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Chicago Neighborhood Events

Lakeview Mayfest

Mid-May

Chicago Seasonal Events

Chicago’s summer festival schedule starts in May with the Lakeview Mayfest. The weekend-long street party combines arts, eats, tunes, brews and more for the ultimate opening to a citywide season of outdoor events. The main stage is packed with Chicago’s hottest bands, starting on Friday evening and going through Sunday night. In between live musical acts, visitors can peruse and purchase work at the artist showcases and indulge in traditional festival fare from the lineup of food stands. Hit up the beer tent for a refreshing beverage to wash down the delicious hometown cuisine.Mayfest culminates with the much anticipated Pet Parade where pet owners bring their four-legged friends to display their cute and cuddliness for all to see. Participants can compete for “Owner Look-a-Like” honors and any pets with a neat trick can show off their talents for a shot at the Best Pet Trick award.

Andersonville Midsommarfest

Mid-June

This north side Chicago street fest is a long-established tradition that began nearly a half-century ago in the quaint Swedish-influenced neighborhood of Andersonville. The event spans two days and includes live musical entertainment, dance troupes, merchant stands, food vendors, children’s activities and much more. There is even a customary folk dance around the Maypole, a time-honored festive practice in Sweden. In addition to being a celebration of the community’s Scandinavian heritage, Midsommarfest is also a carnival of international cuisine and amazing local artisans. Around 50,000 people attend Midcommarfest every year to shop the handcrafted goods at the merchant stands and sample the scrumptious treats at the food booths. Four separate stages, including one family stage, host an array of bands and performers that supply foot-stomping, hand-clapping tunes from early afternoon to night fall.

Chinatown Summer Fair

Late July

There’s no better place in Chicago to experience an authentic Chinese celebration than on Wentworth Avenue in Chinatown. The neighborhood’s main drag is lined with Asian-inspired architecture that makes the perfect setting for the community’s annual summer fair. For a single day, the street is filled with a mix of Chinese and American food tents, local merchants, arts and crafts, and a customary lion dance procession. Live entertainment includes traditional Chinese dancers in full dress, balancing and contortionist teams, musical groups, costumed storytellers, and a number of other performances that highlight Asian-American culture. A children’s corner is even set up at Wentworth Avenue and 24th Place to keep the little tykes occupied and engaged. Families and folks from all walks of life will enjoy this one-of-a-kind Chicago neighborhood festival.

Wicker Park Fest

End of July

North Damen Avenue between North Avenue and Schiller

(773) 384-2672

The artsy Chicago neighborhood of Wicker Park has its own summertime street fair where more than 25,000 visitors come to check out hip bands, tasty cuisine and cool goods for sale. The weekend event is packed with over two dozen bands that rock out for the crowds. The schedule of performers reads like a lineup for Chicago’s trendiest mid-size music venues, which is not surprising considering Wicker Park’s hottest club, Subterranean, helps sponsor the festival.

The music is a big part of Wicker Park Fest, but the munchies are just as important. A number of area restaurants set up shop on Damen for the occasion, dishing up some of the locals’ favorite foods. Ice cold beer, mixed drinks and other thirst quenching beverages are available, making this spirited neighborhood bash a decidedly “adult” affair. 

The Wine Crush in Old Town
Wells Street between North Avenue and Shiller
(773) 868-3010
Mid-September

As the summer comes to a close, Old Town manages to squeeze in one more outdoor festival that attracts the “over 21” crowd with an all-out wine party. For just one day, Wells Street becomes an open air market with art vendors, food stands, live stage performances, and an incredible selection of vintages at the wine tasting pavilions. With over 100 types of wine to try, visitors are happy to take the advice of on-site sommeliers and additional demonstrations provide a crash course in wine tasting for the uninitiated.

The Old Town Wine Crush is a great place to sample bottles from France, Spain, Australia, Chile, Italy, the States and more, but it is also the only spot in Chicago where you can make your own wine – at the Grape Stomping Competition. Take off the shoes, roll up the pant legs, hop into a giant vat of grapes and start crushing away! With your partner, the fastest team to make enough juice to fill half a wine glass wins a bottle of wine and a chance at the championship round. 

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