Puzzling Adventures Customer Photo Calling all Amazing Race enthusiasts! Team up with your fellow adventurers for a fast-paced quest around the city, deciphering questions and piecing together your answers along the way. Can you outsmart the competition and clinch the top spot on 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!

Entertaining for all age groups...

Whether you're a grade-schooler, a young adult, or a senior, our adventures provide enjoyment for everyone. Almost all of our hand-crafted experiences are accessible to wheelchairs and strollers, prioritizing inclusivity. Each adventure is infused with elements of fun and learning, appealing to a wide range of interests and tastes.

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 Mount Pleasant

What are people saying about Puzzling Adventures?

Customer Reviews

This is a great way to explore and learn about a city!
Stacy H.
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 © WheresMichael
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Puzzling Adventures Highlights

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

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Directory

Walking Tour

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

Treasure Hunt

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

Amazing Race

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

Escape Room

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

Scavenger Hunt

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

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