Plan a food-focused trip to Chicago

The best way to get to know Chicago is one meal at a time. This three-day Chicago food itinerary explores the city’s most iconic dishes and under-the-radar restaurants, bakeries, and neighborhood spots that keep locals coming back.

This three-day foodie itinerary covers some of the most celebrated restaurants and beloved hidden gems in the country’s Best Big City. Begin with downtown staples before heading into Chicago’s vibrant neighborhoods for dim sum, authentic Mexican fare, Puerto Rican specialties, and more.

Day 1: Chicago classics and must-try bites

Enjoy a traditional diner breakfast

Ease into the day with a hearty plate at Lou Mitchell’s, a local cornerstone serving breakfast to locals, visitors, and celebrities for more than a century. There’s no better place to kick off a Chicago food tour than at this old-school diner, widely regarded as the unofficial starting point of Route 66.

Anticipate a line, fresh-baked pastries, bottomless coffee, and doughnut holes handed out while you wait. Look forward to a heaping plate of fluffy pancakes and stuffed omelets.

From there, walk to Willis Tower and take the elevator to the 103rd floor to experience a bird’s-eye view of downtown from Skydeck Chicago. Perched more than 1,350 feet above the ground, The Ledge’s glass balconies extend beyond the building, giving you a dramatic look at the cityscape.

Grab an Italian beef in River North

In River North, get your fill of a Chicago staple at Mr. Beef, the legendary Italian beef stand that inspired The Bear. Order the sandwich the Chicago way if you’re up for it: dipped in savory jus, with hot giardiniera or sweet peppers on top. It’s messy, drippy, and exactly the kind of lunch you want when trying one of Chicago’s signature foods.

Afterward, trade the city streets for the river on an architecture cruise with Wendella Tours & Cruises, which runs year-round. The family-owned company has taken passengers along Chicago’s waterways since 1935, with architecture tours showcasing famed historical landmarks, such as the Wrigley Building and Tribune Tower. Choose one of the 90-minute cruises or squeeze in the 45-minute tour before dinner.

Make room for deep dish

Dinner calls for another Chicago classic: deep dish pizza. Iconic pizzerias Lou Malnati’s and Gino’s East both have downtown locations, while Pequod’s is worth the trek to Lincoln Park if you want to try a local favorite. The caramelized-crust pies have earned a devoted following.

Keep in mind a deep dish pie takes 45 minutes or so to bake, and one is usually more than enough for the table, so order a salad or appetizer and settle in.

Finish with the brownie that started it all

Close out the night at the Palmer House, where you can try the original brownie. Invented at the hotel for the 1893 World’s Columbian Exposition, the decadent baked good remains on the menu at Lockwood Restaurant & Bar off the hotel lobby, and you can still order one today. It’s dessert with a side of history.

Day 2: Eat your way through international neighborhoods

Begin with dim sum in Chinatown

Take the Red Line ‘L’ to Cermak-Chinatown to enjoy breakfast in Chicago’s historic Chinatown neighborhood. 

MingHin Cuisine is a Cantonese restaurant that serves Hong Kong-style dim sum throughout the day, so take your time savoring baskets of dumplings, buns, rice rolls, and other small plates. Since dim sum is made for sharing, bring friends and order a bit of everything.

After breakfast, roam through the colorful streets of Chinatown. Walk under the ornate Chinatown Gate on Wentworth Avenue, peruse the gift shops and herbal stores, and look for the bronze zodiac statues at Chinatown Square.

Before leaving, drop by Chiu Quon Bakery, the oldest Chinese bakery in Chicago, for milk tea paired with a coconut cream puff, almond cookies, or a warm Portuguese egg tart.

Check out the top things to do and see in Chinatown.

Wander through Pilsen’s art and food scene

Travel west to nearby Pilsen, where the neighborhood’s creative spirit is proudly on display, from its noteworthy murals to art galleries, boutiques, and colorful storefronts.

Grab lunch at local favorites like La Luna, a colorful and comfortable spot known for its tacos, or Mariscos San Pedro, which serves refined Mexican seafood dishes inside the historic Thalia Hall.

After lunch, explore the free National Museum of Mexican Art, home to one of the largest collections of Mexican art in the country, spanning ancient Mexico through the present.

Discover more activities and restaurants in Pilsen.

Dig through vintage finds in Bridgeport

Continue on to Bridgeport, a South Side neighborhood with a blue-collar streak and growing cultural scene.

It’s the ideal location to hunt for vintage clothes, records, furniture, and other secondhand goods before going to dinner. The galleries and studios at Bridgeport Art Center are also worth a look.

For dinner, book a table at The Duck Inn, housed in a century-old pre-Prohibition tavern. The chef-driven menu changes with the seasons, and the restaurant has an impressive beverage program to match, spotlighting craft beer, cocktails, and wine.

The rotisserie duck is the move, though you may be tempted by the Duck Inn Dog, an upscale take on a Chicago-style hot dog, featuring duck fat and housemade condiments. After dinner, pop over to the cozy Charis Listening Bar for a nightcap with vinyl spinning in the background.

Day 3: Find the best bites from West Town to the West Loop

Line up for a wait-worthy breakfast sandwich

By day, Filipino bakery and restaurant Kasama serves creative pastries, Filipino comfort food, and a viral breakfast sandwich (featured on The Bear).

While there may be a line, the savory sandwich is well worth waiting for, especially when paired with one of the bakery’s sweet treats. By night, Kasama showcases an elevated tasting menu that has earned them two Michelin stars.

After breakfast, spend some time exploring West Town, one of the city’s top gallery districts. Chicago Avenue is a good place to start. Look through curious finds at indie boutiques and vintage stores, and discover the gallery scene alongside public art and longtime cultural institutions.

Try the sandwich Chicago invented

Head northwest toward Humboldt Park for a jibarito, the Chicago-born sandwich made with garlicky fried plantains as a stand-in for bread. Try a chicken or steak jibarito at Papa’s Cache Sabroso or La Bruquena, then wander Paseo Boricua on Division Street, the heart of the neighborhood’s Puerto Rican community.

If you still have a sweet tooth, swing by The Original Rainbow Cone in Wicker Park. The family-run Original Rainbow Cone first opened in Chicago’s Beverly neighborhood in 1926, peddling a five-flavor cone layering chocolate, strawberry, Palmer House, pistachio, and orange sherbet.

Grab dinner in the West Loop, a foodie mecca

A former meatpacking district, the West Loop has become one of Chicago’s most highly regarded dining destinations, with Fulton Market and Randolph Street’s Restaurant Row brimming with award-winning restaurants.

For a classic West Loop experience, join the line atAu Cheval for elevated diner-style offerings like the signature cheeseburger.

Among the neighborhood’s longtime favorites, avec is where Mediterranean flavors meet Midwestern ingredients in a menu designed around shared plates, whileMonteverde brings a global influence to Italian cooking.

Explore more restaurants and places to eat in Chicago.