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

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 © Bobria
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Puzzling Adventures Highlights

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

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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

Treasure Hunt

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

Escape Room

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

Scavenger Hunt

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

Walking Tour

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

Amazing Race

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