Puzzling Adventures Customer Photo Delight in a captivating outdoor odyssey with friends or family with a Puzzling Adventure. Unravel the clandestine wonders of your city. Transform your sightseeing exploration into an immersive 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!

Suitable for all ages...

From grandkids to grandparents, our adventures are designed to entertain and engage everyone. With careful consideration for accessibility, almost all of our experiences are wheelchair and stroller friendly. Each adventure is curated to provide a mix of entertainment and enlightenment, ensuring there's something for every member of your group.

Flexibility to explore at your own tempo...

Thanks to our self-guided adventures, scheduling is a breeze, no reservations required. Whether you're aiming for the top spot or opting for a more relaxed journey, it's entirely up to you. Take the time to dive deeper into each destination or race to be number one, the choice is yours!


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Puzzling Adventures near Old Town

What are people saying about Puzzling Adventures?

Customer Reviews

This was so fun!
Bob A.
Really enjoyed learning things we didn't know about the history and culture of the city.
Dianne M.
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 © OuterBankers
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Puzzling Adventures Highlights

  • No reservations
  • 250+ Locations
  • Accessible
  • Kid friendly
  • Flat rate price
  • Enriching
  • Outdoor activity
  • Exploration
  • Photo Challenges
  • Team building
  • 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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Rendering Map
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directions
20 E Randolph St, Chicago, IL 60601
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Directory

Amazing Race

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

Scavenger Hunt

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

Walking Tour

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

Treasure Hunt

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

Escape Room

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