Chicago Summer Guide

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Explore Chicago’s vibrant summer events with our comprehensive guide. From music festivals to cultural celebrations, discover the must-see highlights of the Windy City’s summer calendar.

GRANT PARK MUSIC FESTIVAL JUNE 12 – AUG. 17

The Grant Park Music Festival has been a part of Chicago summers for 90 years, running Wednesday, Friday and Saturday nights in Millennium Park. This year’s program of 30 free shows includes Haydn, Tchaikovsky and Beethoven, plus a night of American music on the Fourth of July.

African/Caribbean International Festival of Life  July 1-4

The 31st African/Caribbean International Festival of Life and 42nd Chicago Music Awards will be combining this year in the DuSable Museum Garden in Washington Park to celebrate and honor Chicago’s musical diversity, history, and culture. For lovers of R&B, Reggae, Soul, Classic, Funk and even Disco this is a festival not to be missed! 1-day general admission tickets are priced at just $35. 

Chicago Craft Beer Fest July 5-7

Some of the world’s top microbrewers converge on Lincoln Park from July 5-7 for the Chicago Craft Beer Fest. Tickets for a two-hour session start at $35 and come with 12 tastings and a commemorative glass. VIP admission ($75) adds five more tastings and a private seating area. 

Windy City Smokeout July 11-14

Chicago’s premiere country music and barbeque festival is coming back to the United Center with bigger and better headliners, brews and BBQ. Thomas Rhett and Carrie Underwood are set to perform alongside other country music stars. Beyond music, the Windy City Smokeout has gathered all of the world’s best pitmasters for some truly finger lickin’ good barbeque. 

Yacht Club Race to Mackinac July 12 

Since 1898, starting with just five boats the Chicago Yacht Club has been hosting its race to Mackinac island. This event is now a world-class sporting event bringing in sailors from across the country to set sail across The Great Lakes. Head to the Chicago Yacht Club to see the sailors off on this notorious and thrilling race. 

Square Roots Craft Brew and Music Festival July 12-14

Square Roots returns to Lincoln Square this summer bringing live music, family fun, local restaurants and vendors and the best craft beer showcase of any Chicago street fest. This festival will also feature a kid zone family stage alongside dozens of folk bands. 

Chosen Few DJs July 13

Chosen Few DJs picnic and festival is coming to Jackson Park on July 13. This house music festival pays homage to the South Side Sound with sets by popular DJs Wayne Williams, Jesse Saunders, Tony Hatchett, Alan King, Terry Hunter, Mike Dunn and Andre Hatchett. 

West Fest July 12-14

Head out to the eclectic West Town community for three days of cutting edge live music, food from local restaurants, and family and pet friendly fun. West Fest will be filled to the brim with  the best local fine artists and makers and is an excellent way to get to know West Town. 

Southport Art Festival July 13-14

The Southport Art Festival returns to Wrigleyville showcasing a diverse array of visual arts, live performances, and interactive experiences set to captivate the imagination of attendees. This festival will feature an assorted mix of artistic styles and medium with some of the best artists from all over the country participating. 

Pitchfork Music Festival July 19 – 21

Union Park will be transformed into an Indie/Alternative Rock paradise when Pitchfork takes place this July. 1 – day GA tickets start at just $129 with headliners such as 100 Gecs, Carly Rae Jepsen, Muna, Jessie Ware and more all set to take the stage. 

Millennium Park 20th Anniversary July 18-21

Chicago’s centerpiece, Millennium Park, celebrates a milestone birthday on July 18-21! The city has planned a weekend of free events at Pritzker Pavilion, including concerts from Colombian band Fruko y Sus Tesos, the Grant Park Orchestra performing the work of John Williams, rapper (and South Side native) Common and The S&S Chicago Experience, a diverse house music presentation. 

Taste of River North July 19-21

Some of Chicago’s most celebrated restaurants take the spotlight on July 19-21 at the Taste of River North. Stop by on Friday night for a wine tasting or Saturday morning for the dog parade while browsing the works of local artists. The festival benefits the River North Residents Association.

Roscoe Village Burger Fest July 19-21

Roscoe Village will be hosting its 17th Burger Fest from July 19-21. The weekend promises to be an unforgettable patty party, with 11 restaurants vying to win “Best Burger” in “People’s Choice” and “Critic’s Choice” categories. In between the burgers, check out local bands on two stages, arts and crafts vendors and the kids zone. 

Colombian Fest July 19-21

El Gran Festival Colombiano/Colombian Fest Chicago is commemorating a milestone 10th year of the festival with a celebration of Colombian culture on the campus grounds of Northeastern Illinois University. Grupo Niche and Jorge Celedon will be featured at this lively festival which coincides with Colombian Independence Day on July 20. 

Fiesta Del Sol July 25-28 

Since 1974 the Pilsen community has been hosting Fiesta Del Sol; a celebration of the beauty in Latino heritage, history, culture, language and ambition. This four day festival features over 100 booths showcasing some of the best tacos, tamales and tostados in town as well as showcases of up and coming talent. 

Taste of Lincoln Avenue July 26-28

Head to Lincoln Park from July 26-28 for the 40th annual Taste of Lincoln Avenue. Indulge in tasty food while listening to cover and tribute bands, sample Midwestern whiskies on Saturday and wine on Friday and Sunday. There’s even a carnival for the children. The $10 suggested donation benefits the local community development organization. 

Wicker Park Fest July 26-28

Named by the Chicago Tribune as the city’s best summer street festival, Wicker Park Fest, held on July 26-28, distinguishes itself by bringing in nationally known musicians, like headliners Jamila Woods and Superdrag. Animal lovers can check out the Pet Fest, where there will be paw painting, pet portraits and a dog ice cream-eating contest. 

Ginza Festival Chicago July 26-28

The Ginza Holiday Festival is the Midwest Buddhist Temple’s annual fundraising event that has been bringing Japanese American food, culture and entertainment to Chicago’s Old Town neighborhood for over 65 years. The festival will feature delicious specialities like charcoal grilled chicken teriyaki and udon noodles alongside artistic works by local Asian artists. 

Chinatown Summer Fair July 27-28

Attracting more than 40,000 guests annually, the Chinatown Summer Fair is Chicago’s biggest celebration of Far East culture. The fair will be full of Asian performances, kung fu demonstrations, samples from Chinatown’s restaurants, arts & crafts exhibits and so much more.

Argyle Night Market Thursday Evenings in July and August 

Now in its 11th year, Argyle Night Market is a free event featuring food from local restaurants on Uptown’s Argyle St. This part-market, part-street festival also includes live performances of local culture and music. 

Lollapalooza AUG. 1-4

The iconic Lollapalooza returns to its longtime home of Grant Park with more than 170 artists such as Hozier, SZA, The Killers, Blink-182 and Kesha on eight stages. General admission tickets are available for one, two or four days. 

Festa Italiana Aug. 2-4

Embrace the passion, taste the tradition, and celebrate Italy’s finest at Festa Italiana in Naperville. Tickets are available online and in person and include live Italian music all day, a pasta making class, mouth watering Italian food from a variety of vendors and even a meatball eating contest. 

Edison Park Fest Aug. 2-4 

Edison Park Fest started in 1972 as a sidewalk sale, but has grown into one of the most popular neighborhood street festivals in Chicago, welcoming nearly 20,000 attendees throughout the weekend. The festival which has live music, local food vendors, and family friendly fun supports beautification projects through the Edison Park area. 

Retro on Roscoe Aug. 9-11

Retro on Roscoe is a can’t miss event for Chicagoans looking for a blast from the past! The 27th Retro on Roscoe festival utilizes the beautiful tree-lines streets of Roscoe Village to set the scene for artisans, antique vendors, and cool merchants while live oldies music fills the air.

Bud Billiken Parade Aug. 10

For 95 years, the Bud Billiken Parade in Bronzeville has united African Americans through music, food, dance and community. The parade is the second largest in the country, just behind the Rose Bowl. “The Bud” is a celebration of Black pride and history on the South Side.

Chicago Air and Water Show Aug. 10-11

The free Chicago Air and Water Show has been thrilling Chicagoans since 1959. Prepare to be dazzled as brave pilots perform death-defying stunts along the lakefront. Pick a spot at North Avenue Beach for the best view, but get there early. 

Great American Lobster Fest  Aug. 10-11

Live lobsters are being flown to Navy Pier for The Great American Lobster Fest. Enjoy a delectable lobster dinner, live music, and Chicago Air Show visibility until 2 p.m. Fresh seafood at an even fresher price! 

Northalsted Market Days Aug. 10-11

Northalsted Market Days is a weekend long, live music street festival celebrating the vibrant community in Chicago’s Northalsted/Lakeview neighborhood. Market Days, which was labeled by Thrillist as a Can’t Miss Queer Event, features live music on five stages, 250+ vendors, dance exhibitions, drag performances and more!

Printers Row Art Fest Aug. 10-11

The South Loop’s historic Printer’s Row hosts its annual Art Fest on Aug. 10-11 and features works from 95 juried artists in numerous disciplines. With painting classes for adults and a Kids’ Art Zone, everyone can take home something! Admission is free.

Clark After Dark  Aug. 15 

Clark After Dark is River North’s premiere block party celebrating America’s Military service members. The ½ mile long block party brings live music, vendors, local restaurants, and more together in support of the USO of Illinois. 

Glenwood Avenue Arts Fest Aug. 16-18

Held from Aug. 16-18, the Glenwood Avenue Arts Fest will showcase more than 100 artists in Rogers Park. Interact with the artists in their booths and open studios and acquire handmade art and gifts, all while enjoying the diverse street food and music for which the Far North Side is known. 

Taste of Pullman Park Aug. 17

Taste of Pullman Park is part of the Chicago Park District’s Taste of Chicago festival series – a uniquely-Chicago summertime tradition. Stop by Pullman Park to experience an impressive array of eateries showcasing the city’s finest restaurateurs and culinary stars. 

Sangria Festival Aug. 17-18 

Humboldt Park will be transformed into a sangria sanctuary with some of the best local bartenders and mixologists showcasing their signature sangrias. Beyond sangria, there will be live music and dance performances as well as pop-up food stations and a sip and paint experience.

Chicago Jazz Fest 

A Labor Day Weekend tradition, the Jazz Institute of Chicago presents its four-day annual Jazz Festival in Millennium Park. Offering free admission, this festival brings in nationally and internationally renowned musicians while also spotlighting the greats of Chicago’s jazz scene. 

Arc Music Festival Aug. 30 – Sept. 1

House comes home to Union Park with the three–day ARC music festival. Catch sets from Carl Cox, Disclosure, Dom Dolla, Sara Landry and dozens more in an electrifying atmosphere.

North Coast Music Festival Aug. 30 – Sept. 1

North Coast Music Festival at SeatGeek Stadium is an EDM music festival and immersive art experience that is sure to make for a memorable Labor Day weekend. DJ Diesel, Alan Walker, Illenium, Slander and other EDM superstars will be lighting up the festival grounds. 

Taste of Polonia Aug. 30 – Sept. 2

Fiest on kielbasa, pierogi and other authentic Polish dishes at the Taste of Polonia. Held from Aug. 30-Sept. 2 in Jefferson Park on the Northwest Side, it is America’s largest festival of Polish culture, with traditional and modern music, dance and theatrical performances.

West Loop Art Fest Aug. 31 – Sept. 1 

If you are looking for the late summer’s best shopping or an ambient evening stroll, the West Loop Art Festival is returning for its sixth year. With interactive art, children’s crafts and live music this event is sure to delight art lovers of all ages. 

German-American Fest  Sept. 6-7

If a trip to Germany isn’t in the budget for Oktoberfest this year, there is no need to fret! Authentic German cuisine, dance, culture and traditional drinks will be filling the Lincoln Square neighborhood to celebrate Oktoberfest in the city. 

Taste of Chicago Sept. 6-8

Chicago’s famous foodie festival returns to Grant Park on Sept. 6-8! For more than 40 years, Taste of Chicago has brought together restaurants from the North, West and South Sides to celebrate the city’s culinary diversity. Sample iconic Chicago dishes as well as new innovations.

Taste of Greektown Sept. 6-8

If you’re still hungry after eating everything at Taste of Chicago, head to the West Loop. The 34th Taste of Greektown boasts authentic and contemporary takes on Mediterranean cuisine, plus loads of Greek music and dance.

World Dumpling Fest Sept. 9 

Join the Chicago Cultural Association in Logan Square for a one of a kind event featuring dumplings from all around the world. This event features live music, interactive crafts, cultural performances and a diverse array of dumplings. 

Grito Fest Sept. 14-15

El Grito Chicago is a vibrant celebration of Mexican Independence Day. Visitors can head to Grant park and experience Mexican history, culture and gastronomy as well as national and local performers. This year marks the first time in over a decade that this iconic celebration will take place downtown. 

26th Street Mexican Independence Day Parade Sept. 15

Drawing more than 400,00 visitors to Little Village, the 26th Street Mexican Independence Day Parade kicks off Hispanic Heritage Month with colorful floats, mariachi bands and traditional dancing. 

Riot Fest Sept. 20-22

Specializing in alternative and punk, Riot Fest moves to Bridgeview’s SeatGeek Stadium with more than 90 acts, including headliners Fall Out Boy, Beck and Slayer. Between bands, check out RiotLand, an interactive world with all sorts of fun adventures.

Chicago Gourmet Sept. 26-29 

Chicago Gourmet is a culinary experience like no other, set to take place on the stunning Harris Theatre rooftop. Each day of this four-day festival follows a carefully curated theme with Chicago’s most brilliant culinary minds dishing up their best creations. Chicago Gourmet’s mantra is “Amazing cuisine is at the height of fashion.” There is no doubt that this festival will delight all your senses. 

Randolph Street Market Festival Sept. 28-29

Vintage lovers rejoice! Randolph Street Market is returning at the end of the summer bringing vibrant shopping, world-class bites and one-of-a-kind antiques. This festival has been world famous since 2003 and is truly every bargain hunter’s dream.

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