Things to do over Labor Day weekend in Chicago (Updated 2023)

Chicago, USA
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  • Chicago Architecture River Cruise
    Badge of Excellence This experience is highly rated by travelers and has met our top quality standards.

    Chicago Architecture River Cruise

    6548

    Experience one of the world’s most beautiful cities on a cruise down the historic Chicago River. On this architecture cruise, head down the main branch...
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     1 hour 15 minutes  Free Cancellation  Instant Confirmation
    from
    $50.36
    Details
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    $50.36
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  • 90-Minute Chicago River Architecture Tour
    Likely to Sell Out
    Badge of Excellence This experience is highly rated by travelers and has met our top quality standards.

    90-Minute Chicago River Architecture Tour

    2314

    Be inspired by the captivating, visual art that is Chicago’s legendary architecture, and the exceptional architects who created this ever-changing, dynamic legacy for all to...
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     1 hour 30 minutes  Free Cancellation  Instant Confirmation
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    $42
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    $42
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  • Big Bus Chicago Hop-On Hop-Off Tour

    Big Bus Chicago Hop-On Hop-Off Tour

    656

    The lakeside metropolis of Chicago is famous for its striking skyscrapers, world-class museums and colorful history. Explore the “Windy City” at your own pace, with...
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     1 hour  Free Cancellation  Instant Confirmation
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    $48.60
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    $48.60
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  • Chicago CityPASS — Save 40%

    Chicago CityPASS — Save 40%

    351

    Chicago CityPASS® — Discover Chicago's best attractions at one great price with an easy-to-use mobile ticket. Spend less, experience more. Save 40% on prepaid admission to...
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     9 days  Instant Confirmation
    from
    $134
    Details
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    $134
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  • Chicago Crime and Mob Bus Tour
    Likely to Sell Out
    Badge of Excellence This experience is highly rated by travelers and has met our top quality standards.

    Chicago Crime and Mob Bus Tour

    1208

    Escape into Chicago's underworld on a crime and mob tour with stops on-and-off the luxury, climate-controlled bus. Walking tour paths explore historic crime scenes with...
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     90 to 120 minutes  Free Cancellation  Instant Confirmation
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    $46
    Details
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    $46
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  • Chicago Lake and River Architecture Tour
    Likely to Sell Out
    Badge of Excellence This experience is highly rated by travelers and has met our top quality standards.

    Chicago Lake and River Architecture Tour

    741

    An authentic Chicago tradition since 1935, this is the tour that started it all. This unique excursion tells the story of more than 200 years...
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     1 hour 30 minutes  Free Cancellation  Instant Confirmation
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    $42
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    $42
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  • Chicago Sunset Cruise
    Likely to Sell Out
    Badge of Excellence This experience is highly rated by travelers and has met our top quality standards.

    Chicago Sunset Cruise

    407

    The Lake Michigan Sunset Cruise departs near the DuSable (Michigan Avenue) Bridge on Wendella's world class tour boats. The Cruise will navigate from the Chicago...
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     1 hour 30 minutes  Free Cancellation  Instant Confirmation
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    $42
    Details
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    $42
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  • Gangsters and Ghosts Tour in Chicago
    Badge of Excellence This experience is highly rated by travelers and has met our top quality standards.

    Gangsters and Ghosts Tour in Chicago

    2214

    Interested in exploring Chicago from the perspective of ghosts and gangsters? Want to really immerse yourself in the history of this great American city, right...
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     2 hours  Free Cancellation  Instant Confirmation
    from
    $35
    Details
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    $35
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  • Skydeck Chicago Admission Ticket
    Likely to Sell Out

    Skydeck Chicago Admission Ticket

    767

    Gaze upon the city sights from the pinnacle of Chicago, the Skydeck. Located on the 103rd floor of Willis Tower, formerly Sears Tower -- the...
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     90 to 120 minutes  Free Cancellation  Instant Confirmation
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    $44
    Details
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    $44
    Details
  • Lake Michigan Skyline Cruise in Chicago
    Badge of Excellence This experience is highly rated by travelers and has met our top quality standards.

    Lake Michigan Skyline Cruise in Chicago

    383

    Admire all of Chicago's fabulous lakefront sights and attractions on this Lake Michigan boat tour. Cruise along Lake Michigan and take in amazing views of...
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     40 minutes  Free Cancellation  Instant Confirmation
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    $34.93
    Details
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    $34.93
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  • Chicago Architecture Center River Cruise aboard Chicago's First Lady

    Chicago Architecture Center River Cruise aboard Chicago's First Lady

    531

    The Chicago Architecture Center River Cruise aboard Chicago's First Lady has long been the gold standard among all Chicago tour experiences, and is the only...
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     1 hour 30 minutes  Instant Confirmation
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    $57
    Details
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    $57
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  • Skyline Tour Aboard 148 Ft. Schooner Windy - Chicago's Official Tall Ship
    Badge of Excellence This experience is highly rated by travelers and has met our top quality standards.

    Skyline Tour Aboard 148 Ft. Schooner Windy - Chicago's Official Tall Ship

    154

    Leave the hustle and bustle behind! Explore Chicago's shores with a leisurely trip around Lake Michigan. Take in the world-famous skyline, enjoy spectacular views, and...
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     1 hour 15 minutes  Free Cancellation  Instant Confirmation
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    $59
    Details
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    $59
    Details
  • 30 Minute Lake Michigan Speedboat Ride
    Likely to Sell Out

    30 Minute Lake Michigan Speedboat Ride

    121

    Enjoy Chicago’s iconic skyline with an exciting speedboat Tour on Lake Michigan. Departing from Navy Pier, the Lakefront Speedboat Tour is the best way to...
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     30 minutes
    from
    $36.39
    Details
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    $36.39
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  • Field Museum of Natural History Discovery Pass
    Badge of Excellence This experience is highly rated by travelers and has met our top quality standards.

    Field Museum of Natural History Discovery Pass

    5

    Delve deep into the world of natural history with your Field Museum Discovery Pass in Chicago.  Your pass includes access to all general admission exhibits...
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     1 to 8 hours  Free Cancellation  Instant Confirmation
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    $35
    Details
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    $35
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  • Chicago Architecture Boat Tour
    Badge of Excellence This experience is highly rated by travelers and has met our top quality standards.

    Chicago Architecture Boat Tour

    574

    Marvel at the magnificent architecture on the Chicago River with expert tour guides! All ages welcome.Each architecture river tour is narrated by a professional guide...
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     1 hour 30 minutes  Free Cancellation  Instant Confirmation
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    $32
    Details
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    $32
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  • Frank Lloyd Wright Robie House Admission

    Frank Lloyd Wright Robie House Admission

    48

    The Frederick C. Robie House on the University of Chicago campus is considered one of the most important buildings in the history of American architecture....
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     1 hour  Free Cancellation  Instant Confirmation
    from
    $27
    Details
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    $27
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  • 360 CHICAGO Observation Deck Admission (Hancock Center)
    Likely to Sell Out

    360 CHICAGO Observation Deck Admission (Hancock Center)

    292

    The best views of Chicago can be yours at 360 Chicago Observation Deck! Perched 94 stories above the Windy City, the 360 Chicago provides commanding...
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     1 to 4 hours  Free Cancellation  Instant Confirmation
    from
    $30
    Details
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    $30
    Details
  • Chicago Small-Group City Tour with Optional Architecture River Cruise
    Likely to Sell Out
    Badge of Excellence This experience is highly rated by travelers and has met our top quality standards.

    Chicago Small-Group City Tour with Optional Architecture River Cruise

    283

    Enjoy Chicago’s famous sights and fabulous views on this award-winning small-group sightseeing tour of the city. On this tour, you will travel through Chicago with...
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     2 to 4 hours  Hotel pickup offered  Free Cancellation  Instant Confirmation
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    $46.95
    Details
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    $46.95
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  • Underground Donut Tour: Chicago's First Donut Tour
    Badge of Excellence This experience is highly rated by travelers and has met our top quality standards.

    Underground Donut Tour: Chicago's First Donut Tour

    379

    We've always had a passion for donuts, but only recently did we realize just how many others do too. And when looking around, we didn't...
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     2 hours  Free Cancellation  Instant Confirmation
    from
    $54
    Details
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    $54
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  • 2-Hour Guided Segway Tour of Chicago
    Badge of Excellence This experience is highly rated by travelers and has met our top quality standards.

    2-Hour Guided Segway Tour of Chicago

    96

    2 hours of being a kid again!!! Take a Segway tour with us and discover how beautiful Chicago truly is. Ride through some of Chicago's...
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     2 hours  Free Cancellation  Instant Confirmation
    from
    $65
    Details
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    $65
    Details
  • Chicago-Lincoln Park Indoor Skydiving with 2 Flights & Personalized Certificate
    Likely to Sell Out

    Chicago-Lincoln Park Indoor Skydiving with 2 Flights & Personalized Certificate

    33

    When you arrive at the Chicago Lincoln Park indoor skydiving location, get started by putting on your provided gear and going through a specialized training...
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     1 hour 15 minutes  Instant Confirmation
    from
    $98.09
    Details
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    $98.09
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