Photo courtesy Dimmi Dimmi

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 19, 2026

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?

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An Appetite for Adventure

Saturday Night to Sunday Brunch

Photo courtesy of Omakase Yume

Omakase Yume West Loop

Saturday Night Sushi

There are only six seats at Omakase Yume, and chef Sangtae Park serves each bite of pristine nigiri in quick succession in true edomae-style sushi, while his wife Kate Park looks after guests and serves drinks. The quick pace of the meal allows diners to order extra bites of seasonal specialties like yari ika (spear squid), Hokkaido uni, or nodoguro (black throat sea perch) at the end of the 16-course sushi tasting menu if you still have room. You’ll be out of here in less than two hours since Park does three seatings a night, which means there’s plenty of time for an after-dinner drink. For those who prefer beef to raw fish, try the 12-seat all-beef omakase Bonyeon next door.

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La Josie West Loop

An Agave Nightcap

Cross the bridge over the I-90 highway for after-dinner drinks at La Josie, a lively Mexican restaurant specializing in agave spirits, with a collection of more than 100 mezcales, Tequilas, and other rare Mexican drinks from eight states, including raicilla, sotol, and bacanora, all listed in the “agave bible.” It’s easy to grab a seat at one of the restaurant’s three bars — we recommend the rooftop on a nice day. Neat pours, agave flights, and guided tastings are available, or opt for a smooth-drinking mezcal margarita. Chow down on late-night tacos or dessert if you have any room left, including fresh fried churros with chocolate sauce and cajeta ice cream.

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The Duck Inn Bridgeport

Blowout Brunch for the Road

After those cocktails, you’ll wake up ready for an epic brunch. Chef Kevin Hickey had a long career with Four Seasons before opening The Duck Inn in 2014 in the neighborhood he grew up in. Naturally, anything featuring duck is sure to be a hit, whether it’s rotisserie duck hash, Japanese BBQ duck wings, or chile braised duck sopes with fried duck eggs. This will leave you fully sated before your car or train ride back to the airport.

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Middle Brow Brewery and Winery Logan Square

One Last Bevvie

Speaking of trains, if you’re taking the Blue Line to O’Hare, hop off at the California stop and walk less than half a mile to Middle Brown for one last bevvie on your way out of town. Chicago is known for its craft beer scene and this is one of the very best. They make their own beer, natural wine, and pizza dough using exclusively Midwest ingredients. That means dry-farmed and hand-picked West Michigan grapes, and yeast-blended beers made with Illinois, Indiana, and Michigan grains. The communal style tables are great for making new friends, and the sourdough pizzas, topped with meatballs, pesto cream, and kumquat chimichurri, are surely a better airplane snack than anything you’ll find at the airport.

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