Amazing Race near Oakland, Illinois

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?

Embark on a thrilling adventure in Chicago's Millennium Park! Uncover the city's rich history, from its founding in 1837 to its rise as a global hub. Learn about the birth of the Twinkie, the origins of the Wrigley Company, and the legacy of the Pritzker family. Marvel at iconic sculptures like Cloud Gate, cross the BP Bridge, and explore the Art Institute of Chicago. Test your knowledge with fun quizzes, and don't forget to snap a selfie or two!

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About Puzzling Adventures

Seeking an exciting outing with your kids, teens, tweens, other loved ones, or friends?

Engage in a Puzzling Adventure, a blend of a scavenger hunt, an amazing race, and a self-guided walking tour. This innovative outdoor challenge has you exploring sights as you navigate the city route, tackling questions and puzzles to unveil your next steps. Just grab your mobile device and you're set for an fascinating new adventure!

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.

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 Oakland

What are people saying about Puzzling Adventures?

Customer Reviews

This was a great way to spend an afternoon outdoors!
Lynne-Marie A.
Really enjoyed learning things we didn't know about the history and culture of the city.
Dianne M.
We had so much fun we can't wait to try another adventure. Such a fun family activity and a great way to see the city.
Sandi K.
Image © Brima1310
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Puzzling Adventures Highlights

  • Kid friendly
  • Team building
  • Accessible
  • 250+ Locations
  • Photo Challenges
  • Exploration
  • Informative
  • No reservations
  • Flat rate price
  • Enriching
  • Outdoor activity
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Time in the outdoors offers the benefit of mental rest and rejuvenation, it has been shown to improve memory, attention, impulse control, and creativity in the general population. For example, in children, it has led to improved school performance.
McLean Hospital
https://www.mcleanhospital.org/essential/nature
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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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More Information

Available 24 Hours a day 7 days a week

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Directory

Scavenger Hunt

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

Escape Room

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

Treasure Hunt

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

Walking Tour

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

Amazing Race

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