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Lincoln Park Greek Fest

Greek heritage takes center stage at the Lincoln Park Greek Fest from June 3 – 5. Held at St. George Greek Orthodox Church, this annual festival is a celebration of “filoxenia” (aka Greek hospitality and generosity of spirit) featuring traditional Greek food, music, dancing, arts and crafts, and special performances.


Chicago Blues Festival

From June 9 – 12, join more than 500,000 blues fans in Chicago’s Millennium Park for the city’s largest music festival. Completely free and open to the public, the three-day blues jamboree features some of the genre’s most revered musicians while shining a spotlight on the contributions the blues has made to soul, R&B, gospel, rock, and hip hop.


Puerto Rican Festival Chicago

Staged in Humboldt Park — home to the largest Puerto Rican population in the city — from June 10 – 12, this vibrant street fest highlights the diversity of Puerto Rican culture and history with a combo of carnival rides, traditional song and dance performances, a virtual pageant and, of course, food and beverages. Special guest performers at this year’s festival include Lisette Melendez, David Torres, and Boriqua Posse.


Andersonville MidsommarFest

Now in its 56th year, this annual festival celebrating Andersonville’s Swedish culture and history will be held from June 10 – 12 along the Clark Street corridor. This year’s festival will feature more than 50 music and entertainment acts on five stages, including bands such as Sixteen Candles, The Prince Experience, and Dos Santos.


Hyde Park Summer Festival

This popular neighborhood festival marks its 15th anniversary with the perfect pairing: beer and music. Boasting a beer garden chock full of distinctive brewers and a lineup of headliners including rapper Busta Rhymes, DJ Jazzy Jeff, and Chicago native Lupe Fiasco. This year’s event will take place from June 11 – 12 and promises to be among the most memorable yet.


Grant Park Music Festival

This eight-decade-old staple brings classical music to Millennium Park on Wednesdays, Fridays, and Saturdays from June 15 – August 21. This year’s lineup includes a mix of contemporary compositions and classical favorites such as Beethoven’s Eroica Symphony and Tchaikovsky’s Sleeping Beauty, as well as an Independence Day Salute and Cirque Goes to Hollywood featuring live aerialists.


Chicago Pride Fest

The weekend before the 2022 Chicago Pride Parade (June 26), the Chicago Pride Fest returns to the country’s oldest official gayborhood for two days from June 18 – 19. Featuring live music on multiple stages, DJs, dancing, drag shows, a pet parade, local food vendors, and more. This year’s rainbow festival will be headlined by Netta and Inaya Day, among a host of others.


Taste of Chicago

Explore the very best of Chicago’s award-winning cuisine at Taste of Chicago. Pop-ups return this year with food and music events in three Chicago neighborhoods on June 11, 18, and 25 followed by a bite-sized version of the classic lakefront extravaganza from July 8 – 10 at the famed Grant Park. More than 30 eateries and food trucks will be showcased daily alongside three mainstage evening concerts.


Southport Art and Music Fest

From July 9 – 10, experience the art fest that TimeOut Chicago named one of the “Best Festivals in Town.” Held in Chicago’s Southport Corridor, steps away from the iconic Wrigley Field, this two-day festival highlights the work of a diverse group of local artists across multiple disciplines including oil, acrylic, watercolor, jewelry, sculpture, and photography, among others.


Millennium Art Festival

Staged just a few blocks north of Millennium Park, the three-day Millennium Art Festival takes place in the heart of downtown Chicago from July 15 – 17. Sample festival food and libations alongside live music by French singer, Michelet, while perusing an array of original artwork including paintings, ceramics, photography, furniture, and more from over 130 juried artists.


Pitchfork Music Festival

For the last 12 years, Pitchfork Music Festival has set itself apart from other festivals vis-à-vis its unique focus on presenting an edgy multi-genre mix of the best up-and-coming musicians from around the globe alongside diverse vendors, as well as specialty record, poster, and craft fairs. Held on July 15 – 17, this year’s festival promises more of the same with headliners including: The National, Toro y Moi, The Roots, and Japanese Breakfast.


Wicker Park Fest

Dubbed “Chicago’s Best Street Festival of the Summer” by the Chicago Tribune, Wicker Park Fest shines a spotlight on the singular character and musical heritage of its namesake neighborhood with the ultimate street party. On July 22 – 24, expect a weekend festival bubbling over with great local food, arts and crafts, retail vendors, and an eclectic mix of music from more than 30 acts performing across two stages.


Pizza City Fest

While Chicago is known for deep-dish pizza, the inaugural Pizza City Fest -— held on July 23 – 24 — aims to prove the city has so much more to offer. This two-day festival, hosted by James Beard Award-winning food reporter Steve Dolinsky, promises to bring together 39 of the region’s best pizza makers (and one out-of-town guest) for two days of pizza making and appreciation, all under one roof in the West Loop.


Fiesta Del Sol

This four-day, family friendly Mexican festival organized in the heart of Chicago’s vibrant Pilsen neighborhood has grown from a celebration of a successful community action campaign in 1973 into a festive annual tradition attracting over 1 million people. Today, the event spans eight blocks and features top musical talent in addition to over 100 booths showcasing some of the best tacos, tamales, and tostadas in the city from July 28 – 31.  

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Hailed as one of the largest and most recognizable music festivals in the world, Lollapalooza returns to lakefront Grant Park from July 28 – 31. At the latest installment of this epic four-day festival, more than 170 artists are expected to perform across eight stages with headliners including: Dua Lipa, Metallica, Green Day, Kygo, Doja Cat, and Machine Gun Kelly.


Jefferson Park Arts and Music Festival

Jefferson Park Arts and Music Festival — better known to locals as

Jeff Fest — marks its 21st year with another summer weekend full of fun, food, and music from July 29 – 31. Proceeds from this family-friendly event benefit the Jefferson Park Chamber of Commerce, which has worked to advance civic, business, and social interests of the neighborhood since 1939.


Edison Park Fest

Now in its 50th year, what began as a sidewalk sale on Northwest Highway, has morphed into one of the most popular neighborhood street festivals in Chicago. Featuring live music, numerous food vendors, and activities for attendees of all ages, this annual festival held on August 12 – 14, serves as a community fundraiser benefiting beautification projects throughout the area, community programs, and the Edison Park Chamber of Commerce.


RibFest Chicago

As if serving an average of 50,000 pounds of ribs to 60,000 guests over three gloriously smoky, pork-filled days from August 19 – 21 weren’t cause enough, Ribfest Chicago is also a competition in which Chicagoland BBQ masters compete for the title of “Best Ribs” and “People’s Choice” as well as an indie music festival featuring top local and national acts.


Wine and Art Walk at Morton Arboretum

Set among an oasis of magnificent trees and beautiful landscapes, the Morton Arboretum provides the perfect backdrop for an art fair and wine tasting event. From August 19 – 21, sample wine and peruse artwork on display at this juried art show while strolling around Meadow Lake. The fair features photography, woodturning, jewelry, painting, ceramics, fused glass, and more from Midwest artists.


Sangria Festival

The Sangria Festival sets up shop in Humboldt Park for its seventh edition from August 20 – 21. Sip and sample hand-crafted sangrias
from local bartenders and mixologists paired with local Latin eats, while grooving to live music and traditional dance performances, browsing pop-up shops, or getting creative in the festival’s Paint & Sip sangria lounge.


Glenwood Avenue Arts Fest

In its 21st outing on August 20 – 21, this weekend-long arts festival highlights more than 120 local artists along with street food and craft beer in Chicago’s historic Rogers Park neighborhood. In addition, the festival promises live entertainment on two outdoor stages, open studios, performances, and art demonstrations all set along the cobblestone streets of the Glenwood Avenue Arts District.


Taste of Greektown

Experience Greek culture first-hand at the annual Taste of Greektown festival held on August 26 – 28. Join in the celebration as a mix of local Greektown businesses and food vendors come together to showcase authentic Greek cuisine and traditional Mediterranean delicacies alongside lively Greek bands, dance troupes, local musicians, and other on-site activities.


ARC Music Festival

Debuting in 2021 as a celebration of the spirit of house music in the birthplace of the genre, the ARC Music Festival returns to the Chicago over Labor Day weekend (September 2 – 4) with an expanded three-day event featuring some of electronic music’s biggest stars including Carl Cox, Adam Beyer, Gorgon City, Charlotte De Witte, and Fatboy Slim.


Millennium Park Summer Film Series

Pack a picnic and head over to Millennium Park this summer for one of Chicago’s favorite annual events. Taking place on Tuesdays fromnJuly 12 – Aug 30, this film series features blockbusters, award-winning movies, family classics, and cult favorites presented with concert hall quality sound at the spectacular Jay Pritzker Pavilion.


North Coast Music Festival

See off summer at this annual Labor Day weekend (September 2 – 4) music festival which combines a diverse mix of electronic music, hip hop, and rock acts with massive, immersive art installations, elaborately costumed performers, and food vendors to create a whimsical, music-filled wonderland. 2022 headliners include Armin Van Buuren, Diplo and Kaytranada.


Printers Row Lit Fest

If you thought Chicago only did music festivals well, think again. Turn down the volume and turn your attention to the written word at Printers Row Lit Fest on September 10 – 11. Notable as the largest free outdoor literary showcase in the Midwest, this weekend event features amazing authors, speakers, and exhibitors across genres, while simultaneously supporting Chicago’s independent bookstores.


Englewood Jazz Fest

Heralded by critics as not only “the most provocative jazz performance of the year” but also as one of the best free festivals in the City of Chicago, the Englewood Jazz Festival returns to the Hamilton Cultural Center for its 23rd edition from September 15 – 17.


Riot Fest & Carnival

From September 16 – 18, the annual punk rock carnival known as Riot Fest returns to Douglass Park for a raucous three-day extravaganza with headliners My Chemical Romance and the original Misfits featuring Glenn Danzig among other performers. Complete with sideshow acts, rides and a Ferris wheel, Riot Fest is simultaneously one of Chicago’s most popular, most unique and loudest annual events.


Sam Adams Lakeview Taco Fest

The always lively Southport Corridor gets an added injection of spice  when the Sam Adams Lakeview Taco Fest returns to the strip for its ninth edition from September 17 – 18. Sample your way through an array of local taco vendors, explore special beer and taco pairings, take in multiple music stages, and then cast your vote for Chicago’s best taco at this fun foodie affair.

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