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
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Buckingham Fountain Opening Day Events
Chicago's official start of the summer season always coincides with the spectacular splash of the first drops of the iconic Buckingham Fountain. This year's Switch on Summer Kick Off at Buckingham Fountain is set for May 10, 2025. Head to the fountain at 331 E. Randolph from 11:30 … [Read more...] about Buckingham Fountain Opening Day Events
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
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
Andersonville Farmers Market
Wander through one of the city's most colorful markets at Andersonville Farmers Market, running from May 14 to October 22, 2025. Featuring more than 50 vendors, everything sold at the Andersonville Farmers Market is grown or produced within a 200-mile radius, offering the community access to fresh, … [Read more...] about Andersonville Farmers Market
Free and Cheap Easter Events
Easter in Chicago always brings excitement and hope, not just for the holiday but for the warmer weather of the spring season. Easter falls on Sunday, April 20, 2025, this year and events include a variety of Easter egg hunts, photo opps, parties and food specials. Most … [Read more...] about Free and Cheap Easter Events
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
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
Enjoy A Free Latin Jazz Concert
Head to the Humboldt Park neighborhood for a sizzling free concert of Latin jazz music with award-winning musician Richard Pena at the Segundo Ruiz Belvis Cultural Center on April 12, 2025. Richard Pena will perform the world premiere of his new album, "The Latin Side of Jazz Guitar," which … [Read more...] about Enjoy A Free Latin Jazz Concert
