The fun and creativity of chalk art will transform Rogers Park's Howard Street during the annual Chalk Howard Street on August 22, 2026. This free event hosts internationally renowned 2D and 3D artists from around the country Chalk Street Howard is Chicago's only chalk fest … [Read more...] about Chalk Howard Street
Chicago festivals
Taste of Greektown
Chicago's largest celebration of Hellenic culture returns for the 36th annual Taste of Greektown on August 28--30, 2026. Head to the historic Greektown neighborhood to savor Greek food, music and warm hospitality. The hallmark of Taste of Greektown is sampling dishes from the … [Read more...] about Taste of Greektown
Glenwood Avenue Arts Fest
The Rogers Park neighborhood will host the highly anticipated Glenwood Avenue Arts Fest on August 14-16, 2026. Chicago's most diverse community will showcase free live music, art, creative performances, food and crafts by an eclectic array of artists and artisans. Over 120 … [Read more...] about Glenwood Avenue Arts Fest
Chicago House Music Festival and Conference
As the birthplace of house music, Chicago always celebrates and honors this influential art form. The Chicago House Music Festival and Conference will bring the music, history and culture of house music into focus on August 27-30, 2026. The four days of free events will feature live … [Read more...] about Chicago House Music Festival and Conference
Northalsted Market Days
The largest street festival in the Midwest returns to the bustling Lakeview neighborhood for a three-day celebration of music, pride and community. Northalsted Market Days is scheduled for August 7-9, 2026. The 44th annual festival kicks off with over 250 vendors, five stages and all-day … [Read more...] about Northalsted Market Days
Taste of Lincoln Avenue
One of Chicago's most beloved street fests, Taste of Lincoln Avenue, returns to thrill foodies and music lovers alike on July 24-26, 2026. Taking over the intersection of Fullerton and Lincoln Ave., the 42nd annual fest is one of the highlights of the Chicago summer season. Food, arts and … [Read more...] about Taste of Lincoln Avenue
Chinatown Summer Fair
The dynamic colors and traditions of Chinese culture will be the highlight of the Chinatown Summer Fair, scheduled for July 25-26, 2026. This free, family-friendly event offers food, arts and crafts and entertainment for everyone in the historic Chinatown neighborhood. The fair … [Read more...] about Chinatown Summer Fair
Taste of River North
Sample a delicious selection of River North's popular restaurants, dance to live music and absorb the joys of summer at the annual Taste of River North on July 17-18, 2026. This two-day food fest supplies chances to try neighborhood eateries like Lure Fish Bar, Seoul Taco and ,Fogo de Chao, … [Read more...] about Taste of River North
Barrio Arts Festival
The signature festival of the National Museum of Puerto Rican Arts & Culture, the Barrio Arts Fest, returns to Humboldt Park on July 11-12,2026. Immerse yourself in the richness of Puerto Rican culture during this highly anticipated free festival on the grounds of the museum. Dance to the … [Read more...] about Barrio Arts Festival
Chicago Gospel Music Festival
Enjoy the spirit-filled gospel music genre that was created in Chicago at the annual Gospel Music Festival on July 24-25, 2026, in Millennium Park. This beloved fest draws fans from all over the country to hear some of gospel's greatest voices at this free event. A cherished Chicago tradition … [Read more...] about Chicago Gospel Music Festival
Square Roots Festival
Music lovers rejoice, the return of Old Town School of Folk Music's Square Roots Festival is set for July 10-12, 2026. This free, family-friendly music fest celebrates music from around the globe as well as the popular Lincoln Square community. This year's artist line-up of two … [Read more...] about Square Roots Festival
Taste of Chicago
The legendary summer food festival that spawned dozens of similar events across the city, the Taste of Chicago, returns to Grant Park for a showcase of Chicago's culinary diversity on July 8-12 2026. As the biggest free culinary festival in the country, the Taste of Chicago opens in … [Read more...] about Taste of Chicago




















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 