Discover the best things to do in Chicago

90-min Chicago River Architecture Cruise by Wendella

Chicago River cruise boat passing under DuSable Bridge with city buildings in the background.

90-min Chicago River Architecture Cruise by Wendella. Rated 4.9 out of 5 from 557 ratings.From $45

45-min Chicago River Architecture Cruise by Wendella

Chicago River cruise boat passing under a bridge with city skyline.

Official Chicago Architecture Cruise by First Lady

45-min Chicago River Architecture Cruise by Wendella. Rated 4.8 out of 5 from 875 ratings.From $28

Cruise boat on Chicago River passing under Clark Street Bridge.

$57

Official Chicago Architecture Cruise by First Lady. Rated 4.8 out of 5 from 181 ratings.From $57

Dinner cruise boat on Chicago River with illuminated city skyline at night.

Chicago Dinner Cruise

75-Minute Chicago River Architecture Cruise by Shoreline

$112.10

Chicago Dinner Cruise. Rated 4.6 out of 5 from 152 ratings.From $112.10

Tour boat on Chicago River with city skyline and bridge in background.

$39

75-Minute Chicago River Architecture Cruise by Shoreline. Rated 4.4 out of 5 from 116 ratings.From $39

Odyssey Lake Michigan Dinner Cruise

$132.58

Odyssey Lake Michigan Dinner Cruise. Rated 4.6 out of 5 from 74 ratings.From $132.58

90-min Chicago River and Lake Michigan Architecture Cruise by Wendella

Chicago River architecture cruise boat passing under a lift bridge with city skyscrapers in the background.

90-min Chicago River and Lake Michigan Architecture Cruise by Wendella. Rated 4.7 out of 5 from 107 ratings.From $45

Chicago River dinner cruise with city skyline and colorful building lights.

Chicago Fireworks Cruise

$54.76

Chicago Fireworks Cruise. Rated 3 out of 5 from 2 ratings.From $54.76

Chicago River Architecture Cruise

Tour boat on Chicago River with city skyline in background.

Six Flags Great America One Day Tickets

Chicago River Architecture Cruise. Rated 4.8 out of 5 from 321 ratings.From $28

Six Flags: Great America

$46.80

Six Flags Great America One Day Tickets. Rated 4.8 out of 5 from 5 ratings.From $46.80

Chicago Lunch Cruise. Rated 4 out of 5 from 6 ratings.From $62.88

360 Chicago Observation Deck Skip-the-Line Tickets

Couple taking a selfie at Chicago 360 Observation Deck with city skyline view.

$30

360 Chicago Observation Deck Skip-the-Line Tickets. Rated 4.4 out of 5 from 168 ratings.From $30

Why head out with Headout

Curated, not crowded

We bring you experiences worth your time, not hundreds of options to sort through.

Book anytime

Plan ahead or book the night before. There's always a slot when you need one.

Best price, always

We shop around so you don't have to. The best price is right here.

Our guarantee

Every experience is vetted for quality. If something falls short, we fix it.

Top things to do in Chicago

Big Bus Chicago Hop-on Hop-off Tours

from $49

Chicago River Architecture Cruise Tickets

from $30

from $32.50

Willis Tower Skydeck Tickets

from $42.33

Six Flags: Great America

from $46.80

First Lady Cruises Chicago

from $28

Wendella Cruises Chicago

from $28

Shoreline Cruises Chicago

from $32.50

Chicago Architecture Center

from $7

Chicago, your way

Visitor admiring ornate architecture in a historic building with statues and decorative columns.

Architecture Enthusiasts

Couple enjoying a playful moment on a European city street.

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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Chicago Attractions

Six Flags Great America One Day Tickets

Six Flags: Great America

$46.80

Six Flags Great America One Day Tickets. Rated 4.8 out of 5 from 5 ratings.From $46.80

360 Chicago Observation Deck Skip-the-Line Tickets

Willis Tower Skydeck Tickets

$30

360 Chicago Observation Deck Skip-the-Line Tickets. Rated 4.4 out of 5 from 168 ratings.From $30

View from the Skydeck at Willis Tower, Chicago, overlooking the cityscape.

Skydeck Chicago Tickets

$42.33

Skydeck Chicago Tickets. Rated 4.7 out of 5 from 129 ratings.From $42.33

Combo (Save 10%): Chicago Hop-on Hop-off Bus Tour + 360 Chicago Observation Deck Skip-the-Line Tickets

Big Bus Chicago tour and Chicago 360 observation deck view.

Combo (Save 10%): Chicago Hop-on Hop-off Bus Tour + 360 Chicago Observation Deck Skip-the-Line Tickets. Rated 4.5 out of 5 from 469 ratings.From $71.10

Family enjoying view from Chicago 360 Observation Deck with city skyline.

360 Chicago Sip & View

$44

360 Chicago Sip & View. Rated 4.2 out of 5 from 17 ratings.From $44

Go City Chicago Explorer Pass: Choose from 39 Attractions

Family enjoying Chicago skyline view from observation deck.

City Cards

$84

Go City Chicago Explorer Pass: Choose from 39 Attractions. Rated 4.5 out of 5 from 2113 ratings.From $84

Chicago Architecture Center Exhibit Admission

Guests exploring architectural models at the Chicago Architectural Center.

Chicago Architecture Center

Chicago Architecture Center Exhibit Admission. Rated 0 out of 5 from 0 ratings.From $7

Chicago Architecture Center Admission With Walk Through Time Tour

Skyscrapers at 111 E. Wacker Dr. in Chicago with clear blue sky.

Chicago Architecture Center

$35

Chicago Architecture Center Admission With Walk Through Time Tour. Rated 0 out of 5 from 0 ratings.From $35

Chicago Tours

90-min Chicago River Architecture Cruise by Wendella

90-min Chicago River Architecture Cruise by Wendella. Rated 4.9 out of 5 from 557 ratings.From $45

45-min Chicago River Architecture Cruise by Wendella

75-Minute Chicago River Architecture Cruise by Shoreline

45-min Chicago River Architecture Cruise by Wendella. Rated 4.8 out of 5 from 875 ratings.From $28

$39

75-Minute Chicago River Architecture Cruise by Shoreline. Rated 4.4 out of 5 from 116 ratings.From $39

Odyssey Lake Michigan Dinner Cruise

$132.58

Odyssey Lake Michigan Dinner Cruise. Rated 4.6 out of 5 from 74 ratings.From $132.58

90-min Chicago River and Lake Michigan Architecture Cruise by Wendella

90-min Chicago River and Lake Michigan Architecture Cruise by Wendella. Rated 4.7 out of 5 from 107 ratings.From $45

90-min Scenic Sunset Lake Michigan Cruise by Wendella

Cruise boat on Lake Michigan with Chicago skyline at sunset.

90-min Scenic Sunset Lake Michigan Cruise by Wendella. Rated 4.9 out of 5 from 37 ratings.From $45

Chicago Architecture Evening Cruise by Shoreline

Moored tour boats on the Chicago River at sunrise with city skyline.

$46

Chicago Architecture Evening Cruise by Shoreline. Rated 4.9 out of 5 from 36 ratings.From $46

45-Min Lake Michigan Tour by Shoreline

Cruise boat on Lake Michigan with Chicago skyline in the background.

Coach USA One-Way Tickets: Chicago O'Hare Airport to/from Milwaukee City Center

$32.50

45-Min Lake Michigan Tour by Shoreline. Rated 4.4 out of 5 from 14 ratings.From $32.50

Transportation in Chicago

Coach USA bus for one-way tickets from Chicago O'Hare Airport to Milwaukee.

Airport Transfers

$38

Coach USA One-Way Tickets: Chicago O'Hare Airport to/from Milwaukee City Center. Rated 0 out of 5 from 0 ratings.From $38

Cruises in Chicago

90-min Chicago River Architecture Cruise by Wendella

90-min Chicago River Architecture Cruise by Wendella. Rated 4.9 out of 5 from 557 ratings.From $45

45-min Chicago River Architecture Cruise by Wendella

Official Chicago Architecture Cruise by First Lady

45-min Chicago River Architecture Cruise by Wendella. Rated 4.8 out of 5 from 875 ratings.From $28

$57

Official Chicago Architecture Cruise by First Lady. Rated 4.8 out of 5 from 181 ratings.From $57

Chicago Dinner Cruise

75-Minute Chicago River Architecture Cruise by Shoreline

$112.10

Chicago Dinner Cruise. Rated 4.6 out of 5 from 152 ratings.From $112.10

$39

75-Minute Chicago River Architecture Cruise by Shoreline. Rated 4.4 out of 5 from 116 ratings.From $39

Odyssey Lake Michigan Dinner Cruise

$132.58

Odyssey Lake Michigan Dinner Cruise. Rated 4.6 out of 5 from 74 ratings.From $132.58

90-min Chicago River and Lake Michigan Architecture Cruise by Wendella

90-min Chicago River and Lake Michigan Architecture Cruise by Wendella. Rated 4.7 out of 5 from 107 ratings.From $45

Chicago Fireworks Cruise

$54.76

Chicago Fireworks Cruise. Rated 3 out of 5 from 2 ratings.From $54.76

Chicago Specials

Combo (Save 10%): Chicago Hop-on Hop-off Bus Tour + 360 Chicago Observation Deck Skip-the-Line Tickets

Combo (Save 10%): Chicago Hop-on Hop-off Bus Tour + 360 Chicago Observation Deck Skip-the-Line Tickets. Rated 4.5 out of 5 from 469 ratings.From $71.10

Must do things in Chicago

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.

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.

3Chicago River Architecture Cruise Tickets

The Chicago Architecture Foundation Center River Cruise follows the Chicago River through the Loop and along the lake, with licensed architect guides pointing out the city's landmark skyscrapers and design history. Find 90-minute standard cruise tickets, sunset session options, and evening cruise formats here.

4Willis 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.