Hey there, Chicago lovers!
We don’t know about you, but after just enduring another legendary Chicago winter, we think everyone deserves to celebrate the sunshine with food, music, art, and culture!
May is finally here, and that means it’s time for our beautiful city to transform into festival central.
We’re the Ben Lalez Team, and although we’ve been selling real estate for over a decade, we know that a neighborhood’s festival scene is just as important as its property values. The festivals you’ll attend this summer might just lead you to discover your next favorite neighborhood!
In this guide, we’ll cover some of Chicago’s most exciting spring and summer festivals for 2025. Whether you’re a long-time resident or brand new to the city, there’s something magical about experiencing Chicago’s street festivals, lakefront celebrations, and neighborhood parties.
Make sure to bookmark this page so you can come back and reference this list!
May 2025
Lincoln Park Mayfest (Chicago Mayfest)
A lively celebration of the neighborhood’s spirit and talent, featuring local bands, artisan vendors, and plenty of food and beer.
Date: May 16-18
Location: 1000 W. Armitage Ave. (Lincoln Park)
Website: https://chicagoevents.com/event/chicago-mayfest/
Maifest Chicago
A traditional German-American spring festival with beer gardens, live music and dancing (with polka), and German food!
Date: May 29 – June 1
Location: 4521 N. Lincoln Ave (Lincoln Square)
Website: https://www.maifestchicago.com/
Belmont-Sheffield Music Festival
A street music fest in its 40th year in the Lakeview neighborhood, featuring tribute bands, artisan vendors, food and drinks.
Date: May 23-25
Location: 3200 N. Sheffield Ave.
Website: https://chicagoevents.com/event/belmont-sheffield-music-fest/
Mole de Mayo Festival
A popular Pilsen street festival celebrating Mexican cuisine and culture, featuring a mole sauce cook-off, live music, art, and even lucha libre wrestling!
Date: May 24-26
Location: 18th Street & S. Halsted Street
Website: https://www.instagram.com/moledemayofest/
Sueños Music Festival
A big Latin music festival featuring reggaeton, Latin trap, and pop artists.
Date: May 24-25
Location: Grant Park
Website: https://suenosmusicfestival.com/
Do Division Street Festival
A street fest featuring two live music stages booked by local venues, featuring shopping, food, and family activities.
Date: May 30 – June 1
Location: W. Division Street between Damen Ave. and Leavitt St.
Website: https://www.westtownchamber.org/do-division
Make sure to bookmark this page so you can come back and reference this list!
June 2025
Chicago Blues Festival
The largest free blues festival in the world where you can enjoy four days of renowned blues artists on multiple stages.
Date: June 5-8
Location: Millennium Park (plus opening night at the Ramova Theater)
Website: https://www.chicago.gov/city/en/depts/dca/supp_info/chicago_blues_festival.html
Ribfest Chicago
A popular food festival all about BBQ ribs, featuring live rock/country music and kids activities.
Date: June 6-8
Location: Northcenter (4000 N. Lincoln Ave.)
Website: https://www.ribfest-chicago.com/
Lincoln Park Greek Fest
A family-friendly festival featuring authentic Greek food, music, dancing, and cultural exhibits.
Date: June 6-8
Location: St. George Freek Orthodox Church (2701 N. Sheffield Ave.)
Website: https://www.lincolnparkgreekfest.com/
Andersonville Midsommarfest
A street festival in its 59th year, celebrating the neighborhood’s Swedish roots and LGBTQ+ pride, featuring five stages of live music, cultural dance performances, vendors, and international food.
Date: June 13-15
Location: N. Clark St. from Foster to Gregory
Website: https://andersonville.org/midsommarfest/
Taste Of Randolph
A food and music festival featuring Restaurant Row on Randolph Street, with sample dishes from top West Loop restaurants, and two stages with live music.
Date: June 13-15
Location: 900 W. Randolph St.
Website: https://www.tasteofrandolph.org/
Wells Street Art Festival
An art/street festival featuring artists, live music, food, and family activities.
Date: June 14-15
Location: Wells St. between North Ave. and Division St.
Website: https://www.wellsstreetartfest.us/
Chicago Pride Fest
A two-day LGBTQ+ street festival featuring three stages of live music, a pet parade, dance exhibitions, drag shows, and 150+ vendors.
Date: June 21-22
Location: Northalsted on Halsted Street from Addison to Grace St.
Website: https://pridechicago.org/event/chicago-pride-fest-2025/
Puerto Rican Festival & Parade
A celebration of Puerto Rican culture with four days of music, authentic food, carnival rides, and community events.
Date: June 12-15
Location: Humboldt Park (the parade will take place along Division Street)
Website: https://www.puertoricanfest.com/
Taste Of Chicago (June)
A popular food festival featuring local restaurant vendors and entertainment.
Date: June 28
Location: Marquette Park
Website: https://www.chicago.gov/city/en/depts/dca/supp_info/taste_of_chicago.html
Chicago Pride Parade
The city’s massive LGBTQ Pride Parade is in it’s 54th year, featuring 150 colorful floats and marching groups.
Date: June 29
Location: Begins at Montrose & Broadway in Uptown, goes south on Broadway and Halsted, east on Belmont, and ends near Diversey and Cannon Dr.
Website: https://pridechicago.org/
July 2025
Windy City Smokeout
A four-day country music and BBQ festival featuring top country artists, barbecue from acclaimed pitmasters, and craft beer.
Date: July 10-13
Location: United Center parking lot (1901 W. Madison St.)
Website: https://www.windycitysmokeout.com/
Square Roots Festival
A craft beer and music street fest featuring live music, over 30 regional craft beers, and family activities.
Date: July 11-13
Location: Lincoln Square (Lincoln Ave. between Montrose and Wilson)
Website: https://squareroots.org/
Chicago Gospel Music Festival
A festival celebrating gospel music featuring a lineup of acclaimed gospel choirs and artists.
Date: July 12
Location: Millennium Park
Website: https://www.chicago.gov/city/en/depts/dca/supp_info/chicago_gospel_musicfestival.html
Chosen Few Picnic & Festival
An all-day house music party celebrating Chicago house music.
Date: July 12
Location: Jackson Park
Website: https://www.seetickets.us/event/Chosen-Few-Picnic-and-Festival-2025/640918
West Fest
A street festival featuring live music, food and drinks, and family activities.
Date: July 18-20
Location: W. Chicago Ave. and N. Damen Ave.
Website: https://www.westtownchamber.org/west-fest-chicago
Taste Of Chicago (July)
A popular food festival featuring local restaurant vendors and entertainment.
Date: July 19
Location: Pullman Park
Website: https://www.chicago.gov/city/en/depts/dca/supp_info/taste_of_chicago.html
Taste Of Lincoln Avenue
A long-running street festival with live music, food and drink, vendors, dog parade, and family activities.
Date: July 25-26
Location: Along N. Lincoln Ave. around 2500-2700 N.
Website: https://tasteoflincolnchicago.com/
Wicker Park Fest
A large music and arts festival featuring 50 bands on four stages, an arts market, local food trucks, a kids area, and more.
Date: July (not yet announced)
Location: Milwaukee Ave. & North Ave.
Website: https://www.wickerparkbucktown.com/wicker-park-fest/
Chinatown Summer Fair
A weekend festival showcasing Chinese culture, food, and entertainment such as traditional Lion dances, kung fu demonstrations, classical dance, and music performances.
Date: July 26-27
Location: Chinatown
Website: https://ccc-foundation.org/summer-fair/
Fiesta del Sol
One of the largest free Latino festivals in the country, this four-day event features live music, authentic Mexican and Latin American food, carnival rides, art expos, and family activities.
Date: July 31 – August 3
Location: 1400-1600 W. Cermak St.
Website: https://fiestadelsol.org/
Lollapalooza
Chicago’s biggest music festival spans four days and eight stages.
Date: July 31 – August 3
Location: Grant Park
Website: https://www.lollapalooza.com/
August 2025
Taste Of Chicago (August)
A popular food festival featuring local restaurant vendors and entertainment.
Date: August 9
Location: Albany Park
Website: https://www.chicago.gov/city/en/depts/dca/supp_info/taste_of_chicago.html
Northalsted Market Days
An LGBTQ+ summer event that runs two days with five stages of live music, DJs, dancing, food and drink vendors, and arts/crafts.
Date: August 9-10
Location: Northalsted (Halsted St. between Belmont and Addison in Boystown)
Website: https://northalsted.com/events/northalsted-market-days-2024/
Bud Biliken Parade & Picnic
The country’s largest African-American parade features bands, dance teams, floats, and ends with a family picnic and festival in the park.
Date: August 9
Location: King Dr. from 35th St. to Washington Park
Website: https://www.budbillikenparade.org/
Chicago Air & Water Show
A free air show over Lake Michigan featuring the U.S. Navy Blue Angels and U.S. Army Parachute Team (Golden Knights).
Date: August 16-17
Location: North Avenue Beach and along the Lakefront
Website: https://www.chicago.gov/city/en/depts/dca/supp_info/chicago_air_and_watershow.html
Taste Of Greektown
A weekend festival in Greektown celebrating authentic Greek food, music, dance, games, and family fun.
Date: August 22-24
Location: 300 S. Halsted St.
Website: https://chicagoevents.com/event/taste-of-greektown/
Chicago House Music Conference & Festival
A two-day event celebrating the Chicago house scene, featuring a conference (panels and workshops), finishing with a festival with DJs and live performances played into the night.
Date: August 22-23
Location: Chicago Cultural Center (conference) and Millennium Park (festival)
Website: https://www.chicago.gov/city/en/depts/dca/supp_info/house_music0.html
Chicago Jazz Festival
A world-class jazz festival with four days of jazz music.
Date: August 28-31
Location: Chicago Cultural Center and Millennium Park
Website: https://www.chicago.gov/city/en/depts/dca/supp_info/chicago_jazz_festival.html
How To Make The Most Of The Festival Season
Transportation Tips
- Skip the parking: Most festivals have limited or no parking, so consider taking public transit (check out our guide to Chicago’s top neighborhoods for transit access)
- Rideshare drop-off points: Many festivals now have designated rideshare zones, so check festival websites for availability and locations
- Bike-friendly options: Lots of festivals offer bike valet services, so you can pedal your way to the fun and know your bike will be secure
Festival Hacks
- Arrive early: You want to beat the crowds and get first dibs on food before lines form and vendors sell out of popular items
- Bring cash: Even though many vendors accept cards, it’s just a whole lot easier to get by on cash, especially with big lines and connectivity issues
- Prepare for the weather: We all know that Chicago weather can change in an instant, so pack sunscreen, a hat, and a light packable rain jacket
- Comfortable shoes: You’ll likely be doing a lot of walking or standing – this isn’t the time to break out your brand new shoes!
Ready To Find Your Festival Home?
After experiencing the diverse culture of Chicago’s neighborhoods during festival season, you might find yourself falling in love with a particular area and thinking about living there one day.
Whether you’re drawn to the artistic energy of Wicker Park, the cultural richness of Pilsen, or the lakefront vibes of Lakeview, the Ben Lalez Team knows every corner of this amazing city. We can help you find a home that keeps you close to the action all year round!
We’d love to grab a coffee and chat about turning your festival weekend into your everyday reality. Give us a shout, and let’s talk. In the meantime, we’ll see you at the festivals!
