Chicago

The room at Kasama — café by day, tasting menu at night. Photo by Kristin Mendiola, courtesy of Kasama

Guides   Chicago

How to Spend a Perfect 72 Hours Eating Your Way Through Chicago

By

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

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 Café 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 last 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.

Book Now

Proxi West Loop

Photo courtesy of Proxi

Art On The Plate

After checking into your hotel, peruse the impressive Impressionist collection at the Art Institute of Chicago. (Pro tip: Thursday evenings the museum is open until 8 p.m., and admission is free for Illinois residents). Then hop in a car for a short ride to Proxi, where five-time James Beard Award finalist chef Andrew Zimmerman and chef de cuisine Jennifer Kim present a colorful coastal Asian menu focused on open-fire cooking and raw seafood. Think ponzu uni shooters, wood-fired steaks served with your choice of ssamjang butter, soy black garlic jus, or Sichuan salsa verde, and a green curry banana split with fish sauce caramel for dessert. The cocktail list leans tropical and adventurous, with a Thai banana–infused twist on the Manhattan, gin and honey kakigori, and Vietnamese nitro espresso martini.

Book Now

Photo courtesy of Proxi

Kasama Ukrainian Village

Photo courtesy of Kasama

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.

Book Now

Photo courtesy of Kasama

Discover More

The Rundown

How the New Chef at Elia is Redefining Mediterranean Food in Wicker Park

Guides

Eat Your Way Across Chicago’s Award-Nominated Restaurants

The Rundown

The Newly Reimagined Proxi Brings Coastal Asian Flair to the West Loop

New on Resy

Now on Resy: Casa Tulum, Siam Thai, Void, and More Local Favorites

Dish By Dish

Five Dishes To Try At Beity, Chicago’s Lebanese Tasting Menu

The Rundown

Table, Donkey and Stick is an Alpine Retreat in the Heart of Logan Square

New on Resy

Chicago’s Newest Restaurant Openings, Now on Resy

Guides

The Resy Guide to Outdoor Dining in Chicago

The Rundown

Sophia Steak Aims to Bring Chicago a Unique Steakhouse

The Rundown

Meet Cafe Yaya, Now Serving Pastries and Bistro Fare in Lincoln Park

Resy powers the world’s best restaurants, using technology to imagine the future of hospitality.

© 2025 Resy Network, Inc.