Help

United StatesChicago, 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 experiences in Chicago

Cruise boat on Chicago River passing under Clark Street Bridge.
Official Chicago Architecture Cruise by First Lady
Sightseeing Cruises
$57
Official Chicago Architecture Cruise by First Lady. Rated 4.9 out of 5 from 288 ratings.From $57
Free cancellation
Dinner cruise boat on Chicago River with illuminated city skyline at night.
Chicago Dinner Cruise
Dinner Cruises
from
$112.10
Chicago Dinner Cruise. Rated 4.6 out of 5 from 242 ratings.From $112.10
Free cancellation
Guests dining on Odyssey Lake Michigan Dinner Cruise at sunset.
Odyssey Lake Michigan Dinner Cruise
Dinner Cruises
from
$132.58
Odyssey Lake Michigan Dinner Cruise. Rated 4.6 out of 5 from 138 ratings.From $132.58
Chicago River cruise boat at night with city skyline in the background.
Chicago at Night: River & Lake Sightseeing Cruise by First Lady
Sightseeing Cruises
from
$50
Chicago at Night: River & Lake Sightseeing Cruise by First Lady. Rated 4.5 out of 5 from 11 ratings.From $50
Free cancellation
Cruise boat on Lake Michigan with Chicago skyline at sunset.
90-min Scenic Sunset Lake Michigan Cruise by Wendella
Sightseeing Cruises
$45
90-min Scenic Sunset Lake Michigan Cruise by Wendella. Rated 4.8 out of 5 from 53 ratings.From $45
Free cancellation
Fireworks over Chicago River with boats during dinner cruise.
Chicago Fireworks Cruise
Sightseeing Cruises
from
$54.76
Chicago Fireworks Cruise. Rated 3.9 out of 5 from 26 ratings.From $54.76
Free cancellation
Fireworks over Chicago River with boats during dinner cruise.
Chicago Fireworks Dinner Cruises
Sightseeing Cruises
from
$128.49
Chicago Fireworks Dinner Cruises. Rated 3.8 out of 5 from 20 ratings.From $128.49
Chicago River cruise boat with city skyline in the background.
Chicago River & Lake Sightseeing Cruise by First Lady
Sightseeing Cruises
from
$46
Chicago River & Lake Sightseeing Cruise by First Lady. Rated 4.5 out of 5 from 10 ratings.From $46
Free cancellation
Odyssey Chicago River boat cruising on the Chicago River with city skyline.
Odyssey Chicago River Architecture Dinner Cruise
Sightseeing Cruises
from
$139.42
Odyssey Chicago River Architecture Dinner Cruise. Rated 4.6 out of 5 from 56 ratings.From $139.42
Free cancellation
Cruise boat on Lake Michigan with Chicago skyline in the background.
45-Min Lake Michigan Tour by Shoreline
Sightseeing Cruises
from
$32.50
45-Min Lake Michigan Tour by Shoreline. Rated 4.9 out of 5 from 15 ratings.From $32.50
Free cancellation
Sea Dog boat cruising on Lake Michigan with Chicago skyline and Ferris wheel at dusk.
Chicago Sea Dog Fireworks Cruise on Lake Michigan
Sightseeing Cruises
from
$54.76
Chicago Sea Dog Fireworks Cruise on Lake Michigan. Rated 5 out of 5 from 3 ratings.From $54.76
Free cancellation
Guests enjoying drinks on a Lake Michigan dinner cruise with Chicago skyline in the background.
Lake Michigan Dinner Cruise
Dinner Cruises
from
$112.10
Lake Michigan Dinner Cruise. Rated 4.7 out of 5 from 48 ratings.From $112.10
Chicago River cruise with tourists viewing downtown skyscrapers.
Chicago River Architecture Cruise
Sightseeing Cruises
$37
Chicago River Architecture Cruise. Rated 0 out of 5 from 0 ratings.From $37
Downtown Chicago skyline at night with illuminated skyscrapers and a boat on the river.
Chicago Architecture Fireworks Cruises
Sightseeing Cruises
$65
Chicago Architecture Fireworks Cruises. Rated 0 out of 5 from 0 ratings.From $65

What our guests say

Naomi W

United States
Couple
2 weeks ago
Our guide, Claudia, was FABULOUS! She shared details, insights and history with incredible enthusiam. The 1.5 hours was a highlight of our weekend in Chicago.

Official Chicago Architecture Cruise by First Lady

Floretta P

United States
Couple
May 2026

+1 more

The staff is friendly and very nice. Wedding Anniversary and Husband birthday. As for me 14 yrs if chemotherapy enjoying life.

Odyssey Lake Michigan Dinner Cruise

Gomes L

Group
May 2026
Only a cruise like this one lets you take such beautiful photos of Chicago at night. Beyond the cruise itself, there was a great atmosphere on board thanks to the wonderful crew. I highly recommend it!

90-min Scenic Sunset Lake Michigan Cruise by Wendella

Nakisha A

United States
Couple
May 2026
I absolutely loved the view, the food, and the drinks...everyone was so friendly and welcoming...I've never had dinner on the water so that was definitely a great experience, I took my fiancé for his bday and he never been there so that was great seeing his face and how much he loved it 🥰

Odyssey Chicago River Architecture Dinner Cruise

Gabriela S

United States
Group
May 2026
Without a doubt, one of my best experiences. I would take this cruise again and again. We were absolutely delighted—they even wished my sister a happy birthday over the PA system. They made us feel so special. The food was delicious, and we could eat as much as we wanted of everything included, right down to dessert. We don’t speak English, but the staff did their best to make sure we understood everything. They even took a souvenir photo of us—I loved it ❤️ If you visit the area, taking this cruise is the best thing you can do ❤️❤️

Lake Michigan Dinner Cruise

Christopher H

United States
Couple
4 days ago
I really enjoyed the dj. The food was on point. The atmosphere was great. We really enjoyed ourselves. Thanks for the experience.

Chicago Dinner Cruise

Sangjin K

South Korea
Solo
4 days ago
Kind explanation with stunning night view. Boat with classical design. Indoor bar at first floor with some drink. It was a little bit cold after sunset but really good experience.

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

Mercede A

United States
Couple
Last week
I was unable to leave a 1 star this was the worst experience I've ever encountered for $300 this place is a gimmick and please do not do business with this company I have started legal action because we work way to hard for our money for them to steal it ruined my 5th year wedding anniversary

Chicago Fireworks Cruise