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For a city that never sleeps, Chicago has an especially busy weekend ahead. From musical performances to family things to do, you’ll find it all in Windy City. So let’s take a look at some of the top events and attractions you should not miss.
Events Happening This Weekend/Year in Chicago

Live Music Shows
The Chicago music scene is alive and buzzing this weekend with some amazing events. Or check out your favorite artist at the Chicago Theatre, the iconic venue in one of the cities, or discover new ones at one of the city’s many intimate venues. And here are some must-see performances in particular:
- Kendrick Lamar & SZA at Soldier Field – On Friday, June 6, 2025, these Grammy-winning artists will perform together at Soldier Field as part of their Grand National Tour.
- Windy City Smokeout – This country music and BBQ festival will take place from July 10-13, 2025, at the United Center. The lineup includes Kane Brown, Old Dominion, Jon Pardi, Bailey Zimmerman, and Megan Moroney.
- My Chemical Romance at Soldier Field – On Friday, August 29, 2025, the iconic rock band will perform their Black Parade tour at Soldier Field, promising a nostalgic and high-energy show.
Other Chicago Events
- Augmented Chicago: Inaugural Realities (Through November 30, 2025)
- Franz West: Millennium Park (Through November 30, 2025)
- John Akomfrah: Four Nocturnes (Through February 15, 2025)
- Aim High: Soaring with the Tuskegee Airmen (Through January 20, 2025)
- Roger Deakins Photography Exhibition (Through April 30, 2025)
For all events happening this week check out the official listing here:
Broadway in Chicago
If you’re a fan of musical theater, you’re in luck. Broadway in Chicago brings some of the best shows to the city’s stages. This weekend, don’t miss your chance to see:
Currently Running
- Harry Potter and the Cursed Child (Through February 1, 2025)
Venue: James M. Nederlander Theatre
Upcoming Shows
- Come From Away (January 21-26, 2025)
Venue: CIBC Theatre - Shucked (January 7-19, 2025)
Venue: CIBC Theatre - INSIDIOUS: The Further You Fear (February 14-15, 2025)
Venue: CIBC Theatre - CLUE (February 18 – March 2, 2025)
Venue: CIBC Theatre - Beetlejuice (March 11-16, 2025)
Venue: Cadillac Palace Theatre - Titanique (March 25 – May 18, 2025)
Venue: Broadway Playhouse At Water Tower Place - Moulin Rouge! The Musical (April 2-20, 2025)
Venue: Cadillac Palace Theatre
Chicago International Puppet Theater Festival
The Chicago International Puppet Theater Festival is a unique event that showcases the art of puppetry from around the world. This weekend, catch some of the festival’s most exciting performances, including:
- Plexus Polaire’s “Moby Dick” at the Museum of Contemporary Art
- Manual Cinema’s “Frankenstein” at the Chopin Theatre
- Blind Summit’s “The Table” at the Chicago Shakespeare Theater
Best Rooftop Bars in Downtown Chicago

Chicago’s skyline is one of the most iconic in the world, and there’s no better way to take it in than from a rooftop bar. Some of the best spots to enjoy a drink with a view include:
- Cindy’s Rooftop at the Chicago Athletic Association Hotel
- The J. Parker at the Hotel Lincoln
- Raised at the Renaissance Chicago Downtown Hotel
There are several rooftop bars and one is not enough! Start your own rooftop bar crawl by hitting some of the best places in town. Begin at the London House Chicago with a gorgeous view of the river, then to the Wit Hotel’s ROOF on theWit for a lively vibe. For a next-level trendy yet upscale nightcap, hit up Cerise, the Virgin Hotels Chicago rooftop bar.
Family-Friendly Activities in Chicago This Weekend
Maggie Daley Park: Fun for All Ages
Maggie Daley Park is a must-visit destination for families in Chicago. This weekend, take advantage of the park’s many activities, including:
- Mini golf at the Chicago-themed course
- Climbing walls for all skill levels
- Skating ribbon for rollerblading or skating
Interactive Exhibits at the Chicago History Museum
The Chicago History Museum is a great place to learn about the city’s past while having fun. This weekend, check out some of the museum’s interactive exhibits, such as:
- “Chicago: Crossroads of America” – explore the city’s history through artifacts and multimedia displays
- “Facing Freedom” – learn about the struggles and triumphs of the civil rights movement in Chicago
- “The Secret Lives of Objects” – discover the stories behind everyday objects from Chicago’s past
Family-Friendly Events at Millennium Park
Millennium Park is a hub of activity in downtown Chicago, and this weekend is no exception. Bring the whole family to enjoy events like:
- Family Fun Festival – live music, dance performances, and hands-on activities
- Millennium Park Summer Film Series – outdoor movie screenings under the stars
- Lurie Garden – a beautiful urban oasis with guided walks and tours
Experience Chicago’s Famous Architecture
The Chicago Architecture Center has a range of tours that highlight the city’s signature buildings and neighborhoods. This weekend, you can catch one of these often-caught tours:
- River Cruise – a 90-minute tour by boat on the Chicago River
- Walking Tours – explore neighborhoods like the Loop, Gold Coast, or in and around Fulton Market
- Bus Tours – cover more ground with tours by bus of places such as the North Side, South Side, or Frank Lloyd Wright’s Oak Park

Take a Stroll Down Michigan Avenue:
Michigan Avenue is home to some of Chicago’s most famous buildings. Take a leisurely walk down this iconic street and admire architectural gems like:
- Tribune Tower – a neo-Gothic skyscraper with a fascinating history
- Wrigley Building – a beautiful terracotta-clad office building
- Chicago Water Tower – a historic limestone tower that survived the Great Chicago Fire
360 Chicago: Views of the City’s Skyline
For a truly unforgettable experience, head to 360 Chicago (formerly the John Hancock Observatory) on the 94th floor of the John Hancock Center. From this vantage point, you can see up to 55 miles on a clear day. Don’t miss the TILT attraction, which lets you lean out over Michigan Avenue from 1,000 feet up!
Must-Try Restaurants for Chicago Restaurant Week
Top Brunch Spots to Kickstart Your Weekend
Chicago is known for its incredible brunch scene, and this weekend is the perfect time to indulge. Some of the best spots to try include:
- Lula Cafe in Logan Square – known for its farm-to-table fare and cozy atmosphere
- M. Henry in Andersonville – a neighborhood favorite with creative breakfast dishes
- The Bongo Room in Wicker Park – famous for its decadent pancakes and French toast
Hidden Gem Restaurants in Chicago’s Neighborhoods
While downtown Chicago has plenty of great dining options, don’t overlook the city’s neighborhoods. This weekend, venture out to try some of these hidden gems:
- Parachute in Avondale – a Michelin-starred Korean-American restaurant
- Birrieria Zaragoza in Archer Heights – known for its authentic Mexican goat stew
- Mango Pickle in Edgewater – a modern Indian bistro with bold flavors
Taverns and Eateries with a Rich Chicago History
For a taste of old-school Chicago, visit one of the city’s historic taverns or eateries. Some must-try spots include:
- The Berghoff in the Loop – a German restaurant and bar that dates back to 1898
- Twin Anchors in Old Town – a favorite of Frank Sinatra and other celebrities
- The Green Door Tavern in River North – one of the few buildings to survive the Great Chicago Fire
Explore Chicago’s Cultural Scene
Art Institute of Chicago: Current Exhibitions and Events
The Art Institute of Chicago is one of the world’s premier art museums, and this weekend is a great time to visit. Check out current exhibitions like:
- “Monet and Chicago” – a celebration of the city’s long relationship with the famous Impressionist
- “Bisa Butler: Portraits” – stunning quilted portraits that explore African American identity
- “Cosmoscapes: Ink Paintings by Tai Xiangzhou” – intricate landscapes inspired by traditional Chinese art
University of Chicago Campus:
The University of Chicago campus in Hyde Park is home to a variety of cultural institutions and events. This weekend, explore:
- Smart Museum of Art – a free museum with a diverse collection of art from around the world
- Court Theatre – a professional theater company known for its innovative productions
- Oriental Institute Museum – a museum dedicated to the ancient civilizations of the Near East
Hyde Park:
Hyde Park is a vibrant neighborhood on Chicago’s South Side, known for its cultural attractions and community events. This weekend, discover:
- 57th Street Art Fair – one of the oldest juried art fairs in the country
- Hyde Park Art Center – a community art center with exhibitions, classes, and workshops
- Promontory Point – a beautiful park with stunning views of Lake Michigan and the city skyline
Unique Ways to Experience the Chicago River This Weekend
River Cruises: See Chicago from a Different Perspective
The Chicago River runs through the heart of the city, offering a unique perspective on its architecture and history. This weekend, take a river cruise with one of these popular companies:
- Chicago Architecture Foundation River Cruise – a 90-minute tour led by expert docents
- Wendella Boats – offering a variety of tours, including a sunset cruise and a fireworks cruise
- Chicago Line Cruises – a luxurious way to experience the river, with gourmet food and drinks
Riverside Walks and Hidden Gems Along the Chicago Riverwalk
The Chicago Riverwalk is a pedestrian-friendly path along the river’s edge, offering a variety of attractions and activities. This weekend, explore:
- Vietnam Veterans Memorial Plaza – a peaceful spot for reflection and remembrance
- McCormick Bridgehouse & Chicago River Museum – learn about the river’s history and the city’s famous movable bridges
- Urban Kayaks – rent a kayak and paddle down the river for a unique perspective on the city
No matter what your interests are, Chicago has something to offer this weekend. From live music and theater to outdoor adventures and culinary delights, the Windy City is sure to impress. So get out there and explore all that this incredible city has to offer!