Checkpoint Challenges Customer Photo Don't worry about scheduling conflicts! This modern twist on orienteering turns your smartphone into both map and compass, so you can enjoy our courses whenever you want.

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.

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.

Enjoy whenever you want at your own pace...

There is no need to wait for a club meet as our courses are available whenever you are. Enjoyed as either a competitive sport, with rankings for each leg of the course, or a recreational activity, this enriching outdoor pursuit is prefect for any active person or group of adventurers.

Checkpoint Challenges Pacific Junction

What are people saying about Checkpoint Challenges?

Customer Reviews

Great idea! Can't wait to see more locations added.
James
Great idea! Can't wait to see more locations added.
James
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

  • Checkpoints
  • Challenging
  • Flat rate price
  • Contest
  • GPS
  • Compass Reading
  • Race
  • Individuals or groups
  • Team building
  • Active
  • Anytime
  • Running
  • Competition
  • Enriching
  • Outdoors
  • No reservations
  • Physical
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
directions
Humboldt Park, 2631 W Evergreen Ave, Chicago, IL

Directory

Orienteering Event

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

Orienteering Meet

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

Map And Compass Reading

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

Navigation Sport

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

Orienteering Club

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