Puzzling Adventures Customer Photo Inspired by the excitement of the Amazing Race, rally your team for a high-speed pursuit through the city streets, decoding questions and hunting down clues. Only the quickest and sharpest minds will triumph and secure their place atop our Puzzling Adventures leaderboard!

Puzzling Adventures


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About Puzzling Adventures

Searching for an engaging activity to enjoy with your kids, teens, tweens, other family, friends or colleagues?

Step into the world of Puzzling Adventures, a captivating blend of scavenger hunt, self-guided walking tour and an amazing race. Experience the outdoors in a whole new light as you embark on this unique adventure. Navigate the city, solving puzzles and answering questions to uncover your next destination. All you need is a smartphone and an appetite for an unforgettable escapade!

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.

Explore at your leisure, on your terms...

Because our adventures are self-guided you can play any time on any day - no reservations required. Complete the adventure as quickly as possible to win first place or take your time to enjoy the sights, sounds, smells and tastes of the various locations you will visit.

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Puzzling Adventures near Carl Sandburg Village

What are people saying about Puzzling Adventures?

Customer Reviews

This was a great way to spend an afternoon outdoors!
Lynne-Marie A.
This was really fun, it was a nice day and we learned a lot!
Bill S.
I liked how each clue showed us little known facts about the city. It made finding local eateries and sights easy. Very fun!
Taylor V.
Image © Montana Masterminds
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Puzzling Adventures Highlights

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

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Some of the benefits of time spent outside can include improvements in sleep, blood pressure, cognitive function and physical activity, as well as reduced risks of chronic disease, such as type 2 diabetes, cardiovascular disease and cancer.
Harvard University

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directions
20 E Randolph St, Chicago, IL 60601

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Directory

Treasure Hunt

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

Escape Room

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

Scavenger Hunt

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

Walking Tour

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

Amazing Race

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