![]() ![]() Set sail on one of Chicago’s famous boat cruises on our two sparkling waterfronts. Maxwell Street Market: This Sunday market is a Chicago tradition with an eclectic mix of handmade crafts, live music, family fun, and some of the best street food in Chicago.Lincoln Square Greek Fest: Greek food, dance troupes, a Hellenic marketplace, delicious pastries, and more can be found in Lincoln Square all weekend long.Taste of Polonia: This annual Labor Day weekend food fest offers four days of authentic Polish food and beer, live music, dance, performances, and more.The Great American Lobster Fest: Live lobsters are flown in from the East Coast for the Midwest’s largest seafood festival, held at Navy Pier.Chicago Food Truck Festival: Head to Daley Plaza to sample fare from a wide variety of local food trucks on Friday, Sept.Dig into the best local food truck fare, enjoy a lobster roll by the water, and get your fill of traditional Polish or Greek cuisine. Fill up at a food festĬhicago’s culinary community is a melting pot of cultures, and you can get a taste of our diverse dining scene at these Labor Day weekend food events. 4 from 6:30 – 10:30 a.m., followed by a festival for riders in Grant Park. This year’s event takes place on Sunday, Sept. Bike the Drive features a 30-mile loop on the iconic road, inviting bikers to enjoy a long or short ride while taking in views of the lake and city skyline. Jazz in the Court: The scenic Hyde Park neighborhood hosts this free jazz series, wrapping up the season with a performance by Thaddeus Tukes Quartet.īike down Lake Shore Drive Bike the Drive on Lake Shore DriveĮnjoy a scenic ride down Chicago’s stunning DuSable Lakeshore Drive, which is shut down to cars just one day each year.North Coast Music Festival: This annual Labor Day weekend music festival includes electronic music, hip hop and rock acts, plus art installations and food vendors.ARC Music Festival: This new fest in Union Park celebrates house music, a Chicago-born genre, over Labor Day weekend.Chicago Jazz Festival: The oldest of Chicago’s free lakefront music festivals boasts an incredibly diverse lineup in the heart of the loop.This year, the weekend is packed with a diverse line-up of fests - catch a free concert in Millennium Park, dance the night away at a house music festival, listen to jazz in Hyde Park, and more. You can’t do Labor Day in Chicago without checking out one of the city’s annual music festivals. Check out top events and things to do over Labor Day weekend in Chicago. Celebrate the end of the season with boat cruises, dinner on a patio, music under the stars, neighborhood food festivals, cocktails at the beach, and so much more. Summer in Chicago may be coming to an end, but Labor Day weekend is full of ways to enjoy the final days of sunshine and warm weather.
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