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United States
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.

Top things to do

Top experiences in Chicago

What our guests say

Giorgi M

Couple
3 weeks ago
Fantastic way to experience Chicago’s architecture from a completely different perspective. Our guide was knowledgeable, engaging and entertaining, and the 90 minutes passed incredibly quickly. A must-do in Chicago, especially for anyone interested in architecture and the history of the city.

Official Chicago Architecture Cruise by First Lady

Ruhi J

Canada
Couple
3 weeks ago
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

Howard W

United States
Couple
3 weeks ago
I loved it. 10 out of 10! The staff very professional. The DJ was ok and the food was delicious. We had a window seat which made our experience incredible. The View was amazing. Highly recommend.

Odyssey Lake Michigan Dinner Cruise

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

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