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

Thurs. Lunch to Fri. Breakfast

Photo Courtesy Lula Café

Lula Café Logan Square

A Thursday Afternoon Respite

If you’re coming into the city from O’Hare on the Blue Line, hop off at the Logan Square stop and Lula Cafe is just across the park. It’s fitting that this legendary restaurant is your first bite in Chicago – Jason Hammel and team received the Outstanding Hospitality James Beard Award this year and no matter how hangry or disheveled you might be from your travels, you’re sure to be welcomed with open arms. Brunch is served until 3 p.m. and then happy hour begins at 4:30 p.m. Their amaro affogato is the perfect pick-me-up after a long day of travel and the garlicky brown butter pasta Yia Yia is another can’t-miss menu staple.

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Brindille River North

Art On The Plate

After checking into your hotel, peruse the impressive Impressionist collection at the Art Institute of Chicago. Thursday evenings the museum is open until 8 p.m. (admission is free for Illinois residents). Then hop in a car for a short ride to chef Carrie Nahabedian’s French restaurant in River North. Nahabedian was the first woman chef in Chicago to earn a Michelin star (back in 2011 with NAHA) and she continues to prove her chops with signature dishes like chilled foie gras royale and perfectly seared sea scallops with a Robuchon-style potato purée. Her long-time pastry chef Craig Harzewski delivers a stunning sweet finale (his warm baked clafoutis is a sure winner) and you can even take home a box of mignardises and pints of housemade ice cream.

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Kasama Ukrainian Village

Fridays Mean Filipino Breakfast

Kasama is the rare Michelin-starred and James Beard Award-winning restaurant that’s open for breakfast and you’ll want to get here early for a full selection of Genie Kwon’s pastries ranging from Asian-inspired matcha pandan éclairs and ube huckleberry Basque cakes to pecan sticky buns sand foie gras danishes. On the savory side, Tim Flores’ longanisa breakfast sandwich and chicken or mushroom adobo are quick and delicious meals that will fuel you up for a day of exploration. The daytime menu is counter service and first-come, first-served with ample indoor and patio seating. Coffee is from local roaster Dark Matter and there are specialties you won’t find elsewhere like red bean sesame cold brew and a coconut cortadito.

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