Checkpoint Challenges Customer Photo It's no longer necessary to plan around an event! This modern take on orienteering leverages your smartphone for navigation, enabling you to explore our courses whenever it suits you.

Checkpoint Challenges


About Checkpoint Challenges

Do you enjoy walking in the park or going on hikes but want to keep your mind active at the same time?

Get ready for an outdoor adventure like no other with Checkpoint Challenges. Create your own route between the marked points while refining your map reading abilities!

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 Millenium Park

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
Went with my teenage kids and they were really intrigued and want to do this again. Novel way to enjoy the fresh air!
Bella
Always looking for something unusual to do with my girlfriend and this way a hit with both of us!
Noah
Image © Checkpoint Challenges Customer 2025

Checkpoint Challenges Highlights

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


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

Directory

Orienteering Club

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

Orienteering Event

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

Map And Compass Reading

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

Navigation Sport

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

Orienteering Meet

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