Skydeck Chicago: Entry Ticket
Från36,07 €
— 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.
Matches
104
City
Chicago
Total in city
75
Min rating
4.5
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
The Art Institute of Chicago: Fast Pass
Från40 US$
The Field Museum of Natural History: Entry Ticket
Från29 US$
360 Chicago Observation Deck: Entry Ticket
Från30 US$
The Field Museum of Natural History: Pass
Från42 US$
Chicago: Architecture River Cruise from Navy Pier
Från39 US$
Chicago C3® CityPASS®: 3 Attractions of your choice
Från109 US$
Chicago: 45 Minute Architectural Sightseeing Cruise
Från28 US$
Museum Of Contemporary Art (MCA): Entry Ticket
Från22 US$
Lake Michigan & Chicago River: 1.5-Hr Sightseeing Cruise
Från46 US$
Navy Pier Centennial Wheel: Entry Ticket
Från21,1 €
Museum of Illusions Chicago: Entry Ticket
Från43 US$
Museum of Ice Cream Chicago: Entry Ticket
Från43 US$
Chicago: 90 Minute Architecture Sightseeing Cruise
Från45 US$
Flyover Experience in Chicago
Från27,95 US$
Medieval Torture Museum: Entry Ticket
Från35,83 US$
Chicago CityPASS®
Från144 US$
Chicago: Architecture Foundation Center River Cruise aboard Chicago's First Lady
Från57 US$
Chicago Explorer Pass: 2 to 7 Attractions including 360 Chicago
Från84 US$
Chicago: 90-Minute Architecture Tour on the Lake & River
Från45 US$
Chicago Crime & Mob Bus Tour: Criminals, Mobsters and Gangsters
Från49 US$
Balloon Museum® Chicago: EmotionAir Exhibition Entry Ticket
Från44,38 US$
Chicago History Museum: Entry Ticket
Från19 US$
Lake Michigan & Chicago River: 75 Minute Speedboat Cruise
Från72,34 €
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.