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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

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

Cruise boat on Chicago River passing under Clark Street Bridge.
Sightseeing Cruises
Official Chicago Architecture Cruise by First Lady
$57
Official Chicago Architecture Cruise by First Lady. Rated 4.9 out of 5 from 89 ratings.From $57
Free cancellation
Guests dining on Odyssey Lake Michigan Dinner Cruise at sunset.
Dinner Cruises
Odyssey Lake Michigan Dinner Cruise
from
$132.58
Odyssey Lake Michigan Dinner Cruise. Rated 4.7 out of 5 from 25 ratings.From $132.58
Free cancellation
Odyssey Chicago River boat cruising on the Chicago River with city skyline.
Sightseeing Cruises
Odyssey Chicago River Architecture Dinner Cruise
from
$153.08
Odyssey Chicago River Architecture Dinner Cruise. Rated 4.7 out of 5 from 29 ratings.From $153.08
Free cancellation
Cruise boat on Lake Michigan with Chicago skyline at sunset.
Sightseeing Cruises
90-min Scenic Sunset Lake Michigan Cruise by Wendella
$45
90-min Scenic Sunset Lake Michigan Cruise by Wendella. Rated 4.9 out of 5 from 20 ratings.From $45
Free cancellation
Guests enjoying drinks on a Lake Michigan dinner cruise with Chicago skyline in the background.
Dinner Cruises
Lake Michigan Dinner Cruise
from
$112.10
Lake Michigan Dinner Cruise. Rated 4.3 out of 5 from 6 ratings.From $112.10
Free cancellation
Cruise boat on Lake Michigan with Chicago skyline in the background.
Sightseeing Cruises
30-Min Lake Michigan Tour by Shoreline
from
$32.50
30-Min Lake Michigan Tour by Shoreline. Rated 4.2 out of 5 from 11 ratings.From $32.50

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Combos Tickets in Chicago
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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.

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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

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