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

Sat. Night to Sun. 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 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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Dan the Baker / Publican Quality Bread West Loop

Pastries at Publican Quality Bread
Photo courtesy of One Off Hospitality

Sunday Pastries and BYOB

Pre-order pastries a few days in advance from Dan the Baker for pick-up Sunday morning at The Emily Hotel in the West Loop. The lobby is comfortably spacious and if you bring your own tumblers and bottle of … whatever you want to drink on a Sunday morning, you can enjoy a drink with your pastries while people-watching. If you forgot to pre-order, don’t worry. You can also get incredible viennoiserie and breakfast sandwiches at Publican Quality Bread in West Town, although you’ll have to stand in line and there’s not much seating. But the chocolate croissant and cardamom monkey bread are absolutely worth the wait.

The Duck Inn Bridgeport

The Duck Inn’s signature rotisserie duck.
Photo courtesy of the Duck Inn

Ducking Out of Town

Why pastries to start your Sunday? Because you’ll need room 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 chili 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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