Puzzling Adventures Customer Photo If you love the thrill of the Amazing Race, gather your teammates for an adrenaline-fueled dash across the city, tackling questions and hunting for clues. To claim the coveted top spot on our Puzzling Adventures leaderboard, speed and smarts are your ultimate allies!

Puzzling Adventures


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About Puzzling Adventures

Looking for things to do with your date, friends, kids, teenagers, or other family?

Puzzling Adventures are a cross between a scavenger hunt, an amazing race, and a self-guided walking tour. Enjoy this unique outdoor activity and experience sightseeing in a fun new way. Each city route consists of a series of locations that you are guided to where you answer questions or solve puzzles to receive your next instruction. All you need is your own mobile device with a data connection.

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.

Explore at your leisure, on your terms...

Because our adventures are self-guided you can play any time on any day - no reservations required. Complete the adventure as quickly as possible to win first place or take your time to enjoy the sights, sounds, smells and tastes of the various locations you will visit.


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Puzzling Adventures near Shantytown

What are people saying about Puzzling Adventures?

Customer Reviews

Highly recommend to anyone for a fun day out in the city!
Molly C.
Had a blast! Would definitely do it again!
Candice B.
Our family had a lot of fun on the scavenger hunt!
Lynn C.
Image © Coveys 2025

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Puzzling Adventures Highlights

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

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Directory

Treasure Hunt

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

Walking Tour

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

Scavenger Hunt

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

Escape Room

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

Amazing Race

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

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