Chicago is one of the most romantic cities in the American Midwest. This owes to its great combination of neatly planned urban landscapes and a host of leisure options. There are the beautiful parks that line the shores of Lake Michigan, as well as a collection of activities in the city which can bring couples and honeymooners closer.
You can enjoy Chicago’s most romantic places along the lake, and in it, in many ways – be it on a bike for 2 or setting sail and indulging in a romantic dinner cruise. The Centennial Wheel dominates the Chicago skyline and can serve up intimate moments with unforgettable views. For even better views, a helicopter ride takes some beating.
Here, you’ll find more of The Best Romantic Places in Chicago.
Tour Michigan Avenue by horse and carriage
Big and tall Amish workhorses meet big city life in Chicago. They provide memorable carriage tours through the city. A few operators serve Michigan Avenue. For the determined, it can be a most unforgettable way to pop the question. For any couple, it’s a great way to sightsee along the northern shopping section of the Magnificent Mile. Carriage rides at night can be charming, with the pretty shops and small churches along the way. Be sure to make use of the single blanket, for both of you to cuddle up under through the Windy City.
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Ride a glass-bottom gondola on the Centennial Wheel
The Navy Pier is filled with dining and entertainment for all. However, as a couple you can escape on the iconic Centennial Wheel, which rises in the pier’s center, overlooking Lake Michigan. The Ferris wheel offers a wonderful private experience for around $125. This lets you ride in a VIP gondola that’s specially fitted with plush seating and has a glass floor so that you can huddle together and enjoy the thrilling views. In the summer, fireworks synced to music add to the magic on Wednesdays and Saturdays.
Location: Navy Pier, 600 E Grand Ave, Chicago, IL 60611, USA
Open: Daily from 10 am to 8 pm
Phone: +1 800-595-7437
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Tour Chicago by helicopter
The Chicago Helicopter Experience lets you go on a once-in-a-lifetime tour, with unparalleled views above the Windy City and its spectacular lakefront. Daytime tours enable you to take flight and come to eye-level with Chicago’s iconic skyscrapers. Most tours are guided, with the pilot narrating as you fly over the city’s most iconic landmarks. They’ll show you the best photo opportunities around the town, with a few bits of its rich history occasionally thrown in. Night flights are also available, showing you glittering skyline, lit with millions of city lights.
Location: 2420 S Halsted St, Chicago, IL 60608, USA
Open: Daily from 9 am to 10 pm
Phone: +1 312-967-8687
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Set sail across Lake Michigan
As one of the Great Lakes, Lake Michigan is the playground for several majestic yacht and tall ship cruises. Setting sail on the calm waters of the lake can be one of the most surreal experiences for romantics in Chicago. Among the prominent ships are the 114-foot Manitou and the 148-foot tall ship Windy of Chicago, both of which sail the lake by day and in the evenings from Chicago’s Navy Pier. These sailing trips let you take in Chicago’s famous skylines and explore the city’s architectural wonders from the lakefront.
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Check out Chicago’s observation decks
Take your significant other for thrilling sensations from some of the world’s tallest skyscrapers. There’s the SkyDeck Ledge at the Willis Tower on South Wacker Drive. On its 103rd-floor edge, you can step into glass boxes which extend out, with your feet seemingly hovering over at 1,300 feet above the ground. Another observation deck, 360 Chicago, offers a similar sensation from the 94th-floor observatory of the John Hancock Building. Its lookout has a tilting glass enclosure that often has couples clinging to each other for dear life.
Location: 233 S Wacker Dr, Chicago, IL 60606, USA
Open: Daily from 9 am to 10 pm
Phone: +1 312 875 9696
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Stroll through Chicago Botanic Garden
You can find this popular spot in Chicago’s rich collection of beautiful green oases in Glencoe, around a half-hour’s drive north from The Loop. The botanic garden spans over 380 acres, which are filled with 25 display gardens and 4 natural habitats. Among the favorites are the aquatic garden, the bonsai gallery, the Regenstein fruit and vegetable garden, the beautiful and Zen-like Elizabeth Hubert Malott Japanese Garden, and the Model Railroad Garden that families with kids will love.
Location: 1000 Lake Cook Rd, Glencoe, IL 60022, USA
Open: Daily from 7 am to 9 pm
Phone: +1 847 835 5440
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Dine on top of a skyscraper
The skyscraper-filled Windy City has plenty for couples looking for sky-high dining. Among them is the Signature Lounge on the 95th floor of the John Hancock building in Downtown. It offers romantic settings with amazing sunsets, where you can dine and drink to the city’s gradually emerging twinkling lights around the stunning Willis Tower. Cite, an upscale American restaurant with French influences, offers sweeping views of the city and Lake Michigan from the top of Lake Point Tower on North Lake Shore Drive.
Where to stay in Chicago?
Hilton Chicago O’Hare Airport
4-star Chicago hotel with 1 indoor pools, connected to the airport
Food and drink
- Full breakfast (surcharge)
- 2 restaurants
- Bar/lounge
- Coffee shop/café
- Snack bar/deli
- Room service (during limited hours)
Things to do
- Number of indoor pools – 1
- Fitness facilities
- Spa services on site
- Spa treatment room(s)
- Golfing nearby
- Steam room
- Sauna
Working away
- Business center
- Conference space
- Meeting rooms
- Conference center
- Computer station
Services
- 24-hour front desk
- Concierge services
- Dry cleaning/laundry service
- Laundry facilities
- Free grocery shopping service
- Free newspapers in lobby
- Luggage storage
- Wedding services
- Multilingual staff
- Porter/bellhop
Facilities
- Year Built – 1971
- Elevator
- ATM/banking
- Safe-deposit box at front desk
- Designated smoking areas
Accessibility
- Braille or raised signage
- Accessible bathroom
- In-room accessibility
- Roll-in shower
- Assistive listening devices available
- Wheelchair-accessible path to lift
- Wheelchair-accessible pool
- Wheelchair-accessible meeting spaces/business center
- Wheelchair-accessible on-site restaurant
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La Quinta Inn & Suites by Wyndham Chicago Downtown
3-star hotel with restaurant, near Willis Tower
Food and drink
- Restaurant
- Coffee shop/café
- Room service (during limited hours)
Things to do
- Fitness facilities
Working away
- 24-hour business center
- Conference space
- Meeting rooms
- Conference space size (feet) – 1672
- Conference space size (meters) – 155
- Computer station
Services
- 24-hour front desk
- Luggage storage
Facilities
- Year Built – 2009
- Elevator
- Safe-deposit box at front desk
Accessibility
- In-room accessibility
- Wheelchair accessible
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Hyatt Regency McCormick Place
4-star hotel with 1 indoor pools, connected to the convention center, near McCormick Place
Food and drink
- Full breakfast (surcharge)
- 3 restaurants
- 2 bars/lounges
- Coffee shop/café
- Snack bar/deli
- Room service (during limited hours)
Things to do
- Bicycle rentals on site
- Golfing nearby
- Hiking/biking trails nearby
- Kayaking nearby
- Parasailing nearby
- Sailing nearby
- Scooter/moped rentals nearby
- Segway rental/tour nearby
- Water skiing nearby
Working away
- 24-hour business center
- Business center
- Conference space
- Meeting rooms
- Conference space size (feet) – 50000
- Conference space size (meters) – 4645
- Conference center
- Computer station
Services
- 24-hour front desk
- Concierge services
- Tours/ticket assistance
- Dry cleaning/laundry service
- Laundry facilities
- Free newspapers in lobby
- Luggage storage
- Wedding services
- Multilingual staff
- Porter/bellhop
Facilities
- Number of buildings/towers – 2
- Year Built – 1998
- Elevator
- ATM/banking
- Safe-deposit box at front desk
- Designated smoking areas
- Terrace
Accessibility
- Braille or raised signage
- Accessible bathroom
- In-room accessibility
- Roll-in shower
- Wheelchair accessible
- Wheelchair-accessible path of travel
- Wheelchair-accessible parking
- Assistive listening devices available
- Wheelchair-accessible path to lift
- Wheelchair-accessible registration desk
- Raised toilet seat
Location : 2233 S Martin Luther King Dr, Chicago, 60616, IL, United States of America
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