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.

Top things to do
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Top experiences in Chicago
Slide 1 of 1, Cruise boat on Chicago River passing under Clark Street Bridge.

Free cancellation
Slide 1 of 1, Dinner cruise boat on Chicago River with illuminated city skyline at night.

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Slide 1 of 1, Guests dining on Odyssey Lake Michigan Dinner Cruise at sunset.

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Slide 1 of 1, Fireworks over Chicago River with boats during dinner cruise.

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Slide 1 of 1, Cruise boat on Lake Michigan with Chicago skyline at sunset.

Slide 1 of 1, Chicago River cruise boat with city skyline in the background.

Slide 1 of 1, Chicago River cruise boat at night with city skyline in the background.

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Slide 1 of 1, Odyssey Chicago River boat cruising on the Chicago River with city skyline.

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Slide 1 of 1, Sea Dog boat cruising on Lake Michigan with Chicago skyline and Ferris wheel at dusk.

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Slide 1 of 1, Cruise boat on Lake Michigan with Chicago skyline in the background.

Slide 1 of 1, Chicago River cruise with tourists viewing downtown skyscrapers.

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Slide 1 of 1, View from Willis Tower Skydeck in Chicago at sunset.

Slide 1 of 1, Downtown Chicago skyline at night with illuminated skyscrapers and a boat on the river.

What our guests say
O
Ob J
United StatesCouple
5/5
+1 more
Well. I jave never done anything like this before at all ever. So I took the chance and truly enjoyed myself. The food was seasoned well and they had plenty. They also had alot of options of beverages for people who do not drink alcohol. The staff was excited to be there, some even more than us, which makes the overall experience that much better.
Chicago Fireworks Dinner Cruises
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Gianna B
United StatesCouple
5/5
PHENOMENAL!! And legit! Such an amazing experience, amazing food, SO romantic, staff and DJ were very kind! It honestly felt too good to be true at some moments, but it was an amazing experience and I would definitely do it again!
Odyssey Lake Michigan Dinner Cruise
V
Vanessa W
United StatesCouple
5/5
+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
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Jacinda H
United StatesCouple
5/5
The Chicago Architecture Cruise by First Lady was fascinating. Our docent was so knowledgeable about the history, engineering feats, and even some political reasons why and how these amazing skyscrapers were built. The "fun facts" were so intriguing. It is definitely worth your time. P.S. if you go on a sunny day, don't forget your sunscreen.....however if you do forget, they have some on-board to purchase!😉
Official Chicago Architecture Cruise by First Lady
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Cristina K
United StatesCouple
5/5
+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
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Javeah T
United StatesCouple
5/5
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
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Louise H
United StatesSolo
5/5
+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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Shannon H
Couple
5/5
The guide was amazing! He was very funny while being so informative and never crass. The sunset tour was beautiful and I thought it was very smart to offer sweatshirts in the lovely cabin. The bar staff was slammed but still so nice! Would definitely recommend to Chicago natives and out of towners!
Chicago at Night: River & Lake Sightseeing Cruise by First Lady
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