Checkpoint Challenges Customer Photo Don't worry about scheduling conflicts! This modern twist on orienteering turns your smartphone into both map and compass, so you can 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!

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

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

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

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

Navigation Sport

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

Orienteering Event

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

Map And Compass Reading

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

Orienteering Club

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