A Local’s Guide to the Perfect Long Weekend in Chicago

Sample gourmet Ukrainian food, watch a comedy show with puppets, and catch an all-ages jazz show.

A cruise ship makes its way down the river in central Chicago

Chicago’s contemporary architecture is best seen from a river cruise.

Photo By Barry Butler

You might come to Chicago for modernist fine dining, or you might seek a hot dog “dragged through the garden.” It could be Tony Award–winning theater or late-night improv comedy. Or perhaps you want to marvel at soaring skyscrapers or, in summer, dig your toes in Lake Michigan sand. Chicago, rough and refined, gritty and good-humored, welcomes all comers.

After more than 30 years here, I can still travel around my city’s 77 neighborhoods and be surprised by a stoop-front concert, a pop-up market, or a how-did-I-not-know-about-this torta shop. And while I’ve been writing about Chicago for decades, the subject is never static in a city that still seems to channel the words of 19th-century city planner Daniel Burnham: “Make no little plans; they have no magic to stir men’s blood.”

So, come and be stirred. An extended four-day weekend provides enough time to sink your teeth into the meat of Chicago—and still leave you hungry for a return visit.

Thursday: An overview of art and architecture

I counsel visitors to start at the Loop, named for the elevated tracks surrounding this part of downtown, and work their way out. Between the Loop and Lake Michigan, Millennium Park testifies to the city’s motto, “Urbs in horto,” or “City in a garden.” At first glance at this multifaceted public space, the garden seems secondary to art, including Anish Kapoor’s magnetic kidney-bean–shaped sculpture Cloud Gate better known as The Bean, where, like everyone else, you will want to take a warped selfie in its mirrored surface. But go behind the hedges of the Lurie Garden to find “this hidden pocket prairie of native perennials that change colors throughout the seasons,” says Lauren Viera, author of The 500 Hidden Secrets of Chicago. “It’s pretty and quiet.”

Cross the Chicago River via one of its iconic bridges to the River North neighborhood for lunch at Mr. Beef, the iconic Italian beef sandwich shop that inspired the Hulu TV series The Bear. “Italian beef was on its way out, but now it’s got new life,” says Mike Gebert, who writes the local Fooditor newsletter and is writing a book on Chicago restaurant history. Order your sandwich “wet,” “dry,” or “dipped,” the latter immersed in cooking jus for a gloriously messy meal.

After the Great Chicago Fire razed much of the city in 1871, Chicago’s rebuilding produced the skyscraper. Modern and contemporary architecture remains a hallmark of the city, best appreciated through a 90-minute boat tour on the Chicago River run by the Chicago Architecture Center and popular with locals as well as visitors.

If you’re rolling with friends or looking to mingle, backtrack toward Millennium Park to find Cindy’s, a celebratory rooftop bar overlooking the park and lake from the 13th-floor terrace of the Chicago Athletic Association Hotel.

A cyclist riding beside Lake Michigan on the Chicago Lakefront Trail

Bike and Roll Chicago offers bicycle rentals for you to explore Chicago’s Lakefront Trail. The company also runs Segway tours of the city’s highlights.

Photo By Dave Jonasen/Shutterstock

Friday: The outdoors, gourmet Ukrainian food, and improv comedy

Start the day as locals do, using Lake Michigan as fitness inspiration. The 18-mile paved Lakefront Trail is a great workout on a Divvy bike borrowed from the city’s shared bike system or on a more serious model from Bike and Roll Chicago. The path strings together many of the city’s 24 beaches, ideal for wading or doing spontaneous asanas.

With kids in tow, head north to Lincoln Park Zoo to get acquainted with some 200 animal species. Take a walking safari to spot Canadian lynx, Chilean flamingoes, and African penguins. Catch the 11:30 a.m. or 2 p.m. daily feeding at the seal pool.

Continue north along the lakefront path to Montrose Beach, and stop for drinks and live music at The Dock at Montrose Beach, an open-air restaurant and bar beside an expansive stretch of sand.

But save your appetite for dinner at Anelya. The new restaurant from James Beard Award–winning chefs and married partners Beverly Kim and Johnny Clark in the Avondale neighborhood serves gorgeous Ukrainian food. Ukrainian cooks largely staff the kitchen, loading an appetizer cart that’s wheeled tableside with elegant mayo-and-anchovy topped eggs and trout roe tarts, plus reconsidered classics like duck borscht. “You taste borscht, but it’s obviously elevated,” says Gebert. “The presentation is really nice.”

Don’t rush through your Slovenian orange wine, though, because The Second City, Chicago’s seminal improv comedy troop, offers a 10 p.m. show on its mainstage on Fridays and Saturdays. Go to sleep smiling.

Customers relax in Lula Cafe, Chicago

Lula Cafe is the perfect spot to sit with a book and a slice of cake.

Courtesy of Lula Cafe

Saturday: Exploring three distinct neighborhoods

It’s time to stretch to outlying neighborhoods. Among the city’s most distinct quarters, Hyde Park is equal parts college town—home to the University of Chicago—and cultural heavyweight. Start with coffee and pastries at Plein Air Café and Eatery, then stroll to the neighboring Robie House, a landmark by architect Frank Lloyd Wright. If you’re with kids, hit the Griffin Museum of Science & Industry to check out the Apollo 8 moon module and a German U-boat.

In the afternoon, head to the northern Uptown neighborhood and duck into the moody Green Mill Cocktail Lounge, which predates Prohibition, by 3 p.m. That’s when The Paper Machete kicks off, a two-hour variety show mingling stand-up comedy, lip-synching, puppetry, and music. “It is so smart and creative and is a cool way to experience this historic bar,” says Viera. The show is free, but you’ll want to give generously when they pass the hat.

Cap the day with a trip to Logan Square, a destination for dining in the city’s northwest. You could stumble across great bars (Billy Sunday, Longman & Eagle) and restaurants (Mi Tocaya Antojeria), but don’t miss farm-to-table pioneer Lula Cafe. At 25 years old, it’s still winning awards, including a 2024 James Beard Award for Outstanding Hospitality, a nod to its warmth and consistency. “It’s my favorite,” says Viera. “You can walk in and usually sit at the bar or book a table, do the works, and stay for the carrot cake dessert.”

Tre Dita interior & cacio e pepe dish

Bar Tre Dita brings a slice of Tuscany to central Chicago.

Photos by Eric Wolfinger

Sunday: Queuing for breakfast, catching jazz, and toasting the skyline

Lines at brunch joints in Chicago are common, but the one at Kasama in Ukrainian Village isn’t limited to Sundays. Married partners Genie Kwon and Timothy Flores run the place, a Filipino bakery by day, fine-dining restaurant by night. The opportunity to sample a Michelin-starred restaurant for the price of an egg and longanisa sausage sandwich ($11) generates queues. From the restaurant, it’s a quick trip north to walk the Bloomingdale Trail at the 606, a 2.7-mile stretch of abandoned rail line that has been reinvented as a recreational corridor.

Head back downtown to spend time with the Monets and Van Goghs at the Art Institute of Chicago. Then walk several blocks south to the venerable Jazz Showcase—trumpeter Dizzy Gillespie was known to play here annually on his birthday—which welcomes all ages at its Sunday 4 p.m. show.

Save your finale for the swanky Tre Dita Bar in the new St. Regis Chicago, a sinuous 101-story skyscraper designed by prominent architect Jeanne Gang. On the second floor is the Tuscan steakhouse from famed L.A. chef Evan Funke, which debuted in March and has stunning views over the Chicago River. Sit at the bar to appreciate the expert mixologists working from an all-Italian liquor lineup. Believe them when they tell you the ultralight focaccia is a must with whatever you’re drinking.

Where to stay

To immerse yourself in the history and design renown of the city, check into downtown’s Chicago Athletic Association Hotel, a 19th-century neo-Gothic former men’s club with its good old bones restored. A few blocks down Michigan Avenue, the stylish Pendry Chicago occupies a 1929 art deco gem with rooms that boast Insta-worthy views of the Chicago River.

Elaine Glusac is a freelance writer, the Frugal Traveler columnist for the New York Times, and on Instagram @eglusac.
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