Go City Chicago Explorer Pass: Choose from 39 Attractions
Alkaen84 $
— 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
Alkaen36,07 €
45-min Chicago River Architecture Cruise by Wendella
Alkaen28 $
The Art Institute of Chicago: Fast Pass
Alkaen40 $
90-min Chicago River Architecture Cruise by Wendella
Alkaen45 $
Big Bus: Chicago Hop-on Hop-off Bus Tour
Alkaen49 $
The Field Museum of Natural History: Entry Ticket
Alkaen29 $
Skydeck Chicago Tickets
Alkaen42,33 $
360 Chicago Observation Deck Skip-the-Line Tickets
Alkaen30 $
360 Chicago Observation Deck: Entry Ticket
Alkaen30 $
The Field Museum of Natural History: Pass
Alkaen42 $
Chicago: Architecture River Cruise from Navy Pier
Alkaen39 $
Official Chicago Architecture Cruise by First Lady
Alkaen57 $
Chicago C3® CityPASS®: 3 Attractions of your choice
Alkaen109 $
Chicago: Architecture River Cruise from Michigan Avenue
Alkaen46 $
Chicago: 45 Minute Architectural Sightseeing Cruise
Alkaen28 $
Museum Of Contemporary Art (MCA): Entry Ticket
Alkaen22 $
90-min Chicago River and Lake Michigan Architecture Cruise by Wendella
Alkaen45 $
Lake Michigan & Chicago River: 1.5-Hr Sightseeing Cruise
Alkaen46 $
Navy Pier Centennial Wheel: Entry Ticket
Alkaen21,1 €
Museum of Illusions Chicago: Entry Ticket
Alkaen43 $
Chicago Skyline Lake Tour
Alkaen32,5 $
Museum of Ice Cream Chicago: Entry Ticket
Alkaen43 $
Chicago Architecture Evening Cruise by Shoreline
Alkaen46 $
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.