Chicago for couples

Top things to do
Top experiences in Chicago














What our guests say
Louise H
+2 more
Odyssey Chicago River Architecture Dinner Cruise
Shannon H
Chicago at Night: River & Lake Sightseeing Cruise by First Lady
William P
Official Chicago Architecture Cruise by First Lady
Beth J
+6 more
Odyssey Lake Michigan Dinner Cruise
Roberta L
Chicago Fireworks Cruise
Christopher H
Lake Michigan Dinner Cruise
Lucrettia T
90-min Scenic Sunset Lake Michigan Cruise by Wendella
Edgar L
Chicago Dinner Cruise
Browse by themes
Nearby cities to explore










How Headout makes choosing experiences effortless
We curate the best ways to experience
We research and organise all unique experiences - from tickets to tours to special combos - so you get all the choices without the clutter.
We partner with the best
Every supplier is vetted for quality, reliability, and value so you only get top rated experiences. No surprises, no disappointments.
All the best options, in one place
Each experience is thoughtfully organised to give you maximum availability, great value and an easy way to choose.
Book with complete peace of mind
Free cancellations, Flexible payments, and 24/7 support - thoughtfully designed for flexibility, assurance, and total peace of mind.
1/4






