Photo courtesy Dimmi Dimmi

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

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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?

Friday Lunch to Saturday Brunch

Photo courtesy of Niu B

NADU Lincoln Park

Photo courtesy of Nadu

Lincoln Park Double Dinner, Part I

If you like Indian food, you need to try the Keralan curries and Goan seafood at Nadu, where chef Sanchit Sahu received a Michelin Bib Gourmand for his heartfelt interpretation of regional Indian cooking. Each dish is listed with its regional origin in parentheses, so you’ll get a bonus lesson in Indian geography along the way. Nearly half the menu is vegetarian, and there’s a great-value family-style tasting menu for $60 per person, but you might want to order lightly if you’re planning on a second stop. Just save room for warm mawa cake topped with vanilla ice cream and masala tea crumble that rivals any sticky toffee pudding

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Photo courtesy of Nadu

Dimmi Dimmi Lincoln Park

Photo courtesy Dimmi Dimmi

Lincoln Park Double Dinner, Part II

It’s less than a mile to walk from Nadu to Dimmi Dimmi down Sheffield Avenue, which is the perfect distance to digest and mentally transition from Indian to Italian before digging into some pizza and pasta. This cozy neighborhood spot is popular with families, but later in the evening the vibe shifts to a little more romantic. The sheep’s milk ricotta gnudi pomodoro and chicken or eggplant parmesan are must orders. Fresh mozzarella and sausages are made from scratch, and if you befriend  your server, you might be doing housemade limoncello shots with dessert.

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Photo courtesy Dimmi Dimmi

Green City Market Lincoln Park

Photo courtesy of Green City Farmers Market

Saturday Morning at the Market

Rise early and head to Green City Market April through November to see Chicago’s best farmers market in action, and catch the city’s top chefs picking up produce that might end up on your plate in a few hours. Snack on samples, pick up some pastries or cheese for later and do a few cartwheels in the grass while enjoying live music and chef demos. If you’re visiting outside of farmers market season, it’s probably cold, so sleep in and enjoy coffee and room service at your hotel. Many of Chicago’s better hotels proudly serve local roasters, or venture outside for coffee at Fairgrounds Cafe for a selection of artisan roasters and specialty drinks with five locations around town.

Photo courtesy of Green City Farmers Market