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Chicago Attractions

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    • Popular things to do

    1

    Couple lying on glass ledge at SkyDeck, Willis Tower, overlooking Chicago skyline.

    Willis 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.
    from $ 42.33

    2

    Family enjoying the view from 360 Chicago observation deck.

    360 Chicago

    Observation Decks
    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.
    from $ 27

    3

    Roller coaster loop at Six Flags: Great America with riders in orange seats.

    Six Flags: Great America

    Browse this collection of tickets to Six Flags Great America, home to some of the most thrilling rides in the Midwest. From heart-pounding roller coasters like Goliath and Raging Bull to family-friendly attractions and the splashes of Hurricane Harbor water park, there’s something for everyone.
    from $ 46.80

    4

    Chicago Architecture Center facade with city reflections and pedestrians.

    Chicago Architecture Center

    Unlock the stories behind Chicago’s world-famous skyline at the Chicago Architecture Center. Dive into interactive exhibits, then step out on guided walking tours like Must-See Chicago or Walk Through Time. Perfect for architecture lovers and curious explorers, these experiences reveal the design genius that shaped the Windy City.
    from $ 15

    Top experiences in Chicago

    Free cancellation
    Couple taking a selfie at Chicago 360 Observation Deck with city skyline view.
    360 Chicago Observation Deck Skip-the-Line Tickets
    360 Chicago
    from
    $27
    360 Chicago Observation Deck Skip-the-Line Tickets. Rated 4.4 out of 5 from 165 ratings.From $27
    Riders upside down on Maxx Force roller coaster at Six Flags Great America.
    Six Flags Great America One Day Tickets
    Six Flags: Great America
    from
    $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
    Willis Tower Skydeck Tickets
    from
    $42.33
    Skydeck Chicago Tickets. Rated 4.8 out of 5 from 129 ratings.From $42.33
    Free cancellation
    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
    Combo
    from $76
    $68.40
    10% off
    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 461 ratings.From $68.40
    Free cancellation
    Family enjoying Chicago skyline view from observation deck.
    Go City Chicago Explorer Pass: Choose from 39 Attractions
    City Cards
    from
    $84
    Go City Chicago Explorer Pass: Choose from 39 Attractions. Rated 4.5 out of 5 from 2113 ratings.From $84
    Free cancellation
    Family enjoying view from Chicago 360 Observation Deck with city skyline.
    360 Chicago Sip & View
    360 Chicago
    from
    $44
    360 Chicago Sip & View. Rated 4.2 out of 5 from 18 ratings.From $44
    Free cancellation
    Guests exploring architectural models at the Chicago Architectural Center.
    Chicago Architecture Center Exhibit Admission
    Chicago Architecture Center
    $15
    Chicago Architecture Center Exhibit Admission. Rated 0 out of 5 from 0 ratings.From $15
    Free cancellation
    Skyscrapers at 111 E. Wacker Dr. in Chicago with clear blue sky.
    Chicago Architecture Center Admission With Walk Through Time Tour
    Chicago Architecture Center
    $35
    Chicago Architecture Center Admission With Walk Through Time Tour. Rated 0 out of 5 from 0 ratings.From $35
    Free cancellation
    Chicago mirror maze experience with Go City All-Inclusive Pass.
    Go City Chicago All-Inclusive Pass: Choose from 39 Attractions
    City Cards
    from
    $149
    Go City Chicago All-Inclusive Pass: Choose from 39 Attractions. Rated 4.4 out of 5 from 2130 ratings.From $149
    Free cancellation
    Guided group walking under Calder's Flamingo sculpture in Chicago.
    Architecture Center Admission with Must-See Chicago Walking Tour
    Chicago Architecture Center
    $35
    Architecture Center Admission with Must-See Chicago Walking Tour. Rated 0 out of 5 from 0 ratings.From $35

    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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    What our guests say

    Julian S

    United States
    Couple
    3 weeks ago
    Without a doubt, my best experience in this wonderful city was with Headout! The Skydeck experience was amazing!

    Skydeck Chicago Tickets

    Sarantuya B

    United States
    Group
    Apr 2026
    We just came from Mongolia. Visit the skydeck. We did very enjoyed our time there . It's beautiful place i would love the place. We have small businesses in our country, we did beautiful pictures for our business product. Thankyou Chicago!

    Skydeck Chicago Tickets

    Wei J

    United States
    Couple
    3 weeks ago
    The observation deck is high enough to view the whole city, also close enough to the water/beach to enjoy the beautiful blues.

    360 Chicago Observation Deck Skip-the-Line Tickets

    Karen S

    Colombia
    Solo
    Mar 2026

    +1 more

    It's a magical viewpoint. You can see the whole city, and the view to the side is breathtaking. Highly recommended. No lines and super fast!!! Plus, the information is available in English and Spanish.

    360 Chicago Observation Deck Skip-the-Line Tickets

    Fabrice C

    Couple
    May 2026
    This was awesome. Since I arrived well before the scheduled time, a staff member updated my reservation on his own, and I was able to start the tour right away. It was really cool—not too crowded—and I got some great photos of Chicago. I highly recommend this tour.

    Combo: Chicago Hop-on Hop-off Bus Tour + 360 Chicago Observation Deck Skip-the-Line Tickets

    Martha P

    United States
    Couple
    Mar 2026
    It was really fast to buy the tickets, even the greeter told us how to save with the tickets. The services, the facilities, and the recommendations were really good.

    Combo: Chicago Hop-on Hop-off Bus Tour + 360 Chicago Observation Deck Skip-the-Line Tickets