From lollipop chicken wings to Vienna hot dogs (Chicago-style, of course), the Windy City knows its food — and so do we. So, grab your appetite and let our food-focused itinerary take you through a perfect weekend in Chicago.

By Alina Dizik | June 22, 2022 (Updated August 14, 2025)

Hold the deep-dish pizza — or at least save room after a few bites. Chicago restaurants are serving up some of the country’s most ambitious dishes in recent years. And let’s not forget that the city also hosts the coveted James Beard Awards each spring. Add that to walkable neighborhoods, waterfront views and world-class museums, and you’ve got a recipe for an ideal weekend to enjoy the Chicago food scene.

Friday

Morning

Ease into your stay by enjoying a leisurely morning at your hotel, the storied Palmer House, a Hilton Hotel. Situated at the center of the Theater District, Palmer House boasts one of the best locations in the city. Stroll around the block and grab a tomato, basil, and ricotta puff pastry and hot coffee from Goddess and the Baker to kickstart your day.

Afternoon

The Chicago River, which connects to Lake Michigan, is a hot spot for both locals and tourists with opportunities for biking and walking along the waterfront. Next, head down to the Riverwalk for up-close views of the city’s most iconic buildings.

If you’re in the mood for fancier fare, settle in for a leisurely waterfront lunch at RPM Seafood, a swanky Chicago restaurant that serves specials including truffle scrambled eggs, miso black cod, and cheese-baked focaccia on its multi-level terrace.

Evening

Explore the nightlife, murals, and dining opportunities of Chicago’s artsy Pilsen neighborhood, shaped by generations of Mexican Americans who call it home. Stop into historic Thalia Hall, a landmark building, which houses Dusek’s Tavern for perfectly executed fare, including wood-roasted trout and a griddled double cheeseburger. End the night at Punch House, a basement cocktail bar, or Tack Room, a piano bar, which are also in the same building.

Saturday

With miles of sandy lakefront, Lake Michigan’s city beaches draw in a weekend crowd, and for good reason. It’s easy to rent bikes for a ride along the lake, dip your toes in the sand or people-watch along the waterfront. Dive into an egg sandwich (with a view) at Caffe Oliva, which overlooks Ohio Street Beach.

Afternoon

Spend the afternoon exploring works at the Museum of Contemporary Art Chicago near the city’s Magnificent Mile. The museum has one of the world’s largest collections of contemporary living artists and features works realized through canvas, film and sculpture. Don’t leave without trying Marisol Restaurant & Bar. Named after a Venezuelan-American artist, the Michelin-recommended space offers farm-to-table brunch from local chef Jason Hammel.

Evening

Explore the used bookstores, consignment shops, and indie boutiques in the buzzy Wicker Park neighborhood. For a casual dinner, try Big Star, a neighborhood institution offering fresh tacos on handmade tortillas, churro ice cream pops, and melted queso fundido in a refurbished 1940s gas station.

Sunday

Morning

Your last morning in Chicago calls for elevated comfort food at Little Goat Diner, guaranteed to provide enough Sunday sustenance after a long night out. After your meal, save time to explore Randolph Street, dubbed Restaurant Row for its many glitzy eateries. The former meatpacking district is also packed with art galleries, shops, and plenty of entertainment.

Afternoon

Close out the weekend on a high note — with a ride on the iconic Centennial Wheel at Navy Pier. With breathtaking views of the city skyline and Lake Michigan, the Ferris wheel is a must-see during any season. Little ones in tow? Checkout Navy Pier’s Chicago Children’s Museum which offers a Tinkering Lab and Treehouse Trails enchanted forest play space.

Evening

One last stop before you go: Grab a quick bite at Pat’s Pizza, a thin tavern-style pizza that’s been a city staple since 1950. The square-cut pizza is a viable contender to the deep-dish and a popular pick with locals — try Pat’s Special Pizza (sausage, peppers, onions, and mushrooms) for a dinner that’s sure to please.

Best of all, the pies are extra-large, so you can even stash leftovers to enjoy back home.