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, a Chicago-based journalist specializing in luxury travel, food, wine, and wellness. She writes about hotels and restaurants for The Wall Street Journal, Fine Dining Lovers, The Telegraph, and Travel + Leisure.

Updated: May 20, 2025

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 Lake Shore 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
An Appetite for Adventure

Fri. Lunch to Sat. Brunch

Photo courtesy of Niu B

Niu B Sushi & Noodle Bar South Loop

Museums and Maki

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, stop for sushi and noodles at Niu B, a 15-minute walk away. Chef Jimmy Cao’s pan-Asian menu also features teriyaki, tempura, and wok-fried favorites, but we favor his creative signature maki in the summer and a cozy bowl of heartwarming ramen come winter. Weekday lunch bento boxes are a great value, and a side of taro fries with black garlic mayo for the table is always a good idea.

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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.

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Bar Parisette Palmer Square

Roast chicken at Bar Parisette — Photo courtesy of Bar Parisette

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.

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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.

Cafe Yaya Lincoln Park

Brunch, Mediterranean Style

Just a mile northwest of the farmers market in Lincoln Park is a cheerful new all-day cafe from the team behind Michelin-starred Galit. Middle Eastern flavors permeate the menu, with shakshuka served with “so many fresh herbs,” lamb merguez sausage and egg on a challah roll, and a rich quiche on a flaky boreka dough crust. Housemade pastries include chai morning buns, cherry chocolate mahleb scones, and cardamom kouign-amanns. After loading up on carbs, head back to Lincoln Park and meander through Lincoln Park Zoo or the Peggy Notebaert Nature Museum to work up your appetite for dinner.

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