Checkpoint Challenges Customer Photo No more scheduling conflicts! This revolutionary orienteering experience uses your smartphone as both map and compass, giving you the freedom to enjoy our courses whenever you choose.

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!

Orienteering in the Digital Age...

Much like traditional orienteering, each course consists of a series of points on a map that must be visited in sequence. Participants choose their routes between checkpoints and return to the Start. However, instead of using a large paper map, your smartphone will display only the current map segment with a compass overlay, progress updates, and hints to avoid 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 Lake View

What are people saying about Checkpoint Challenges?

Customer Reviews

This is a must do for anybody who likes hiking, map reading, or orienteering!
Evan
Great idea! Can't wait to see more locations added.
James
Yes, I got lost, but I was soon back on track! I loved the whole experience but especially the helpful warning when I got too far off course :-)
Liam
Image © Checkpoint Challenges Customer

Checkpoint Challenges Highlights

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

After surveying 158 people ages 18 to 87, researchers concluded that orienteering may be more beneficial than physical activity alone. That's because exercising while navigating activates the parts of the brain our ancestors used for hunting and gathering, but which are largely dormant now as people rely on GPS to find their way around.
Time Magazine

Mapping Humboldt Park, 2631 W Evergreen Ave, Chicago, IL
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Humboldt Park, 2631 W Evergreen Ave, Chicago, IL

Directory

Orienteering Meet

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

Map And Compass Reading

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

Orienteering Event

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

Orienteering Club

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

Navigation Sport

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