Checkpoint Challenges

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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.

Orienteering in the modern era...

Similar to traditional orienteering, each course is a series of points marked on a map that must be visited in order. Participants select their own paths between checkpoints, ultimately returning to the Start. However, instead of a large paper map, your phone displays only the current course segment with an integrated compass, progress updates, and hints to keep you from getting lost.

Select your own time and pace...

No need to wait for club meetings as our courses are available whenever you're ready. Engage in competitive action with rankings for each leg or enjoy as a recreational activity. This enriching outdoor pursuit is perfect for any active person or adventurous group.

Checkpoint Challenges Pennock

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

Checkpoint Challenges Highlights

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

The main finding of this study was that Orienteering was more effective than Hiking in terms of developing gait and cognitive adaptations.

Science Direct

https://www.sciencedirect.com/science/article/abs/pii/S0167494323002790

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

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Humboldt Park, 2631 W Evergreen Ave, Chicago, IL

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Orienteering Club

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

Orienteering Event

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

Navigation Sport

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

Map And Compass Reading

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

Orienteering Meet

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