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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.

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Top experiences in Chicago

What our guests say

Elisabetta B

Group
Last week
The cruise is very, very well organized; the staff were punctual and professional. Above all, it is much more comprehensive than others, as it offers a view of the city from both the lake and the river. Truly spectacular. The guide on board was very knowledgeable. I highly recommend it.

Chicago River & Lake Sightseeing Cruise by First Lady

Anne M

United Kingdom
Couple
Last week
Jean, our guide, was fabulous! Such a wealth of knowledge conveyed in an interesting and humorous style. Thoroughly recommend!

Official Chicago Architecture Cruise by First Lady

Michael S

United States
Solo
2 weeks ago

+1 more

I enjoyed going so far out into Lake Michigan for all the pictures I could handle of the Chicago coastline! It was absolutely beautiful! Did I mention this was the Night Cruise? It was beyond exquisite! It was so great, in fact, I had to video call my family and show them THIS part of my journey! They were so excited and impressed! Also, our guide Doug was awesome! The info and history he had about the various buildings and locations gave me the truest sense of a tour that kept me interested and wanting to come back for more! Thank you for bringing him on-board with us! Even with his mandated quota of bad jokes!

Chicago at Night: River & Lake Sightseeing Cruise by First Lady

Ronald J

United States
Couple
2 weeks ago
We booked a dinner on the didn't know what boat it was. Once we kept walking and found out it was the Spirit of Chicago, we got aboard and thanked them for the grace period. After being shown to our seats, we got to enjoy the amazing view of the city. It was our anniversary and Destiny treated very well! I totally forgot it was a buffet and couldn't have been more happier. The food was really out of this world. The variety, the flavors, it was a whole experience. We hopped on the dance floor for a bit, ordered more (pretty large) drinks, and went outside to take pictures of the sunset. Amazing experience... Can't wait to do it again!

Lake Michigan Dinner Cruise

Susan N

United States
Couple
3 weeks ago

+3 more

We had a gorgeous and wonderful evening celebrating my birthday. Lauren, our server, was fabulous. We had a great starter, Mediterranean plate. The 3 course meal was delicious. We enjoyed great music, dancing, cocktails and wine list. Great evening all the way around.

Odyssey Lake Michigan Dinner Cruise

Chantal H

United States
Couple
3 weeks ago
I very much enjoyed the cruise, but it ended up being a lot longer than expected and we had to go to dinner afterwards so if I had known it was gonna be more than 90 minutes, I don't know if I would have planned it so close to dinner. They had explained that this cruise was gonna be a little different but I didn't hear why they said it was gonna be different. We had to pull over a couple times to stop so I don't know what was going on. The views of the buildings and the sunset were really nice. I couldn't really hear what they were saying about the buildings & the history of them because we sat downstairs but if I was to do this again, I would try and get a better seat so I can hear them hear them speaking about what we're seeing.

90-min Scenic Sunset Lake Michigan Cruise by Wendella

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

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