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!

Puzzling Adventures

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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!

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 Fifty Acres

What are people saying about Puzzling Adventures?

Customer Reviews

This was a great way to spend an afternoon outdoors!
Lynne-Marie A.
Very enjoyable!
Kelly L.
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 © Fight or Flight Club

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Puzzling Adventures Highlights

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

Treasure Hunt

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

Escape Room

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

Walking Tour

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

Amazing Race

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

Scavenger Hunt

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