Discover the best things to do in Chicago

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

45-min Chicago River Architecture Cruise by Wendella

$28

45-min Chicago River Architecture Cruise by Wendella. Rated 4.9 out of 5 from 553 ratings.From $28

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

90-min Chicago River Architecture Cruise by Wendella

90-min Chicago River Architecture Cruise by Wendella. Rated 4.9 out of 5 from 347 ratings.From $45

Odyssey Lake Michigan Dinner Cruise

$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.

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

Odyssey Chicago River boat cruising on the Chicago River with city skyline.

Odyssey Chicago River Architecture Dinner Cruise

Willis Tower Skydeck Tickets

$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.

Skydeck Chicago Tickets

$42.33

Skydeck Chicago Tickets. Rated 4.7 out of 5 from 113 ratings.From $42.33

Lake Michigan Dinner Cruise

$121.65

Lake Michigan Dinner Cruise. Rated 0 out of 5 from 0 ratings.From $121.65

Hop-on Hop-off Tours Chicago

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

Big Bus: Chicago Hop-on Hop-off Bus Tour. Rated 4.6 out of 5 from 298 ratings.From $45

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

360 Chicago Observation Deck Skip-the-Line Tickets

$30

360 Chicago Observation Deck Skip-the-Line Tickets. Rated 4.3 out of 5 from 152 ratings.From $30

Cruise boat on Lake Michigan with Chicago skyline at sunset.

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 18 ratings.From $45

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

90-min Chicago River and Lake Michigan Architecture Cruise by Wendella. Rated 4.7 out of 5 from 56 ratings.From $45

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

360 Chicago Sip & View

$44

360 Chicago Sip & View. Rated 4.1 out of 5 from 16 ratings.From $44

Top things to do in Chicago

Big Bus Chicago Hop-on Hop-off Tours

from $45

Chicago River Architecture Cruises

from $30

from $45

Willis Tower Skydeck Tickets

from $42.33

First Lady Cruises Chicago

from $28

Wendella Cruises Chicago

from $28

Chicago Architecture Center

from $15

Chicago, your way

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

Architecture Enthusiasts

Couple examining a map in a city setting, ideal for first-time visitors.

How Headout makes choosing experiences effortless

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Chicago Attractions

Willis Tower Skydeck Tickets

Skydeck Chicago Tickets

$42.33

Skydeck Chicago Tickets. Rated 4.7 out of 5 from 113 ratings.From $42.33

360 Chicago Observation Deck Skip-the-Line Tickets

$30

360 Chicago Observation Deck Skip-the-Line Tickets. Rated 4.3 out of 5 from 152 ratings.From $30

360 Chicago Sip & View

$44

360 Chicago Sip & View. Rated 4.1 out of 5 from 16 ratings.From $44

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

from $75

$67.50

10% off

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 449 ratings.From $67.50

The Art Institute of Chicago

The Art Institute of Chicago Tickets

$40

The Art Institute of Chicago Tickets. Rated 0 out of 5 from 0 ratings.From $40

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 2112 ratings.From $84

Go City Chicago All-Inclusive Pass: Choose from 39 Attractions

Chicago mirror maze experience with Go City All-Inclusive Pass.

City Cards

$149

Go City Chicago All-Inclusive Pass: Choose from 39 Attractions. Rated 4.4 out of 5 from 2130 ratings.From $149

Chicago Architecture Center

Guests exploring architectural models at the Chicago Architectural Center.

Chicago Architecture Center Exhibit Admission

$15

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

Chicago Tours

45-min Chicago River Architecture Cruise by Wendella

$28

45-min Chicago River Architecture Cruise by Wendella. Rated 4.9 out of 5 from 553 ratings.From $28

90-min Chicago River Architecture Cruise by Wendella

90-min Chicago River Architecture Cruise by Wendella. Rated 4.9 out of 5 from 347 ratings.From $45

Odyssey Lake Michigan Dinner Cruise

$136.68

Odyssey Lake Michigan Dinner Cruise. Rated 5 out of 5 from 1 ratings.From $136.68

Hop-on Hop-off Tours Chicago

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

Big Bus: Chicago Hop-on Hop-off Bus Tour. Rated 4.6 out of 5 from 298 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 18 ratings.From $45

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 56 ratings.From $45

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

Combo

from $75

$67.50

10% off

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 449 ratings.From $67.50

Go City Chicago Explorer Pass: Choose from 39 Attractions

City Cards

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

$84

Go City Chicago Explorer Pass: Choose from 39 Attractions. Rated 4.5 out of 5 from 2112 ratings.From $84

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

45-min Chicago River Architecture Cruise by Wendella

$28

45-min Chicago River Architecture Cruise by Wendella. Rated 4.9 out of 5 from 553 ratings.From $28

90-min Chicago River Architecture Cruise by Wendella

90-min Chicago River Architecture Cruise by Wendella. Rated 4.9 out of 5 from 347 ratings.From $45

Odyssey Lake Michigan Dinner Cruise

$136.68

Odyssey Lake Michigan Dinner Cruise. Rated 5 out of 5 from 1 ratings.From $136.68

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

Odyssey Chicago River Architecture Dinner Cruise

$147.62

Odyssey Chicago River Architecture Dinner Cruise. Rated 4.7 out of 5 from 21 ratings.From $147.62

Lake Michigan Dinner Cruise

$121.65

Lake Michigan Dinner Cruise. Rated 0 out of 5 from 0 ratings.From $121.65

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 18 ratings.From $45

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 56 ratings.From $45

Chicago Specials

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

Combo

from $75

$67.50

10% off

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 449 ratings.From $67.50

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.

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.

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.