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 632 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

$28

45-min Chicago River Architecture Cruise by Wendella. Rated 4.9 out of 5 from 984 ratings.From $28

Cruise boat on Chicago River passing under Clark Street Bridge.

$57

Official Chicago Architecture Cruise by First Lady. Rated 4.9 out of 5 from 227 ratings.From $57

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

Chicago Dinner Cruise

$112.10

Chicago Dinner Cruise. Rated 4.7 out of 5 from 191 ratings.From $112.10

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.

75-Minute Chicago River Architecture Cruise by Shoreline

90-min Chicago River and Lake Michigan Architecture Cruise by Wendella. Rated 4.8 out of 5 from 126 ratings.From $45

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

$39

75-Minute Chicago River Architecture Cruise by Shoreline. Rated 4.5 out of 5 from 134 ratings.From $39

Chicago Fireworks Dinner Cruises

Fireworks over Chicago River with boats during dinner cruise.

$112.10

Chicago Fireworks Dinner Cruises. Rated 3.9 out of 5 from 7 ratings.From $112.10

Odyssey Lake Michigan Dinner Cruise

$132.58

Odyssey Lake Michigan Dinner Cruise. Rated 4.7 out of 5 from 103 ratings.From $132.58

Sea Dog Cruise on Lake Michigan

Chicago River with tour boats and bridges in downtown Chicago.

$35.72

Sea Dog Cruise on Lake Michigan. Rated 5 out of 5 from 6 ratings.From $35.72

360 Chicago Observation Deck Skip-the-Line Tickets

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

$27

360 Chicago Observation Deck Skip-the-Line Tickets. Rated 4.5 out of 5 from 166 ratings.From $27

Chicago Fireworks Cruise

$54.76

Chicago Fireworks Cruise. Rated 4.3 out of 5 from 12 ratings.From $54.76

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 40 ratings.From $45

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 $27

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 $15

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

360 Chicago Observation Deck Skip-the-Line Tickets

Six Flags Great America One Day Tickets

$27

360 Chicago Observation Deck Skip-the-Line Tickets. Rated 4.5 out of 5 from 166 ratings.From $27

Six Flags: Great America

Willis Tower Skydeck Tickets

$46.80

Six Flags Great America One Day Tickets. Rated 4.8 out of 5 from 6 ratings.From $46.80

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

Skydeck Chicago Tickets

$42.33

Skydeck Chicago Tickets. Rated 4.8 out of 5 from 129 ratings.From $42.33

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

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 4.6 out of 5 from 463 ratings.From $68.40

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 18 ratings.From $44

Chicago Architecture Center Exhibit Admission

Guests exploring architectural models at the Chicago Architectural Center.

Chicago Architecture Center

$15

Chicago Architecture Center Exhibit Admission. Rated 0 out of 5 from 0 ratings.From $15

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 632 ratings.From $45

45-min Chicago River Architecture Cruise by Wendella

$28

45-min Chicago River Architecture Cruise by Wendella. Rated 4.9 out of 5 from 984 ratings.From $28

Odyssey Lake Michigan Dinner Cruise

75-Minute Chicago River Architecture Cruise by Shoreline

$132.58

Odyssey Lake Michigan Dinner Cruise. Rated 4.7 out of 5 from 103 ratings.From $132.58

$39

75-Minute Chicago River Architecture Cruise by Shoreline. Rated 4.5 out of 5 from 134 ratings.From $39

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

90-min Chicago River and Lake Michigan Architecture Cruise by Wendella. Rated 4.8 out of 5 from 126 ratings.From $45

90-min Scenic Sunset Lake Michigan Cruise by Wendella

90-min Scenic Sunset Lake Michigan Cruise by Wendella. Rated 4.9 out of 5 from 40 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 38 ratings.From $46

Big Bus: Chicago Hop-on Hop-off Bus Tour

Hop-on Hop-off Tours Chicago

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

$49

Big Bus: Chicago Hop-on Hop-off Bus Tour. Rated 4.7 out of 5 from 301 ratings.From $49

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 632 ratings.From $45

45-min Chicago River Architecture Cruise by Wendella

$28

45-min Chicago River Architecture Cruise by Wendella. Rated 4.9 out of 5 from 984 ratings.From $28

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

90-min Chicago River and Lake Michigan Architecture Cruise by Wendella. Rated 4.8 out of 5 from 126 ratings.From $45

Chicago Dinner Cruise

$112.10

Chicago Dinner Cruise. Rated 4.7 out of 5 from 191 ratings.From $112.10

Chicago Fireworks Cruise

$54.76

Chicago Fireworks Cruise. Rated 4.3 out of 5 from 12 ratings.From $54.76

90-min Scenic Sunset Lake Michigan Cruise by Wendella

75-Minute Chicago River Architecture Cruise by Shoreline

90-min Scenic Sunset Lake Michigan Cruise by Wendella. Rated 4.9 out of 5 from 40 ratings.From $45

Chicago at Night: River & Lake Sightseeing Cruise by First Lady

$39

75-Minute Chicago River Architecture Cruise by Shoreline. Rated 4.5 out of 5 from 134 ratings.From $39

Chicago River cruise boat at night with city skyline in the background.

$50

Chicago at Night: River & Lake Sightseeing Cruise by First Lady. Rated 5 out of 5 from 1 ratings.From $50

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 4.6 out of 5 from 463 ratings.From $68.40

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.