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Chicago

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117 mi 188 km of trail 5 Featured Runs

Easy Trails 31 Trails Intermediate Trails 1 Trail Hard Trails 0 Trails

Food & Drink

After the Run: Local Favorites

Rootstock Delicious food to pair with an impressive liquor selection or wines from around the world.
Flying Saucer Love it- remember CASH ONLY
Puerto Rico Food and Liquors Junior takes care of his customers! Best curated beer selection around these parts.
Fatso's Last Stand Try the Mac and Cheese
Bite Café Try the mashbrown from our 100 Best list: The search for the perfect hash browns ends at Bite, where a patty of skin-on potato mash is always fried to a golden crisp.
Kasia's Polish Delicatessen Pierogi lovers unite! While these polish treats are Kasia's most popular star, delicious Polish food of all varieties can be found here---just like in our sister city of Warsaw.
Uncle Mike's Place Try the Filipino breakfast!
1700 W Grand Ave, Chicago IL — (312) 226-5318
Parson's Chicken & Fish I just watched a server here pick her butt.
Yuzu Sushi and Robata Grill Oh yeah and its BYOB just so you know.
Fifolet Pretty authentic Cajun (New Orleans) food and cocktails!
Handlebar This biker bar (bikes not motorcycles) in Wicker Park specializes in vegetarian fare.
2311 W North Ave, Chicago IL — (773) 384-9546
Flo get there early for brunch on the weekends, enjoy coffee on the house while you wait
Smoke Daddy Best mac & cheese.
Big Star Try the michelada from our 100 Best list: We know it contains Tecate, Cholula and Valentina hot sauces, and Maggi. Oh, and we’re certain it's delicious, alleviates hangovers & might just cure cancer.
1531 N Damen Ave, Chicago IL — (773) 235-4039
Dove's Luncheonette Enchilada with a Fried Egg was awesome, so was the Pozole.
1545 N Damen Ave, Chicago IL — (773) 645-4060
Irazu I'm a bit milkshake crazy, so I always get an oatmeal & banana shake. Always.
Stan's Donuts & Coffee Must try their biscoff donut. Best ever!!!
1560 N Damen Ave, Chicago IL — (773) 360-7386
Kanela Breakfast Club I highly recommend anything on the menu with their homemade chorizo. It amazing.
Antique Taco ...or as I like to call it, Etsy Taco.
Piece Brewery and Pizzeria The crispy pies hold a lot of weight, so after you choose your pizza style—red, white or New Haven plain—start picking toppings. (If you’re really going New Haven–style, try one with clams and bacon.)
1927 W North Ave, Chicago IL — (773) 772-4422

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Featured Runs in Chicago - 5

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Trails in Chicago - 27

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9.7 mi 15.6 km
#1 Yellow Trail
Willow Springs, IL
9.7 mi 15.6 km Willow Springs, IL
Unknown
Update
Maywood, IL
15.7 mi 25.2 km Maywood, IL
Unknown
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0.3 mi 0.5 km
#3 Outer Loop
Lincolnwood, IL
0.3 mi 0.5 km Lincolnwood, IL
Unknown
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0.3 mi 0.5 km
#4 Inner Loop
Lincolnwood, IL
0.3 mi 0.5 km Lincolnwood, IL
Unknown
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7.3 mi 11.8 km
#5 Red Trail
Riverside, IL
7.3 mi 11.8 km Riverside, IL
Unknown
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3.7 mi 5.9 km
#6 Black Trail
Lyons, IL
3.7 mi 5.9 km Lyons, IL
Unknown
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1.0 mi 1.5 km
#7 Black Loop
Lyons, IL
1.0 mi 1.5 km Lyons, IL
Unknown
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2.6 mi 4.2 km
#8 Tan Trail
Palos Hills, IL
2.6 mi 4.2 km Palos Hills, IL
Unknown
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1.5 mi 2.4 km
#9 Orange Trail
Willow Springs, IL
1.5 mi 2.4 km Willow Springs, IL
Unknown
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3.9 mi 6.3 km
#10 Brown Trail
Willow Springs, IL
3.9 mi 6.3 km Willow Springs, IL
Unknown
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Northfield, IL
15.3 mi 24.6 km Northfield, IL
Unknown
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Northfield, IL
8.4 mi 13.5 km Northfield, IL
Unknown
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Morton Grove, IL
0.8 mi 1.3 km Morton Grove, IL
Unknown
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Morton Grove, IL
0.9 mi 1.4 km Morton Grove, IL
Unknown
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, IL
0.6 mi 1.0 km , IL
Unknown
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1.2 mi 1.9 km
#16 Brown Unpaved
, IL
1.2 mi 1.9 km , IL
Unknown
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1.8 mi 2.8 km
#17 Blue Loop
North Riverside, IL
1.8 mi 2.8 km North Riverside, IL
Unknown
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8.4 mi 13.6 km
#18 Major Taylor Trail
Riverdale, IL
8.4 mi 13.6 km Riverdale, IL
Unknown
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Willow Springs, IL
3.3 mi 5.3 km Willow Springs, IL
Unknown
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Prospect Heights, IL
18.0 mi 28.9 km Prospect Heights, IL
Unknown
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5.1 mi 8.2 km
#21 Yellow Paved
, IL
5.1 mi 8.2 km , IL
Unknown
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, IL
0.9 mi 1.5 km , IL
Unknown
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, IL
1.2 mi 2.0 km , IL
Unknown
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, IL
0.3 mi 0.4 km , IL
Unknown
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2.1 mi 3.3 km
#25 Brown Unpaved
, IL
2.1 mi 3.3 km , IL
Unknown
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1.8 mi 3.0 km
#26 Blue Unpaved
, IL
1.8 mi 3.0 km , IL
Unknown
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1.0 mi 1.6 km
#27 Black Loop
Evergreen Park, IL
1.0 mi 1.6 km Evergreen Park, IL
Unknown
Update

Photos of Chicago - 10

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