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!

Puzzling Adventures


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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!

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.

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 Boystown

What are people saying about Puzzling Adventures?

Customer Reviews

Highly recommend to anyone for a fun day out in the city!
Molly C.
Fun fun fun! great way to experience a new area!
Rhonda R.
We had a great time. Great bonding experience for the whole family.
Angie B.
Image © Tree Gals 2025
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Puzzling Adventures Highlights

  • No reservations
  • Flat rate price
  • Kid friendly
  • Team building
  • Exploration
  • Outdoor activity
  • Enriching
  • Accessible
  • Informative
  • Photo Challenges
  • 250+ Locations
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As little as 5 minutes of outdoor activity can help improve your self-esteem. This is especially true if you're near water or green space. And it's not high-intensity exercise that does it best. More relaxed activity like a walk, bike ride, or work in the garden seems to work even better.
Web MD

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directions
20 E Randolph St, Chicago, IL 60601
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Directory

Scavenger Hunt

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

Walking Tour

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

Amazing Race

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

Treasure Hunt

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

Escape Room

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

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