No need to wait for a meet that fits your schedule! This innovative new take on orienteering uses your smartphone as both map and compass and allows you to enjoy any of our courses whenever you choose.

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.

Next Generation Orienteering

Like conventional orienteering, each course includes a sequence of map points that must be visited in order. Participants select their own routes between checkpoints, eventually returning to the Start. Instead of a full-size paper map, though, your phone will show only the current course segment, complete with an integrated compass, progress details, and hints to keep you oriented.

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 West Loop

What are people saying about Checkpoint Challenges?

Customer Reviews

This is a must do for anybody who likes hiking, map reading, or orienteering!

Evan

Did this solo and really enjoyed it. Going to take some friends out next time!

Dave

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

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

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

https://brighterworld.mcmaster.ca/articles/dementia-fighter-how-orienteering-helps-the-brain/

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Humboldt Park, 2631 W Evergreen Ave, Chicago, IL

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Navigation Sport

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

Orienteering Club

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

Orienteering Meet

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

Map And Compass Reading

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

Orienteering Event

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