Go City Chicago Explorer Pass: Choose from 39 Attractions
DesdeUSD 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
122
City
Chicago
Total in city
122
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
45-min Chicago River Architecture Cruise by Wendella
DesdeUSD 28
90-min Chicago River Architecture Cruise by Wendella
DesdeUSD 45
Combo (Save 10%): Chicago Hop-on Hop-off Bus Tour + 360 Chicago Observation Deck Skip-the-Line Tickets
DesdeUSD 71.1
Big Bus: Chicago Hop-on Hop-off Bus Tour
DesdeUSD 49
Skydeck Chicago Tickets
DesdeUSD 42.33
360 Chicago Observation Deck Skip-the-Line Tickets
DesdeUSD 30
Official Chicago Architecture Cruise by First Lady
DesdeUSD 57
90-min Chicago River and Lake Michigan Architecture Cruise by Wendella
DesdeUSD 45
Chicago Skyline Lake Tour
DesdeUSD 32.5
Chicago Architecture Evening Cruise by Shoreline
DesdeUSD 46
90-min Scenic Sunset Lake Michigan Cruise by Wendella
DesdeUSD 45
360 Chicago Sip & View
DesdeUSD 44
30-Min Lake Michigan Tour by Shoreline
DesdeUSD 32.5
Lake Michigan & Chicago River: 75 Minute Speedboat Cruise
DesdeUSD 84.74
The Chicago Theatre Tour Experience
DesdeUSD 30
The Art Institute of Chicago: Skip The Line Ticket + Semi-Private Guided Tour
DesdeUSD 90.1
Chicago: Underground Pedway & the Loop Guided Walking Tour
DesdeUSD 35
Chicago: Premier Dinner Cruise on Lake Michigan
DesdeUSD 132.57
Chicago: Craft Brewery Barrel Bus Tour
DesdeUSD 99.6
Tiffany in Chicago: Guided Tour
DesdeUSD 30
Chicago: Food and Prohibition Architecture Guided Tour
DesdeUSD 99
Lake Michigan Chicago: 2-Hr Sightseeing Cruise with Lunch
DesdeUSD 94.31
Chicago: 48-Hour Hop-on Hop-off Bus + Architecture Cruise
DesdeUSD 99
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.