Skydeck Chicago: Entry Ticket
De la36,07 EUR
— 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
De la40 USD
The Field Museum of Natural History: Entry Ticket
De la29 USD
360 Chicago Observation Deck: Entry Ticket
De la30 USD
The Field Museum of Natural History: Pass
De la42 USD
Chicago: Architecture River Cruise from Navy Pier
De la39 USD
Chicago C3® CityPASS®: 3 Attractions of your choice
De la109 USD
Chicago: 45 Minute Architectural Sightseeing Cruise
De la28 USD
Museum Of Contemporary Art (MCA): Entry Ticket
De la22 USD
Lake Michigan & Chicago River: 1.5-Hr Sightseeing Cruise
De la46 USD
Navy Pier Centennial Wheel: Entry Ticket
De la21,1 EUR
Museum of Illusions Chicago: Entry Ticket
De la43 USD
Museum of Ice Cream Chicago: Entry Ticket
De la43 USD
Chicago: 90 Minute Architecture Sightseeing Cruise
De la45 USD
Flyover Experience in Chicago
De la27,95 USD
Medieval Torture Museum: Entry Ticket
De la35,83 USD
Chicago CityPASS®
De la144 USD
Chicago: Architecture Foundation Center River Cruise aboard Chicago's First Lady
De la57 USD
Chicago Explorer Pass: 2 to 7 Attractions including 360 Chicago
De la84 USD
Chicago: 90-Minute Architecture Tour on the Lake & River
De la45 USD
Chicago Crime & Mob Bus Tour: Criminals, Mobsters and Gangsters
De la49 USD
Balloon Museum® Chicago: EmotionAir Exhibition Entry Ticket
De la44,38 USD
Chicago History Museum: Entry Ticket
De la19 USD
Lake Michigan & Chicago River: 75 Minute Speedboat Cruise
De la72,34 EUR
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.