Go City Chicago Explorer Pass: Choose from 39 Attractions
Από84 $
— For two
Romantic Σικάγο for couples
Plan an unforgettable trip for two. We've pulled the highest-rated experiences in Σικάγο — sunset cruises, private dinners, rooftop viewpoints, and intimate shows — all rated 4.5 stars or higher by real couples.
See all Σικάγο
Date-night approved, top-rated.
Matches
118
City
Σικάγο
Total in city
118
Min rating
4.5
About this list
Why this shortlist
Σικάγο 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 Σικάγο for couples
45-min Chicago River Architecture Cruise by Wendella
Από28 $
90-min Chicago River Architecture Cruise by Wendella
Από45 $
Combo (Save 10%): Chicago Hop-on Hop-off Bus Tour + 360 Chicago Observation Deck Skip-the-Line Tickets
Από71,1 $
Big Bus: Chicago Hop-on Hop-off Bus Tour
Από45 $
Skydeck Chicago Tickets
Από42,33 $
360 Chicago Observation Deck Skip-the-Line Tickets
Από30 $
Official Chicago Architecture Cruise by First Lady
Από57 $
90-min Chicago River and Lake Michigan Architecture Cruise by Wendella
Από45 $
Chicago Skyline Lake Tour
Από32,5 $
Chicago Architecture Evening Cruise by Shoreline
Από46 $
90-min Scenic Sunset Lake Michigan Cruise by Wendella
Από45 $
360 Chicago Sip & View
Από44 $
30-Min Lake Michigan Tour by Shoreline
Από32,5 $
Lake Michigan & Chicago River: 75 Minute Speedboat Cruise
Από84,74 $
The Chicago Theatre Tour Experience
Από30 $
The Art Institute of Chicago: Skip The Line Ticket + Semi-Private Guided Tour
Από90,1 $
Chicago: Underground Pedway & the Loop Guided Walking Tour
Από35 $
Chicago: Premier Dinner Cruise on Lake Michigan
Από132,57 $
Chicago: Craft Brewery Barrel Bus Tour
Από99,6 $
Tiffany in Chicago: Guided Tour
Από30 $
Chicago: Food and Prohibition Architecture Guided Tour
Από99 $
Lake Michigan Chicago: 2-Hr Sightseeing Cruise with Lunch
Από94,31 $
Chicago: 48-Hour Hop-on Hop-off Bus + Architecture Cruise
Από99 $
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.