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💪 Remember: This is about experiencing Chicago's food culture, not just counting calories!
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ℹ️ Chicago is one of the flattest major cities in the U.S., making this route relatively easy elevation-wise. The elevation ranges from 579 ft at Lake Michigan to about 600 ft inland.
The Loop
Mile 0.0
World's largest food festival (when running). Historic Grant Park location represents Chicago's food culture showcase.
Fun fact: Started in 1980 with 75,000 attendees. At its peak, drew over 3 million visitors. Features samples from hundreds of Chicago restaurants.
Magnificent Mile
Mile 0.5
Ice cream bar covered in thick chocolate coating. The original premium ice cream bar.
Fun fact: Invented in 1956 by Leo Stefanos at his Chicago candy shop to keep his kids from running into traffic for ice cream. Named after a local dove bird.
River North
Mile 0.8
All-beef frank on poppy seed bun with yellow mustard, chopped onions, bright green relish, tomato wedges, pickle spear, sport peppers, and celery salt. NEVER ketchup!
Fun fact: Chicago has more hot dog restaurants than McDonald's, Wendy's, and Burger Kings combined. The 'no ketchup' rule is taken seriously by Chicagoans.
River North
Mile 1.2
Shrimp baked in garlic butter with breadcrumbs and sherry. Rich, decadent, old-school Chicago fine dining.
Fun fact: Created at DeJonghe's Hotel and Restaurant (1899-1923) by Belgian brothers Henri and Pierre DeJonghe. It's pure turn-of-the-century Chicago elegance.
River North
Mile 1.5
Thick-crust pizza with layers built in reverse: crust, cheese, toppings, chunky tomato sauce on top. Baked in a deep round pan.
Fun fact: Invented in 1943 at Pizzeria Uno by Ike Sewell and Ric Riccardo. A slice can weigh over half a pound.
Des Plaines (Chicagoland)
Mile 2.8
Hot dog-sausage hybrid: all-beef hot dog wrapped in bacon or sausage casing, served on bun with classic Chicago toppings.
Fun fact: Named after Charles Prasky, who created this hybrid at his Des Plaines hot dog stand.
Norwood Park
Mile 3.5
Bright neon green sweet pickle relish made with sport peppers. The distinctive color comes from blue food coloring mixed with yellow relish.
Fun fact: The shocking neon green color is intentional! Vienna Beef created this iconic relish specifically for Chicago hot dogs.
Lincoln Park
Mile 3.8
Chicago's premier sustainable farmers market. Checkpoint for fresh local produce and artisanal foods.
Fun fact: Founded in 1998, it's Chicago's only year-round farmers market and focuses on sustainable farming. Many top chefs shop here.
Lincoln Park
Mile 4.2
Bright lime-green colored soda with a sweet, citrus-vanilla flavor. Chicago's unofficial soft drink.
Fun fact: Created in 1919 by the Schoenhofen Brewing Company. After Prohibition ended, it became the official soda of Chicago hot dog stands.
Lakeview
Mile 4.8
Waffle-doughnut hybrid: waffle batter pressed into a doughnut shape, deep-fried, and topped with glaze or toppings.
Fun fact: Created in 2013 at Waffles Cafe. It predated the cronut craze and is a Chicago original pastry innovation.
Wrigleyville
Mile 5.5
Caramel-coated popcorn and peanuts. 'Buy me some peanuts and Cracker Jack!'
Fun fact: Invented in Chicago in 1893, introduced at the World's Columbian Exposition. The name possibly came from the slang 'crackerjack' meaning excellent. Immortalized in 'Take Me Out to the Ball Game'.
Andersonville
Mile 5.8
Notoriously bitter wormwood-based liqueur. Drinking it is considered a Chicago rite of passage.
Fun fact: Marketed with the tagline 'Malört, I'll have another!' The typical reaction is an instant grimace. Chicagoans dare visitors to try it.
Uptown
Mile 6.5
Classic Chicago cocktail made with bourbon, orange liqueur, lime juice, and grenadine. Prohibition-era favorite.
Fun fact: Popular during the Jazz Age at speakeasies like The Green Mill, allegedly frequented by Al Capone.
Dunning
Mile 7.2
Rich, creamy Chicago-style cheesecake with shortbread crust. The original 'Eli's Original Plain' is legendary.
Fun fact: Created by Eli Schulman in 1980 for the opening of his restaurant Eli's The Place for Steak. A 2,000-pound Eli's cheesecake was served at President Obama's inauguration.
West Loop
Mile 8.5
Chicago-made sausage brand known for quality meat products. Historic Chicago meat-packing industry representative.
Fun fact: Founded in 1919, Parker House became synonymous with Chicago's meatpacking prowess during the Union Stock Yards era.
University Village
Mile 9.1
Historic open-air market, Chicago's oldest (since 1847). Checkpoint representing Chicago's market culture.
Fun fact: Maxwell Street was the Ellis Island of Chicago, where immigrants started businesses. It's where the blues were electrified and where Chicago street food was born.
Little Italy
Mile 9.3
Thinly sliced roast beef on Italian roll, dipped in jus (gravy), topped with giardiniera or sweet peppers. Order it 'wet' (extra jus), 'dipped' (whole sandwich in jus), or 'dry'.
Fun fact: Invented in the 1930s by Italian immigrants who needed to stretch meat further during tough economic times. The sandwich gained fame in the 2024 TV show 'The Bear'.
University Village
Mile 9.6
Grilled Polish sausage on bun with grilled onions and yellow mustard. A street food classic.
Fun fact: Named after the historic Maxwell Street Market, Chicago's oldest open-air market dating to 1847. Vendors would grill sausages 24/7.
Little Italy
Mile 9.8
Bone-in chicken and potato wedges roasted with garlic, oregano, white wine, and olive oil. Sometimes served with peas.
Fun fact: Named after Mount Vesuvius, created at The Vesuvio Restaurant on Chicago's West Side in the 1930s. It's on nearly every Italian-American restaurant menu in Chicago.
Pilsen
Mile 10.2
Iconic Chicago BBQ and soul food spot famous for rib tips, hot links, and no-frills South Side BBQ culture.
Fun fact: Known for its pink pig logo and no-nonsense counter service. It embodies authentic Chicago neighborhood BBQ culture.
Ukrainian Village
Mile 11.2
Deep-fried dough pocket filled with cheese, tomato sauce, and sometimes sausage. Like a pizza calzone meets empanada.
Fun fact: Invented in the 1970s by Iltaco Foods, sold primarily at South and West Side carryouts. It's uniquely Chicago.
Humboldt Park
Mile 11.8
Puerto Rican sandwich using flattened fried plantains instead of bread, filled with steak, lettuce, tomato, and garlic mayo.
Fun fact: Invented in Chicago in 1996 by Juan Figueroa at Borinquen Restaurant. The name comes from 'jíbaro', meaning Puerto Rican highlander.
Wicker Park
Mile 12.5
Brandy-based cocktail with Champagne, orange curaçao, and a sugar-rimmed glass dipped in orange bitters.
Fun fact: Appears in 'The Bartender's Manual' (1900). The sugared rim is dipped in bitters, creating a beautiful red rim.
South Loop
Mile 15.5
Cultural checkpoint honoring the guidebook that captured working-class Chicago food culture through the eyes of police officers.
Fun fact: The book 'The Beat Cop's Guide to Chicago Eats' documents authentic neighborhood spots that cops recommend - the real Chicago.
Bridgeport
Mile 16.2
Scrambled eggs with fried bell peppers on Italian bread. A Chicago Italian staple, especially during Lent.
Fun fact: Traditional Lenten meal for Italian-American families, eaten on Fridays when meat was forbidden.
Bronzeville
Mile 16.8
Sweet, tangy, slightly spicy BBQ-ketchup hybrid sauce, bright orange in color. Essential with fried chicken and fries.
Fun fact: Unique to Chicago's South and West Sides, particularly at fried chicken joints. Harold's Chicken popularized it starting in 1950.
West Englewood
Mile 17.5
Chicago tamale on hot dog bun with chili. Sometimes called a 'Father-in-law' if you add a hot dog too.
Fun fact: The name comes from the joke that like a mother-in-law, it's both hot and steamy! Created on Chicago's South Side.
Ashburn
Mile 18.2
Thin, crispy crust cut into squares (party cut), often with fennel-heavy sausage. The 'other' Chicago pizza that locals actually eat more often.
Fun fact: Tavern-style is actually what most Chicagoans eat regularly, not deep-dish. It's designed to be shared at bars with beer.
Greater Grand Crossing
Mile 19.5
Ribs and rib tips with a distinctive aquarium smoker method, served with tangy-sweet sauce and white bread. Chicago's unique BBQ style features smoky, charred edges.
Fun fact: Chicago BBQ uses aquarium smokers (visible through glass) and is known for 'rib tips' - the ends of spare ribs, which are more affordable and extra flavorful.
Hyde Park
Mile 20.8
Sweeter, tangier alternative to mayonnaise. You either love it or hate it, but it's a Chicago creation.
Fun fact: Invented by Kraft Foods in 1933 at the Chicago World's Fair (Century of Progress). Over 7 million jars sold in the first year.
The Loop
Mile 26.2
Final checkpoint celebrating Chicago's culinary culture: from Michelin stars to street food, from immigrant traditions to modern innovation.
Fun fact: Chicago has more restaurants per capita than any US city except San Francisco. It's home to multiple James Beard winners and maintains authentic immigrant food traditions.