23 Things You Have to Do in Chicago This Year
These are the must-hit festivals, concerts, events, and most fun things to do in Chicago this year.
Summers in Chicago are what people flock to the city for. You can’t beat a day at the beach (we know it’s a lake but we’ll never call it that), jamming out at an outdoor concert with the skyline sparking in the background (we see you Lollapalooza and Pitchfork), or sipping a cold beverage while wandering the stalls of a neighborhood street festival (there’s one practically every weekend across the city). But the truth is, there’s no shortage of things to do throughout the year. Each season has its own charm and until you’ve experienced them all, you can’t really say you know Chicago. Even in winter, the Windy City remains somehow underrated.
So pack your bag and tailor your travel around food, sports, culture and/or music—Chicago has it all. Here's a list of the city’s best events all year long.
January
January 15–26, 2025
Various locations
One of the city’s most unique displays of arts and culture is the International Puppet Fest, which features a range of puppetry styles from around the world. During the 2024 season artists from Belgium, Chile, Norway, Germany, Indonesia, Kenya, Mexico, and Poland put on shows for 11 days in various locations across Chicago. Performances ranged from family-friendly works on small stages to an adults-only, late night puppet cabaret. In the beginning, the festival was held only once, every other year. Due to its growing popularity, it is now held each year. It’s one of my favorite festivals of the year and the creativity on display somehow makes the winter easier to bear. Shows sell out quickly so if you see one you like, don’t hesitate to book.
Ready to go? Book here.
February
February 8–17, 2025
McCormick Place
Founded in 1901, this is the oldest auto show in North America. The event features the latest car models, concept cars, and the latest automotive technology (think of it as the Stark Expo for cars). Visitors have the chance to test drive cars indoors and outdoors, and virtual reality allows for stimulated car experiences. The show kicks off with a first look, black-tie gala that raises millions of dollars for local charities.
Ready to go? Book here.
March
March 15, 2025
Loop
In The Fugitive, that iconic movie synonymous with Chicago, Harrison Ford's Dr. Richard Kimble eludes arrest by Tommy Lee Jones' character by blending in with parade go-ers during the St. Patrick’s Day Parade. The parade is more than 175 years old and each year it grows larger and larger as people pack the streets flocking to see the Chicago River dyed emerald green. The chaotic energy of St. Patrick’s Day in Chicago is unmatched. Expect bars to be packed, an unruly amount of Malort to be consumed, and lots of green to be worn. This Loop party is family-friendly and tame. Locals know to head down to Beverly for the South Side Irish Parade for more of a party vibe.
Ready to go? This event is free.
April
April 24–27, 2025
River North
Art lovers from all over the world descend on Chicago and flock to Navy Pier each year for EXPO CHICAGO. The four-day art fair brings in gallery owners, artists, collectors, curators, and fans together for art viewing and programming across the city. Events pop-up in various galleries and art museums, including the Art Institute of Chicago and the Museum of Contemporary Art, for the city’s premier art event.
Ready to go? Book here.
May
May 24–25, 2025
Loop
When the music festival Sueños debuted in Grant Park, it brought in more than 45,000 guests to enjoy the pulsating beats of reggaetoneros Wisin y Yandel, J Balvin, Myke Tower, and Ozuna. It was an iconic cultural moment for Latinos as they danced and partied in the heart of Chicago’s downtown in this first-of-its-kind event. This year event organizers signed a five-year contract with the city so expect it to bring in the most popular artists in Latin music. This year’s headliners included Young Miko, Peso Pluma, Rauw Alejandro, and Maluma.
Ready to go? Book here.
June
June 2025 Dates TBD
West Loop
The Taste of Chicago is one of the city’s largest and longest standing neighborhood festivals. It features three blocks of local food, beverages, and vendors, as well as two live performance stages to entertain more than 50,000 attendees in one of the city’s most popular neighborhoods.
Ready to go? This event is free.
June 14–15, 2025
Old Town
The Old Town Art Fair, which began in 1950, is a staple of the Northside and the oldest fair of its kind. More than 30,000 art lovers descend on the lakefront neighborhood to get a look at the work of over 220 artists. The shutdown of numerous streets creates a block party effect for a five-block radius. I lucked out in college having a friend who lived on Wells, a main street of the fair, where I could enjoy the activities and brief respite (including a bathroom) if I needed to. For those without a local in the area, plan your visit around mealtime and enjoy the view from one of several local restaurants in the area.
Ready to go? This event is free.
July
July 10–13 2025
West Loop
For fans of country music, BBQ, and craft beer, there’s no better place to be than the Windy City Smokeout. The festival is run by Lettuce Entertain You, which means you can expect great food and quality service. Expect live music from top performers. Past headliners include Carrie Underwood, Zac Brown Band, and Luke Bryan.
Ready to go? Book here.
July 2025 Exact Dates TBD
Pilsen
Located in the Mexican enclave of Pilsen, Fiesta del Sol is one of the largest Latino street festivals of its kind. More than 1 million attendees come to the four days festival to roam endless stalls of local vendors, go on the carnival rides, or soak in the art exhibits. Admission is free and profits made are reinvested into the community through scholarship programs. In my experience, most vendors take credit cards, but it’s best to carry cash to avoid disappointment.
Ready to go? This event is free.
July 5–6 2025
Loop
The excitement of NASCAR hits the streets of Chicago as speed racers zoom through the city’s downtown streets with the skyline serving as the backdrop. Unlike traditional NASCAR races held on oval tracks, the Chicago Street Race circuit features a 12-turn, 2.2-mile track that weaves through the Loop, providing a challenging and scenic route for drivers and a one-of-a-kind experience for fans. Check the weather to ensure you’re dressed appropriately for the outdoor event. The first year the event had heavy rains and left many guests wishing they wore rain boots as they waded through wet fields and muddy waters (I know because I was one of them).
Ready to go? Book here.
July 25–27, 2025
Bridgeport
In this town you’re either a Cubs or Sox fan. “Chicago fans,” usually get laughed at for their non-committal, lukewarm stance on which team they claim (take it from personal experience). The rivalry runs deep here and each year fans get the chance to go head-to-head and brag that their team is better when the two MLB teams face off against each other in a best of three series that takes place twice a year—once on each team’s home turf. It doesn’t matter where each team is in the ranking. When these two teams play each other for the Crosstown Cup, these wins (and losses) are all that matter.
Ready to go? Book here.
August
August 9, 2025
Washington Park/Bronzeville
Marching bands, dance troupes, drill teams, elected officials, and the occasional celebrity are among the participants of the Bud Billiken Parade, which is synonymous with the end of summer. Founded in 1929 by Robert S. Abbott, founder of the Chicago Defender newspaper, to celebrate Black culture, the parade is one of the oldest and largest of its kind. Bud is a fictional guardian of children and the spirit of education. Oprah Winfrey, Duke Ellington, then-Senator Barack Obama, Michael Jordan, and Muhammad Ali, are among the famous faces to have participated in the parade.
Ready to go? This event is free.
August 9–10, 2025
Northalsted
One of the biggest and most anticipated events of the summer is Market Days, the largest LGBTQ+ event in the Midwest. More than 200 vendors gather selling their arts and crafts, clothing, jewelry and food. Beer gardens are set-up throughout and each night culminates with live music. Past event headliners include Olivia Newton-John, Salt-N-Pepa, and En Vogue.
Ready to go? This event is free.
September
September 14, 2025
Little Village
More than 400,000 people gather each year in what’s known as “the Mexico of the Midwest,” to celebrate Mexico’s Independence Day. The parade kicks off from the historic Little Village Arch on 26th street and Albany Avenue and continues on through two-and half-miles of the neighborhood's business corridor (the second-highest grossing shopping district in the city). Expect mariachi bands, folklórico dancers and charros on horseback.
Ready to go? This event is free.
September 2025 Dates TBD
Loop
The Taste of Chicago is the largest food festival in the city and one of the most beloved events. It’s changed over the years and mini versions of the original pop-up in the neighborhoods. One thing that hasn’t changed? There’s something for everyone’s palette. Restaurant partners include 90 Miles Cuban Café, Badou Senegalese Cuisine, Billy Goat Tavern, Churro Factory (Xurro), and Connie's Pizza.
Ready to go? This event is free.
September 2025 Dates TBD
South Loop
A literary festival made for book lovers. The Printers Row Lit Fest celebrates books, authors, and the writing process. The (mostly) outdoor event is free and the largest of its kind in the Midwest. Attendees can browse hundreds of books for sale, attend speaker panels and author discussion, or participate in writing workshops. The festival is family-friendly with a number of children activities throughout the day. Submissions to participate open in spring 2025.
Ready to go? This event is free.
2025 Dates TBD
Various Locations
Destinos, Chicago’s international Latino theater festival, produced by the Chicago Latino Theater Alliance returns for its seventh season with various productions throughout the city. Expect performers from Brazil, Chile, Argentina, Puerto Rico, and Mexico, in addition to U.S. and Chicago's hometown companies presenting new works. The line-up is set to be announced in the summer of 2025.
Ready to go? Book here.
October
October 2025 Dates TBD
Various locations
The Chicago International Film Festival is North America's longest-running competitive international film festival. For more than 60 years the prestigious festival has been a launching pad for filmmakers. Creatives from more than 50 countries are represented throughout. Martin Scorsese, Steven Spielberg, Oliver Stone, and Alfonso Cuarón are notable alums who got their start at CIFF.
Ready to go? Book here.
October 12, 2025
Various locations
Nothing beats waking up on race day in Chicago and walking down to the course to cheer runners on. The 26.2 mile course goes through Chinatown, Greektown, the Loop, and up Lake Shore Drive, and it’s where world-records are set (Ruth Chepngetich of Kenya smashed the world record by nearly two minutes in 2024). People say running the marathon is the best way to see the city. I’ve done it once, and I have to agree. If that’s not for you, then just grab your breakfast, a chair and hit the course. Make a day of it. With nearly 50,000 runners from all over the world, you never know who you might see going the distance. Kevin Hart and Tyler Cameron are among the race’s celebrity runners.
Ready to go? This event is free.
October 11-12, 2025
Ravenswood
Hit up Malt Row, a craft brewing corridor in Ravenswood, for the 12th annual Oktoberfestivary hosted by Begyle Brewing and Dovetail Brewery. Enjoy the dip in temps with live music, food trucks and lots of beer. The festival is free to attend but a $5 donation is suggested. Proceeds benefit The Friendship Center, a local food pantry serving the community for more than 50 years. The event is family friendly.
Ready to go? This event is free.
November
November 22–December 24, 2024
2025 Dates TBD
Loop, Wrigleyville and Aurora at RiverEdge Park
Red and white striped tents, alongside little brown huts, mark the open air Christkindlmarket. Inspired by the Christmas markets of Germany, this maze of stalls attracts more than 2 million visitors each year across all three markets. It’s a perfect way to kick-off the holiday season. Grab a pal, a hot cup of cider, and take your time strolling through rows of ornaments, breads, wines and chocolate. The market is free, and the signature boot mug runs up to $23.
Ready to go? This event is free.
November 15, 2024–January 5, 2025
Lincoln Park
Don’t let the cold stop you from seeing the Lincoln Park Zoo lit up at night for the holidays. It’s an easy way to break up the winter monotony. Dress warm and avoid driving if you can (I lived in the area for several years and the traffic in and out moves at a crawl). The zoo is free but for this special event, the cost is $7-10 per person, depending on the day. ZooLights will not be open Thanksgiving Day, Christmas Eve, Christmas Day, and New Year’s Eve so plan accordingly.
Ready to go? Book here.
December
December 5–7, 2024
West Loop
This is by far one of the most beautiful Christmas events of the season. In Old St. Pat’s, the Music Ministry gathers to host a holiday concert (complete with orchestral and choral performances.) in a backlit church stacked with poinsettias and festive decor. It’s one of my favorite events of the season. The moment you walk up to the entrance is when the feeling of being in a movie begins. Tickets go on sale November 1 and don’t forget to dress up for the occasion!
Ready to go? Book here.
Ximena N. Beltran Quan Kiu is a Thrillist contributor.