Checkpoint Challenges Customer Photo No need to wait for an event 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.

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 Sheffield

What are people saying about Checkpoint Challenges?

Customer Reviews

This was a really cool way to explore the park and it took me places I never would have gone otherwise!
Sophia
Went with my teenage kids and they were really intrigued and want to do this again. Novel way to enjoy the fresh air!
Bella
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 2025

Checkpoint Challenges Highlights

  • Challenging
  • Flat rate price
  • GPS
  • Team building
  • Physical
  • Enriching
  • Contest
  • Individuals or groups
  • Race
  • Running
  • No reservations
  • Compass Reading
  • Active
  • Competition
  • Outdoors
  • Anytime
  • Checkpoints
Scientists find unusual outdoor activity can help stave off dementia. Researchers studied orienteering, an outdoor sport that exercises mind and body and can also train the brain, helping fight cognitive decline. Now scientists say that the sport - which draws on athleticism, navigational skills and memory - could be useful as an intervention or preventive measure to fight cognitive decline related to dementia.
The Independent


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Humboldt Park, 2631 W Evergreen Ave, Chicago, IL

Directory

Map And Compass Reading

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

Orienteering Meet

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

Navigation Sport

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

Orienteering Club

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

Orienteering Event

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