Chicago loves celebrations. especially when there are cocktails and food involved. Enjoy drinks, eats, live music, a watch party and other entertainment at the free Kentucky Derby celebration on May 3, 2025, at Time Out Market Chicago. Deck yourself out in your best Kentucky Derby … [Read more...] about Kentucky Derby Celebration at Time Out Market
spring events
Things To Do In Chicago in May
With spring weather warming up more consistently and the lakefront thawing into lovely aquamarine waves, May is a favorite time to explore Chicago before the large summer tourist crowds arrive. Consider these free or low-cost activities for your Chicago May adventures. Besides the essential … [Read more...] about Things To Do In Chicago in May
Ina Mae Tavern Music Festival
Celebrate the high-energy spirit of New Orleans with live blues, jazz and dance rhythms, Creole food, cocktails and a joyful time in the Wicker Park neighborhood at Ina Mae Tavern Music Festival on April 24-27, 2024. Prepare for a non-stop four-day party at Ina Mae's Music Festival, which … [Read more...] about Ina Mae Tavern Music Festival
Mexico Fest at Navy Pier
The colors, music, dance and traditions of Mexico will light up Navy Pier during the exciting three-day events of Mexico Fest, scheduled for May 2-4, 2025. Dance along to noted dance troupes like Ballet Folklorico de Chicago and move to the rhythms of bands like Mariachi Estrellas de Chicago … [Read more...] about Mexico Fest at Navy Pier
Pullman Railroad Days
Explore the historic world of railcars and their glamorous history during Chicago's biggest rail-themed event, Pullman Railroad Days, on May 17 and 18, 2025, in the Pullman neighborhood. Step inside elegant Pullman railroad cars from the early 20th century and learn about passenger trains, … [Read more...] about Pullman Railroad Days
Chicago Mayfest in Lincoln Park
Beer, food and cover bands are the hallmarks of the city's first festival of the summer, Chicago Mayfest. This year's 28th annual edition continues the tradition from May 16-18, 2025, in the Lincoln Park neighborhood. This year's fest will kick off at Armitage and Sheffield and … [Read more...] about Chicago Mayfest in Lincoln Park
Mole De Mayo Festival in Pilsen
Head to the historic Mexican neighborhood of Pilsen to explore the joys of the traditional chocolate-based dish of mole, at the 16th annual Mole De Mayo fest from May 24-26, 2025. Restaurants and chefs will offer their best recipes for the rich sauce served over enchiladas or meats … [Read more...] about Mole De Mayo Festival in Pilsen
Celebrate German Culture at Chicago Maifest
Welcome spring at the traditional German celebration of the season, Maifest Chicago. The 26th annual festival runs from May 29 to June 1, 2025, in the heart of Chicago's German community in Lincoln Square. Chow down on lots of German food and witness a traditional keg tapping, maypole … [Read more...] about Celebrate German Culture at Chicago Maifest
Timeout Market Chicago Easter Event
Hop over to Timeout Market Chicago for a family-friendly Easter at the Market event on April 20, 2025, in the West Loop neighborhood. Dress in your festive spring attire and join in the fun-filled activities. Hunt for eggs on the second floor of the market, sample tasty treats at … [Read more...] about Timeout Market Chicago Easter Event
Celebrate Spring with a Bonfire at Andersonville’s Valborg
Join the Swedish tradition of welcoming spring and banishing winter with a roaring bonfire, music, poetry, food and dance at the second annual Valborg in the Andersonville neighborhood on April 30, 2025. Sit around the bonfire and toss the worries you've written down into the flames to kick … [Read more...] about Celebrate Spring with a Bonfire at Andersonville’s Valborg
Chicago Rum Festival
Explore the varied tastes, histories and complexities of rum during the 8th annual Chicago Rum Festival in the Logan Square neighborhood on April 26, 2025. Rum connoisseurs, casual consumers and industry professionals will mingle at this annual event that includes rum tastings, workshops, … [Read more...] about Chicago Rum Festival
Norwood Park Egg Hunt
Put on your super-sleuth gear for this popular annual event that scatters 10k eggs for participants to discover. The Norwood Park Egg Hunt kicks off on Saturday, April 12, 2025, Pick up a map at the Depot and hop around from business to business around the corridor to search for eggs and … [Read more...] about Norwood Park Egg Hunt
