Chicago, the Windy City, is a vibrant metropolis that effortlessly blends urban sophistication with Midwestern charm. Known for its iconic skyline, world-class museums, deep-dish pizza, and rich cultural history, Chicago is a destination that offers something for everyone. Whether you’re a foodie, an architecture enthusiast, a sports fan, or simply someone looking to explore a new city, Chicago will captivate you with its energy and diversity.
Planning a trip to Chicago can feel overwhelming, especially if you only have one week to experience everything this incredible city has to offer. But don’t worry—this Chicago Itinerary is designed to help you make the most of your time. From must-see attractions to hidden gems, this guide will walk you through the perfect one-week Chicago adventure.
One Week Chicago Itinerary
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Important Things to Know Before Visiting Chicago
Before diving into your Chicago Itinerary, here are a few essential tips to keep in mind:
- Weather: Chicago experiences all four seasons, with cold, snowy winters and hot, humid summers. Spring and fall are ideal for pleasant weather.
- Currency: The U.S. Dollar (USD) is the local currency. Credit cards are widely accepted, but it’s always good to carry some cash for smaller vendors.
- Language: English is the primary language spoken in Chicago.
- Safety: Like any major city, be mindful of your surroundings, especially at night. Stick to well-lit, populated areas.
- Tipping: Tipping is customary in the U.S. Aim for 15-20% at restaurants and a few dollars for hotel staff and taxi drivers.
Getting In and Out of Chicago Airport
Chicago is served by two major airports: O’Hare International Airport (ORD) and Midway International Airport (MDW).
- O’Hare is one of the busiest airports in the world and is located about 17 miles northwest of downtown.
- Midway is smaller and located about 10 miles southwest of downtown.
Transportation Options:
- CTA Trains: The Blue Line connects O’Hare to downtown, while the Orange Line connects Midway. Both are affordable and efficient.
- Taxis/Rideshares: Taxis and rideshare services like Uber and Lyft are readily available.
- Shuttles: Many hotels offer shuttle services from the airport.
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Is Going to Chicago for a Week Worth It?
Absolutely! A week in Chicago gives you enough time to explore the city’s top attractions, indulge in its culinary delights, and even take a day trip or two. Whether you’re strolling along the Lakefront Trail, marveling at the architecture, or catching a game at Wrigley Field, you’ll find plenty to keep you entertained.
One Week Chicago Itinerary — What to Do?
Here’s a day-by-day breakdown of the perfect Chicago Itinerary:
Day 1: Arrival and Downtown Exploration
Your first day in Chicago is all about getting acquainted with the city’s vibrant downtown area. After arriving and settling into your hotel, you’ll dive into some of Chicago’s most iconic landmarks and neighborhoods. Here’s a detailed breakdown of how to make the most of your first day in the Windy City:
Morning: Arrival and Check-In
- Arrive in Chicago: Whether you’re flying into O’Hare or Midway, follow the transportation tips mentioned earlier to get to your hotel.
- Check-In: Drop off your luggage and freshen up. If your room isn’t ready yet, most hotels will store your bags for you.
- Grab a Coffee: Start your day with a caffeine boost at a local café. Try Intelligentsia Coffee in the Loop or Sawada Coffee in West Loop for a trendy vibe.
Midday: Millennium Park and The Loop
- Millennium Park: Head to this iconic park, a must-see on any Chicago Itinerary.
- Cloud Gate (The Bean): Snap photos of this reflective sculpture, one of Chicago’s most famous landmarks.
- Jay Pritzker Pavilion: Admire the stunning outdoor concert venue designed by Frank Gehry.
- Lurie Garden: Stroll through this serene urban garden for a peaceful escape.
- Lunch at The Gage: Just across from Millennium Park, this gastropub offers hearty American fare with a view of the park.
Afternoon: Grant Park and Buckingham Fountain
- Grant Park: Walk south from Millennium Park into Grant Park, often referred to as “Chicago’s front yard.”
- Buckingham Fountain: This grand fountain is one of the largest in the world and a perfect spot for photos.
- Maggie Daley Park: If you’re traveling with kids, this park features a climbing wall, mini-golf, and a playground.
- Art Institute of Chicago (Optional): If you’re an art lover, consider visiting this world-class museum, home to masterpieces like American Gothic and A Sunday on La Grande Jatte.
Evening: Dinner and Nighttime Stroll
- Dinner at The Purple Pig: Located on the Magnificent Mile, this restaurant is known for its Mediterranean-inspired small plates. Try the milk-braised pork shoulder or the charcuterie board.
- Magnificent Mile: After dinner, take a leisurely stroll along this famous stretch of Michigan Avenue. Window-shop at luxury boutiques or stop by the Water Tower Place for some retail therapy.
- Chicago Riverwalk: End your day with a peaceful walk along the Chicago Riverwalk. The city lights reflecting on the water make for a magical experience.
Optional Add-Ons
- Skydeck at Willis Tower: If you’re up for it, head to the Skydeck for stunning nighttime views of the city. The glass ledge is a thrilling experience!
- Theatre or Comedy Show: Check out what’s playing at the Chicago Theatre or catch a comedy show at The Second City, where legends like Tina Fey and Stephen Colbert got their start.
Pro Tips for Day 1
- Wear Comfortable Shoes: You’ll be doing a lot of walking, so make sure your footwear is up to the task.
- Layer Up: Chicago weather can be unpredictable, especially near the lake. Bring a light jacket or sweater.
- Stay Hydrated: Keep a water bottle handy, especially if you’re visiting in the summer.
Day 1 sets the tone for your Chicago Itinerary, giving you a taste of the city’s architecture, culture, and culinary delights. By the end of the day, you’ll already be falling in love with the Windy City!
Day 2: Architecture and River Cruise
Chicago is renowned for its stunning architecture, and Day 2 of your Chicago Itinerary is dedicated to exploring the city’s skyline and architectural marvels. From a scenic river cruise to towering skyscrapers, this day will leave you in awe of Chicago’s design and innovation. Here’s a detailed plan for your second day in the Windy City:
Morning: Architecture River Cruise
- Breakfast at Wildberry Pancakes and Café: Start your day with a hearty breakfast at this popular spot near Millennium Park. Try their signature berry pancakes or savory omelets.
- Chicago Architecture Foundation River Cruise:
- Why It’s a Must: This 90-minute cruise along the Chicago River is consistently rated as one of the best ways to experience the city’s architecture.
- What You’ll See: Learn about iconic buildings like the Willis Tower, the Wrigley Building, and the Tribune Tower, as well as the history behind Chicago’s architectural evolution.
Booking Tip: Book your tickets in advance (Book Here) to secure your spot, especially during peak seasons.
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Midday: Willis Tower and The Loop
- Willis Tower Skydeck:
- Overview: Head to the Skydeck on the 103rd floor of the Willis Tower (formerly the Sears Tower) for panoramic views of the city and beyond.
- The Ledge: Step out onto the glass-bottomed ledge for a thrilling experience—it’s not for the faint of heart!
- Pro Tip: Arrive early to avoid long lines, or consider purchasing a Fast Pass for quicker access.
- Lunch at Revival Food Hall: Located in the heart of the Loop, this food hall offers a variety of options, from sushi to barbecue. It’s a great spot to refuel after your Skydeck adventure.
Afternoon: Chicago Riverwalk and Architectural Gems
- Chicago Riverwalk:
- Stroll Along the River: After lunch, take a leisurely walk along the Chicago Riverwalk. This pedestrian-friendly path is lined with restaurants, bars, and public art installations.
- Kayaking (Optional): If you’re feeling adventurous, rent a kayak and explore the river from a different perspective.
- Marina City and Merchandise Mart:
- Marina City: These iconic corncob-shaped towers are a must-see for architecture enthusiasts.
- Merchandise Mart: Once the largest building in the world, this massive structure is a hub for design and innovation.
Evening: Dinner and Nighttime Views
- Dinner at Cindy’s Rooftop:
- Location: Located atop the Chicago Athletic Association Hotel, Cindy’s offers stunning views of Millennium Park and Lake Michigan.
- What to Try: Their seasonal menu features dishes like roasted chicken and fresh seafood, paired with creative cocktails.
- The Signature Lounge at the 96th:
- Why Go: End your day with drinks at this iconic lounge in the John Hancock Center. The views are unparalleled, and it’s a more affordable alternative to the observation deck.
- Pro Tip: Arrive before sunset to watch the city transition from day to night.
Optional Add-Ons
- Frank Lloyd Wright’s Robie House: If you’re a fan of architecture, consider taking a short trip to Hyde Park to see this Prairie-style masterpiece.
- The Rookery Building: Visit this historic building in the Loop to see its stunning light-filled atrium designed by Frank Lloyd Wright.
Pro Tips for Day 2
- Dress Comfortably: You’ll be walking and exploring all day, so wear comfortable shoes and weather-appropriate clothing.
- Bring a Camera: The architecture and views are incredibly photogenic, so don’t forget your camera or smartphone.
- Stay Hydrated: Keep a water bottle with you, especially if you’re visiting in the summer.
Day 2 of your Chicago Itinerary is all about appreciating the city’s architectural brilliance and enjoying its stunning skyline. By the end of the day, you’ll have a deeper understanding of why Chicago is considered one of the world’s greatest architectural cities.
Day 3: Museums and Lakefront
Day 3 of your Chicago Itinerary is all about immersing yourself in the city’s world-class museums and enjoying its beautiful lakefront. From iconic art collections to interactive science exhibits, Chicago’s museums are a treasure trove of knowledge and inspiration. Pair that with the serene beauty of Lake Michigan, and you’ve got a day that’s both enriching and relaxing. Here’s a detailed plan for your third day in the Windy City:
Morning: Art Institute of Chicago
- Breakfast at Yolk: Start your day with a delicious breakfast at Yolk, known for its creative twists on classic dishes. Try their red velvet French toast or savory skillet options.
- Art Institute of Chicago:
- Why It’s a Must: This museum is one of the oldest and largest art museums in the U.S., home to an impressive collection of artworks from around the world.
- Highlights:
- American Gothic by Grant Wood
- A Sunday on La Grande Jatte by Georges Seurat
- Thorne Miniature Rooms
- Modern Wing featuring contemporary art
- Pro Tip: Purchase tickets online in advance (Book Here) to skip the lines.
- Lunch at the Museum Café: Refuel at the museum’s on-site café, which offers a variety of sandwiches, salads, and pastries.
Afternoon: Museum Campus and Lakefront
- Museum Campus: After lunch, head to Chicago’s Museum Campus, a lakefront park that houses three of the city’s top museums.
- Field Museum:
- Highlights: Sue the T. rex, ancient Egyptian artifacts, and interactive exhibits on natural history.
- Pro Tip: Check out the special exhibitions, which often feature fascinating topics like dinosaurs or ancient civilizations.
- Shedd Aquarium:
- Highlights: Beluga whales, dolphins, and the Caribbean Reef exhibit.
- Pro Tip: Don’t miss the aquatic show, which is both entertaining and educational.
- Adler Planetarium:
- Highlights: Space exhibits, the Doane Observatory, and stunning views of the skyline.
- Pro Tip: If you’re short on time, prioritize the planetarium’s sky shows, which are truly out of this world.
- Field Museum:
- Lunch Option: If you prefer to eat outside the museums, try Café Muse near the Field Museum for a quick bite.
Late Afternoon: Lakefront Trail and Navy Pier
- Lakefront Trail:
- What to Do: Rent a bike or take a leisurely walk along this 18-mile trail that hugs the shores of Lake Michigan. The views of the lake and skyline are breathtaking.
- Pro Tip: Divvy bikes are available for rent throughout the city, making it easy to explore the trail.
- Navy Pier:
- Why Visit: This iconic pier is a hub of activity, featuring attractions, restaurants, and shops.
- Highlights:
- Centennial Wheel: Ride this Ferris wheel for panoramic views of the city and lake.
- Crystal Gardens: A beautiful indoor botanical garden.
- Polk Bros Park: A great spot to relax and enjoy the waterfront.
- Pro Tip: Visit in the late afternoon to catch the sunset over the lake.
Evening: Dinner and Nighttime Entertainment
- Dinner at Giordano’s:
- Why It’s a Must: No trip to Chicago is complete without trying its famous deep-dish pizza. Giordano’s is one of the best spots to indulge in this cheesy, saucy delight.
- What to Try: The classic cheese or sausage deep-dish pizza.
- Navy Pier Fireworks (Seasonal): If you’re visiting in the summer, stick around Navy Pier for their weekly fireworks display. It’s a magical way to end your day.
- Alternative Option: If fireworks aren’t happening, head to The Violet Hour in Wicker Park for craft cocktails in a speakeasy-style setting.
Optional Add-Ons
- Peggy Notebaert Nature Museum: Located in Lincoln Park, this museum focuses on nature and the environment, with a butterfly haven as its star attraction.
- Chicago History Museum: Learn about the city’s rich history, from the Great Chicago Fire to its role in the Civil Rights Movement.
Pro Tips for Day 3
- Wear Comfortable Shoes: You’ll be walking a lot, especially if you explore the Lakefront Trail.
- Bring Layers: The lakefront can be breezy, even on warm days, so bring a light jacket or sweater.
- Stay Hydrated: Keep a water bottle with you, especially if you’re biking or walking along the trail.
Day 3 of your Chicago Itinerary combines culture, history, and natural beauty, giving you a well-rounded experience of the city. By the end of the day, you’ll have a deeper appreciation for Chicago’s artistic and scientific contributions, as well as its stunning lakefront setting.
Day 4: Neighborhood Exploration
Chicago is a city of neighborhoods, each with its own unique character, history, and charm. Day 4 of your Chicago Itinerary is all about stepping away from the downtown hustle and immersing yourself in the local vibe. From trendy boutiques to historic landmarks, today’s adventures will take you through some of Chicago’s most beloved neighborhoods. Here’s a detailed plan for your fourth day in the Windy City:
Morning: Wicker Park and Bucktown
- Breakfast at Dove’s Luncheonette: Start your day in Wicker Park at this cozy diner known for its Southern-inspired dishes. Try the chicken tamales or the waffle with smoked maple syrup.
- Explore Wicker Park:
- What to Do: This trendy neighborhood is a hub for artists, musicians, and foodies.
- Shopping: Browse unique boutiques along Milwaukee Avenue, such as Una Mae’s for vintage finds or Mildblend Supply Co. for denim.
- Street Art: Don’t miss the colorful murals scattered throughout the area.
- The 606 Trail: Walk or bike along this elevated trail for great views of the neighborhood.
- What to Do: This trendy neighborhood is a hub for artists, musicians, and foodies.
- Coffee Break at Wormhole Coffee: Stop by this quirky café for a latte and a dose of 80s nostalgia.
Midday: Logan Square
- Lunch at Lula Café: Head to Logan Square for lunch at this farm-to-table restaurant, a neighborhood staple. Their seasonal menu features dishes like roasted vegetable bowls and house-made pasta.
- Explore Logan Square:
- What to Do: This hip neighborhood is known for its historic boulevards, vibrant arts scene, and laid-back vibe.
- Logan Boulevard: Stroll along this tree-lined street and admire the historic mansions.
- Logan Square Farmers Market (Seasonal): If you’re visiting on a Sunday, check out this popular market for local produce and artisanal goods.
- The Logan Theatre: Catch an indie film or just admire the vintage marquee.
- What to Do: This hip neighborhood is known for its historic boulevards, vibrant arts scene, and laid-back vibe.
Afternoon: Lincoln Park
- Lincoln Park Zoo:
- Why Visit: This free zoo is one of the oldest in the U.S. and home to a wide variety of animals, from lions to penguins.
- Highlights: The Regenstein Center for African Apes and the Kovler Lion House.
- Peggy Notebaert Nature Museum (Optional): Located near the zoo, this museum focuses on nature and the environment, with a butterfly haven as its star attraction.
- Lincoln Park Conservatory:
- What to Do: Wander through this beautiful greenhouse filled with exotic plants and flowers.
- Pro Tip: The conservatory is free to enter and a peaceful escape from the city buzz.
Evening: Dinner and Nightlife in West Loop
- Dinner at Girl & the Goat:
- Why It’s a Must: This award-winning restaurant by Chef Stephanie Izard is a culinary gem.
- What to Try: The wood oven-roasted pig face or the goat empanadas.
- Pro Tip: Reservations fill up fast, so book well in advance (Book Here).
- Nightlife in West Loop:
- The Aviary: For a unique cocktail experience, visit this upscale bar known for its inventive drinks and theatrical presentations.
- Haymarket Pub & Brewery: If you’re a beer lover, this spot offers a great selection of craft brews.
Optional Add-Ons
- Pilsen: If you’re interested in art and culture, head to Pilsen to explore its vibrant murals and visit the National Museum of Mexican Art.
- Andersonville: This charming neighborhood is known for its Swedish heritage, eclectic shops, and cozy cafés.
Pro Tips for Day 4
- Use Public Transit: The CTA Blue Line and buses make it easy to hop between neighborhoods.
- Wear Comfortable Shoes: You’ll be walking a lot, so make sure your footwear is up to the task.
- Bring a Reusable Bag: If you plan to shop at local boutiques or farmers markets, a reusable bag will come in handy.
Day 4 of your Chicago Itinerary is all about discovering the city’s diverse neighborhoods and experiencing their unique flavors and cultures. By the end of the day, you’ll have a deeper appreciation for the local life that makes Chicago so special.
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Day 5: Sports and Entertainment
Chicago is a city that lives and breathes sports and entertainment. Whether you’re a die-hard sports fan, a music lover, or just someone looking for a fun day out, Day 5 of your Chicago Itinerary has something for everyone. From catching a game at a historic ballpark to enjoying world-class performances, this day is all about experiencing the city’s vibrant energy. Here’s a detailed plan for your fifth day in the Windy City:
Morning: Game Day or Museum Morning
- Breakfast at Batter & Berries: Start your day with a hearty breakfast at this popular spot known for its French toast flights and savory omelets.
- Option 1: Catch a Game at Wrigley Field (Seasonal):
- Why It’s a Must: Wrigley Field, home of the Chicago Cubs, is one of the oldest and most iconic ballparks in the U.S.
- What to Do:
- Arrive early to explore the surrounding Wrigleyville neighborhood, filled with bars, restaurants, and Cubs memorabilia shops.
- Grab a hot dog and a beer inside the stadium and soak in the electric atmosphere.
- Pro Tip: Check the Cubs’ schedule and book tickets in advance (Book Here).
- Option 2: Visit Guaranteed Rate Field (Seasonal):
- Why Go: Home of the Chicago White Sox, this stadium offers a more modern experience with great views of the field.
- Pro Tip: If you’re not visiting during baseball season, consider taking a stadium tour to learn about the team’s history.
- Option 3: Museum Morning:
- Field Museum: If sports aren’t your thing, spend the morning exploring this world-class natural history museum. Don’t miss Sue the T. rex!
- Shedd Aquarium: Dive into the underwater world with exhibits featuring beluga whales, dolphins, and tropical fish.
Midday: Lunch and Neighborhood Exploration
- Lunch at Big Star: Located in Wicker Park, this trendy spot is known for its tacos and margaritas. Try the al pastor tacos and a classic margarita.
- Explore Wrigleyville (If You’re Not at the Game):
- What to Do: Walk around the neighborhood, grab a drink at Murphy’s Bleachers, and soak in the lively atmosphere.
- Alternative Option: Chinatown:
- What to Do: Visit Chinatown for a delicious dim sum lunch at MingHin Cuisine and explore the neighborhood’s shops and landmarks, like the Nine Dragon Wall.
Afternoon: Entertainment Options
- Option 1: Chicago Theatre Tour:
- Why It’s a Must: This historic theater is a Chicago landmark, known for its stunning architecture and rich history.
- What to Do: Take a guided tour to learn about the theater’s past and see its beautiful interiors.
- Option 2: Second City Comedy Show:
- Why Go: This legendary comedy club has launched the careers of stars like Tina Fey and Stephen Colbert.
- What to Do: Catch an improv or sketch comedy show for a night of laughs.
- Pro Tip: Book tickets in advance (Book Here).
- Option 3: Millennium Park Concert:
- Why Go: If you’re visiting in the summer, check out a free concert at the Jay Pritzker Pavilion in Millennium Park.
- Pro Tip: Bring a picnic blanket and enjoy the music under the stars.
Evening: Dinner and Nightlife
- Dinner at Au Cheval:
- Why It’s a Must: This West Loop spot is famous for its decadent burgers, often hailed as some of the best in the country.
- What to Try: The double cheeseburger with thick-cut bacon and a side of fries.
- Pro Tip: Be prepared for a wait, as this place is always busy.
- Nightlife in River North:
- The Violet Hour: Head to this speakeasy-style bar for expertly crafted cocktails in a chic setting.
- Howl at the Moon: If you’re in the mood for live music and a party atmosphere, this dueling piano bar is a great choice.
Optional Add-Ons
- United Center Tour: If you’re a basketball or hockey fan, take a tour of the United Center, home of the Chicago Bulls and Blackhawks.
- Chicago Symphony Orchestra: For a more refined evening, catch a performance by one of the world’s leading orchestras.
Pro Tips for Day 5
- Check Schedules: Whether it’s a game, concert, or show, make sure to check schedules and book tickets in advance.
- Dress Comfortably: If you’re attending a game or outdoor event, wear comfortable clothing and shoes.
- Arrive Early: Popular venues like Wrigley Field and Second City can get crowded, so arrive early to secure a good spot.
Day 5 of your Chicago Itinerary is all about embracing the city’s love for sports and entertainment. Whether you’re cheering on the Cubs, laughing at a comedy show, or enjoying a live concert, you’ll experience the vibrant energy that makes Chicago so special.
Day 6: Day Trip
After five days of exploring Chicago’s bustling streets and iconic landmarks, Day 6 of your Chicago Itinerary is the perfect opportunity to venture beyond the city limits and discover the surrounding areas. Whether you’re interested in nature, history, or architecture, there are plenty of fantastic day trip options within easy reach of Chicago. Here’s a detailed plan for your sixth day in the Windy City:
Option 1: Indiana Dunes National Park
- Why Go: Just an hour’s drive from Chicago, Indiana Dunes offers stunning beaches, hiking trails, and breathtaking views of Lake Michigan.
- What to Do:
- Hike the Trails: Explore trails like the 3 Dunes Challenge or the Cowles Bog Trail for scenic views and diverse landscapes.
- Relax on the Beach: Spend some time soaking up the sun at West Beach or Kemil Beach.
- Visit the Visitor Center: Learn about the park’s history and ecosystems at the Paul H. Douglas Center.
- Lunch: Pack a picnic or grab a bite at a local café in Chesterton, a charming nearby town.
- Pro Tip: Bring comfortable hiking shoes, sunscreen, and plenty of water.
Option 2: Evanston and Northwestern University
- Why Go: Located just north of Chicago, Evanston is a picturesque town known for its historic homes, vibrant downtown, and Northwestern University.
- What to Do:
- Explore Northwestern University: Stroll through the beautiful campus and visit the Block Museum of Art.
- Downtown Evanston: Shop at unique boutiques and enjoy a meal at one of the many restaurants.
- Grosse Point Lighthouse: Visit this historic lighthouse and learn about its role in maritime history.
- Lunch: Try Farmhouse Evanston for farm-to-table dishes or Buffalo Joe’s for classic wings and burgers.
- Pro Tip: Take the Metra Union Pacific North Line from Chicago for an easy and scenic ride to Evanston.
Option 3: Oak Park and Frank Lloyd Wright
- Why Go: Oak Park is a historic suburb known for its connection to famed architect Frank Lloyd Wright.
- What to Do:
- Frank Lloyd Wright Home and Studio: Take a guided tour of Wright’s former home and studio, where he designed many of his early works.
- Unity Temple: Visit this UNESCO World Heritage Site, one of Wright’s most iconic buildings.
- Hemingway Museum: Learn about the life and works of Ernest Hemingway, who was born in Oak Park.
- Lunch: Stop by Petersen’s Ice Cream for a sweet treat or Molly’s Cupcakes for delicious baked goods.
- Pro Tip: The Green Line L train provides easy access to Oak Park from downtown Chicago.
Option 4: Starved Rock State Park
- Why Go: Located about 90 minutes from Chicago, Starved Rock is known for its stunning canyons, waterfalls, and hiking trails.
- What to Do:
- Hike the Trails: Explore trails like St. Louis Canyon or French Canyon for beautiful views and waterfalls.
- Visit the Lodge: Check out the historic Starved Rock Lodge and enjoy a meal at its restaurant.
- Boat Tours (Seasonal): Take a scenic boat tour along the Illinois River.
- Lunch: Dine at the Starved Rock Lodge Restaurant, which offers hearty American fare with a view.
- Pro Tip: Wear sturdy shoes and bring a camera to capture the park’s natural beauty.
Evening: Return to Chicago
- Dinner at The Publican: After your day trip, head back to Chicago and enjoy dinner at this popular West Loop spot known for its farm-to-table dishes and extensive beer list.
- Relax: Spend the evening unwinding at your hotel or exploring a nearby neighborhood like River North or Logan Square.
Pro Tips for Day 6
- Plan Ahead: Check the weather and pack accordingly, especially if you’re heading to a park or outdoor area.
- Transportation: Depending on your destination, consider renting a car or using public transit. The Metra and CTA are convenient options for nearby suburbs.
- Timing: Start your day early to make the most of your trip and avoid traffic.
Day 6 of your Chicago Itinerary offers a refreshing change of pace, allowing you to explore the natural beauty and cultural richness of the areas surrounding the city. Whether you’re hiking through canyons, touring historic homes, or relaxing on a beach, you’ll return to Chicago with unforgettable memories and a deeper appreciation for the region.
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Day 7: Shopping and Farewell
Your final day in Chicago is all about savoring the last moments of your trip, indulging in some retail therapy, and bidding farewell to the Windy City. Day 7 of your Chicago Itinerary is designed to be relaxed yet memorable, giving you a chance to pick up souvenirs, enjoy one last deep-dish pizza, and reflect on your incredible week in Chicago. Here’s a detailed plan for your seventh day:
Morning: Shopping on the Magnificent Mile
- Breakfast at The Bongo Room: Start your day with a decadent breakfast at this popular spot known for its creative pancakes and French toast. Try the white chocolate and caramel pretzel pancakes—they’re a fan favorite!
- The Magnificent Mile:
- Why It’s a Must: This iconic stretch of Michigan Avenue is a shopper’s paradise, featuring everything from luxury boutiques to flagship stores.
- What to Do:
- Luxury Shopping: Visit high-end stores like Tiffany & Co., Gucci, and Nordstrom.
- Flagship Stores: Check out the multi-level Nike Chicago or the Apple Store for the latest tech.
- Souvenirs: Stop by Chicago Sports Depot for Cubs or Bulls memorabilia, or Local Goods Chicago for unique, locally made gifts.
- Pro Tip: Wear comfortable shoes and bring a reusable shopping bag for your purchases.
Midday: Lunch and Last-Minute Explorin
- Lunch at Portillo’s: No trip to Chicago is complete without trying a Chicago-style hot dog or Italian beef sandwich. Portillo’s is a local favorite for both.
- Millennium Park (Optional): If you missed it earlier in the week or want to revisit, take a final stroll through Millennium Park and snap a few more photos with The Bean.
- Chicago Cultural Center:
- Why Visit: This beautiful building is home to free art exhibits, stunning architecture, and the world’s largest Tiffany stained-glass dome.
- Pro Tip: Check out the center’s event schedule for any last-minute performances or tours.
Afternoon: Relax and Reflec
- Lakefront Trail: If you have some extra time, take a leisurely walk or bike ride along the Lakefront Trail. The views of Lake Michigan and the skyline are the perfect backdrop for reflecting on your trip.
- Navy Pier (Optional): If you didn’t get a chance to visit earlier, spend some time at Navy Pier. Ride the Centennial Wheel or simply enjoy the waterfront atmosphere.
Evening: Farewell Dinner
- Dinner at Lou Malnati’s: End your trip with one last deep-dish pizza experience. Lou Malnati’s is a Chicago institution, known for its buttery crust and rich tomato sauce.
- What to Try: The classic Malnati Chicago Classic with sausage or the Lou’s Veggie for a lighter option.
- Dessert at Garrett Popcorn Shops: Pick up a bag of their famous Chicago Mix (a blend of caramel and cheese popcorn) for a sweet and savory treat to enjoy on your way home.
Optional Add-Ons
- Skydeck at Willis Tower: If you haven’t already, visit the Skydeck for a final panoramic view of the city.
- The Signature Lounge at the 96th: Sip a cocktail while enjoying breathtaking views of the city skyline.
Pro Tips for Day 7
- Pack Smart: Make sure you leave room in your luggage for souvenirs, or consider shipping items home if needed.
- Check Out Early: If you have a late flight, ask your hotel to store your luggage so you can explore without carrying bags.
- Transportation to the Airport: Plan ahead for your trip to O’Hare or Midway. The CTA Blue Line (to O’Hare) and Orange Line (to Midway) are affordable and efficient options.
One Week Chicago Itinerary
As your week in Chicago comes to an end, take a moment to reflect on all the incredible experiences you’ve had. From exploring world-class museums and iconic landmarks to indulging in the city’s culinary delights and vibrant neighborhoods, your Chicago Itinerary has given you a taste of everything the Windy City has to offer.
Chicago is a city that leaves a lasting impression, and we hope this guide has helped you make the most of your time here. Whether you’re already planning your next visit or simply reminiscing about your adventures, one thing is certain: Chicago will always welcome you back with open arms.
Safe travels, and until next time, farewell from the Windy City!
Ready to plan your trip? Use the booking links provided throughout this guide to secure your accommodations and activities, and start counting down the days to your Chicago adventure!
Where to Eat in Chicago?
Chicago’s food scene is legendary. Here are some must-try spots:
- Deep-Dish Pizza: Giordano’s, Lou Malnati’s, Pequod’s
- Hot Dogs: Portillo’s, Superdawg
- Fine Dining: Alinea, Smyth, Oriole
- Casual Eats: Au Cheval, Big Star, Publican
Where to Stay During One Week in Chicago
Choosing the right place to stay is crucial for making the most of your Chicago Itinerary. The Windy City offers a wide range of accommodations, from luxury hotels to budget-friendly options, each with its own unique charm and advantages. Whether you want to be in the heart of downtown or prefer a quieter neighborhood, here’s a detailed guide to help you decide where to stay during your one-week trip to Chicago.
Best Areas to Stay in Chicago
1. The Loop (Downtown)
- Why Stay Here: The Loop is the heart of Chicago’s downtown, making it perfect for first-time visitors who want to be close to major attractions like Millennium Park, the Art Institute, and the Chicago Riverwalk.
- Pros:
- Central location with easy access to public transit.
- Walking distance to iconic landmarks.
- Plenty of dining and entertainment options.
- Cons:
- Can be noisy and crowded, especially during peak hours.
- Higher prices compared to other neighborhoods.
- Recommended Hotels:
2. River Nort
- Why Stay Here: River North is known for its vibrant nightlife, art galleries, and proximity to the Magnificent Mile. It’s a great choice for those who want a mix of culture and entertainment.
- Pros:
- Close to shopping, dining, and nightlife.
- Easy access to public transit.
- Trendy and energetic atmosphere.
- Cons:
- Can be noisy at night due to the nightlife scene.
- Slightly more expensive than other areas.
- Recommended Hotels:
3. West Loop
- Why Stay Here: West Loop is a foodie’s paradise, home to some of Chicago’s best restaurants and the famous Randolph Street Restaurant Row. It’s also close to Greektown and Fulton Market.
- Pros:
- Incredible dining options, from casual eateries to fine dining.
- Trendy and up-and-coming neighborhood.
- Close to downtown without the hustle and bustle.
- Cons:
- Limited hotel options compared to downtown.
- Slightly farther from major tourist attractions.
- Recommended Hotels:
4. Wicker Park/Bucktown
- Why Stay Here: These neighborhoods are perfect for travelers who want a more local, artsy vibe. Wicker Park and Bucktown are known for their trendy boutiques, street art, and hipster culture.
- Pros:
- Unique shopping and dining experiences.
- Laid-back and creative atmosphere.
- Affordable compared to downtown.
- Cons:
- Farther from major tourist attractions.
- Limited luxury hotel options.
- Recommended Hotels:
5. Lincoln Park
- Why Stay Here: Lincoln Park is a residential neighborhood with a relaxed vibe, perfect for families or those who want to escape the downtown hustle. It’s home to the Lincoln Park Zoo and the Lakefront Trail.
- Pros:
- Quiet and family-friendly.
- Close to nature and outdoor activities.
- Great dining and shopping options.
- Cons:
- Farther from downtown attractions.
- Limited hotel options.
- Recommended Hotels:
Budget-Friendly Options
If you’re looking to save on accommodations, consider these budget-friendly options:
- Freehand Chicago (Book Here): A stylish hostel with private rooms and dorms, located in River North.
- HI Chicago Hostel (Book Here): A clean and affordable hostel in the South Loop, close to public transit.
Luxury Options
For those seeking a more luxurious stay, these hotels offer top-notch amenities and service:
- Four Seasons Hotel Chicago (Book Here): Located on the Magnificent Mile, this hotel offers stunning views and world-class service.
- The Peninsula Chicago (Book Here): A five-star hotel with a spa, rooftop terrace, and fine dining options.
Pro Tips for Choosing Where to Stay
- Consider Your Itinerary: Choose a neighborhood that’s close to the attractions you plan to visit most.
- Book Early: Chicago is a popular destination, so book your accommodations well in advance, especially during peak seasons.
- Check for Deals: Look for package deals or discounts on hotel booking websites.
- Read Reviews: Check guest reviews to ensure the hotel meets your expectations.
No matter where you choose to stay, Chicago’s diverse neighborhoods and accommodations ensure you’ll find the perfect home base for your Chicago Itinerary. Enjoy your stay in the Windy City!
Disclosure: Some links in this post are affiliate links. If you make a purchase through one of these links, we may earn a small commission (at no extra cost to you!). We’re very grateful when you use our links to make a purchase:-).
More Tips for Visiting Chicago in 2025
Chicago is a city that’s constantly evolving, and visiting in 2025 promises to be an exciting experience with new attractions, events, and trends. To help you make the most of your trip, here are some additional tips and insights tailored for your Chicago Itinerary in 2025.
1. Plan Ahead for Major Events
Chicago hosts a variety of festivals, concerts, and sporting events throughout the year. Here are some highlights to consider for 2025:
- Lollapalooza (August): This world-famous music festival takes over Grant Park with performances by top artists. Book tickets and accommodations early if you plan to attend.
- Chicago Air and Water Show (August): Watch jaw-dropping aerial stunts along the lakefront. It’s free to attend!
- Chicago Marathon (October): If you’re visiting in October, be aware that this major event draws thousands of runners and spectators, so plan your transportation accordingly.
- Holiday Markets (November-December): Christkindlmarket and other holiday markets are a must-visit for festive shopping and treats.
2. Embrace Sustainable Travel
Chicago is making strides toward sustainability, and you can contribute by:
- Using Public Transit: The CTA trains and buses are an eco-friendly way to get around. Consider purchasing a Ventra Card for unlimited rides.
- Biking: Rent a Divvy bike and explore the city’s extensive bike lanes and trails, including the Lakefront Trail.
- Supporting Green Businesses: Look for restaurants and hotels with eco-friendly practices, such as The Hoxton and Soho House Chicago.
3. Explore New Attractions
Chicago is always adding new attractions and experiences. Here are a few to look out for in 2025:
- The 78: This massive development along the Chicago River will feature new parks, residential spaces, and cultural venues.
- Obama Presidential Center: Scheduled to open in Jackson Park, this center will celebrate the legacy of President Barack Obama and feature exhibits, gardens, and community spaces.
- Expanded Riverwalk: The Chicago Riverwalk continues to grow, with new restaurants, bars, and public art installations.
4. Stay Connected with Technology
- Free Wi-Fi: Take advantage of free Wi-Fi hotspots in parks, libraries, and public spaces.
- Apps to Download:
- Transit Stop: For real-time CTA updates.
- Divvy Bikes: For bike rentals and station locations.
- OpenTable: For restaurant reservations.
- Citymapper: For navigating the city like a local.
5. Be Weather-Ready
Chicago’s weather can be unpredictable, so pack accordingly:
- Winter (December-February): Bundle up with layers, a heavy coat, gloves, and a hat. Snow and ice are common.
- Spring (March-May): Bring a light jacket and umbrella for rain showers.
- Summer (June-August): Wear lightweight clothing, sunscreen, and stay hydrated. Be prepared for humidity.
- Fall (September-November): Pack layers and a jacket for cooler evenings.
6. Save Money with CityPASS
If you plan to visit multiple attractions, consider purchasing a Chicago CityPASS. It includes discounted entry to top sites like the Shedd Aquarium, Skydeck Chicago, and the Field Museum.
7. Try New Food Trends
Chicago’s food scene is always evolving. In 2025, keep an eye out for:
- Plant-Based Dining: More restaurants are offering vegan and vegetarian options. Try Chicago Diner or Alinea’s plant-based tasting menu.
- Global Flavors: Explore diverse cuisines in neighborhoods like Pilsen (Mexican), Devon Avenue (Indian), and Argyle Street (Vietnamese).
- Pop-Up Restaurants: Look for temporary dining experiences and food trucks offering unique dishes.
8. Respect Local Culture
- Tipping: Tipping is customary in the U.S. Aim for 15-20% at restaurants and a few dollars for hotel staff and taxi drivers.
- Public Etiquette: Be mindful of personal space, especially on public transit, and avoid loud conversations in quiet areas.
- Support Local Businesses: Shop at independent boutiques and dine at locally owned restaurants to support the community.
9. Stay Safe
- Be Aware of Your Surroundings: Stick to well-lit, populated areas, especially at night.
- Emergency Numbers: Dial 911 for emergencies.
- Travel Insurance: Consider purchasing travel insurance for peace of mind.
10. Capture Memories
- Photography Tips:
- Visit the Chicago Riverwalk at sunrise for stunning reflections.
- Capture the skyline from Adler Planetarium or the 606 Trail.
- Use a wide-angle lens for iconic shots of The Bean and Millennium Park.
- Journaling: Keep a travel journal to document your experiences and favorite moments.
By following these tips, you’ll be well-prepared to enjoy everything Chicago has to offer in 2025. Whether you’re exploring new attractions, savoring the latest food trends, or simply soaking in the city’s vibrant energy, your Chicago Itinerary is sure to be unforgettable. Safe travels!
Getting Around Chicago
Navigating Chicago is relatively easy thanks to its well-connected public transportation system, bike-friendly streets, and walkable neighborhoods. Whether you’re exploring downtown or venturing into the city’s diverse districts, here’s a detailed guide to help you get around during your Chicago Itinerary.
Public Transportation
1. CTA Trains (The “L”)
- Overview: The Chicago Transit Authority (CTA) operates the city’s elevated and subway train system, known as the “L.” It’s one of the most efficient ways to get around.
- Key Lines:
- Red Line: Runs north-south, connecting downtown to neighborhoods like Wrigleyville and Hyde Park.
- Blue Line: Runs northwest to downtown and O’Hare Airport.
- Brown Line: Loops through downtown and heads north to Lincoln Park and Albany Park.
- Green Line: Connates downtown to the West Side and South Side.
- Orange Line: Runs from downtown to Midway Airport.
- Fares:
- Single ride: 2.50(withVentraCard)or2.50(withVentraCard)or3 (cash).
- Unlimited passes: 1-day (5),3−day(5),3−day(15), 7-day ($20).
- Pro Tip: Download the Transit Stop app for real-time train updates and schedules.
2. CTA Buses
- Overview: CTA buses complement the train system, providing access to areas not served by the “L.”
- Key Routes:
- #146 Marine-Michigan: Connects downtown to Lincoln Park and Uptown.
- #151 Sheridan: Runs along the lakefront, offering scenic views.
- Fares: Same as the train system.
- Pro Tip: Use the Citymapper app to plan your bus routes and track arrivals.
3. Metra Rail
- Overview: Metra trains are ideal for traveling to suburban areas or taking day trips.
- Key Lines:
- Union Pacific North: Connects downtown to Evanston and other northern suburbs.
- BNSF Line: Runs to western suburbs like Naperville.
- Fares: Vary by distance; check the Metra website for pricing.
- Pro Tip: Metra trains are less frequent than the “L,” so check the schedule in advance.
Biking
1. Divvy Bikes
- Overview: Chicago’s bike-share program offers thousands of bikes at hundreds of stations across the city.
- Costs:
- Single ride: $3.30 for 30 minutes.
- Day pass: $15 for unlimited 3-hour rides.
- Annual membership: $108 (great for frequent visitors).
- Pro Tip: Use the Divvy Bikes app to locate stations and check bike availability.
2. Bike Lanes and Trails
- Lakefront Trail: An 18-mile trail along Lake Michigan, perfect for biking with stunning views.
- The 606: An elevated trail through Wicker Park, Bucktown, and Humboldt Park.
- Protected Bike Lanes: Many streets, like Dearborn and Milwaukee Avenue, have dedicated bike lanes.
Rideshares and Taxis
1. Uber and Lyft
- Overview: Rideshare services are widely available and convenient for short trips or late-night travel.
- Pro Tip: Use promo codes for first-time users to save on rides.
2. Taxis
- Overview: Traditional taxis are still an option, though they’re less common than rideshares.
- How to Hail: Look for yellow cabs or use the Curb app to book one.
- Fares: Start at $3.25, with additional charges per mile and for waiting time.
Walking
1. Downtown Chicago
- Overview: The Loop and surrounding areas are highly walkable, with wide sidewalks and pedestrian-friendly streets.
- Key Areas:
- Magnificent Mile: Perfect for shopping and sightseeing.
- Millennium Park: Easy to explore on foot.
- Chicago Riverwalk: A scenic route for strolling.
- Pro Tip: Wear comfortable shoes and be mindful of traffic when crossing streets.
Driving
1. Renting a Car
- When to Rent: Only necessary if you plan to explore suburbs or take day trips outside the city.
- Parking:
- Street parking can be hard to find and expensive.
- Use apps like SpotHero to reserve parking spots in advance.
- Pro Tip: Avoid driving downtown during rush hour (7-9 AM and 4-6 PM).
2. Toll Roads
- Overview: Some highways, like the Illinois Tollway, require toll payments.
- Payment Options: Use an I-PASS or pay online within 7 days.
Airport Transportation
1. O’Hare International Airport (ORD)
- CTA Blue Line: The most affordable option, taking about 45 minutes to downtown.
- Taxis/Rideshares: Cost around 40−40−50 to downtown.
- Shuttles: Many hotels offer shuttle services.
2. Midway International Airport (MDW)
- CTA Orange Line: Takes about 25 minutes to downtown.
- Taxis/Rideshares: Cost around 30−30−40 to downtown.
Pro Tips for Getting Around Chicago
- Ventra Card: Purchase a reloadable Ventra Card for seamless access to CTA trains and buses.
- Avoid Rush Hour: Public transit and roads can get crowded during peak hours.
- Stay Alert: Keep an eye on your belongings, especially in crowded areas.
- Use Apps: Download Transit Stop, Citymapper, and Divvy Bikes for real-time updates and route planning.
With these transportation options and tips, you’ll have no trouble navigating Chicago during your Chicago Itinerary. Whether you’re hopping on the “L,” biking along the lakefront, or strolling through downtown, getting around the Windy City is part of the adventure!
One Week Chicago Itinerary: In Conclusion
A week in Chicago is the perfect amount of time to experience the city’s highlights and immerse yourself in its unique culture. From iconic landmarks to hidden gems, this Chicago Itinerary ensures you’ll leave with unforgettable memories. So pack your bags, book your tickets, and get ready to fall in love with the Windy City!
Disclosure: Some links in this post are affiliate links. If you make a purchase through one of these links, we may earn a small commission (at no extra cost to you!). We’re very grateful when you use our links to make a purchase:-).
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