City Features: Chicago's best eats, runs, and sights

By San Diego Guide and Chicago Manager Chelsey Stone

While interviewing Chicago Guides Rebecca Greenberg and Lauren Hooks as well as Read & Run’s Allison Yates, Chelsey asked for their ultimate recommendations for the best food, running, and sights in Chicago. Whether you’re in town for the Chicago Marathon this October or plan on visiting the city soon, check out these recommendations from one runner to another.

Where the locals eat 

Like many runners, we’re a frugal group who love healthy, nutritious food that fuels our runs, so we like to cook a lot of meals ourselves. But when pressed for their favorite places to eat out, our crew came up with some great places, in a variety of neighborhoods throughout the city.

Becca’s recommendations 

Guide Becca

"There’s sort of a neighborhood for everything. Try the deep dish pizza if you have to [more on this below], but there’s some really good Italian spots in Little Italy."

"Hotel Lincoln [points to it as we happened to be coming up to it on our run] has got 12 different bars and restaurants. But the rooftop has amazing cocktails, and you can see all of the city."

"I always recommend going to a brewery. District Brew Yards has Around the Bend, one of my favorite breweries. The place is a little expensive, but it’s by the pour and you get to try 4 different breweries. It’s in the middle of the West Loop. In the summer, it has huge outdoor seating, board games, music.

Allison’s recommendations

Read & Run’s Allison

If you think you know Chicago style pizza, think again. Read & Run led a run based on Steve Dolinsky’s The Ultimate Chicago Pizza Guide and the book covers Chicago’s pizza history and where to get the best slice.

“At Robert’s Pizza and Dough Co. Robert uses as many local ingredients as possible, and he has even been using the same yeast starter for over 25 years. When he goes on vacation, he has a yeast babysitter. He has really great combinations and very creative pizzas that he does all himself. He’ll be walking around the restaurant and come talk to you and say hi. I truly think that pizza is amazing. It's more tavern style, but it's cut into triangles, so it's technically contemporary but very good.” The good news for visitors, this spot is right downtown. You might not expect to get a really good pizza spot so close to the epicenter of Chicago’s tourism, but for those staying downtown, this place is a half mile walk to Michigan Ave. and the Mag Mile.

If we're still talking about pizza though. Pizza Friendly Pizza in Ukranian Village on Western Ave. They’ve got really good and affordable slices and beer. They're right next door to The Empty Bottle, which has free shows on Mondays. They have a lot of up and coming artists but they've also historically had shows of people who became very famous. It's grungy, almost a seedy looking place, but very accessible to listen to live music of all types.

Lauren’s recommendations

Guide Lauren

“When you’re newer to a city, you want to try all of the Chicago restaurants.” Her favorite spots to play tourist are Range in Lincoln Park. She said eating there was “one of the best experiences ever. They have a very seasonal menu. The chef comes over to your table and talks with you. Great drinks, good vibes, great atmosphere.” But Lauren warns to make your reservation now as they can book up.

Another of her favorites is Gather.

Chelsey’s recommendations

Chelsey (left) and Allison (right) at a Read & Run event

My favorite post-20 miler breakfast spot is Tweet in Uptown. It’s a popular place, so be prepared to wait it out in the bar with a well-deserved mimosa. They know you’re hungry after all that waiting though, so they give you a tasty fruit cup and toast right when they seat you; it keeps you from getting too hangry while waiting for your order.

The Chicago Marathon takes runners down S Wentworth Ave., right by Chiu Quon Bakery in Chinatown, combining the opportunity to check out the course and grab something delicious to eat. They have tons of buns, cookies, and cakes on display; just remember your eyes are bigger than your stomach. I’ve been known to order in excess after a run around nearby Ping Tom Memorial Park.

Chiu Quon Bakery

If you are staying downtown, try Aster Hall, a food court in a swanky shopping mall where you can sample many of Chicago’s finest like Small Cheval (petite version of the famous Au Cheval), a Chicago-style hotdog, ramen, and more. And if you’re thinking you’re recommending a food court like my mom did after I suggested it for my post-Chicago Marathon dinner, I promise, it’s not your typical mall food court.

Where the locals run

Becca Greenberg: "I really like to go up N Clark St. and down N Lincoln Ave.; you see a weird cross-section of the city, a combination of schools and houses, music and theaters and bars, and everything in between. You pass Wrigley Field. How often can you go on a run and pass a major league field? Though sometimes it’s not a great idea to run through the crowd entering or leaving the stadium."

The Lakefront is a runner’s paradise, and no wonder. It’s an 18-mile long path with almost no intersections (a few stop-signed areas, where you have the right of way, and crossings with the separated bike path). Some of my favorite spots on or right off of the Lakefront Trail include Promontory Point on the south side, Montrose Bird Sanctuary on the north side, and Northerly Island in the center. Allison agreed and described them best:

Promontory Point is my absolute favorite spot on the lakefront for so many reasons. It has great views and I love the type of people who go there. Because of the University of Chicago, it's a really intellectual crowd, so I like overhearing their conversations. You can hear a lot of different languages there. And it's great for community barbecuing.”

Montrose Bird Sanctuary feels like an urban city where nature is uniting and thriving together. I feel the same about Northerly Island. I love that you cannot hear the city but see it and feel so far away but also you're very close.”

Skokie Sculpture Park

My favorite routes are anywhere along the Chicago River. You can of course run on the famous Chicago Riverwalk and while it’s not very long, you can add distance by going north or south on the Lakefront Trail. The North Shore Channel Trail will take you right along the river and up to the Skokie Sculpture Park. You can also run from the Eleanor Street Boathouse to the Canal Riverwalk Park, it’ll just require some running on the streets to connect.

Chicago River at Lathrop Homes

Where the locals hang out

Allison provided neighborhood attractions that won’t necessarily be on every list of things to do…

“One of my favorite places to take people is Shit Fountain. I take everybody there because it tells a really fun story. It’s a great example of how you can have something so funky in a pretty standard neighborhood. And people just love it and it became a beloved by the community feature. Jerzy S. Kenar is the artist. He does a lot of religious art, but apparently he has ties to the Daley family via a priest because he's very Catholic. And Daley came to the unveiling of Shit Fountain.
Andersonville: “I love neighborhoods with concentrated strips of restaurants, bars, and culture. There’s the Swedish American Museum. Their children's section is so fun, but it’s for any age. It's meant to mimic what the neighborhood used to be, which was Swedish. I also love that they have some dive bars, amazing Middle Eastern grocery stores and restaurants all in one concentrated area, and of course Women and Children First bookstore.”

See Chicago through our guides

There are, of course, just about a million websites for recommended eating and sight-seeing in Chicago, but our guides and community have curated the above list for with their fellow runners in mind. We hope you enjoy our favorite spots in Chicago just as much as we do.

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