The room at Kasama — café by day, tasting menu at night. Photo by Kristin Mendiola, courtesy of Kasama

How to Spend a Perfect 72 Hours Eating Your Way Through Chicago

By Amber Gibson August 22, 2024

The Windy City is known for its sports teams, hearty food, world-class museums, friendly locals and majestic architecture, which you can best appreciate while speeding down Lakeshore Drive or cruising the Chicago River with the Chicago Architecture Foundation River Cruise. You might be stopping by Chicago on your way between coasts, and it’s a worthy weekend getaway, especially in summer and autumn.

If you only have 72 hours on the ground – Thursday afternoon through Sunday brunch – there’s a lot of ground to cover. Luckily, the grid system makes the city easy to navigate and public transportation is a convenient way to move between neighborhoods, and even get downtown from the airport (Blue Line downtown from O’Hare or Orange Line from Midway).

Here’s a greatest hits list to get you to some iconic culinary treasures, but you can also check our Resy Hit List for the buzziest places to dine right now, and guides for every taste. Are you hungry yet?

Amber Gibson is a Chicago-based journalist specializing in travel, food, and wine. Her work has appeared in Departures, Food & Wine, Saveur, Bon Appétit, and Travel + Leisure. Follow her here; follow Resy, too.

Resy Presents
Tables Worth a Trip

Fri. Lunch to Sat. Brunch

Photo courtesy of Apolonia

Apolonia South Loop

Museums and Mediterranean Fare

Head to Chicago’s 57-acre Museum Campus park after breakfast, where you can choose between the Field Museum of Natural History, Shedd Aquarium or Adler Planetarium, the country’s first planetarium. Learn about the stars, the seas and meet Máximo the Titanosaur, who surely could throw down in an eating contest. When you’re peckish again, Michelin Bib Gourmand recipient Apolonia is a quick car ride away for wood-fired Mediterranean fare and housemade pasta. You might see chef Stephen Gillanders at the pass, plating grilled branzino or yogurt marinated chicken. Start with the black truffle puff bread to share and save room for pastry chef Tatum Sinclair’s desserts, including warm bomboloni and one of the best tiramisus in the city.

Table, Donkey and Stick

4.7 · European · $$

Palmer Square

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Bavette's Bar & Boeuf - Chicago

4.9 · Steakhouse · $$$

River North

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Cellar Door Provisions Logan Square

Photos by David Raine Photography, courtesy of Cellar Door Provisions.

Friday-Night Wine Twofer (Part I)

We’re doing a wine bar one-two punch tonight for dinner, so get ready for snacky bites and trying some new bottles (mostly European) you’ve never heard of before. This Logan Square staple originally began as a daytime coffee shop and cafe when it opened a decade ago and has always been known for their country bread. Start with the famous bread and cultured butter paired with a glass of natural wine or cider. Consider ordering an interesting wine first and then choosing food to pair with your wine, whether it’s tempura daikon cakes, grilled oyster mushrooms, or plump potato gnocchi. The menu here changes frequently but you can count on simply prepared food with bold flavors served with zero pretension.

Table, Donkey and Stick

4.7 · European · $$

Palmer Square

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Bavette's Bar & Boeuf - Chicago

4.9 · Steakhouse · $$$

River North

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Bar Parisette Palmer Square

Friday-Night Wine Twofer (Part II)

It’s time for more wine (or a cocktail, if you need a changeup). Stroll a mile south — or take a five minute Uber — to this bustling French bistro where wine does indeed rule the day. Bring friends so you can order bottles to share – the markups here are much lower than at other restaurants in the city and there are good deals galore. The shredded carrot salad is an excellent snack to start as you peruse the menu. Housemade charcuterie comes from sister restaurant Table, Donkey and Stick and you can’t go wrong with bistro classics like steak frites and roast chicken.

Table, Donkey and Stick

4.7 · European · $$

Palmer Square

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Bavette's Bar & Boeuf - Chicago

4.9 · Steakhouse · $$$

River North

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Green City Market Lincoln Park

Photo courtesy of Green City Farmers Market

Saturday Morning at the Market

Rise early and head to Green City Market April through November to see Chicago’s best farmers market in action, and catch the city’s top chefs picking up produce that might end up on your plate in a few hours. Snack on samples, pick up some pastries or cheese for later and do a few cartwheels in the grass while enjoying live music and chef demos. If you’re visiting outside of farmers market season, it’s probably cold, so sleep in and enjoy coffee and room service at your hotel. Many of Chicago’s better hotels proudly serve local roasters, or venture outside for coffee at Fairgrounds Cafe for a selection of artisan roasters and specialty drinks with five locations around town.

Table, Donkey and Stick

4.7 · European · $$

Palmer Square

Book Now

Bavette's Bar & Boeuf - Chicago

4.9 · Steakhouse · $$$

River North

Book Now

Armitage Alehouse Chicago

Brunch, British Style

Just a mile west of the farmers market in Lincoln Park is a posh but brooding British pub by the Hogsalt hospitality team (Bavette’s, Au Cheval), with elaborate 1920s vintage furniture and décor. Brunch is a lively affair, with boozy masala chai, Belgian-style crispy Liège waffles, malt vinegar fish and chips, and a hefty full English breakfast with decadent blood sausage. If you arrive too late for brunch (after 2 p.m.), there’s always an afternoon snack menu that’s offered in the front bar room too. Head back to Lincoln Park and meander through Lincoln Park Zoo or the Peggy Notebaert Nature Museum to work up your appetite for dinner.