Puzzling Adventures Customer Photo Take your friends or family on a fun outdoor journey with a Puzzling Adventure. Explore your city and discover some of its hidden secrets. Enjoy sightseeing in a whole new way!

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

Hunting for a new experience with your kids, teens, family, or your significant other?

Indulge in a Puzzling Adventure, a fusion of self-guided tour, scavenger hunt, and The Amazing Race. Delight in this outdoor escapade, exploring the city in a refreshing way. Follow the route by deciphering clues and tackling challenges to unlock the next phase of your journey. All you need is your mobile device and you're all set for an entertaining new adventure!

Entertaining for all age groups...

Whether you're a grade-schooler, a young adult, or a senior, our adventures provide enjoyment for everyone. Almost all of our hand-crafted experiences are accessible to wheelchairs and strollers, prioritizing inclusivity. Each adventure is infused with elements of fun and learning, appealing to a wide range of interests and tastes.

Embark on your journey, your way, your time...

As 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 pace.


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Puzzling Adventures near Printers Row

What are people saying about Puzzling Adventures?

Customer Reviews

Had a lot of fun walking around, answering questions and being silly!
Eric G.
Had a blast! Would definitely do it again!
Candice B.
We had so much fun we can't wait to try another adventure. Such a fun family activity and a great way to see the city.
Sandi K.
Image © Brima1310

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Puzzling Adventures Highlights

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

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Time in the outdoors offers the benefit of mental rest and rejuvenation, it has been shown to improve memory, attention, impulse control, and creativity in the general population. For example, in children, it has led to improved school performance.
McLean Hospital

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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

Walking Tour

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

Treasure Hunt

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

Scavenger Hunt

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

Escape Room

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

Amazing Race

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