18 Best Chicago Festivals in 2023 (By a Local)

Curious about the best festivals in Chicago? There is an endless list of festivals for anyone who’s planning a visit to the Windy City.

As a local of Chicago for the past five years, I can tell you that attending Chicago festivals should be at the top of every list of stuff to do in Chicago.

Whether you’re looking for live music, dancing, or amazing food, there’s a festival in Chicago for you. In this guide, I’ll break down my picks for the 18 best festivals in Chicago!

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18 Best Festivals in Chicago

Taste of Chicago

Sample the best food of the Windy City!

📍 Google Maps | Phone: (312) 744-3316 | Website | 📅 Dates: September 8 – 10 2023 | Entrance: free (tickets for food are sold in strips of 14 for $10)

If you’re a foodie, this is definitely the festival for you. Taste of Chicago takes place soon after July 4 in Grant Park on Randolph St. You’ll get to sample deep dish pizza, Chicago-style hot dogs, cheesecake, and much more.

You can try all the classic Chicago foods, but also international cuisine and novel creations as well. With more than 3 million annual attendees, Taste of Chicago is the largest free outdoor festival dedicated to food in the world.

Don’t want to buy the full portion at your favorite Chicago restaurant? This is a great way to sample and try them all. Dozens of the best Chicago restaurants participate in the Taste of Chicago each year, including food trucks.

Local artists also perform, which makes for a fun backdrop for your smorgasbord.

👉 Pro Tip: Not going to be around during the three-day event in July? Watch for the bite sized version pop-up events in June, taking place in different neighborhoods within Chicago.

Chicago Blues Festival

Take in blues performances and learn about this profound genre

📍 Google Maps | Phone: (312) 744-3370 | Website | 📅 Dates: June 8 – 11, 2023 | Entrance: free

Always taking place in early June in Millennium Park, the Chicago Blues Festival is one of the world’s biggest music festivals. It lasts for three days, and people who attend can watch live music performances free of charge. If you want to support this free Chicago festival, buy food and drinks from local vendors.

Over half a million fans every year who come from around the globe for this June event. You’ll hear different kinds of blues here, including Motown, soul, and funk. It includes performances from known artists, such as Etta James and B.B. King, as well as new up-and-comers.

In other events, learn about the history of blues music in this city, dubbed the “Blues Capital of the World,” by pursuing information stations.

🛎️ Need a Hotel? Blues fans may want to consider booking a hotel like The Langham Chicago ahead of time – it’s walking distance from Millennium Park!

Chicago Jazz Festival

Listen to and learn about jazz music in Grant Park on Randolph St.

📍 Google Maps | Phone: (312) 744-3315 | Website | 📅 Dates: August 31 – September 3, 2023 | Entrance: free

The Chicago Jazz Festival is an opportunity for both famous and rising jazz artists from around the world to perform. This popular Chicago festival is held every year during Labor Day weekend in Grant Park.

The Chicago Jazz Festival aims to provide access to jazz music for everyone around and to raise awareness of the art of jazz. This festival has been part of the summer music lineup of Chicago for over four decades, having featured iconic jazz artists such as Duke Ellington and John Coltrane.

If you get thirsty while grooving away to the music, grab refreshments at the concessions tent, situated east of the Jay Pritzker Pavilion.

Chicago Air and Water Show

Watch awesome stunts in the air and water by the Chicago lakefront!

📍 Google Maps | Phone: (312) 744-3315 | Website | 📅 Dates: August 19 & 20, 2023 | Entrance: free

The Chicago Air and Water show was established in 1959. The show is held every year in mid-August for two days on Lake Michigan, and is hosted by the city government. It is the largest free show of its kind in the United States.

You can see all sorts of amazing aeronautic performances, including daredevil pilots, parachute groups, boat demos, diving stunts, and many more events.

Every year, more than two million people come to see both civilian and military pilots, including the US Navy Blue Angels, participating in this show, and you’ll be able to see the exhibitions from almost anywhere on the lakefront of Chicago. 

👉 Pro Tip: There are many angles from which you can watch this show. You can reserve a cabana space or just find a spot on one of the downtown Chicago beaches, watch it from a lakefront boat cruise, or even get a bird’s-eye view of the action from 360 CHICAGO.

Wicker Park Fest

Enjoy eclectic food and music in one of Chicago’s coolest neighborhoods!

📍 Google Maps | Website | 📅 Dates: July 22 – 24, 2023 | Entrance: $10 donation

Named “Chicago’s Best Street Festival of the Summer” by the Chicago Tribune, the Wicker Park Fest is one of the most popular festivals in Chicago. This annual event is a reflection of the cultural vibrancy of this neighborhood, including the musical heritage, vivacious nightlife, and eclectic array of culinary offerings.

This three-day street festival takes place in July, with four stages of live music and entertainment for people of all ages. More than 50 musical groups will be featured, and there is an entire area that is devoted to more events centering around art and installations.

You can enjoy food from over 80 food vendors, including neighborhood artisans, boutiques, and restaurants.

📚 Related Reading: Wicker Park is an excellent place to stay for your trip to Chicago. If you want to see other options, check out my guide to the best areas to stay in Chicago!

Pitchfork Music Festival

Listen to indie music being performed for the first time!

📍 Google Maps | Website | 📅 Dates: July 21 – 23, 2023 | Entrance: $109 for one day passes, $239 for three day passes

Taking place in downtown Chicago, on the slopes of Union Park on Randolph St., the three-day summer festival combines art, music, and food in one location. Pitchfork is a popular music blog in Chicago that organizes the event annually. You can see the talent of amateur and professional artists from all over Chicago.

This is a great event if you want to hear indie music that you’ve never heard before. In addition to all of the musical talent, there are nonprofit booths, a pop-up craft fair, and food stalls to quench your hunger.

👉 Pro Tip: Many Chicagoans see it as a tradition to bike to Union Park for this festival, although you can take the CTA as well.

Riot Fest

Jam out to metal, punk, rock, hip hop, and more for days!

📍 Google Maps | Website | 📅 Dates: Sept. 15 – 17, 2023 | Entrance: Starts at $289.98 for three day passes

Established in 2005, Riot Fest takes place in Douglass Park every year. This three day festival is known for booking guest performances, full album performances, and reunions.

This Douglass Park festival is one of the biggest independently-owned music festivals in the United States, focusing on punk, rock, hip hop, and alternative rock, among other genres.

👉 Pro Tip: Riot Fest became so popular that it led to spin-off editions in Denver and Toronto.

Windy City Smokeout

Listen to country music while enjoying BBQ and beer!

📍 Google Maps | Website | 📅 Dates: Jul. 13 – 16, 2023 | Entrance: $299 for four day passes, $59.95 – $99.95 for one day, free for kids 10 and under

Love country music, barbecue, and beer? Then this late summer festival is the place for you. Taking place in the United Center, you’ll get to hear live entertainment from your favorite country artists and enjoy delicious barbecue (from the top pitmasters in the world!) and refreshing beer during this four day festival. There’s even a barbecue brunch!

Logan Square Arts Festival

Experience Logan Square in all its glory!

📍 Google Maps | Website | 📅 Dates: June 23 – 25, 2023 | Entrance: free

This annual June event takes place on Milwaukee Avenue in Logan Square Monument Park. It has been going on for 12 years, and it celebrates everything that makes this friendly, eclectic, diverse neighborhood what it is.

Many very talented local merchants and artists give this June festival a lot of unique colors. The festival contains two stages where live music is played by many popular bands. Local food vendors serve popular eats, as well as beer, wine, and spirits.

Since its inception in 2009, this June festival has raised tens of thousands of dollars for nonprofit organizations in the neighborhood.

🚗 How to Get There: You can get to Logan Square via the CTA Blue Line. As with all areas where there is a significant distance from the city center (and thus extremely efficient public transportation options), you may want to use Discover Cars if you need to rent a car.

Jefferson Park Arts & Music Festival

Enjoy music of local classic rock artists!

📍 Google Maps | Phone: (773) 685-3316) | Website | 📅 Dates: Aug. 4 – 6, 2023 | Entrance: $7 for adults, free for children under 13 who are with an adult

Taking place in the well-loved Jefferson Memorial Park, the summer weekend festival affectionately dubbed as “Jeff Fest” involves family fun, live music, and delicious food. There’s even a Kids’ Zone on the north side of Jefferson Park with many cool activities for kids and families. This includes the Community Stage, which brings acclaim to local artists.

As with any good music festival, there’s plenty of dancing too. Dance troupes from the Chicago Music and Arts Academy will be performing on the last day of this weekend festival.

Grant Park Music Festival

Learn to appreciate classical music with this 10-week summer series

📍 Google Maps | Phone: (312) 742-7638 | Website | 📅 Dates: June 14 – Aug. 19, 2023 | Entrance: free

Unlike many Chicago festivals, this is a 10-week concert series taking place in Jay Pritzker Pavilion on Randolph St. within Millennium Park. The Grant Park Chorus and Grant Park Symphony Orchestra give performances on select days within this 10-week period, in addition to guest conductors and performers.

There are also docents that will answer questions and give educational talks during the open rehearsals of the chorus and orchestra that take place before the performances. It’s definitely one of the best things to do in Chicago during the summers!

👉 Pro Tip: If you want to get good lawn seats, try to get to one of these events an hour early.

Chicago House Music Festival

Celebrate house music in the city where it was born!

📍 Google Maps | Phone: (312) 616-0600 | Website | 📅 Dates: June 23 – 24, 2023 | Entrance: free

This festival, taking place in Millennium Park on Randolph St., features live music and DJs that exhibit all of the styles and sounds of house music, a genre that found its inception in Chicago and has gone on to be very influential when it comes to dance music around the world.

People from around the United States come to this weekend festival, which starts with an industry conference with seminars on interesting topics that relate to this genre.

West Fest Chicago

Experience an eclectic array of local events in West Town

📍 Google Maps | Phone: (312) 850-9390 | Website | 📅 Dates: July 7 – 9 2023 | Entrance: $10 donation (optional)

West Fest Chicago stands out among other festivals because it is locally planned in West Town, and it is made up almost entirely of local talent and offerings, including local restaurants, live music from local fine artists, and more.

There’s even something from the dog lovers, with Pet Fest on Saturday and Sunday – this includes paw painting, a dog obstacle course, and many pet related demos. Kid Fest is also a part of this event, including many quality activities for families and kids.

December Christkindlmarket

Celebrate the holidays with German food and fare!

📍 Google Maps | Phone: (312) 494-2175 | Website | 📅 Dates: Sept. 19 – December 24, 2022 | Entrance: free

Arguably the most popular holiday tradition in the windy city is Christkindlmarket at Daley Plaza in downtown Chicago. This is a German inspired village setting that sells authentic food, beverages, and other cool items. 

This is a great way for families to make special holiday memories. It’s more than just a visit to a German market – the combination of shiny Christmas ornaments, festive music, and smells of hot spiced wine and fresh pretzels will really put you in the holiday spirit!

Lincoln Park Uncorked

Stroll through Armitage Street and Halsted Street while sipping fine wines and enjoying fine fare!

📍 Google Maps | Phone: (773) 880-5200 | Website | 📅 Dates: May 10, 2023 | Entrance: $44-60

Although most festivals in this city take place in the summer, there are some great ones in the spring. This is the perfect spring festival for wine lovers, located in the Lincoln Park neighborhood.

Basically, you get to take a leisurely walk through Armitage Street and Halsted Street, while enjoying sample pours of fine wine, light food, and in-store specials in the local shops.

Chicago Comic & Entertainment Expo

Travel to an alternate dimension with anime and cosplay!

📍 Google Maps | Phone: 800-354-4003 | Website | 📅 Dates: Mar. 31 – Apr. 2, 2023 | Entrance: $47.75-57.75 for one day, $107.75 for three days

This convention, affectionately known as C2E2, is the largest pop culture convention in the Midwest. Taking place at McCormick Place, this is an amazing convention for anyone who is a fan of comics, graphic novels, anime, video games, manga, and other aspects of popular culture. There are many famous guests and an intense cosplay competition as well. 

Memorial Day Wreath Laying Ceremony and Parade

Honor those who have served our country on Memorial Day Weekend!

📍 Google Maps | Website | 📅 Dates: May 27, 2023 | Entrance: free

If you are looking for something to do on Memorial Day weekend, you may want to attend this Saturday morning parade in order to honor the men and women who sacrificed their lives in order to protect the freedom of the United States. The parade starts by going down State Street, and then the wreath laying ceremony takes place at Daley Plaza.

👉 Read Next: 17 Best Day Trips from Chicago

Lollapalooza

Enjoy the energy and unforgettable performance of the biggest music festival in Chicago!

📍 Google Maps | Website | 📅 Dates: Aug 3 – 6, 2023 | Entrance: $130 for one day, $380 for four days

No list of festivals in Chicago would be complete without Lollapalooza. This is the biggest music festival in Chicago, lasting for four days every summer in Grant Park on Randolph St.

Festival-goers get to enjoy amazing live musical performances from some of the best groups and artists in the world with a backdrop of a scenic lakefront and a Windy City summer.

The Lollapalooza account has even tweeted about the possibility of watching your favorite band play from a Ferris wheel, showing their innovative spirit. They find a way to make the festival amazing every summer, with tons of alternative rock, techno, and hip hop events.

👉 Read Next: 20 Best Museums in Chicago

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I hope you found my guide to the best Chicago festivals helpful! There really is something for everyone here, especially for music lovers.

If you’re looking for other things to do while you’re here between festivals, bookmark our guide on the best things to do in Chicago!