Checkpoint Challenges Customer Photo Similar to orienteering, this physical and mental outdoor activity combines exercise and navigation into an engaging competition for active people of all skill and fitness levels.

Checkpoint Challenges

About Checkpoint Challenges

Do you enjoy hiking or long walks in the park but also want to keep your mind stimulated?

Checkpoint Challenges will take you off the beaten path for an outdoor adventure like no other. Choose your own route between the marked points while perfecting your map reading skills.

Contemporary Orienteering...

Just like in classic orienteering, each course comprises a sequence of points on a map that must be visited sequentially. Participants determine their own routes between these checkpoints and eventually return to the Start. However, rather than using a full-size paper map, your smartphone will show only the current map segment with a built-in compass, progress tracking, and hints to help you stay on track.

Your schedule, your tempo...

There's no need to wait for a club meet, as our courses are always available. Whether you enjoy the competitive rankings for each leg or prefer a leisurely recreational activity, this enriching outdoor sport is ideal for active individuals and adventurous groups.

Checkpoint Challenges Simons

What are people saying about Checkpoint Challenges?

Customer Reviews

Why did it take so long for this to be invented. Well done and thank you!
Ava
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

  • Running
  • Active
  • Compass Reading
  • Individuals or groups
  • GPS
  • Contest
  • Challenging
  • Checkpoints
  • Anytime
  • Flat rate price
  • Outdoors
  • Team building
  • No reservations
  • Physical
  • Enriching
  • Competition
  • Race

Remarkably, even a single orienteering session improved spatial memory in our study participants. This suggests that participating in orienteering, even infrequently, could enhance spatial abilities, with the potential to delay their decline with age.
McMaster University Canada


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Humboldt Park, 2631 W Evergreen Ave, Chicago, IL

Directory

Navigation Sport

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Map And Compass Reading

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

Orienteering Club

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

Orienteering Event

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

Orienteering Meet

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