Checkpoint Challenges Customer Photo No need to adjust your schedule for an event! This innovative way to orienteer uses your smartphone for navigation, letting you enjoy our courses whenever you want.

Checkpoint Challenges


About Checkpoint Challenges

Are you passionate about hiking or walking in the park but also looking to challenge your mind?

Checkpoint Challenges offers an unmatched outdoor adventure experience. Plot your unique course between checkpoints while working on your map reading skills!

A new version of Orienteering......

Like traditional orienteering, each course consists of a sequence of points marked on a map that must be visited in sequence. Participants choose their own route between the checkpoints, eventually returning back to the Start location. However, instead of a full-size paper map, your smartphone will only show you the current map segment with an intergated compass along with details on your progess and hints to prevent you getting lost.

Have fun on your schedule and at your speed...

Skip the club meet! our courses are ready whenever you are. Enjoy them competitively, with rankings for each segment, or as a recreational pastime. This enriching outdoor experience is ideal for active people and adventure groups alike.


Checkpoint Challenges Whiskey Point

What are people saying about Checkpoint Challenges?

Customer Reviews

Great idea! Can't wait to see more locations added.
James
Great idea! Can't wait to see more locations added.
James
I can't believe this isn't more popular! Such a rewarding experience.
Olivia
Image © Checkpoint Challenges Customer 2025

Checkpoint Challenges Highlights

  • Race
  • Team building
  • Compass Reading
  • Competition
  • Individuals or groups
  • Checkpoints
  • Flat rate price
  • Challenging
  • Active
  • Outdoors
  • Physical
  • No reservations
  • Anytime
  • GPS
  • Contest
  • Enriching
  • Running
Scientists find unusual outdoor activity can help stave off dementia. Researchers studied orienteering, an outdoor sport that exercises mind and body and can also train the brain, helping fight cognitive decline. Now scientists say that the sport - which draws on athleticism, navigational skills and memory - could be useful as an intervention or preventive measure to fight cognitive decline related to dementia.
The Independent

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Humboldt Park, 2631 W Evergreen Ave, Chicago, IL

Directory

Map And Compass Reading

Near West Side Map And Compass Reading Killgubbin Map And Compass Reading East Garfield Park Map And Compass Reading Logan Square Map And Compass Reading Simons Map And Compass Reading Printers Row Map And Compass Reading Cabrini Addition Map And Compass Reading Magnificent Mile Map And Compass Reading Swedentown Map And Compass Reading Central Park Map And Compass Reading Lincoln Park Map And Compass Reading Mccormickville Map And Compass Reading Ravenswood Gardens Map And Compass Reading Grayland Map And Compass Reading Garibaldi Square Map And Compass Reading North Center Map And Compass Reading Pilsen Map And Compass Reading Grace Abbott Homes Map And Compass Reading Wolcotts And Bushnells Additions Map And Compass Reading East Village Map And Compass Reading West Town Map And Compass Reading Streeterville Map And Compass Reading Sheffield & Depaul Map And Compass Reading South Lawndale Map And Compass Reading Avondale Map And Compass Reading Cityfront Center Map And Compass Reading Cragin Map And Compass Reading Kinzies Addition Map And Compass Reading Hermosa Map And Compass Reading West Loop Map And Compass Reading Canal Trustees Map And Compass Reading Fifty Acres Map And Compass Reading Six Corners Map And Compass Reading Greektown Map And Compass Reading Boystown Map And Compass Reading Little Italy Uic Map And Compass Reading Kelvyn Grove Map And Compass Reading Cuyler Map And Compass Reading Mandell Map And Compass Reading Hanson Park Map And Compass Reading Little Hell Map And Compass Reading Carpenters Addition Map And Compass Reading Marshall Field Garden Apartments Map And Compass Reading Pennock Map And Compass Reading Little Sicily Map And Compass Reading Whiskey Point Map And Compass Reading Moreland Map And Compass Reading Garfields Map And Compass Reading Carl Sandburg Village Map And Compass Reading Mid North District Map And Compass Reading Pacific Junction Map And Compass Reading Millenium Park Map And Compass Reading Belgravia Terrace Map And Compass Reading Olsen Hansen Row Houses Map And Compass Reading Pine Grove Map And Compass Reading Shantytown Map And Compass Reading California Park Map And Compass Reading River North Map And Compass Reading Maplewood Courts Map And Compass Reading Gold Coast Map And Compass Reading Conleys Patch Map And Compass Reading Robert Brooks Homes Map And Compass Reading Bricktown Map And Compass Reading Irving Park Map And Compass Reading Lombard Tree Map And Compass Reading Cityfront Place Map And Compass Reading Wrigleyville Map And Compass Reading Austin Map And Compass Reading Humboldt Park Map And Compass Reading Rush & Division Map And Compass Reading Bohemian California Map And Compass Reading Ukrainian Village Map And Compass Reading Towertown Map And Compass Reading Buena Park Map And Compass Reading West Ravenwood Map And Compass Reading Duncans Addition Map And Compass Reading Loop Map And Compass Reading Jane Addams Homes Map And Compass Reading Bucktown Map And Compass Reading Garfield Park Map And Compass Reading Maplewood Map And Compass Reading Near North Side Map And Compass Reading Hamlin Park Map And Compass Reading Frances Cabrini Homes Map And Compass Reading Swede Town Map And Compass Reading Lower West Side Map And Compass Reading West Garfield Park Map And Compass Reading Fort Dearborn Addition Map And Compass Reading Ravenswood Manor Map And Compass Reading Claremont Cottages Map And Compass Reading Lake View Map And Compass Reading North Lawndale Map And Compass Reading Belmont Park Map And Compass Reading Old Town Map And Compass Reading Humboldt Map And Compass Reading William Green Homes Map And Compass Reading Belmont Cragin Map And Compass Reading United Center Map And Compass Reading Crawford Map And Compass Reading Wicker Park Map And Compass Reading

Navigation Sport

Ukrainian Village Navigation Sport Jane Addams Homes Navigation Sport Killgubbin Navigation Sport Lower West Side Navigation Sport Little Sicily Navigation Sport Claremont Cottages Navigation Sport East Garfield Park Navigation Sport Swede Town Navigation Sport Mid North District Navigation Sport Cityfront Center Navigation Sport Canal Trustees Navigation Sport North Center Navigation Sport Whiskey Point Navigation Sport Carl Sandburg Village Navigation Sport Sheffield & Depaul Navigation Sport Garibaldi Square Navigation Sport Belmont Cragin Navigation Sport Irving Park Navigation Sport Carpenters Addition Navigation Sport Ravenswood Gardens Navigation Sport Maplewood Courts Navigation Sport Conleys Patch Navigation Sport Near West Side Navigation Sport Avondale Navigation Sport Millenium Park Navigation Sport West Garfield Park Navigation Sport Boystown Navigation Sport Buena Park Navigation Sport Bucktown Navigation Sport Crawford Navigation Sport Frances Cabrini Homes Navigation Sport Simons Navigation Sport West Town Navigation Sport Fifty Acres Navigation Sport Grace Abbott Homes Navigation Sport Ravenswood Manor Navigation Sport Magnificent Mile Navigation Sport Swedentown Navigation Sport Pine Grove Navigation Sport Grayland Navigation Sport Rush & Division Navigation Sport Logan Square Navigation Sport Little Hell Navigation Sport Robert Brooks Homes Navigation Sport Duncans Addition Navigation Sport Mandell Navigation Sport Kelvyn Grove Navigation Sport Olsen Hansen Row Houses Navigation Sport William Green Homes Navigation Sport Cragin Navigation Sport West Loop Navigation Sport California Park Navigation Sport Streeterville Navigation Sport Belmont Park Navigation Sport United Center Navigation Sport Shantytown Navigation Sport Printers Row Navigation Sport South Lawndale Navigation Sport Lake View Navigation Sport Mccormickville Navigation Sport Near North Side Navigation Sport Kinzies Addition Navigation Sport Hanson Park Navigation Sport Cityfront Place Navigation Sport Humboldt Park Navigation Sport Wolcotts And Bushnells Additions Navigation Sport Greektown Navigation Sport Gold Coast Navigation Sport Garfields Navigation Sport Belgravia Terrace Navigation Sport Hermosa Navigation Sport Loop Navigation Sport North Lawndale Navigation Sport Cabrini Addition Navigation Sport Lombard Tree Navigation Sport Bohemian California Navigation Sport Humboldt Navigation Sport East Village Navigation Sport Fort Dearborn Addition Navigation Sport Bricktown Navigation Sport Central Park Navigation Sport Garfield Park Navigation Sport Marshall Field Garden Apartments Navigation Sport Little Italy Uic Navigation Sport Pennock Navigation Sport Pilsen Navigation Sport Lincoln Park Navigation Sport Wicker Park Navigation Sport Austin Navigation Sport Cuyler Navigation Sport Pacific Junction Navigation Sport Old Town Navigation Sport Wrigleyville Navigation Sport Six Corners Navigation Sport West Ravenwood Navigation Sport Hamlin Park Navigation Sport River North Navigation Sport Towertown Navigation Sport Moreland Navigation Sport Maplewood Navigation Sport

Orienteering Meet

Bricktown Orienteering Meet California Park Orienteering Meet Hermosa Orienteering Meet Ravenswood Manor Orienteering Meet Near North Side Orienteering Meet Greektown Orienteering Meet Lower West Side Orienteering Meet Mandell Orienteering Meet Cityfront Place Orienteering Meet Killgubbin Orienteering Meet Central Park Orienteering Meet Carl Sandburg Village Orienteering Meet Crawford Orienteering Meet Wolcotts And Bushnells Additions Orienteering Meet River North Orienteering Meet Garibaldi Square Orienteering Meet Little Hell Orienteering Meet Pine Grove Orienteering Meet Old Town Orienteering Meet United Center Orienteering Meet Mid North District Orienteering Meet Garfield Park Orienteering Meet Little Italy Uic Orienteering Meet Humboldt Park Orienteering Meet Rush & Division Orienteering Meet Wicker Park Orienteering Meet South Lawndale Orienteering Meet Olsen Hansen Row Houses Orienteering Meet Printers Row Orienteering Meet Pacific Junction Orienteering Meet Belmont Park Orienteering Meet North Lawndale Orienteering Meet Cabrini Addition Orienteering Meet Marshall Field Garden Apartments Orienteering Meet Swedentown Orienteering Meet East Garfield Park Orienteering Meet Hamlin Park Orienteering Meet Lake View Orienteering Meet Bucktown Orienteering Meet Carpenters Addition Orienteering Meet Near West Side Orienteering Meet Maplewood Orienteering Meet Conleys Patch Orienteering Meet Bohemian California Orienteering Meet Fifty Acres Orienteering Meet Lombard Tree Orienteering Meet West Town Orienteering Meet Belmont Cragin Orienteering Meet Towertown Orienteering Meet Cragin Orienteering Meet Grayland Orienteering Meet Belgravia Terrace Orienteering Meet Ravenswood Gardens Orienteering Meet Whiskey Point Orienteering Meet Garfields Orienteering Meet Irving Park Orienteering Meet Magnificent Mile Orienteering Meet Millenium Park Orienteering Meet North Center Orienteering Meet Maplewood Courts Orienteering Meet Swede Town Orienteering Meet Sheffield & Depaul Orienteering Meet Logan Square Orienteering Meet Cuyler Orienteering Meet Humboldt Orienteering Meet Ukrainian Village Orienteering Meet Wrigleyville Orienteering Meet East Village Orienteering Meet Streeterville Orienteering Meet Buena Park Orienteering Meet West Ravenwood Orienteering Meet Mccormickville Orienteering Meet Fort Dearborn Addition Orienteering Meet Grace Abbott Homes Orienteering Meet Jane Addams Homes Orienteering Meet Simons Orienteering Meet Loop Orienteering Meet Shantytown Orienteering Meet Robert Brooks Homes Orienteering Meet Kelvyn Grove Orienteering Meet Pennock Orienteering Meet Moreland Orienteering Meet William Green Homes Orienteering Meet Little Sicily Orienteering Meet West Loop Orienteering Meet Duncans Addition Orienteering Meet Canal Trustees Orienteering Meet West Garfield Park Orienteering Meet Boystown Orienteering Meet Lincoln Park Orienteering Meet Hanson Park Orienteering Meet Austin Orienteering Meet Frances Cabrini Homes Orienteering Meet Kinzies Addition Orienteering Meet Gold Coast Orienteering Meet Cityfront Center Orienteering Meet Avondale Orienteering Meet Claremont Cottages Orienteering Meet Pilsen Orienteering Meet Six Corners Orienteering Meet

Orienteering Event

Irving Park Orienteering Event Bricktown Orienteering Event Little Hell Orienteering Event Streeterville Orienteering Event Kelvyn Grove Orienteering Event Garibaldi Square Orienteering Event Greektown Orienteering Event Whiskey Point Orienteering Event Loop Orienteering Event Humboldt Park Orienteering Event Logan Square Orienteering Event Six Corners Orienteering Event South Lawndale Orienteering Event Mandell Orienteering Event Near North Side Orienteering Event Buena Park Orienteering Event Lombard Tree Orienteering Event North Center Orienteering Event Ukrainian Village Orienteering Event Cuyler Orienteering Event Avondale Orienteering Event Humboldt Orienteering Event West Ravenwood Orienteering Event Carpenters Addition Orienteering Event Central Park Orienteering Event Old Town Orienteering Event Little Sicily Orienteering Event Rush & Division Orienteering Event Bohemian California Orienteering Event Olsen Hansen Row Houses Orienteering Event Duncans Addition Orienteering Event Printers Row Orienteering Event Bucktown Orienteering Event Little Italy Uic Orienteering Event Maplewood Orienteering Event Pacific Junction Orienteering Event Fort Dearborn Addition Orienteering Event West Town Orienteering Event Crawford Orienteering Event Cityfront Center Orienteering Event Wrigleyville Orienteering Event Jane Addams Homes Orienteering Event Wicker Park Orienteering Event Pennock Orienteering Event United Center Orienteering Event Swedentown Orienteering Event Belgravia Terrace Orienteering Event Lower West Side Orienteering Event Canal Trustees Orienteering Event Towertown Orienteering Event Grayland Orienteering Event East Village Orienteering Event Mccormickville Orienteering Event Maplewood Courts Orienteering Event Conleys Patch Orienteering Event Grace Abbott Homes Orienteering Event Marshall Field Garden Apartments Orienteering Event Ravenswood Gardens Orienteering Event Gold Coast Orienteering Event Lincoln Park Orienteering Event Austin Orienteering Event California Park Orienteering Event Garfields Orienteering Event William Green Homes Orienteering Event Cityfront Place Orienteering Event Belmont Cragin Orienteering Event North Lawndale Orienteering Event Robert Brooks Homes Orienteering Event Pilsen Orienteering Event Mid North District Orienteering Event Magnificent Mile Orienteering Event Cragin Orienteering Event Fifty Acres Orienteering Event Frances Cabrini Homes Orienteering Event Sheffield & Depaul Orienteering Event Shantytown Orienteering Event Hermosa Orienteering Event Garfield Park Orienteering Event Carl Sandburg Village Orienteering Event Near West Side Orienteering Event Ravenswood Manor Orienteering Event Swede Town Orienteering Event Hamlin Park Orienteering Event West Garfield Park Orienteering Event Millenium Park Orienteering Event Simons Orienteering Event East Garfield Park Orienteering Event Belmont Park Orienteering Event Hanson Park Orienteering Event Wolcotts And Bushnells Additions Orienteering Event Cabrini Addition Orienteering Event Boystown Orienteering Event Moreland Orienteering Event River North Orienteering Event Killgubbin Orienteering Event Kinzies Addition Orienteering Event Claremont Cottages Orienteering Event Pine Grove Orienteering Event Lake View Orienteering Event West Loop Orienteering Event

Orienteering Club

Old Town Orienteering Club North Lawndale Orienteering Club South Lawndale Orienteering Club Streeterville Orienteering Club Maplewood Courts Orienteering Club Wolcotts And Bushnells Additions Orienteering Club North Center Orienteering Club Olsen Hansen Row Houses Orienteering Club Bricktown Orienteering Club Wrigleyville Orienteering Club Near West Side Orienteering Club Avondale Orienteering Club Claremont Cottages Orienteering Club Humboldt Park Orienteering Club Magnificent Mile Orienteering Club Killgubbin Orienteering Club Austin Orienteering Club Kinzies Addition Orienteering Club Kelvyn Grove Orienteering Club Grace Abbott Homes Orienteering Club Swede Town Orienteering Club Cityfront Place Orienteering Club Grayland Orienteering Club East Village Orienteering Club Carpenters Addition Orienteering Club Whiskey Point Orienteering Club Crawford Orienteering Club Humboldt Orienteering Club Duncans Addition Orienteering Club Six Corners Orienteering Club Bucktown Orienteering Club Garfields Orienteering Club Marshall Field Garden Apartments Orienteering Club Fifty Acres Orienteering Club Near North Side Orienteering Club United Center Orienteering Club Wicker Park Orienteering Club Ukrainian Village Orienteering Club Hamlin Park Orienteering Club Belgravia Terrace Orienteering Club East Garfield Park Orienteering Club Sheffield & Depaul Orienteering Club Ravenswood Manor Orienteering Club Belmont Park Orienteering Club Mccormickville Orienteering Club Lower West Side Orienteering Club William Green Homes Orienteering Club Cityfront Center Orienteering Club Cragin Orienteering Club Hanson Park Orienteering Club Greektown Orienteering Club Pacific Junction Orienteering Club Gold Coast Orienteering Club Frances Cabrini Homes Orienteering Club Little Italy Uic Orienteering Club West Garfield Park Orienteering Club Central Park Orienteering Club Millenium Park Orienteering Club Lincoln Park Orienteering Club Ravenswood Gardens Orienteering Club Boystown Orienteering Club West Loop Orienteering Club Bohemian California Orienteering Club Mandell Orienteering Club Robert Brooks Homes Orienteering Club California Park Orienteering Club Little Sicily Orienteering Club Moreland Orienteering Club Loop Orienteering Club Rush & Division Orienteering Club Maplewood Orienteering Club Printers Row Orienteering Club West Ravenwood Orienteering Club Pine Grove Orienteering Club Canal Trustees Orienteering Club Cabrini Addition Orienteering Club Lake View Orienteering Club Mid North District Orienteering Club Conleys Patch Orienteering Club Hermosa Orienteering Club Fort Dearborn Addition Orienteering Club Logan Square Orienteering Club Garibaldi Square Orienteering Club Simons Orienteering Club River North Orienteering Club Belmont Cragin Orienteering Club Buena Park Orienteering Club Jane Addams Homes Orienteering Club Cuyler Orienteering Club Shantytown Orienteering Club Swedentown Orienteering Club West Town Orienteering Club Pennock Orienteering Club Towertown Orienteering Club Garfield Park Orienteering Club Little Hell Orienteering Club Carl Sandburg Village Orienteering Club Irving Park Orienteering Club Lombard Tree Orienteering Club Pilsen Orienteering Club