Puzzling Adventures Customer Photo Embark on an exhilarating outdoor escapade with a Puzzling Adventure. Uncover the enigmatic mysteries of your city with an interactive sightseeing experience!

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

Seeking an exciting outing with your kids, teens, tweens, other loved ones, or friends?

Engage in a Puzzling Adventure, a blend of a scavenger hunt, an amazing race, and a self-guided walking tour. This innovative outdoor challenge has you exploring sights as you navigate the city route, tackling questions and puzzles to unveil your next steps. Just grab your mobile device and you're set for an fascinating new adventure!

Fun for all ages...

Kids, teens, tweens, young adults, seniors, groups, couples, or individuals. Almost all of our adventures are designed to be wheelchair and stroller friendly and all are carefully crafted to be entertaining and informative with something to appeal to everyone.

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 Mount Pleasant

What are people saying about Puzzling Adventures?

Customer Reviews

Highly recommend to anyone for a fun day out in the city!
Molly C.
This was a great experience!
Natalie M.
We had a great time. Great bonding experience for the whole family.
Angie B.
Image © Brima1310
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Puzzling Adventures Highlights

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

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There are a lot of studies that show even just sitting under a tree every day, lowers our stress, which can then, in turn, lower blood pressure, heart rate and those stress hormones, like cortisol. There's a natural calming effect created by breathing in fresh air and focusing on the sounds and sights around you. It's even proven to help people suffering from anxiety and depression. There's studies that are ongoing about how that could potentially help people who have ADHD. It's been shown it can improve our memory even so it could be even more cognitively active when we come back from being outside.
CBS News

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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

Scavenger Hunt

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

Treasure Hunt

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

Amazing Race

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

Escape Room

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

Walking Tour

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