Celebrate Poetry Month and all the notable literary stars that Chicago has birthed at the 27th annual Chicago Poetry Fest at the Harold Washington Library on April 27, 20226. Enjoy a day of free poetry events for all ages and backgrounds at this engaging event. Attend poetry workshops, listen … [Read more...] about Chicago Poetry Festival
spring events
View Cherry Blossoms in Chicago
The delicate blooms of cherry blossom trees are a beloved marker of the spring season but you don't have to travel to Japan to enjoy them. Chicago's cherry blossom season typically runs from late April to early May in Jackson Park. Head to Hyde Park and the Garden of the … [Read more...] about View Cherry Blossoms in Chicago
Lincoln Park Conservatory Spring Flower Show
Even though the winter still lingers in Chicago, you can pretend Spring is already here at the annual Lincoln Park Conservatory Spring Flower Show. The 2026 show is called "Jewels of Spring" and runs through May 10, 2026. Take in the beauty of flowers and plants and the color … [Read more...] about Lincoln Park Conservatory Spring Flower Show
Jarvis Square Egg Hunt and Live Music
Head to Rogers Park to celebrate the spring season with an egg hunt around Jarvis Square, accompanied by high-energy live music with a fun-filled Jarvis alfresco event on April 4, 2026. Stroll around the lively block between Jarvis and Greenview and enjoy refreshments from local restaurants, … [Read more...] about Jarvis Square Egg Hunt and Live Music
Chicago Hosts International Jazz Day with Free Concerts and Events
Commemorating 15 years of jazz music's role in fostering peace and intercultural dialogue, International Jazz Day is celebrated in 190 countries around the globe. On April 30, 2026, Chicago will host an all-star global concert, directed by the city's own and International Jazz Day founder, Herbie … [Read more...] about Chicago Hosts International Jazz Day with Free Concerts and Events
Discounted Tickets at the Chicago Latino Film Festival
The variety and broad appeal of Latin American cinema will be showcased during the 42nd annual Chicago Latino Film Festival from April 16-27, 2026. Viewers will be transported to Ecuador, Venezuela, Brazil, Puerto Rico, Argentina and many other countries during this exciting … [Read more...] about Discounted Tickets at the Chicago Latino Film Festival
One of a Kind Spring Show
Get ready for spring by browsing handmade home goods, art, clothing, jewelry, gourmet products and more at the One of a Kind spring show at theMART, April 24-26, 2026. Explore the work of over 350 artists and designers from all over North America during the annual spring show. This is an … [Read more...] about One of a Kind Spring Show
Kentucky Derby Celebration at Time Out Market
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
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 on the Cheap is a member of Living on the Cheap, a network of websites published by frugalistas, journalists and consumer advocates. Find practical advice on saving money on groceries, travel and shopping, plus tips from our experts on how to live the good life for less at 