Orienteering Event near Fort Dearborn Addition, Illinois

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

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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 Fort Dearborn Addition

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 2025

Checkpoint Challenges Highlights

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

Aerobic exercise releases chemicals in the brain that foster the growth of new brain cells. And when you use a map and connect it to landmarks, you stimulate growth between brain cells.

Harvard University Medical School

https://www.health.harvard.edu/blog/orienteering-great-exercise-and-better-thinking-skills-202307102953

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Humboldt Park, 2631 W Evergreen Ave, Chicago, IL

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Orienteering Club

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

Map And Compass Reading

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

Orienteering Event

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

Orienteering Meet

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

Navigation Sport

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