Puzzling Adventures Customer Photo Explore the city with your nearest and dearest, embarking on a Puzzling Adventure. Uncover hidden gems and elevate your sightseeing journey with a dash of intrigue and excitement!

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!

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.

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 Harbor Square

What are people saying about Puzzling Adventures?

Customer Reviews

This was so fun!
Bob A.
Had a blast! Would definitely do it again!
Candice B.
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 © Mom and the Kids
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Puzzling Adventures Highlights

  • Photo Challenges
  • 250+ Locations
  • Outdoor activity
  • Flat rate price
  • Team building
  • Enriching
  • Exploration
  • Kid friendly
  • Informative
  • Accessible
  • 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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Mapping 20 E Randolph St, Chicago, IL 60601

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directions
20 E Randolph St, Chicago, IL 60601

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Directory

Amazing Race

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

Escape Room

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

Scavenger Hunt

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

Walking Tour

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

Treasure Hunt

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