Become a Member

Get access to more than 30 brands, premium video, exclusive content, events, mapping, and more.

Already have an account? Sign In

Become a Member

Get access to more than 30 brands, premium video, exclusive content, events, mapping, and more.

Already have an account? Sign In

Brands

Travel

Triathlon Tour Guide: Chicago

A world-class race venue in a modern Midwestern metropolis: Chicago is our kind of town.

For access to all of our training, gear, and race coverage, plus exclusive training plans, FinisherPix photos, event discounts, and GPS apps, sign up for Outside+.

A world-class race venue in a modern Midwestern metropolis: Chicago is our kind of town.

Half-Day Adventure

Explore Chi-town
Power up in the morning with a latte from Heritage General Store, a combination of coffee bar and bike art gallery (Heritagebicycles.com). The warm and friendly shop is also a studio for custom steel bikes inspired by vintage aesthetics—they’re not very aero but sure are fun to ride. In the afternoon, take a walk to The Centered Chef to swap recipes and race stories. Established in 2005 by triathlete Ryan Hutmacher, the culinary school offers short and fun cooking classes such as “Athlete Performance Nutrition” and “Vegan Cooking & Baking 101” (Centeredchef.com).

Free Coffee and Beer!

Bike-shop Bliss
New multisport store Live Grit not only has an array of swim-bike-run gear and apparel in the West Loop, it also acts as a pre- or post-ride hangout spot with free coffee and beer. Check out the shop’s calendar for upcoming events when you’re in town (Livegrit.com).

Multisport Meetups

Train Like a Local
Despite its big-city traffic, Chicago is a bike-friendly city. The Chicago Tri Club has several popular training routes outlined on its website (Chicagotriclub.com), including the Saturday “Muffin Ride,” a 50-mile ride beginning near Wrigley Field and looping to Highland Park for a breakfast treat before returning to the start. To log some open water time, meet up with the “Lake Monsters” at Ohio Street Beach. This fun-loving group of swimmers, led by swim coaches at Open Water Chicago, brave the waves of Lake Michigan on summer weekends (Openwaterchicago.com). Many swimmers stay for a brick run on the Lakefront Trail, a 19-mile stretch of shared-use path under the striking Chicago skyline.

Run This Town

A Night Out
If you’re the type to mix running and revelry, meet up with the Chicago Hash House Harriers, a raucous “drinking club with a running problem” with meetups around Chicago almost every night (Chicagohash.com). If you (or your spouse) would rather spend the night sans sweat, there is no shortage of fun (and free!) events in Millennium Park each night, from live jazz concerts in the Jay Pritzker Pavilion to sunset strolls through the Lurie Gardens. Go on a Wednesday or Saturday night for the best view of the fireworks show from nearby Navy Pier. Afterward, head to The Gage (Thegagechicago.com), a vintage tavern with upscale comfort food and whiskey tasting flights.

Race It! Adding to an already full calendar of triathlon events (including the popular Transamerica Chicago Triathlon), the Windy City will become the first U.S. city to host an ITU World Triathlon Series Grand Final in 2015. Want to follow in the footsteps of ITU stars Gwen Jorgenson and Javier Gomez? Sign up for the age-group races, taking place September 2015 (Chicago.triathlon.org). The course loops along the shores of Lake Michigan, blazing past Chicago landmarks Soldier Field and the Art Institute of Chicago before finishing at the iconic Buckingham Fountain.

Go: In the summer or fall, when the city compensates for its brutal winters with an abundance of lakefront running, patio dining and outdoor festivals.

Stay: At Hotel Palomar, a boutique hotel in the River North neighborhood, mere steps away from the lakefront paths and most of the city’s landmarks, including the Magnificent Mile, Navy Pier and the Chicago Gallery District (Hotelpalomar-chicago.com). This fitness-friendly hotel schedules free weekly group runs and barre classes on the 17th floor poolside terrace. Seeking a solitary savasana? The concierge will deliver yoga equipment to your room.

Dine: Chicagoans love their thick-crust pizza, especially when topped with meat and cheese at Lou Malnati’s (Loumalnatis.com). Wash your pie down with a hometown brew, like Anti-Hero IPA from Revolution Brewing Company.

Though Chicago is known for its pizza pies, locals say Gene’s Sausage Shop is the true taste of the town (Genessausageshop.com). The historic delicatessen showcases the city’s Polish roots with traditional sausages and pierogies (dumplings stuffed with sweet or savory fillings).

RELATED PHOTOS: 2014 ITU WTS Chicago Age Group Race

More Triathlon Tour Guides.