4.5(2.1k)
Go City Chicago Explorer Pass: Choose from 39 Attractions
Chicago
From$84
For two
Romantic Chicago for couples
Plan an unforgettable trip for two. We've pulled the highest-rated experiences in Chicago: sunset cruises, private dinners, rooftop viewpoints, and intimate shows. All rated 4.5 stars or higher by real couples.
See all Chicago
Date-night approved, top-rated.
About this list
Why this shortlist
Chicago is one of the world's great date-night cities, and the shortlist below reflects it. Every experience here has been rated 4.5★ or higher, which means real couples went, loved it, and said so afterwards.
Book any of them in under two minutes with free cancellation on most options. Anniversary, proposal, or just a Friday night. You're covered.
Shortlist
Romantic Chicago for couples
4.4(2.1k)Go City Chicago All-Inclusive Pass: Choose from 39 Attractions
Chicago
From$149
4.7(575)The Art Institute of Chicago: Fast Pass
Chicago
From$40
4.6(335)The Field Museum of Natural History: Entry Ticket
Chicago
From$29
4.6(301)Big Bus: Chicago Hop-on Hop-off Bus Tour
Chicago
From$49
4.3(308)360 Chicago Observation Deck: Entry Ticket
Chicago
From$30
4.8(114)Official Chicago Architecture Cruise by First Lady
Chicago
From$57
4.7(126)Skydeck Chicago Tickets
Chicago
From$42.33
4.5(145)75-Minute Chicago River Architecture Cruise by Shoreline
Chicago
From$46
4.4(162)360 Chicago Observation Deck Skip-the-Line Tickets
Chicago
From$30
4.6(127)Chicago C3® CityPASS®: 3 Attractions of your choice
Chicago
From$109
4.2(181)Navy Pier Centennial Wheel: Entry Ticket
Chicago
From$24.72
4.8(93)Chicago: Architecture River Cruise from Navy Pier
Chicago
From$46
4.7(72)90-min Chicago River and Lake Michigan Architecture Cruise by Wendella
Chicago
From$45
4.2(93)Museum Of Contemporary Art (MCA): Entry Ticket
Chicago
From$22
4.5(64)Museum of Illusions Chicago: Entry Ticket
Chicago
From$43
4.6(58)Flyover Experience in Chicago
Chicago
From$27.95
4.0(94)Museum of Ice Cream Chicago: Entry Ticket
Chicago
From$43
4.2(66)Balloon Museum® Chicago: EmotionAir Exhibition Entry Ticket
Chicago
From$44.38
4.2(64)Santa’s Village Amusement & Water Park: Any Day Ticket
Chicago
From$45.13
4.6(42)Chicago CityPASS®
Chicago
From$144
5.0(27)Chicago Architecture Evening Cruise by Shoreline
Chicago
From$46
4.9(23)90-min Scenic Sunset Lake Michigan Cruise by Wendella
Chicago
From$45
4.8(21)Medieval Torture Museum: Entry Ticket
Chicago
From$35.83
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Before you book
FAQ
- Are these experiences suitable for anniversaries or proposals?
- Yes. Anything marked private or sunset is especially popular for special occasions. Get in touch after booking if you'd like to add a surprise.