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

Whether you’re drawn to Chicago for its modernist fine dining or the classic hot dog “dragged through the garden,” you might find yourself captivated by Tony Award-winning theater or late-night improv. Perhaps it’s the allure of towering skyscrapers, or in the summer, the chance to feel the sand of Lake Michigan between your toes. Chicago, both rugged and sophisticated, embraces everyone.

Having spent over 30 years here, I still discover surprises around my city’s 77 neighborhoods, from impromptu concerts on stoops to pop-up markets and hidden torta shops. Although I’ve chronicled Chicago for decades, its vibrancy is ever-evolving, echoing the vision of 19th-century city planner Daniel Burnham: “Make no little plans; they have no magic to stir men’s blood.”

So, come and be inspired. A leisurely four-day weekend gives you ample opportunity to delve into the essence of Chicago—and still leave you eager for more.

Thursday: A Dive into Art and Architecture

I recommend that visitors begin their journey in the Loop, named for the elevated train tracks encircling this area of downtown, and then explore outward. Nestled between the Loop and Lake Michigan, Millennium Park embodies the city’s motto, “Urbs in horto,” or “City in a garden.” At first glance, this dynamic public space seems to prioritize art, highlighted by Anish Kapoor’s captivating kidney-bean-shaped sculpture Cloud Gate, commonly known as The Bean, where you'll undoubtedly want to capture a quirky selfie in its reflective surface. However, venture behind the hedges of the Lurie Garden to discover “this hidden pocket prairie of native perennials that change colors with the seasons,” as Lauren Viera describes in The 500 Hidden Secrets of Chicago. “It’s beautiful and serene.”

Cross the Chicago River via one of its iconic bridges to reach the River North neighborhood, where you can enjoy lunch at Mr. Beef, the legendary Italian beef sandwich shop that inspired the Hulu series The Bear. “Italian beef was fading away, but now it’s experiencing a resurgence,” notes Mike Gebert, author of the local Fooditor newsletter and a forthcoming book on Chicago's restaurant scene. Choose your sandwich style—“wet,” “dry,” or “dipped,” with the latter soaked in cooking jus for a wonderfully messy experience.

Following the devastation of the Great Chicago Fire in 1871, the city’s reconstruction introduced the skyscraper. Today, modern and contemporary architecture defines the skyline, best appreciated on a 90-minute boat tour along the Chicago River offered by the Chicago Architecture Center, popular among both locals and tourists.

If you’re out with friends or eager to meet new people, head back toward Millennium Park to discover Cindy’s, a vibrant rooftop bar with stunning views of the park and lake from the 13th-floor terrace of the Chicago Athletic Association Hotel.

Friday: Embrace the outdoors, savor gourmet Ukrainian cuisine, and enjoy improv comedy

Begin your day like a local, drawing fitness motivation from Lake Michigan. The 18-mile paved Lakefront Trail is perfect for a workout, whether on a Divvy bike from the city’s bike-sharing program or a high-performance model from Bike and Roll Chicago. This scenic route connects many of the city’s 24 beaches, ideal for wading or spontaneous yoga poses.

If you have kids with you, head north to Lincoln Park Zoo to meet around 200 animal species. Take a leisurely stroll to spot Canadian lynx, Chilean flamingoes, and African penguins. Don’t miss the daily feedings at the seal pool at 11:30 a.m. or 2 p.m.

Continue your journey north along the lakefront path to Montrose Beach, where you can enjoy drinks and live music at The Dock at Montrose Beach, an open-air restaurant and bar nestled beside a vast sandy stretch.

Make sure to save room for dinner at Anelya. This new restaurant, brought to you by James Beard Award-winning chefs and married couple Beverly Kim and Johnny Clark in the Avondale neighborhood, showcases exquisite Ukrainian cuisine. The kitchen is primarily staffed by Ukrainian cooks who bring around an appetizer cart filled with elegant mayo-and-anchovy topped eggs, trout roe tarts, and reimagined classics like duck borscht. “You taste borscht, but it’s obviously elevated,” remarks Gebert. “The presentation is truly impressive.”

Savor your Slovenian orange wine slowly, as The Second City, Chicago’s iconic improv comedy troupe, presents a 10 p.m. show on its main stage every Friday and Saturday. Drift off to sleep with a smile on your face.

Saturday: Discovering three unique neighborhoods

It’s time to venture into the surrounding neighborhoods. Hyde Park stands out as a unique blend of college town, home to the University of Chicago, and a cultural heavyweight. Begin your day with coffee and pastries at Plein Air Café and Eatery, then take a leisurely walk to the nearby Robie House, a notable landmark designed by architect Frank Lloyd Wright. If you’re accompanied by children, don’t miss the Griffin Museum of Science & Industry to explore the Apollo 8 moon module and a German U-boat.

In the afternoon, make your way to the northern Uptown neighborhood and step into the atmospheric Green Mill Cocktail Lounge, a venue that has been around since before Prohibition, just in time for the 3 p.m. start of The Paper Machete. This two-hour variety show blends stand-up comedy, lip-syncing, puppetry, and music. “It’s incredibly clever and creative—a fantastic way to enjoy this historic bar,” says Viera. The show is free, but be prepared to contribute when they pass around the collection hat.

End your day with a visit to Logan Square, a hotspot for dining in the city’s northwest. You might discover fantastic bars like Billy Sunday and Longman & Eagle, as well as eateries such as Mi Tocaya Antojeria, but make sure to stop by Lula Cafe, a farm-to-table pioneer. Now 25 years old, it continues to earn accolades, including a 2024 James Beard Award for Outstanding Hospitality, recognizing its warmth and reliability. “It’s my favorite,” shares Viera. “You can casually sit at the bar or reserve a table, enjoy a full meal, and indulge in their carrot cake for dessert.”

Sunday: Waiting in line for breakfast, enjoying jazz, and admiring the skyline

Queues for brunch are a common sight in Chicago, but the line at Kasama in Ukrainian Village is a daily occurrence. Co-owned by married partners Genie Kwon and Timothy Flores, this spot transforms from a Filipino bakery by day to a fine-dining restaurant by night. The chance to experience a Michelin-starred dining experience for just $11, featuring an egg and longanisa sausage sandwich, attracts a crowd. After dining, take a short walk north to the Bloomingdale Trail at the 606, a 2.7-mile repurposed rail line turned recreational path.

Return downtown to immerse yourself in masterpieces by Monet and Van Gogh at the Art Institute of Chicago. Then, stroll a few blocks south to the historic Jazz Showcase, a venue known for hosting trumpeter Dizzy Gillespie’s birthday performances, which welcomes all ages to its Sunday 4 p.m. show.

Conclude your day at the stylish Tre Dita Bar in the new St. Regis Chicago, a striking 101-story skyscraper designed by renowned architect Jeanne Gang. On the second floor, you’ll find a Tuscan steakhouse from celebrated L.A. chef Evan Funke, which opened in March and offers breathtaking views of the Chicago River. Sit at the bar to watch talented mixologists craft drinks from an entirely Italian liquor selection. Don’t miss their recommendation of the ultralight focaccia to complement your beverage.

Where to stay

For a deep dive into the city’s rich history and celebrated design, stay at the Chicago Athletic Association Hotel, a beautifully restored 19th-century neo-Gothic former men’s club. Just a few blocks down Michigan Avenue, the chic Pendry Chicago resides in a stunning 1929 art deco building, offering rooms with Instagram-worthy views of the Chicago River.