32 Best Festivals in Chicago in 2025 (By a Local)

👉 Jump to: January | February | March | April | May | June | July | August | September | October | November | December

Chicago festivals range from large-scale music festivals to neighborhood street festivals, seasonal celebrations, and more. There’s truly a festival for everyone, no matter the time of year.

As a Chicago, Illinois local, I love checking out festivals and taking advantage of Chicago’s fun-filled events — which make for some of the best things to do in the city. This guide covers the top festivals, month by month. 

1 Chicago Festival in January

Chicago Restaurant Week 

A city-wide event where Chicago restaurants offer set-price menus and deals. 

📅 January/February | Chicago Restaurant Week Website 

Restaurant Week is a city-wide event taking place every January-February for about two weeks. Hundreds of Chicago restaurants offer fixed-price menus for breakfast, brunch, lunch, and dinner. 

This is an awesome opportunity to try new restaurants and affordably dine at some of Chicago’s most sought-after establishments.

2 Chicago Festivals in February

Chicago Theatre Week

Get discounted tickets to over 100 productions at theaters across Chicago.

📅 February | Chicago Theatre Week Website 

Chicago Theatre Week features over 100 theater productions offering discounted tickets. This citywide event is hosted at theaters scattered across Chicagoland. Some tickets go for as low as $15 and $30. 

Chicago Auto Show

An enormous auto event that showcases a diverse range of vehicles.

📅 February | 📍 Google Maps | Chicago Auto Show Website 

The Chicago Auto Show has been running for over 100 years and is the biggest auto show in North America. This event showcases domestic and imported vehicles and takes place at McCormick Place. Tickets are $17 for adults.

1 Chicago Festival in March

St. Patrick’s Day Parade and River Dyeing

Experience the Chicago River dyed green, a parade, and buzzing bar crawls across the city at this iconic annual event. 

📅 March 17, 2025 | Chicago St. Patrick’s Day Website 

St. Patrick’s Day is a huge deal in Chicago. The Chicago River gets dyed bright green and there’s a festive parade that takes place on Columbus Drive between Balbo and Monroe. Several organized pub crawls also take place across Chicago.

1 Chicago Festival in April

EXPO Chicago

An international modern and contemporary art event at Navy Pier.

📅 TBD 2026 | 📍 Google Maps | Expo Chicago Website 

EXPO Chicago is a modern and contemporary art event that takes place in Festival Hall at Navy Pier. The event exhibits art from around the world and includes talks, on-site installations, and more. Single-day admission is $35. 

📚 Related Reading: Museum of Contemporary Art Chicago

4 Chicago Festivals in May

Mayfest

This Lincoln Park festival kicks off summer with music, food, and more. 

📅 TBD 2026 | 📍 Google Maps | Mayfest Website 

Mayfest is a family-friendly Lincoln Park festival meant to support the neighborhood and kick off the summer festival season, which is one of the best times to visit Chicago. This festival includes musical performances, art demonstrations, food, and drinks. A $10 donation is suggested. 

Renegade Craft Fair

A fun local makers market takes place in different Chicago neighborhoods throughout the year.

📅 May 18-19, September 6-7, & December 20-21, 2025 | Renegade Craft Fair Website 

The Renegade Craft Fair is a huge, free, and totally local makers market that hosts creators from around Chicagoland. You can find everything from home decor to clothing and antiques at Renegade. Different neighborhoods around Chicago host the fair each season.

👉Pro Tip: Renegade Craft Fair is also hosting a pop-up at the 2024 Pitchfork Music Festival.

Sueños Music Festival

An energetic Reggaeton and Latin music festival in Grant Park. 

📅 May 23rd & 24th, 2026 | 📍 Google Maps | Sueños Music Festiva Website 

Sueños Music Festival is a huge Reggaeton and Latin music festival that takes place in Grant Park. Performances are by popular Latin artists and upcoming talent. The event includes local food and drink vendors. 2-Day general admission tickets are $310.

Randolph Street Market

A large and diverse vintage market that takes place twice a year in the West Loop.

📅 May 25-26, September 27-28, 2025 | 📍 Google Maps | Randolph Street Market Website 

Randolph Street Market is a large indoor-outdoor vintage market that takes place twice a year on Randolph Street in the popular Chicago neighborhood of West Loop. There are countless makers and vintage vendors selling everything from clothing to furniture and art. There’s food and live music, too. General admission is $12. 

7 Chicago Festivals in June

Chicago Blues Festival 

Chicago’s free and iconic blues festival takes place each year in Millennium Park. 

📅 June 5 – 8, 2025 | 📍 Google Maps | Chicago Blues Festival Website 

The Chicago Blues Festival is one of Chicago’s largest and most iconic music festivals. After all, Chicago has a rich history with blues music. This 4-day free admission festival takes place in Millennium Park and features performances by renowned blues musicians and up-and-coming artists. 

📚 Related Reading: Free Things to Do in Chicago

Andersonville Midsommarfest

A family-friendly summer festival that celebrates the Swedish culture, tradition, and heritage of Andersonville. 

📅 June 13-15, 2025 | 📍 Google Maps | Andersonville Midsommarfest Website 

Andersonville’s Midsommarfest is a beloved local street festival that celebrates Swedish culture and tradition. You can try international foods, dance around the Maypole, and more. This festival is family-friendly and has a suggested $10 entry donation. 

Grant Park Music Festival

This classical music series takes place all summer long at Jay Pritzker Pavilion. 

📅 June 11 – August 16, 2025 | 📍 Google Maps | Grant Park Music Festival Website 

Grant Park Music Festival is a classical music event that takes place all summer long at Jay Pritzker Pavilion in Millennium Park. This family-friendly summer music series includes classical music performances each week. Entrance is free. 

Taste of Randolph

A food and music street festival in the trendy West Loop neighborhood. 

📅 June 16-18, 2025 | 📍 Google Maps | Taste of Randolph Website 

Taste of Randolph is a street festival that takes place on Randolph Street in the West Loop, where some of Chicago’s most popular restaurants are located. This festival features two stages and performances by fairly large names in music. It’s a fun way to enjoy great food and music in one place. A $10 donation is suggested for entry. 

Chicago Pride Fest 

A 2-day festival full of performances in the Northalsted neighborhood. 

📅 June 21-22, 2025 | 📍 Google Maps | Chicago Pride Fest Website 

Chicago Pride Fest takes place in Northalsted, Chicago’s historically LGBTQ+ neighborhood. The festival is chock-full of drag, dance, and musical performances. There are numerous food and merchandise vendors, too. A donation of $15 is suggested for entry. 

Chicago Pride Parade

This North Side parade is one of Chicago’s largest and most vibrant parades. 

📅 June 29, 2025 | 📍 Google Maps (Start Location) | Chicago Pride Parade Website 

The Chicago Pride Parade takes place on Chicago’s North Side and is filled with vibrant floats, decorations, and upbeat energy. It begins at the intersection of Montrose and Broadway and ends at the intersection of Diversey and Sheridan in Lincoln Park. 

Chicago SummerDance 

Take free dance lessons and listen to live music at this summer-long event that takes place throughout Chicago. 

📅 June – September 2025 | Chicago SummerDance Website 

Chicago SummerDance is a city-wide dance event where people of all ages can enjoy free dance lessons and live music. This summer event is free and takes place at different parks throughout Chicago. 

5 Chicago Festivals in July

Millennium Park Summer Music Series

A free summer music series with a diverse range of performances at Jay Pritzker Pavilion.

📅 June 26 – August 7, 2025  | 📍 Google Maps | Millennium Park Summer Music Series Website 

Millennium Park Summer Music Series is one of Chicago’s most popular summer events for all ages. This music series is free and features performances by artists from a diverse range of styles and genres. It takes place at Jay Pritzker Pavilion on Mondays and Thursdays. 

👉 Add the Millennium Park Summer Music Series to your Chicago itinerary if you’re visiting in the summer! Get a free, printable version of our itinerary here. 

Millennium Park Summer Film Series

A free outdoor summer movie event for all ages that takes place at Jay Pritzker Pavilion. 

📅 July 1 – August 26, 2025 | 📍 Google Maps | Millennium Park Summer Film Series Website 

Millennium Park Summer Film Series is a free summer event series that takes place on Thursdays at Jay Pritzker Pavilion. People of all ages can come and enjoy everything from cult classics to family-friendly films. 

Windy City Smokeout

Enjoy barbecue, beer, and country music right outside the United Center. 

📅 July 10-13, 2025 | 📍 Google Maps | Windy City Smokeout Website 

Windy City Smokeout is a barbecue, beer, and music festival that takes place in the lot of the United Center. This food-fueled festival features performances by country music artists and barbecue by top pitmasters. Single-day general admission is $66 plus fees. 

Wicker Park Fest

This unique Wicker Park street festival includes live music, food, and local merchandise. 

📅 July 25-27, 2025 | 📍 Google Maps | Wicker Park Fest Website 

Wicker Park Fest is a street festival that takes place in Chicago’s artsy, eclectic Wicker Park neighborhood. Expect an awesome lineup of musical performances across genres as well as local food and merchandise vendors. It’s suitable for all ages. A $10 entry donation is suggested. 

3 Chicago Festivals in August

Lollapalooza 

This famous music festival with impressive headliners takes place in Chicago’s Grant Park every year. 

📅 July 31 – Aug 3, 2025 | 📍 Google Maps | Lollapalooza Website 

Lollapalooza is one of the biggest music festivals in the world. Every August Lollapalooza takes over Grant Park and features an impressive lineup of the world’s most popular artists. Previous headliners have included Billie Eilish, the Red Hot Chili Peppers, Kendrick Lamar, and others. Single-day passes range anywhere from $200-$400 and up. 

👉Pro Tip: Lollapalooza is one of many festivals that can create serious traffic in downtown Chicago. Read my travel tips and guide on how to get around Chicago to help you navigate the chaos. 

Chicago Air and Water Show

An impressive air and water show with airplane stunts that takes place on Chicago’s lakefront. 

📅 August 16 – 17, 2025 | 📍 Google Maps | Chicago Air and Water Show Website 

The Chicago Air and Water Show is an annual summer event for the whole family to enjoy. It’s the oldest and largest free air and water show in the country and features impressive plane stunts by pilots. North Avenue Beach is the best place to catch the show. 

Chicago Jazz Festival

This free jazz event brings live music to Millennium Park and Chicago neighborhoods. 

📅 August 28-31, 2025 | 📍 Google Maps | Chicago Jazz Festival Website 

The Chicago Jazz Festival is a free annual music event. Each year’s lineup includes performances by local and renowned jazz musicians. The main performances are at Jay Pritzker Pavilion in Millennium Park but there are neighborhood shows, too. 

3 Chicago Festivals in September

Taste of Chicago

This fun food festival takes over Grant Park and features food vendors from all around Chicago.

📅 September 5-7, 2025 | 📍 Google Maps | Taste of Chicago Website 

Taste of Chicago is a foodie festival that takes place in Grant Park. It includes popular Chicago food vendors and a range of international cuisines. There’s live music and fun events like karaoke and dancing. Admission is free. 

Riot Fest

This Douglass Park music festival features rock and punk performances.

📅 September 19-21, 2025 |📍 Google Maps | Riot Fest Website 

Riot Fest is a rock and punk music festival that takes place in Douglass Park. It often features reunion and full album performances. The festival includes carnival rides, food, and more. A 2-day pass is just over $200. 

Jack’s Pumpkin Pop-Up

Enjoy fall festivities at this seasonal pop-up with pumpkins, games, and more, located by Goose Island. 

📅 TBD, 2025 | 📍 Google Maps | Jack’s Pumpkin Pop-Up Website 

Jack’s Pumpkin Pop-Up is a fall and Halloween-themed event that takes place near Goose Island. The 6-week pop-up is open to all ages and includes a corn maze, photo ops, carnival games, food and drinks, and of course, pumpkins (and more). Tickets start at $22. 

1 Chicago Festivals in October

Chicago International Film Festival

See feature films and short films at different theaters across Chicago. 

📅 October 15 – 26, 2025 | Chicago Film Festival Website 

The Chicago International Film Festival is the “longest-running competitive film festival” in North America [source]. The festival showcases feature films and short films from around the world and across genres. It takes place at different theaters around Chicago. Tickets range from $60 up to $380. 

4 Chicago Festivals in November

The Wintrust Magnificent Mile Lights Festival

One million lights illuminate downtown Chicago during this holiday parade. 

📅 November 22, 2025 | 📍 Google Maps | Magnificent Mile Website 

The Wintrust Magnificent Mile Lights Festival is the biggest night parade in the country. It takes place down Michigan Avenue (better known as “The Magnificent Mile”) and features Disney characters, large balloons, performances, and of course, infinite holiday lights. 

Chicago Thanksgiving Parade

A festive downtown Chicago parade to kick off Thanksgiving. 

📅 November 28, 2025 | Chicago Thanksgiving Parade Website 

The Chicago Thanksgiving Parade takes place in downtown Chicago on State Street between Ida B. Wells Drive and Randolph Street. The parade includes turkey-themed floats, live music, giant balloons, and so much more. 

ZooLights at Lincoln Park Zoo

Walk through colorful light displays and enjoy festivities at the Lincoln Park Zoo. 

📅 TBD | 📍 Google Maps | Lincoln Park Zoo Website 

Lincoln Park ZooLights is a family-friendly event that takes place in the evening hours at Lincoln Park Zoo throughout the holiday season. Colorful light displays illuminate the zoo while holiday music plays and events like ice carving take place. Tickets are $7-$10 depending on the day. 

Christkindlmarket Chicago

This European-style Christmas market sells festive crafts and decor and has two Chicago locations. 

📅 TBD | Christkindlmarket Website 

Christkindlmarket is a European-style Christmas market that takes place in downtown Chicago and Wrigleyville. It’s a fun and festive place to pick up gifts like ornaments, German Christmas carousels, nutcrackers, and more. There’s food and drinks to enjoy. Entrance is free. 

1 Chicago Festivals in December

Light Up the Lake at Navy Pier

Head to Navy Pier for interactive holiday activities on the lakefront. 

📅 TBD | 📍 Google Maps | Navy Pier Website 

Light Up the Lake is an indoor-outdoor holiday event at Navy Pier. You can enjoy ice skating, festive light displays, holiday-themed rides, and more. There’s something for adults and kids alike. Tickets start at $15 for children and $27 for adults. 

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Chicago’s diverse lineup of festivals is truly one of the best parts of living in the Windy City. Have you been to any of these festivals? Are there any I missed? Let us know in the comments! Next up, read our guide on where to stay in Chicago!

(Featured Image Credit: Peter James Sampson / Shutterstock.com)