Puzzling Adventures Customer Photo Immerse yourself in the captivating realm of Puzzling Adventures, where self-guided tours merge seamlessly with interactive puzzles and questions. Reveal the city's secrets while sharpening your mental acuity. Enjoy urban exploration with a twist!

Embark on a thrilling adventure in Chicago's Millennium Park! Uncover the city's rich history, from its founding in 1837 to its rise as a global hub. Learn about the birth of the Twinkie, the origins of the Wrigley Company, and the legacy of the Pritzker family. Marvel at iconic sculptures like Cloud Gate, cross the BP Bridge, and explore the Art Institute of Chicago. Test your knowledge with fun quizzes, and don't forget to snap a selfie or two!

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About Puzzling Adventures

Are you ready for a fun outdoor activity with your family, friends, or a special someone?

Embark on a Puzzling Adventure, a combintation of scavenger hunt, amazing race, and self-guided tour. Immerse yourself in this one-of-a-kind outdoor experience, discovering city sights in an exciting new way. Traverse the route by answering questions or solving riddles. All that's required is your mobile device and your desire to enjoy an unforgettable journey!

Perfect for all generations...

Whether you're spending special time with your friends, children, parents, grandchildren, or grandparents, our adventures are tailored to accommodate everyone. Our wheelchair and stroller-friendly experiences are crafted to be both entertaining and informative, appealing to a diverse audience. With activities designed to engage all ages, Puzzling Adventures goal is to provide a memorable experience for everybody who participates.

Play on your own schedule at your own pace...

Since our adventures are self-guided, you have the freedom to play whenever suits you with no need for reservations. Whether you're racing for first place or savoring each moment, the choice is yours. Immerse your senses in all of the locations you'll encounter, all at your own speed.


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Puzzling Adventures near Prairie Shores

What are people saying about Puzzling Adventures?

Customer Reviews

This was a great way to spend an afternoon outdoors!
Lynne-Marie A.
Had a blast! Would definitely do it again!
Candice B.
This was so much fun! What a great adventure!
Michele P.
Image © Brima1310
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Puzzling Adventures Highlights

  • Team building
  • Enriching
  • No reservations
  • Outdoor activity
  • 250+ Locations
  • Photo Challenges
  • Accessible
  • Flat rate price
  • Informative
  • Kid friendly
  • Exploration

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Spending time outdoors can improve overall health and wellness. The outdoors offers many opportunities to be physically active. Time outdoors may also promote mental health and stress reduction.
Centers for Disease Control and Prevention

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Mapping 20 E Randolph St, Chicago, IL 60601

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directions
20 E Randolph St, Chicago, IL 60601
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Directory

Amazing Race

Humboldt Amazing Race Killgubbin Amazing Race Armour Square Amazing Race Millenium Park Amazing Race Greektown Amazing Race Cleaverville Amazing Race Duncans Addition Amazing Race Canalport Amazing Race Park Row Amazing Race Cityfront Center Amazing Race Bucktown Amazing Race Wicker Park Amazing Race Oakland Amazing Race Logan Square Amazing Race Fort Dearborn Addition Amazing Race Mckinley Park Amazing Race Olsen Hansen Row Houses Amazing Race Douglas Amazing Race Printers Row Amazing Race Lake View Amazing Race Bridgeport Amazing Race Oakenwald Amazing Race Streeterville Amazing Race Robert Brooks Homes Amazing Race Wolcotts And Bushnells Additions Amazing Race Harbor Square Amazing Race South Commons Amazing Race Maplewood Amazing Race Garfield Park Amazing Race United Center Amazing Race Swede Town Amazing Race Little Hell Amazing Race Lake Meadows Amazing Race Mount Pleasant Amazing Race Museum Campus Amazing Race Chinatown Amazing Race Lincoln Park Amazing Race Magnificent Mile Amazing Race Canal Trustees Amazing Race Lower West Side Amazing Race Old Town Amazing Race Frances Cabrini Homes Amazing Race East Garfield Park Amazing Race Near West Side Amazing Race Cabrini Addition Amazing Race Prairie Shores Amazing Race Hamlin Park Amazing Race Near North Side Amazing Race Belgravia Terrace Amazing Race Bohemian California Amazing Race Towertown Amazing Race Film Row Amazing Race Grant Village Amazing Race Mid North District Amazing Race West Loop Amazing Race Ducktown Amazing Race Claremont Cottages Amazing Race Marshall Field Garden Apartments Amazing Race Central Station Amazing Race Little Italy Uic Amazing Race Kinzies Addition Amazing Race Maplewood Courts Amazing Race Carl Sandburg Village Amazing Race South Branch Addition Amazing Race Sheffield & Depaul Amazing Race Gold Coast Amazing Race Grace Abbott Homes Amazing Race Jane Addams Homes Amazing Race Boystown Amazing Race Rush & Division Amazing Race Conleys Patch Amazing Race Cityfront Place Amazing Race Garibaldi Square Amazing Race Pilsen Amazing Race Stateway Gardens Historical Amazing Race Chicago Amazing Race Locks Amazing Race Ida B Wells Housing Project Amazing Race Little Sicily Amazing Race William Green Homes Amazing Race Shantytown Amazing Race Victor A Olander Homes Amazing Race West Town Amazing Race Burnham Place Amazing Race Fifty Acres Amazing Race River North Amazing Race Loop Amazing Race East Village Amazing Race Mccormickville Amazing Race Dearborn Homes Amazing Race Grant Park Amazing Race Near South Side Amazing Race Carville Amazing Race Ukrainian Village Amazing Race Bronzeville Amazing Race Carpenters Addition Amazing Race Prairie Avenue Courts Amazing Race Fuller Park Amazing Race Aldine Square Amazing Race Prairie Courts Amazing Race

Scavenger Hunt

Mckinley Park Scavenger Hunt Olsen Hansen Row Houses Scavenger Hunt Central Station Scavenger Hunt West Town Scavenger Hunt Film Row Scavenger Hunt Logan Square Scavenger Hunt Lincoln Park Scavenger Hunt Chinatown Scavenger Hunt Aldine Square Scavenger Hunt South Commons Scavenger Hunt Maplewood Courts Scavenger Hunt William Green Homes Scavenger Hunt Near West Side Scavenger Hunt Ida B Wells Housing Project Scavenger Hunt Garfield Park Scavenger Hunt Harbor Square Scavenger Hunt Humboldt Scavenger Hunt Mount Pleasant Scavenger Hunt Jane Addams Homes Scavenger Hunt Streeterville Scavenger Hunt Cityfront Center Scavenger Hunt Maplewood Scavenger Hunt Bridgeport Scavenger Hunt Wicker Park Scavenger Hunt Bohemian California Scavenger Hunt Fifty Acres Scavenger Hunt Locks Scavenger Hunt Gold Coast Scavenger Hunt Victor A Olander Homes Scavenger Hunt Douglas Scavenger Hunt Sheffield & Depaul Scavenger Hunt Killgubbin Scavenger Hunt Marshall Field Garden Apartments Scavenger Hunt Belgravia Terrace Scavenger Hunt Prairie Shores Scavenger Hunt Kinzies Addition Scavenger Hunt Cityfront Place Scavenger Hunt Carville Scavenger Hunt Grant Park Scavenger Hunt United Center Scavenger Hunt Armour Square Scavenger Hunt Old Town Scavenger Hunt Printers Row Scavenger Hunt Ducktown Scavenger Hunt Frances Cabrini Homes Scavenger Hunt Little Italy Uic Scavenger Hunt Cabrini Addition Scavenger Hunt Oakland Scavenger Hunt East Village Scavenger Hunt Conleys Patch Scavenger Hunt Stateway Gardens Historical Scavenger Hunt Pilsen Scavenger Hunt Bucktown Scavenger Hunt Loop Scavenger Hunt Little Hell Scavenger Hunt Park Row Scavenger Hunt Burnham Place Scavenger Hunt Fuller Park Scavenger Hunt Duncans Addition Scavenger Hunt Hamlin Park Scavenger Hunt Chicago Scavenger Hunt Near South Side Scavenger Hunt Carl Sandburg Village Scavenger Hunt West Loop Scavenger Hunt Millenium Park Scavenger Hunt Lake Meadows Scavenger Hunt Oakenwald Scavenger Hunt Claremont Cottages Scavenger Hunt Shantytown Scavenger Hunt Magnificent Mile Scavenger Hunt Greektown Scavenger Hunt Little Sicily Scavenger Hunt Cleaverville Scavenger Hunt Museum Campus Scavenger Hunt Dearborn Homes Scavenger Hunt Lower West Side Scavenger Hunt Bronzeville Scavenger Hunt Boystown Scavenger Hunt Near North Side Scavenger Hunt Carpenters Addition Scavenger Hunt River North Scavenger Hunt Ukrainian Village Scavenger Hunt East Garfield Park Scavenger Hunt Grant Village Scavenger Hunt Fort Dearborn Addition Scavenger Hunt Canalport Scavenger Hunt Prairie Avenue Courts Scavenger Hunt Mccormickville Scavenger Hunt South Branch Addition Scavenger Hunt Towertown Scavenger Hunt Canal Trustees Scavenger Hunt Lake View Scavenger Hunt Prairie Courts Scavenger Hunt Swede Town Scavenger Hunt Mid North District Scavenger Hunt Wolcotts And Bushnells Additions Scavenger Hunt Grace Abbott Homes Scavenger Hunt Rush & Division Scavenger Hunt Garibaldi Square Scavenger Hunt Robert Brooks Homes Scavenger Hunt

Treasure Hunt

Little Sicily Treasure Hunt Prairie Shores Treasure Hunt Old Town Treasure Hunt Dearborn Homes Treasure Hunt Stateway Gardens Historical Treasure Hunt Prairie Courts Treasure Hunt Oakland Treasure Hunt West Loop Treasure Hunt Maplewood Treasure Hunt Marshall Field Garden Apartments Treasure Hunt Central Station Treasure Hunt Chicago Treasure Hunt Canal Trustees Treasure Hunt Printers Row Treasure Hunt Grant Village Treasure Hunt Robert Brooks Homes Treasure Hunt Bronzeville Treasure Hunt Boystown Treasure Hunt Carville Treasure Hunt Chinatown Treasure Hunt Douglas Treasure Hunt Belgravia Terrace Treasure Hunt Bridgeport Treasure Hunt Locks Treasure Hunt Wolcotts And Bushnells Additions Treasure Hunt Loop Treasure Hunt Harbor Square Treasure Hunt Pilsen Treasure Hunt Ducktown Treasure Hunt Jane Addams Homes Treasure Hunt Lower West Side Treasure Hunt Carpenters Addition Treasure Hunt Burnham Place Treasure Hunt Lake Meadows Treasure Hunt Garfield Park Treasure Hunt Bucktown Treasure Hunt Little Italy Uic Treasure Hunt Rush & Division Treasure Hunt Grace Abbott Homes Treasure Hunt Carl Sandburg Village Treasure Hunt Fuller Park Treasure Hunt Garibaldi Square Treasure Hunt Sheffield & Depaul Treasure Hunt Fort Dearborn Addition Treasure Hunt Wicker Park Treasure Hunt Frances Cabrini Homes Treasure Hunt United Center Treasure Hunt Fifty Acres Treasure Hunt Armour Square Treasure Hunt Cabrini Addition Treasure Hunt Millenium Park Treasure Hunt West Town Treasure Hunt Cityfront Place Treasure Hunt Near West Side Treasure Hunt Near South Side Treasure Hunt Grant Park Treasure Hunt Gold Coast Treasure Hunt Mccormickville Treasure Hunt Ida B Wells Housing Project Treasure Hunt Bohemian California Treasure Hunt Aldine Square Treasure Hunt Mount Pleasant Treasure Hunt Hamlin Park Treasure Hunt River North Treasure Hunt Film Row Treasure Hunt Mid North District Treasure Hunt Lincoln Park Treasure Hunt Prairie Avenue Courts Treasure Hunt Near North Side Treasure Hunt Oakenwald Treasure Hunt Olsen Hansen Row Houses Treasure Hunt Victor A Olander Homes Treasure Hunt Cleaverville Treasure Hunt Maplewood Courts Treasure Hunt Logan Square Treasure Hunt Lake View Treasure Hunt South Branch Addition Treasure Hunt Streeterville Treasure Hunt Museum Campus Treasure Hunt Ukrainian Village Treasure Hunt Little Hell Treasure Hunt Humboldt Treasure Hunt Duncans Addition Treasure Hunt East Garfield Park Treasure Hunt Swede Town Treasure Hunt Conleys Patch Treasure Hunt Canalport Treasure Hunt East Village Treasure Hunt Magnificent Mile Treasure Hunt William Green Homes Treasure Hunt Shantytown Treasure Hunt Greektown Treasure Hunt Towertown Treasure Hunt Claremont Cottages Treasure Hunt Park Row Treasure Hunt Mckinley Park Treasure Hunt South Commons Treasure Hunt Kinzies Addition Treasure Hunt Killgubbin Treasure Hunt Cityfront Center Treasure Hunt

Walking Tour

Wicker Park Walking Tour East Village Walking Tour Little Sicily Walking Tour Lake View Walking Tour Gold Coast Walking Tour Canal Trustees Walking Tour South Commons Walking Tour Greektown Walking Tour Loop Walking Tour Pilsen Walking Tour Duncans Addition Walking Tour Near West Side Walking Tour Killgubbin Walking Tour Grace Abbott Homes Walking Tour Garfield Park Walking Tour Millenium Park Walking Tour Mount Pleasant Walking Tour Bridgeport Walking Tour Streeterville Walking Tour Magnificent Mile Walking Tour South Branch Addition Walking Tour Belgravia Terrace Walking Tour Aldine Square Walking Tour United Center Walking Tour Carville Walking Tour William Green Homes Walking Tour Bucktown Walking Tour Cityfront Place Walking Tour Museum Campus Walking Tour West Town Walking Tour Swede Town Walking Tour Little Italy Uic Walking Tour Cleaverville Walking Tour Armour Square Walking Tour Oakenwald Walking Tour Prairie Shores Walking Tour Chicago Walking Tour Grant Village Walking Tour Towertown Walking Tour Bohemian California Walking Tour Old Town Walking Tour Prairie Avenue Courts Walking Tour Boystown Walking Tour Ukrainian Village Walking Tour Mccormickville Walking Tour Carl Sandburg Village Walking Tour Bronzeville Walking Tour Logan Square Walking Tour West Loop Walking Tour Near North Side Walking Tour Shantytown Walking Tour Robert Brooks Homes Walking Tour Park Row Walking Tour Lower West Side Walking Tour Garibaldi Square Walking Tour Marshall Field Garden Apartments Walking Tour Cityfront Center Walking Tour Fifty Acres Walking Tour Sheffield & Depaul Walking Tour Near South Side Walking Tour Dearborn Homes Walking Tour Central Station Walking Tour Fort Dearborn Addition Walking Tour Lake Meadows Walking Tour Douglas Walking Tour Canalport Walking Tour Victor A Olander Homes Walking Tour Prairie Courts Walking Tour Stateway Gardens Historical Walking Tour Conleys Patch Walking Tour Grant Park Walking Tour Carpenters Addition Walking Tour Fuller Park Walking Tour River North Walking Tour Kinzies Addition Walking Tour Maplewood Courts Walking Tour Humboldt Walking Tour Film Row Walking Tour Locks Walking Tour Mckinley Park Walking Tour Printers Row Walking Tour Rush & Division Walking Tour Oakland Walking Tour Claremont Cottages Walking Tour Ducktown Walking Tour Harbor Square Walking Tour Chinatown Walking Tour Hamlin Park Walking Tour Burnham Place Walking Tour Cabrini Addition Walking Tour Wolcotts And Bushnells Additions Walking Tour Frances Cabrini Homes Walking Tour Olsen Hansen Row Houses Walking Tour Jane Addams Homes Walking Tour Ida B Wells Housing Project Walking Tour Lincoln Park Walking Tour Little Hell Walking Tour Maplewood Walking Tour East Garfield Park Walking Tour Mid North District Walking Tour

Escape Room

Bohemian California Escape Room Maplewood Escape Room Canalport Escape Room Near South Side Escape Room Mccormickville Escape Room Near North Side Escape Room Fifty Acres Escape Room Lincoln Park Escape Room Cityfront Place Escape Room South Branch Addition Escape Room Lake View Escape Room Mount Pleasant Escape Room Fort Dearborn Addition Escape Room East Garfield Park Escape Room Cityfront Center Escape Room Swede Town Escape Room Millenium Park Escape Room Little Hell Escape Room Gold Coast Escape Room Little Italy Uic Escape Room Wolcotts And Bushnells Additions Escape Room Ducktown Escape Room Magnificent Mile Escape Room Kinzies Addition Escape Room Humboldt Escape Room Conleys Patch Escape Room Prairie Shores Escape Room Cabrini Addition Escape Room Jane Addams Homes Escape Room Grant Park Escape Room Locks Escape Room Chinatown Escape Room Wicker Park Escape Room Museum Campus Escape Room Boystown Escape Room Towertown Escape Room Lake Meadows Escape Room Carpenters Addition Escape Room Mckinley Park Escape Room United Center Escape Room Oakland Escape Room Park Row Escape Room River North Escape Room Victor A Olander Homes Escape Room Burnham Place Escape Room West Loop Escape Room Sheffield & Depaul Escape Room Garibaldi Square Escape Room Ida B Wells Housing Project Escape Room Canal Trustees Escape Room Bucktown Escape Room Pilsen Escape Room Bridgeport Escape Room Ukrainian Village Escape Room Prairie Avenue Courts Escape Room Killgubbin Escape Room Douglas Escape Room Loop Escape Room Marshall Field Garden Apartments Escape Room Old Town Escape Room Mid North District Escape Room Aldine Square Escape Room Chicago Escape Room Lower West Side Escape Room Little Sicily Escape Room Near West Side Escape Room Shantytown Escape Room Bronzeville Escape Room Dearborn Homes Escape Room Carl Sandburg Village Escape Room Carville Escape Room South Commons Escape Room Grace Abbott Homes Escape Room Cleaverville Escape Room Rush & Division Escape Room Prairie Courts Escape Room Logan Square Escape Room Hamlin Park Escape Room West Town Escape Room Olsen Hansen Row Houses Escape Room Belgravia Terrace Escape Room Garfield Park Escape Room Frances Cabrini Homes Escape Room Stateway Gardens Historical Escape Room Streeterville Escape Room East Village Escape Room Film Row Escape Room William Green Homes Escape Room Fuller Park Escape Room Claremont Cottages Escape Room Central Station Escape Room Maplewood Courts Escape Room Grant Village Escape Room Printers Row Escape Room Greektown Escape Room Armour Square Escape Room Duncans Addition Escape Room Harbor Square Escape Room Oakenwald Escape Room Robert Brooks Homes Escape Room

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