Go City Chicago Explorer Pass: Choose from 39 Attractions
DariUS$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.
Matches
117
City
Chicago
Total in city
117
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
Skydeck Chicago: Entry Ticket
Dari€36,07
45-min Chicago River Architecture Cruise by Wendella
DariUS$28
The Art Institute of Chicago: Fast Pass
DariUS$40
90-min Chicago River Architecture Cruise by Wendella
DariUS$45
Big Bus: Chicago Hop-on Hop-off Bus Tour
DariUS$49
The Field Museum of Natural History: Entry Ticket
DariUS$29
Skydeck Chicago Tickets
DariUS$42,33
360 Chicago Observation Deck Skip-the-Line Tickets
DariUS$30
360 Chicago Observation Deck: Entry Ticket
DariUS$30
The Field Museum of Natural History: Pass
DariUS$42
Chicago: Architecture River Cruise from Navy Pier
DariUS$39
Official Chicago Architecture Cruise by First Lady
DariUS$57
Chicago C3® CityPASS®: 3 Attractions of your choice
DariUS$109
Chicago: Architecture River Cruise from Michigan Avenue
DariUS$46
Chicago: 45 Minute Architectural Sightseeing Cruise
DariUS$28
Museum Of Contemporary Art (MCA): Entry Ticket
DariUS$22
90-min Chicago River and Lake Michigan Architecture Cruise by Wendella
DariUS$45
Lake Michigan & Chicago River: 1.5-Hr Sightseeing Cruise
DariUS$46
Navy Pier Centennial Wheel: Entry Ticket
Dari€21,1
Museum of Illusions Chicago: Entry Ticket
DariUS$43
Chicago Skyline Lake Tour
DariUS$32,5
Museum of Ice Cream Chicago: Entry Ticket
DariUS$43
Chicago Architecture Evening Cruise by Shoreline
DariUS$46
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.