Processing your payment

Headout logo. Link to home.
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 things to do

First Lady Cruises Chicago
First Lady Cruises Chicago
from $28
Wendella Cruises Chicago
Wendella Cruises Chicago
from $28

Top experiences in Chicago

Free cancellation
Odyssey Chicago River boat cruising on the Chicago River with city skyline.
Sightseeing Cruises
Odyssey Chicago River Architecture Dinner Cruise
from
$147.62
Odyssey Chicago River Architecture Dinner Cruise. Rated 4.9 out of 5 from 9 ratings.From $147.62
Free cancellation
Guests dining on Odyssey Lake Michigan Dinner Cruise at sunset.
Dinner Cruises
Odyssey Lake Michigan Dinner Cruise
from
$136.68
Odyssey Lake Michigan Dinner Cruise. Rated 5 out of 5 from 1 ratings.From $136.68
Free cancellation
Guests enjoying drinks on a Lake Michigan dinner cruise with Chicago skyline in the background.
Dinner Cruises
Lake Michigan Dinner Cruise
from
$121.65
Lake Michigan Dinner Cruise. Rated 0 out of 5 from 0 ratings.From $121.65
Cruise boat on Chicago River passing under Clark Street Bridge.
Sightseeing Cruises
First Lady's Chicago Architecture Boat Tour
$57
First Lady's Chicago Architecture Boat Tour. Rated 4.9 out of 5 from 46 ratings.From $57
Free cancellation
Cruise boat on Lake Michigan with Chicago skyline at sunset.
Sightseeing Cruises
90-min Scenic Sunset Lake Michigan Cruise
$45
90-min Scenic Sunset Lake Michigan Cruise. Rated 4.9 out of 5 from 17 ratings.From $45

Browse by themes

Museums in Chicago
Chicago City Cards
Landmarks in Chicago
Observation Decks in Chicago
View all Chicago Attractions
Guided Tours in Chicago
Hop-on Hop-off Tours Chicago
View all Chicago Tours
Airport Transfers in Chicago
Public Transport Tickets in Chicago
Shared Airport Transfers
View all Transportation in Chicago
Sightseeing Cruises in Chicago
Dinner Cruises in Chicago
View all Cruises in Chicago
Combos Tickets in Chicago
View all Chicago Specials

Nearby cities to explore

See all
Things to do in Nashville
United States
Things to do in Atlanta
United States
Things to do in Washington DC
United States
Things to do in Philadelphia
United States
Things to do in New York
United States
Things to do in Myrtle Beach
United States
Things to do in Charleston
United States
Things to do in Savannah
United States
Things to do in Dallas
United States
Things to do in New Orleans
United States

How Headout makes choosing experiences effortless

We curate the best ways to experience

We research and organise all unique experiences - from tickets to tours to special combos - so you get all the choices without the clutter.

We partner with the best

Every supplier is vetted for quality, reliability, and value so you only get top rated experiences. No surprises, no disappointments.

All the best options, in one place

Each experience is thoughtfully organised to give you maximum availability, great value and an easy way to choose.

Book with complete peace of mind

Free cancellations, Flexible payments, and 24/7 support - thoughtfully designed for flexibility, assurance, and total peace of mind.

1/4

We curate the best ways to experience
We partner with the best
All the best options, in one place
Book with complete peace of mind

We've served 48 million+ guests and we are here for you

48 million+

Happy customers across 10,000+ experiences

In the media

Featured and recommended by the best brands

24 x 7 help center

Have a question? Live chat with local experts anywhere, anytime