As temperatures rise, the city comes alive with incredible things to do, and none are more exciting than Chicago street festivals. The city hosts a vibrant calendar of summer events that make every day in the Windy City magical. From food festivals to cultural celebrations, Chicago has street festivals for everyone this summer.
Finding all of the best events this summer can be hard, but this complete guide to street festivals and summer events in Chicago is all you need.
May
May 12, 2023: Manifest Urban Arts Festival
May 12 – 14, 2023: Chicago Mayfest
May 13, 2023: Switch on Summer
May 26 – 28, 2023: Mole de Mayo Festival
May 29, 2023: Chicago Spring Tequila Tasting Festival
May 27, 2023: Chicago Memorial Day Parade
May 27 – 28, 2023: Belmont-Sheffield Music Fest
May 27 – 28, 2023: Sueños Festival
May – October 2023: Chicago City Markets

June
June 2 – 4, 2023: Do Division Street Fest
June 2 – 4, 2023: Lincoln Park Greek Fest
June 3, 2023: Chicago Gospel Music Festival
June 3 – 4, 2023: Windy City Hot Dog Fest
June 3 – 4, 2023: Annual 57th Street Art Fair
June 8 – 11, 2023: Chicago Blues Festival
June 9 – 11, 2023: Andersonville Midsommarfest
June 10, 2023: Vegandale Fest
June 10 – 11, 2023: Old Town Art Fair
June 10 – 11, 2023: Heat Wave Music Festival
June 10 – 11, 2023: Wells Street Art Festival
June 17 – 18, 2023: Hyde Park Summer Fest
June 14 – Aug 19, 2023: Grant Park Music Festival
June 16 – 18, 2023: Taste of Randolph Street
June 17 – 18, 2023: Chicago Pride Fest
June 17 – 18, 2023: Gold Coast Art Fair
June 22 – 23, 2023: Ravenswood On Tap
June 22 – August 21, 2023: Millennium Park Summer Music Series
June 24 – 25, 2023: Miche Festival
June 24 – 25, 2023: Logan Square Arts Festival
June 23 – 24, 2023: Pride In The Park Chicago
June 23 – 25: Summer Smash 2023

July
July 1 – 4, 2023: African/Caribbean International Festival Of Life
July 7 – 9, 2023: Square Roots Craft Brew and Music Festival
July 7 – 9, 2023: Roscoe Village Burger Fest
July 8: Chosen Few DJs Picnic & Music Festival
July 8 – 9, 2023: Southport Art & Music Fest
July 11 – August 29, 2023: Millennium Park Summer Film Series
July 14 – 16, 2023: Millennium Art Festival
July 13 – 16, 2023: Windy City Smokeout
July 15 – September 10, 2023: Chicago SummerDance
July 21 – 23, 2023: Taste of Lincoln Avenue
July 21 – 23, 2023: Pitchfork Music Festival
July 29 – 30, 2023: Chinatown Summer Fair
July 29 – 30, 2023: Chicago Food Truck Festival
July 22 – 23, 2023: Chicago Margarita Festival
July 27 – 30, 2023: Fiesta Del Sol
July 29th & 30th: Annual Silver Room Block Party

August
August 3 – 6, 2023: Lollapalooza
August 4 – 6, 2023: Jeff Fest
August 11 – 13, 2023: Ginza Festival
August 12 – 13, 2023: Printers Row Lit Fest
August 12 – 13, 2023: Northalsted Market Days
August 11 – 13, 2023: Retro On Roscoe
August 11 – 13, 2023: Edison Park Fest
August 12, 2023: Bud Billiken Parade
August 12 & 13, 2023: My House Music Festival
August 17, 2023: Clark After Dark
August 18 – 20, 2023: Ribfest Chicago
August 19 & 20: Chicago Air & Water Show
August 19 & 20: Great American Lobster Fest
August 25 – 27, 2023: Taste Of Greektown
August 26, 2023: Chalk Howard Street

September
September 1 – 3, 2023: North Coast Music Festival
September 1 – 3, 2023: ARC Music Festival
September 1 -3, 2023: Taste of Polonia
August 19 & 20, 2023: Chicago Jazz Festival
September 1 – 4, 2023: African Festival of the Arts
September 2 – 3, 2023: West Loop Art Fest
September 8 – 10, 2023: Taste of Chicago
September 9, 2023: World Dumpling Fest
September 9 – 10, 2023: Printers Row Lit Fest
September 15- 17, 2023: Riot Fest & Carnival
September 16 – 17, 2023: Lakeview East Festival of the Arts
September 23 – 24, 2023: Hyde Park Jazz Festival
September 16 – 17, 2023: Sam Adams’ Lakeview Taco Fest
September 21 – 24, 2023: Chicago Gourmet
September 22 – 24, 2023: Oktoberfest Chicago
September 22 – October 1: World Music Festival Chicago
September 30 – October 1, 2023: Apple Fest
September 2023: Throwback Music Festival
September 2023: Mexican Independence Parade
September 2023: 80th Street Renaissance Festival

October
October 6 – 8, 2023: Lincoln Park Wine Festival
October 14 – 15, 2023: Open House Chicago.
Tips for Attending a Chicago Street Festival
Attending a street festival in Chicago is a great way to explore the city and have fun. By using this guide to plan ahead, you can make the most of your festival experience. Here are some other tips to make your festival experience the best yet:
- Bring cash: Some street festivals ask for cash “donations” as an alternative to an entry fee. Be sure to have some on hand so that you can enter the festival with ease.
- Visit the website: Find out performance windows, vendors, and other things to expect from street festivals by visiting their website beforehand so you know what to expect when you arrive.
- Taking public transit: This is the easiest way to get around as streets are often closed down for blocks and even miles in some instances
- Dress comfortably: This is key for the festival season. Dress in layers and wear comfortable shoes. More often than not you will be standing. The temperatures may also increase or drop throughout the day, dressing in layers will make sure you enjoy festivities all day long.
- Travel Light: Take only the essentials with you to the festival like your phone, sunglasses, an extra charger, and a refillable water bottle. There is often security at festivals and bags will sometime be checked, so leave any extras or things that you wouldn’t want to lose at home.
- Coordinate a meetup spot: If you plan to attend a festival with a group of friends, determine a designated meetup spot before, during, and after the festival. This is important to establish should someone lose their phone or get “caught up” in the festival spirit.
Even if you are a first-time festival-goer, you should feel confident that you can have a great time now that you know the inside tricks and tips. So what are you waiting for? Get out there and get to the Chicago Street Festival – you won’t regret it!
With this guide, you won’t go wrong with any festival you choose this summer in Chicago. Need more details on my favorites from the list? Be sure to check outThe Best Festivals in Chicago: According to The Haute Seeker