Chicago summer festivals guide

Start making weekend plans filled with food, music and art with our guide to Chicago summer festivals and street parties
Photograph: Neal O'Bryan
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Once the weather in Chicago starts warming up, the streets fill with people and the city's summer festival season gets started. Looking for things to do this weekend? May through September, there’s more than likely a festival for that. Whether you want to dance the night away to live music, hunt down the most impeccable burger in Chicago or taste as many local brews as possible, these summer fests have something for you. Don't get too stuffed though, because these Chicago summer festivals offer some of the best, and most worldly food available all year long. So what’re you waiting for?

RECOMMENDED: Things to do in the summer in Chicago



Chicago summer festivals in May 2018

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Photograph: Tessa Marshall
Things to do, Festivals

Kids and Kites Festival

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Celebrate the arrival of spring at this free, outdoor family-friendly festival at Cricket Hill in Lincoln Park, where kids can fly a kite or watch professional demonstrations. Free paper kites will be provided, but families will also be able to purchase more intricate flying creations from a variety of vendors.

Photograph: Jaclyn Rivas
Things to do, Festivals

Lincoln Park Wine Fest

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Sample more than 100 wines from all over the world while listening to classical music at the second annual Lincoln Park Wine Fest. Yes, it doesn't get much more sophisticated than this. Our advice? Cozy up to the most nicely dressed person in attendance and ask them to take you for a post-fest ride on their yacht.

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Things to do, Festivals

Skokie Festival of Cultures

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Take a tour of the world at this popular festival in Skokie, which features ethnic music, dance, food and arts. Attendees won't have trouble finding ways to celebrate cultural diversity at this free event, with activities like an international beer tasting competition and plenty of games for kids and families.

Shopping

Randolph Street Market Festival

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More than 200 vendors hawk their antique housewares, furniture, ephemera, clothing and more at this indoor-outdoor festival. Stop in for vintage clothes and jewelry, a vinyl swap meet, a fancy food market and global goods bazaar or bring your own items for appraisal. This event typically occurs on the last weekend of each month. During the warm-weather months of May–September, the market adds an outdoor area, offering even more vintage shopping and a beer garden.

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The 36th annual IML weekend culminated in the coronation of International Mr. Leather 2014 in a contest at the Harris Theater.
Photograph: Marzena Abrahamik
LGBT

International Mr. Leather Weekend

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Rooted in a 1979 bar contest, this four-day event features parties, a fetish and leather market, a physique competition, a sexy shoe-polishing competition and, of course, the annual crowning of International Mr. Leather. In additional to the daily Leather Market, there are the big evening events: the Opening Ceremonies, Physique Competition, International Mr. Leather Contest, IML Victory Celebration Party, and the Black and Blue Ball. 

Bike the Drive
Photograph: John Lankford
Things to do

Bike the Drive

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Have you ever dreamed of cruising down Lake Shore Drive on your bicycle? Bike the Drive makes that dream a reality for one day this year, closing down the popular lakefront thoroughfare to cars early on a Sunday morning. Participants can bike from Bryn Mawr Avenue to the Museum of Science industry (and back) during the five hours of car-free riding.

Chicago summer festivals in June 2018

Music, Classical and opera

Chicago Gospel Music Festival

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The city's annual celebration of gospel music welcomes national touring acts and up-and-coming local talent to Millennium Park for two days of uplifting songs and hymns. Lineup to be announced.

CAKE
Photograph: courtesy CAKE
Things to do, Conventions

CAKE: Chicago Alternative Comics Expo

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For readers of independent comics and small press publications, there's no event more sweet than CAKE (short for the Chicago Alternative Comics Expo). Each year, the convention brings creators and fans to the Center on Halsted for two days of panels, workshops and, of course, shopping. 

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Things to do, Festivals

57th Street Art Fair

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The oldest juried craft fair in Hyde Park features paintings, sculptures, jewelry and ceramics from more than 200 artists. The event features pop-up artist talks as well as an artist-at-work area, where attendees can observe the process of creation. Attendees can shop for artwork created in a variety of mediums, including glass, jewelry, leather, photography, printmaking, painting, sculpture, wood, ceramics or fiber.

Cyclists strip down and cruise through Chicago during the World Naked Bike Ride​
Photograph: Max Herman
Things to do

World Naked Bike Ride

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The annual clothing-optional bike ride takes over the streets of Chicago, attracting hundreds of scantily clad riders who help raise awareness about cyclists and positive body image. Check-in for the ride begins at 6pm in the West Loop and the ride usually runs from 8pm-11pm—for specific route details (typically announced the day of the event) check ChicagoNakedRide.org.

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Taste of Randolph
Photograph: Max Herman
Things to do, Festivals

Taste of Randolph

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In the heart of restaurant row, on the same streets as some of Chicago's (and America's) best-known restaurants, this West Loop fest boasts six blocks of food, drink and music. Lineup to be announced. 

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Photograph: Sara Mays
Things to do, Festivals

Chicago Pride Fest

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Prep for the following weekend's annual Pride Parade with Chicago's LGBT community at this celebration. The event offers musical entertainment and food and drinks from local vendors, right in the heart of Boystown. 

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Windy City LakeShake Country Music Festival, June 20, 2015 at Northerly Island, Chicago.
Photographer: cousindaniel.com
Music, Music festivals

Country LakeShake Festival

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For country music fans in Chicago, there's no bigger event than the Country LakeShake Festival on Northerly Island. Headliners at this year's fest include The Voice judge (and Sexiest Man Alive, according to People magazine) Blake Shelton, singer-songwriter Dierks Bentley and bro-country duo Florida Georgia Line. In a city where most festivals tend to ignore country music, this is the hootenanny that Nashville devotees have been waiting for.

Photograph: Greater Ravenswood Chamber of Commerce
Things to do, Festivals

Ravenswood on Tap

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The stretch of Ravenswood Avenue that calls itself "Malt Row" hosts this annual festival, which prominently features the neighborhood's diverse craft brewing scene. You'll find beer from Band of Bohemia, Begyle Brewing, Dovetail, Empirical, Half Acre and more, in addition to food from local restaurants and live music.

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Shopping

Randolph Street Market Festival

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More than 200 vendors hawk their antique housewares, furniture, ephemera, clothing and more at this indoor-outdoor festival. Stop in for vintage clothes and jewelry, a vinyl swap meet, a fancy food market and global goods bazaar or bring your own items for appraisal. This event typically occurs on the last weekend of each month. During the warm-weather months of May–September, the market adds an outdoor area, offering even more vintage shopping and a beer garden.

The inaugural Mamby on the Beach music festival brought electronic acts and DJs to Oakwood Beach on July 12, 2015.
Photographer: Cousin Daniel
Music, Music festivals

Mamby on the Beach

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If you can't afford a vacation to the ocean this summer, you can at least enjoy some music with sand beneath your toes at Mamby on the Beach. The lakefront festival takes place on Oakwood Beach, and typically features a mix of indie, electronic and hip-hop acts.

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Chicago summer festivals in July 2018

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Photograph: Zach Weiss
Things to do, Festivals

Bristol Renaissance Faire

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Have a jolly olde time and butcher your favorite European accent as you engage in live-action fantasy play, enjoy interactive riddles, cheer on your favorite jousting knight or revel in period performances from 1574. The festival takes place Saturdays, Sundays and Labor Day in July, August and early September.

Brothers Osborne
Photograph: Courtesy Universal Music Group Nashville
Things to do, Festivals

Windy City Smokeout

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Spend a weekend eating barbecue and listening to country music at the Windy City Smokeout, which fills a parking lot with some of the country's best pitmasters and musicians. Sample smoked meats cooked by BBQ masters from Texas, Georgia, North Carolina and Tennesee while you listen to twangy tunes from the likes of Brett Eldredge, Brothers Osborne, Ashley McBryde and Aaron Lewis. Dust off your cowboy hat, tie a bib around your neck and dig into this weekend of delicious meat and music.

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Things to do, Festivals

Roscoe Village Burger Fest

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It's no secret that we unabashedly love burgers, so you can imagine how much we're anticipating Roscoe Village's annual celebration of succulent, beef patty cuisine. Loosen your belt and prepare to taste grilled creations from local restaurants while enjoying live music and ample libations. 

Photograph: Kaitlin Hetterscheidt
Things to do, Festivals

Chinatown Summer Fair

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Chinatown celebrates the arrival of summer at this annual event, featuring food, art and music from the Far East. The festival opens with a traditional Lion Dance Procession and continues with performances, kung fu demonstrations and cuisine from Chinatown restaurants.

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Things to do, Festivals

Southport Art Festival

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The Southport Corridor hosts its annual two-day art festival, bringing together a variety of artists and local vendors near neighborhood landmarks like the Music Box Theatre. Guests can peruse pieces, shop at Southport Avenue stores or get up early and enjoy the annual Gospel Brunch on Sunday morning.

Things to do, Festivals

Taste of River North

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This riverfront bash offers samples of dishes from trendy area restaurants like Farmhouse, Taco Joint and El Hefe in addition to great view of the skyline. The shindig also includes a family fun area and live music.

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Photograph: Matt Lief Anderson
Music, Music festivals

Pitchfork Music Festival

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If you're searching for a fest that showcases rising bands, underground legends and mainstream performers with strong independent roots, look no further than the Pitchfork Music Festival. This Union Park fest is best described as a laid-back weekend of musical discovery. Headlining acts include Aussie psych outfit Tame Impala, folk-rockers Fleet Foxes and R&B singer Ms. Lauryn Hill (performing her 1998 debut The Miseducation of Lauryn Hill). You'll want to show up early to catch sets from funk legend Chaka Khan, electronic duo Mount Kimbie, experimental collective This is Not This Heat and host of other compelling performers.

Things to do, Festivals

BenFest

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If you're really lucky, you'll walk away from BenFest with $10,000 in your pocket. Even if you don't win the cash raffle, there's still plenty to see and do at this annual benefit for the St. Benedict Parish in North Center, including live music and a 3-on-3 basketball tournament for the kids.

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The Art Institute of Chicago.
Photograph: Courtesy Art Institute of Chicago
Things to do, Festivals

Art Institute of Chicago Block Party

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The Art Institute of Chicago hosts its very first Block Party celebration, inviting guests to learn about the museum while enjoying exhibitions, activities, presentations, gallery tours, live music and more. The evening is headlined by performances from guitarist Jeff Parker and local jazz musician Ben LaMar Gay.

Things to do, Festivals

Chicago Craft Beer Festival

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Foamy, flat macrobrewed suds in a plastic cup not exactly your idea of a good time? Unleash your inner sophisticate at this Lincoln Park fest, which serves up more than 70 local, regional and national craft beers from 35 brewers. Purchase tickets before making your way to the tasting session each day from 11:30am–4pm—each ticket is good for one 3 ounce sample of beer. Once you've got a buzz going, admire some lawns or catch a band at the nearby Sheffield Music Festival and Garden Walk.

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Chicago summer festivals in August 2018

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Photograph: Zach Weiss
Things to do, Festivals

Bristol Renaissance Faire

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Have a jolly olde time and butcher your favorite European accent as you engage in live-action fantasy play, enjoy interactive riddles, cheer on your favorite jousting knight or revel in period performances from 1574. The festival takes place Saturdays, Sundays and Labor Day in July, August and early September.

Lollapalooza 2017
Photograph: Neal O'Bryan
Music, Music festivals

Lollapalooza

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Taking over Grant Park for four days each summer, Lollapalooza is Chicago's largest music festival, attracting an estimated 100,000 attendees each day. This year, the Weeknd, Bruno Mars, Jack White and Arctic Monkeys headline the fest, topping a bill that includes acts like St. Vincent, Franz Ferdinand, Tyler, the Creator and more. With more than 180 artists, grub from local eateries and plenty of beer, this is the kind of weekend that Chicago summers were made for. RECOMMENDED: Check out photos and reviews from Lollapalooza

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Flashback Weekend
Photograph: Courtesy Flashback Weekend
Things to do, Conventions

Flashback Weekend Chicago Horror Convention

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Let out a few blood-curdling screams during Flashback Weekend, an annual convention that celebrates gory slasher flicks, cinematic monsters and horror films. Confirmed guests at this year's event include Brad Dourif—better known as the voice of Chucky in the Child's Play film series. Of course, you'll also be able to dig through a terrifying amount of classic movie memorabilia or show off your creepiest outfit at a horror-themed costume contest. 

Things to do, Festivals

Jeff Fest Arts and Music Festival

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Grab your djembe and head to Jefferson Park, where a drum circle is just one of the many highlights of this annual community festival. This year's live music lineup is filled with homages to classic rock, including Pink Floyd tribute act Echoes of Pompeii, ZZ Top cover band Eliminator and Led Zeppelin devotees Kashmir. 

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Edge Fest
Photograph by Jeremy Bressman
Things to do, Festivals

Edge Fest

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This is not a celebration of U2's guitarist, instead the "edge" here is Edgewater. This year, the 'hood hosts a long weekend of wholesome family entertainment featuring tons of interactive, kid-friendly activities including karaoke night. Vendors willl serve up the anticipated array of festival foods (corn dogs, funnel cakes, blintzes, donuts), while local artists display handmade goods and crafts.

Things to do, Festivals

Illinois State Fair

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Come for the fried festival fare, stay for the Butter Cow—the fair's unofficial icon and Paula Deen's life-long dream, a life-size cow sculpture made of 500 pounds of butter. The annual State Fair features carnival rides, auto races, livestock competitions and (separately ticketed) concerts from the likes of Ludacris, 311, Foreigner and more. Really, there's no better excuse to make the trip to our state's capital.

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Chicago Hot Dog Fest
Photograph: Stephen Jensen
Things to do, Festivals

Chicago Hot Dog Fest

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The Chicago History Museum organizes this celebration of one of the city's most famous dishes, serving creative franks from the likes of Byron's, Chicago's Dog House, Edzo's and more. While you're chowing down on neon green relish and sport pepper, you can listen to live music or attend a lecture that will teach you about the history of the Chicago-style hot dog.

Festival Cubano
Photograph: Courtesy Festival Cubano
Things to do, Festivals

Festival Cubano

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Back in Riis Park, the three-day Festival Cubano brings together musician, dancers and food for a weekend of cultural celebration. Begin by checking out the festival's 30 Cuban vendors, who will be serving dishes such as jibarito sandwhiches, ropa vieja, lechón and tostones. Once you're full, play a game of dominos, shop for a hand-rolled cigar, watch boxing matches or catch a performance from Cuban stars like Willy Chirino and Jerry Rivera.

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Retro on Roscoe
Photograph: Courtesy Retro on Roscoe
Things to do, Festivals

Retro on Roscoe

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Antique vendors and classic cars fill six blocks of Roscoe Village at this throwback street market, where everything old is new again. The music lineup is equally nostalgic, featuring tribute acts like Too White Crew, Trippin Billies, American English and 16 Candles. 

Photograph: G Nagata
Things to do, Festivals

Ginza Holiday Festival

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Celebrate Japanese culture, food and entertainment at the 63rd annual Ginza Holiday. Meet and buy crafts from master craftsmen (called Waza), who will be flown in from Tokyo to share their skills. Live martial arts, cultural songs, classical dances and Japanese food (teriyaki, sushi, Spam musubi, Hawaiian shave ice and more) give Chicago a taste of Japan. 

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Chicago summer festivals in September 2018

Rebirth Brass Band | Northcoast | September 1, 2012
Photograph: Chandler West
Music, Jazz

Chicago Jazz Festival

icon-location-pin Millennium Park
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Chicago may be best known for its blues musicians, but these days it's more of a jazz city. The annual Chicago Jazz Festival celebrates contemporary improvisers and legendary players with four days of free concerts at the Chicago Cultural Center and Millennium Park. The festivities typically include tributes to notable jazz figureheads, an influx of international acts and visits from musicians who got their start in Chicago's jazz scene.

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Ryan Bourque
Things to do, Festivals

Taste of Polonia

icon-location-pin Jefferson Park
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Feast on potato pancakes, kielbasa, pierogi and more at this Polish celebration during Labor Day weekend. After you've stuffed yourself, dance to some polka music, watch a cover band or play a few rounds of bingo.

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Music, Music festivals

North Coast Music Festival

icon-location-pin West Loop
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The other big festival in Union Park (the one that doesn't rhyme with Itchpork) leans heavy on EDM, jam and rap. Booked by some of the same folks behind Spring Awakening and Mamby on the Beach, North Coast offers up a mix of hip-hop and EDM acts.

Windy City Wine Festival
Photograph courtesy of Windy City Wine Festival
Things to do, Festivals

Windy City Wine Festival

icon-location-pin Grant Park
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Sample more than 300 wines from around the world at this annual sommelier extravaganza at Buckingham Fountain in Grant Park. Area restaurants and caterers will be serving up their signature dishes while bands provide musical accompaniment to your wine tasting journey.

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Photograph: Neal O'Bryan
Music, Music festivals

Riot Fest

icon-location-pin North Lawndale
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It's the social event of the season for anyone with a denim jacket covered in patches hanging in their closet. Riot Fest brings punk, metal, indie acts to Douglas Park, setting up stages amid circus attractions, games and a sideshow. The 2018 lineup has not yet been announced.

Things to do, Festivals

German-American Fest

icon-location-pin Lincoln Square
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Grab a plastic stein and munch on a pretzel at this annual Lincoln Square celebration of Deutschland heritage. The street party features plenty of German food, music and dancing as well as the Von Steuben Parade on Saturday at 2pm.

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Art

Edgewater Fall Art Fair

icon-location-pin Edgewater
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Children's art and creativity come with a hyperlocal focus at the 3rd Annual Edgewater Fall Art Fair. Local schools showcase student artwork programs through gallery exhibitions, while smaller-size budding Rembrandts can face- and finger-paint at the Children’s Activity Corner. This family friendly fest includes a children's music talent showcase, costume contest, pet parade. Adults can enjoy the beer garden as well.  

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Photograph: Max Herman
Things to do, Festivals

Chicago Gourmet

icon-location-pin Millennium Park
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The annual three-day fest kicks off Friday with its Hamburger Hop throwdown. Walk in to Millennium Park and waddle out once you've stuffed your face at cooking demos, tasting pavilions and a wine sampling. The 2018 vendor lineup has not yet been announced.

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