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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

Willis Tower Skydeck Tickets
Willis Tower Skydeck Tickets
from $42.33
First Lady Cruises Chicago
First Lady Cruises Chicago
from $28
Wendella Cruises Chicago
Wendella Cruises Chicago
from $28
Shoreline Cruises Chicago
Shoreline Cruises Chicago
from $32.50

Top experiences in Chicago

Free cancellation
Cruise boat on Lake Michigan with Chicago skyline at sunset.
Sightseeing Cruises
90-min Scenic Sunset Lake Michigan Cruise
4.9(15)
Rated 4.9 out of 5.0 from 15 ratings.
$45
Free cancellation
Cruise boat on Lake Michigan with Chicago skyline in the background.
Sightseeing Cruises
45-Min Lake Michigan Tour
NEW
$32.50
Cruise boat on Chicago River passing under Clark Street Bridge.
Sightseeing Cruises
First Lady's Chicago Architecture Boat Tour
4.9(19)
Rated 4.9 out of 5.0 from 19 ratings.
$56
Selling out fast
View from Willis Tower Skydeck in Chicago at sunset.
Observation Decks
Chicago Night Tour with Skydeck & Architecture Cruise
NEW
$169
Free cancellation
Guests enjoying drinks on a Lake Michigan dinner cruise with Chicago skyline in the background.
Dinner Cruises
Lake Michigan Dinner Cruise
NEW
from
$176.32
Free cancellation
Guests dining on Odyssey Lake Michigan Dinner Cruise at sunset.
Dinner Cruises
Odyssey Lake Michigan Dinner Cruise
NEW
from
$135.31
Free cancellation
Odyssey Chicago River boat cruising on the Chicago River with city skyline.
Sightseeing Cruises
Odyssey Chicago River Architecture Dinner Cruise
NEW
from
$203.65

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