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Discover the best things to do in Chicago

A curated collection of the city’s top-rated tours, iconic attractions, and unmissable things to do.
Discover the best things to do in Chicago

Top experiences in Chicago

Free cancellation
Chicago River cruise boat passing under a bridge with city skyline.
Sightseeing Cruises
45-min Chicago River Architecture Cruise by Wendella
from
$28
45-min Chicago River Architecture Cruise by Wendella. Rated 4.9 out of 5 from 553 ratings.From $28
Free cancellation
Chicago River cruise boat passing under DuSable Bridge with city buildings in the background.
Sightseeing Cruises
90-min Chicago River Architecture Cruise by Wendella
$45
90-min Chicago River Architecture Cruise by Wendella. Rated 4.9 out of 5 from 347 ratings.From $45
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
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 48 ratings.From $57
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 4.7 out of 5 from 21 ratings.From $147.62
View from the Skydeck at Willis Tower, Chicago, overlooking the cityscape.
Willis Tower Skydeck Tickets
Skydeck Chicago Tickets
from
$42.33
Skydeck Chicago Tickets. Rated 4.7 out of 5 from 113 ratings.From $42.33
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
Free cancellation
big bus: chicago hop-on hop-off bus tour-1
Hop-on Hop-off Tours Chicago
Big Bus: Chicago Hop-on Hop-off Bus Tour
from
$45
Big Bus: Chicago Hop-on Hop-off Bus Tour. Rated 4.6 out of 5 from 298 ratings.From $45
Free cancellation
Couple taking a selfie at Chicago 360 Observation Deck with city skyline view.
360 Chicago
360 Chicago Observation Deck Skip-the-Line Tickets
from
$30
360 Chicago Observation Deck Skip-the-Line Tickets. Rated 4.3 out of 5 from 152 ratings.From $30
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 18 ratings.From $45
Free cancellation
Chicago River architecture cruise boat passing under a lift bridge with city skyscrapers in the background.
Sightseeing Cruises
90-min Chicago River and Lake Michigan Architecture Cruise by Wendella
$45
90-min Chicago River and Lake Michigan Architecture Cruise by Wendella. Rated 4.7 out of 5 from 56 ratings.From $45
Free cancellation
Family enjoying view from Chicago 360 Observation Deck with city skyline.
360 Chicago
360 Chicago Sip & View
from
$44
360 Chicago Sip & View. Rated 4.1 out of 5 from 16 ratings.From $44

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

Must do things in Chicago

Big Bus Chicago Hop-on Hop-off Tours

1Big Bus Chicago Hop-on Hop-off Tours

Experience Chicago like never before with a Big Bus tour. Marvel at architectural wonders like the Willis Tower, explore cultural gems at Millennium Park and soak in stunning skyline views from Navy Pier. Get a combo ticket to the 360 Chicago Observatory and make the best of your stay in the city.
360 Chicago

2360 Chicago

Discover Chicago's skyline in all its glory at 360 Observation Deck! Marvel at iconic landmarks, like Willis Tower and Lake Michigan, and witness the city's architectural wonders and breathtaking sunset views.
Willis Tower Skydeck Tickets

3Willis Tower Skydeck Tickets

Embark on an exhilarating adventure as you stand on the Skydeck's breathtaking glass ledge, suspended 1,353 feet above the vibrant city of Chicago. Ensure your spot by securing tickets that grant you exclusive access to this awe-inspiring experience.
First Lady Cruises Chicago

4First Lady Cruises Chicago

First Lady Cruises Chicago operates a fleet of elegant boats; each with open‑air upper decks, climate‑controlled lower salons, upscale marble restrooms and a full bar. As the only official cruise partner of the Chicago Architecture Center, they deliver expert‑led river and lake sightseeing, enchanting sunset and fireworks voyages, plus fully customizable private charters for groups large or small.

What our guests say

Frangelith B

United States
Group
Feb 2026



+1 more

It was a nice experience. The view he gives us from Chicago was spectacular, and the attention incredible. I give 100 points to this beautiful place

360 Chicago Observation Deck Skip-the-Line Tickets

Ashleigh P

United States
Solo
Jan 2026


I loved this experience! I went alone and all of the employees were super kind and welcoming. I haven't been to the skydeck in over 10 years so it was great to go back and see the amazing views of Chicago!!

Skydeck Chicago Tickets

Sweta J

United States
Couple
Jan 2026


My mom is visiting Chicago for first time and taking her to the cruise and showing her the city was one of thing on my bucket list.

45-min Chicago River Architecture Cruise by Wendella

Chetna D

United States
Couple
Dec 2025



+1 more

I absolutely loved this tour! The JBL speakers were fantastic and made it so easy to hear the guide clearly, even in a busy and noisy environment. The tour guide was incredibly knowledgeable and shared information in such a fun, engaging, and effortless way that it really stayed with me. I still remember interesting facts like the Chicago River being 22 feet wide and how it turns green on St. Patrick’s Day. The clear sound from the JBL speakers and the amazing guide together made this tour truly memorable and enjoyable.

90-min Chicago River Architecture Cruise by Wendella

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