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Chicago, United States

Chicago for couples

Rediscover love in Chicago with our curated experiences and tours tailor-made for couples. Be it something adventurous or romantic, we’ve got you covered.
Couple enjoying a playful moment on a European city street.

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Top experiences in Chicago

What our guests say

Stacy S

United States
Group
4 days ago

+2 more

Beautiful day on the Chicago River, the volunteer docent Bob was great and explained things in a way that was easy to understand so we actually learned a little bit more about architecture today. Clean bathrooms, comfy chairs that tilted back which really did help since you're looking up most of the time!

Official Chicago Architecture Cruise by First Lady

Paul M

United States
Couple
Last week

+2 more

Food was great...atmosphere was great, music was great....and the staff was very welcoming...i will do this again!!! Cannot beat the views of they city!!

Odyssey Lake Michigan Dinner Cruise

Ruhi J

Canada
Couple
Aug 2026
The 45-minute Lake Michigan sunset cruise was amazing!! The views of the Chicago skyline at sunset were beautiful, and the whole cruise was very relaxing and enjoyable. Shoreline organized everything really well, and the staff were friendly and welcoming. Definitely a great way to experience Chicago from the water!

45-Min Lake Michigan Tour by Shoreline

Ob J

United States
Couple
Aug 2026

+1 more

The night started out rainy with more thunderstorms predicted and rough waves. The stage was set for a not so desirable evening. Once we boarded the ship out spirits were high and excited about celebrating our 25th wedding anniversary. The food was good and most importantly the staff had amazing upbeat attitudes. As the boat was rocking on some rough waves some of the staff was dancing with the rock of the ship, it was smooth like some real movie scene type of vibe. During dinner the rain began and it cleared up just in time for the fireworks which we just splendid. The crew opened up the top deck as the fireworks began an all guest were able to take some stunning pictures of the skyline and the fireworks. We had a great t8me and recommend this cruise.

Chicago Fireworks Dinner Cruises

Vanessa W

United States
Couple
Jul 2026

+1 more

Overall, the boat cruise was a great experience\. The food was delicious, the staff was friendly and attentive, and the scenery and atmosphere were beautiful\. Everything was set up nicely and had the potential to be an amazing time\. Unfortunately, the DJ completely ruined the vibe\. The music selection was terrible, there was no energy, and it never got the crowd engaged\. On a cruise like this, the DJ really sets the tone for the entire experience, and this one missed the mark\. If the cruise gets a new DJ, I would definitely recommend it\. Everything else was great, but the entertainment needs a major upgrade\.

Lake Michigan Dinner Cruise

Cristina K

United States
Couple
Jul 2026

+1 more

It was a great easy ride around the city thanks to the captain. We liked how you timed the cruise so people could see the sunset just in time. Boarding was easy. The guide was informative but not intrusive in letting people enjoy the view to the nice music. It was a very pleasant experience and I will recommend to anyone I know who is visiting Chicago. It was truly the highlight of my visit.

90-min Scenic Sunset Lake Michigan Cruise by Wendella

Javeah T

United States
Couple
Jul 2026
such a great time, the tour guide was great the driver was great, the music was on point and went along with the excursions going on i loved it would visit again

Chicago Sea Dog Fireworks Cruise on Lake Michigan

Louise H

United States
Solo
Jul 2026

+2 more

Our evening on the Odyssey Chicago River Architecture Dinner Cruise was unforgettable. The views of Chicago’s iconic skyline and historic buildings were breathtaking, and the narration made the city’s architecture come alive. The staff was genuinely warm and attentive, the meal was delicious, and the atmosphere on board felt both elegant and relaxed. Watching the city lights reflect on the river while enjoying dinner with friends was a perfect experience. I would gladly recommend this cruise to anyone looking for a memorable way to experience Chicago.

Odyssey Chicago River Architecture Dinner Cruise