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

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.

Bonyeon

4.8 · Korean Steakhouse · $

West Loop Gate

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Cindy's Rooftop

4.5 · American · $$$

The Loop

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Milk Room The Loop

A Speakeasy Saturday Wrap

Walk across the river towards Millennium Park for after-dinner drinks at Milk Room, an eight-seat speakeasy inside the Chicago Athletic Association that’s been named one of the best hotel bars in the country at Tales of the Cocktail’s 2024 Spirited Awards. You’ll feel like you stepped back in time to the Prohibition era with esoteric ingredients and pours available from rare bottles you’d be hard-pressed to find anywhere else. Drinks can easily reach $50 a glass, but the intimate custom cocktail experience is worth it. Ideally, you’ll book a reservation in advance, but if there’s a waitlist, head across the street to snap a selfie at Chicago’s Instagram-favorite Cloud Gate sculpture by British artist Anish Kapoor while you wait for a seat at the bar. Or head upstairs to Cindy’s Rooftop for great Millennium Park views as a back-up plan.

Bonyeon

4.8 · Korean Steakhouse · $

West Loop Gate

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Cindy's Rooftop

4.5 · American · $$$

The Loop

Book Now

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.

Bonyeon

4.8 · Korean Steakhouse · $

West Loop Gate

Book Now

Cindy's Rooftop

4.5 · American · $$$

The Loop

Book Now

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.