As a born-and-bred Midwesterner, I have always considered Chicago my go-to big city. Even as an East Coast transplant, the Windy City regularly calls me back to see museum exhibitions, explore its quirky neighborhoods, take long walks along the shores of Lake Michigan and—most importantly—eat.
At first glance, Chicago’s cuisine might not appear very friendly to gluten-free diners. If you look beyond the legendary pizza and hot dogs, however, you’ll find some of the best gluten-free fare in the nation. From deep-dish pizza to donuts to diners, Chicago continually impresses.
Do gluten free right at
Eating my way through Chicago usually involves more calories than I care to count, so it’s important for me to offset a few indulgent meals and snacks with long walks through the city. No matter where my route takes me, though, my first stop is always the same.
Do-Rite Donuts is well-known in Chicago, thanks to its wonderful cake donuts and fried chicken sandwiches. While many of the offerings here are off limits for gluten-free diners, Do-Rite has a special gluten-free menu that includes no fewer than five donut varieties. This tiny donut shop even does its baking in-house and uses separate equipment for its gluten-free donuts, which means you can enjoy these delicious all-day goodies without worry.
At both Do-Rite locations, you can take your pick from gluten-free Valrhona Chocolate Glazed, Cinnamon & Sugar, Pistachio Meyer Lemon, Maple Bacon or Birthday Cake donuts. Perfect with a hot cup of coffee, the Pistachio Meyer Lemon donut is worth an early morning trip into Chicago’s downtown Loop any day.
Discover public art in
After fueling up for the day, it’s time to start exploring Chicago’s parks. Located right on the shores of Lake Michigan and in the center of Chicago, Millennium Park is one of my favorite places to work off a donut or two. Start on the north side and catch interactive highlights like the Crown Fountain and Cloud Gate. Better known as The Bean, this reflective sculpture offers one of the most popular photo opportunities in Chicago.
Depending on when you visit, you might catch a festival or a seasonal event in Millennium Park. Take a stroll through the Lurie Garden to see what’s blooming, spin by the Jay Pritzker Pavilion to see who’s playing, or just enjoy the view of the city’s skyline from this urban oasis.
This expansive green space is also home to the Art Institute of Chicago, which has something new to see each time I visit. Whether you’re a fan of medieval arms and armor, ancient Chinese bronzes or groundbreaking contemporary art, you’ll find something to love at the Art Institute.
Dig into deep-dish pizza
or vegan sammies
After a long walk through the park, it’s time for lunch. With so many options, you’ll have to make some hard decisions. If it’s your first visit to Chicago, you won’t want to miss out on the city’s world-famous deep-dish pizza. Several of the most popular pizza joints in the area offer thin-crust gluten-free pies, but for the real deal, make your way to one of the three Chicago’s Pizza locations. This pizza parlor uses a separate oven and prep spaces to prepare its special pies, so gluten-free diners can feel confident that these pizzas are both mouth-watering and safe to eat.
Go classic with a Chicago Supreme deep dish, which includes pepperoni, mushrooms, green peppers and plenty of mozzarella cheese nestled in a buttery crust. Or take your pizza experience to new heights with a stuffed Chicago Vegetarian, which is essentially a deep-dish pizza with an extra layer of dough on top. After trying one of these delicious stuffed pies, I’ll never look at gluten-free pizza the same way again.
If you’re in the mood for something a little lighter, pay a visit to The Chicago Diner, which has served hearty vegetarian and vegan food like piled-high sandwiches, grain bowls and veggie meatloaf for over 30 years. This venerable institution also has a gluten-free menu, which boasts options like my favorite, Portabella Truffle Melt with marinated mushrooms and white truffle aioli, or the Soul Bowl with seasoned quinoa and blackened tofu. The gluten-free menu even indicates items prepared in shared fryers, so everyone can make informed dining choices.
For a quick bite, go to Cassava in Chicago’s Lake View neighborhood. Almost everything at this completely gluten-free café centers on the cassava root, a common ingredient in South American cuisine. Owner Jorge Flores and his team make Ecuadoran-style empanadas and Brazilian cheese bread with cassava flour and pack them with grass-fed beef and flavorful vegetables. Here the emphasis is on good health and nutritious ingredients, a welcome departure from many of Chicago’s rich treats.
Have a grand time
at Navy Pier
After a filling lunch, my favorite places to stretch my legs are Navy Pier and the nearby Museum Campus. These waterfront destinations are packed with both indoor and outdoor attractions, so they’re great places to spend the afternoon no matter the weather. Young travelers as well as kids at heart will love everything, from the eye-catching Ferris wheel to the aquarium to the dinosaur models.
On a nice day, head to the Navy Pier’s Centennial Wheel, where you can grab a ticket to soar high above the city. Get the complete boardwalk experience with rides on the carousel, Light Tower Ride and Pepsi Wave Swinger®. Challenge the kids to a round of mini golf or hop aboard a sightseeing cruise and see Chicago from a whole new vantage point.
South of Navy Pier and Millennium Park, Grant Park is home to the Museum Campus as well as the dramatic Buckingham Fountain, which wows spectators with water shows from the spring through the fall.
At the Shedd Aquarium, you’re in for an underwater adventure. Get lost in the immersive environments that mimic the Great Lakes and the Caribbean Sea, or spot jellyfish and rare frogs in special exhibits. If you’re traveling with natural history buffs, don’t miss the Field Museum, where you can step back nearly 5 billion years in time. Get face to face with Sue the Tyrannosaurus rex, check out an ancient Egyptian tomb or see touring exhibits from around the world.
Indulge your sweet tooth
When I need an afternoon pick-me-up, there’s no place I’d rather be than Chicago’s Defloured®. Located in the city’s friendly Andersonville neighborhood, this bakery couldn’t be more welcoming—or more gluten free. From the cookies to the lemon bars to the cake pops to the custom layer cakes, everything on the premises is completely gluten free. Owner Johanna VanDorf believes, “Everyone has a right to dessert,” and I couldn’t agree more.
At Defloured, all of the goodies are equal parts tasty and fun, which can make it hard to pick just one. Try the signature Winkies, chocolate sandwich cookies with marshmallow cream, the frosted vegan oatmeal cookies or the mind-boggling Bomber Bars, which feature a graham crust with a Reese’s peanut butter cup and Heath bar center topped with a sprinkling of potato chips. Of course, dessert isn’t the only course on the menu here. The bakery also prepares savory quiches and scones on weekends, although no stop at Defloured is complete without a sweet treat or two.
Get blown away by the windy city
I love getting a good bird’s-eye view of a city, especially one that’s as dense as Chicago. It’s a fun way to see how neighborhoods connect, spot unknown buildings and parks, and gain a new perspective on a city. In my experience, the John Hancock Center’s 360 CHICAGO is the best place to see Chicago from above. Not only are the lines here short or even nonexistent, but the 94th-floor observation deck also tends to be relatively low-key, making it the ideal place to watch the sun slowly set.
Just one magnificent mile south of 360 CHICAGO and only a couple of blocks from the Chicago River, Sunda is my pick for a nice dinner in Chicago. If you’ve ever hesitated to dine at a Japanese, Chinese or Thai restaurant due to unknown ingredients or fears of cross-contamination, rest assured that Executive Chef Jess DeGuzman and his team prepare creative New Asian dishes with careful attention to food allergens.
Start with a light bite like the Thai-inspired Bang! Bang! Salad, or go for Sunda’s specialty, the Sweet Potato Caterpillar. Almost too attractive to eat, this vegan sushi roll is filled with roasted sweet potato and Asian pear and topped with black garlic and roasted red pepper puree.
Start planning your next Chicago getaway
Each time I visit Chicago, I find myself making a mental list of what to do on subsequent trips. Next spring, I’ll be seeking out some of the Windy City’s only gluten-free hot dogs at U.S. Cellular Field, home of the White Sox. In any season, I can’t wait to take a guided tour of Chicago’s legendary architecture, explore public art in Wicker Park, peruse local shops in Bucktown, and try the gluten-free bagels and weekend brunch at Wheat’s End Café. With so much to do and so many new places constantly changing the landscape, it’s no wonder Chicago is one of my favorite cities to explore.
Travel Editor Anna Sonnenberg is a food and travel writer who has journeyed around the world gluten free since being diagnosed with celiac disease in 2012. She launched her website, glutenfreejetset.com, in 2013.