Cloud Gate shimmers beneath the fading light of downtown dusk.
Illinois office of tourism
Connect with Chicago’s riches, from its sprawling lakefront, legendary culinary scene and charmingly unique neighborhoods.
Weekends are when Chicago comes to life, buzzing with a palpable energy of fun. Chicagoans take great pride in their city and love exploring it to the fullest. Whether that’s enjoying the fresh, calm waters of Lake Michigan, meandering through one of the city’s many world-class museums or taking in the many architectural wonders of the city, Chicago weekends are packed with a seemingly endless array of fun things to do for all ages. Read on for a handy guide to making the most of your weekend in Chicago.
Traveler’s Tip: Take the hassle out of planning your Chicago getaway with AAA TripCanvas. This free tool helps you create a custom itinerary featuring iconic sights, such as Navy Pier, the Art Institute, and Millennium Park. Plus, AAA Members save on top Chicago hotels, dining, attractions and Hertz car rentals.
As night approaches, the Chicago Riverwalk glows with urban charm.
The Loop: The heart of Chicago’s downtown district, The Loop is the perfect weekend launch pad. You’re near many of the city’s top attractions like Millennium Park, The Art Institute of Chicago and the Chicago Riverwalk, all easily accessible by public transit. The Loop is also home to the Theatre District, an excellent spot for catching a weekend matinee or evening performance.
River North: An easy walk from The Loop, River North is a hub for foodies, art lovers and night owls looking for a hopping nightlife scene. Art galleries and showrooms line the streets alongside some of the city’s most popular restaurants and chic cocktail lounges. The neighborhood is excellent for a weekend night out with live music venues, comedy clubs and buzzy rooftop bars.
Colorful murals bring the streets of Wicker Park to life.
Wicker Park: Local, artsy and effortlessly cool, Wicker Park is a hub for Chicago’s creatives. Stroll the streets and discover cool cafes, bookstores and record shops. The shopping here is the best for eclectic finds in the neighborhood’s vintage stores and indie boutiques. Colorful murals adorn many of the area's walls, transforming the neighborhood into a vibrant living outdoor gallery. Some of the can’t-miss street art includes “Greetings from Chicago” and the “Wicker Park Mural” by Richard Haas.
The city meets the lake—North Avenue Beach from a new perspective.
adobe stock
Lakefront Lounging: In Chicago, it’s all about the lake. Lake Michigan is the city’s sprawling body of water that feels like an ocean, but there’s no salt and no tide. Swim comfortably for hours with water that won’t sting your eyes, no jellyfish or sharks to worry about and temperatures in the height of summer that can reach the upper 70s Fahrenheit. Summer weekends mean beach days at the lively North Avenue Beach, where you can enjoy swimming, volleyball and people-watching. For something a little quieter, Ohio Street Beach is more family-friendly and close to Navy Pier.
The best way to see the city? On two wheels along the lakefront.
choose chicago \ abel arciniega
Getting Active: In a city that loves the outdoors, the Chicago Lakefront Trail is the ideal spot to begin. This bustling byway stretches 18.5 miles along Lake Michigan, connecting beaches, parks and top skyline views. Walk, bike or rollerblade along the well-kept paths. Another popular trail is the newer 606 Trail. The former elevated rail line was transformed in 2015 into a 2.7-mile greenway, perfect for a leisurely walk through Bucktown, Logan Square and Wicker Park. Get down to the waterline and learn a few things along the way, with Chicago’s unique guided architect kayak tours. Companies like Urban Kayaks and Kayak Chicago offer guided kayak tours throughout the Chicago River and Lake Michigan.
Chicago’s skyline framed by the beauty of Lincoln Park.
The City’s Backyard: Chicago’s parks are lovely escapes from the buzz of the city. Millennium Park is most known for the stunning Cloud Gate (locally known as "The Bean") and the quirky spouting faces of Crown Fountain, two top selfie spots in the Loop. Pack a picnic and enjoy the many free seasonal concerts at the Jay Pritzker Pavilion. During the winter months, this is the best place in the city to ice skate with its perfect skyline backdrop. Lincoln Park in the city’s North Side is a family favorite, especially with its always free, always open Lincoln Park Zoo, where you’ll find yourself within feet of African lions, red pandas and gorillas. Stroll Lincoln Park’s scenic Nature Boardwalk and tour the beautiful and historic Lincoln Park Conservatory, free just like the zoo.
Honoring stories that shape generations at the DuSable Museum.
World-Class Art Museums: Chicago is home to a remarkable array of museums, featuring famous masterpieces, ancient artifacts and illuminating permanent exhibitions. The Art Institute of Chicago is the city’s top destination for art enthusiasts. Founded in 1879, the Art Institute houses over 300,000 artworks spanning 5,000 years. The most famed of the collection includes Grant Wood’s “American Gothic,” Edward Hopper’s “Nighthawks” and Georges Seurat’s “A Sunday Afternoon on the Island of La Grande Jatte.” The DuSable Black History Museum and Education Center is the country’s oldest independent museum dedicated to the history, culture and art of African Americans. The museum houses a permanent collection of over 15,000 pieces of art and memorabilia. For the most unique and boundary-pushing art, the Museum of Contemporary Art Chicago is the city’s vibrant hub. The museum is home to ever-changing exhibitions and galleries, featuring a permanent collection that includes works by modern artists such as Andy Warhol, Jeff Koons and Alexander Calder.
Experiencing the beauty and curiosity of the beluga whale at Shedd Aquarium.
Science in the City: The Field Museum is Chicago’s premier natural history museum, most notable for Sue, the largest and best-preserved Tyrannosaurus rex skeleton ever discovered. Nearby, the Shedd Aquarium is a great way to spend a weekend day immersed in aquatic wonders. The highlight here is the Abbott Oceanarium, home to whales, dolphins and penguins. The Museum of Science and Industry is a top destination for families, featuring permanent exhibits that include a recreation of a working coal mine and a walk-through of a real German World War II submarine.
Scenic Skyscrapers: The city’s skyline is dotted with unique, stunning skyscrapers, some of which date back more than 130 years. Get the full story with all the fascinating details on one of Chicago’s renowned architecture river cruises. This is the definitive way to trace the history of Chicago’s urban design.
Information about attractions, restaurants and other businesses was accurate at the time of publication. Offerings, hours and availability may change, and some locations may have closed since. We recommend checking directly with the business before visiting.
