Dive into the joy of the season with a visit to the Ravenswood Costume Crawl, filled with Halloween-themed fun, seasonal goods, treats and drinks on October 28, 2026. This thrill-filled event will transform Ravenswood's Montrose Avenue of shops and restaurants into a spooky space for sipping, … [Read more...] about Ravenswood Costume Crawl
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Haunted Halsted Halloween Parade
The ultimate Chicago Halloween celebration kicks off with the 30th Annual Haunted Halsted Halloween Parade and costume contest on October 31, 2026. Throw together your most creative, witty costume for the dramatic spectacle of the Haunted Halsted Halloween Parade. Prepare to see … [Read more...] about Haunted Halsted Halloween Parade
Chicago Free and Cheap Fall Events
After the close of the beloved Summertime Chicago season, the fun continues with a hearty lineup of activities that celebrate the flavors, scents and visions of fall. As the red and gold foliage reflects off the lake, the city vibrates with autumn fests, apple-picking events, Oktoberfest and artisan … [Read more...] about Chicago Free and Cheap Fall Events
Free World Music Wednesday Concerts
The new season for World Music Wednesday has been announced! Every Wednesday, through December 9, 2026, at 8:00 pm, the Old Town School of Folk Music will host a free concert series, World Music Wednesdays, featuring musicians from all around the world. Culture and countries represented … [Read more...] about Free World Music Wednesday Concerts
Jack’s Pumpkin Pop Up
Wander through pumpkin patches and corn mazes while you enjoy the season at Chicago's largest fall festival, Jack's Pumpkin Pop Up, located near Goose Island, from September 19 to November 1, 2026. The large number of all-ages festivities make Jack's one of the most popular fall excursions. … [Read more...] about Jack’s Pumpkin Pop Up
First Lady Fall Cruises
One of Chicago's most iconic experiences is sailing on the scenic Chicago Architecture Center (CAC) River Cruise aboard First Lady and absorbing the city's stunning skyline while learning about its design history. The fun continues through the fall, with cruises floating along the shore … [Read more...] about First Lady Fall Cruises
Riverwalk Fall Fest
Experience the beauty of the fall season with the Chicago River as the backdrop at the Island Party Hut Fall Fest on the Chicago Riverwalk on Saturdays, September 19- October 31, 2026. Enjoy autumn festivities like hay rides on the river, pumpkin patches and eating apple cider donuts along … [Read more...] about Riverwalk Fall Fest
Free Lincoln Park Zoo Fall Fest
Celebrate the joys of autumn in the fun-filled setting of Lincoln Park Zoo during the tenth annual Lincoln Park Zoo Fall Fest, September 25-November 1, 2026. Step into the vibrant world of pumpkins, harvest mazes and fall photo ops during this family-friendly event. Admission to the zoo is … [Read more...] about Free Lincoln Park Zoo Fall Fest
Cheap and Chic: $7 Cocktails at Cache 310
Chicago is filled with bars and lounges that deliver tasty but pricey drinks and cocktails. Patrons at downtown bars can expect to spend $14-$20 for basic mixed drinks but there's a new bar in town that offers style, a charming atmosphere and elevated cocktails for only $7. Inspired by … [Read more...] about Cheap and Chic: $7 Cocktails at Cache 310
Jazz in the Court
The Hyde Park neighborhood celebrates South Side jazz traditions with free outdoor concerts in Harper Court on the first Fridays of the summer months. Enjoy free live music in the heart of the historic community This year's dates are June 5, 2026. July 10, 2026, August 7, 2026, and September … [Read more...] about Jazz in the Court
Visit the Obama Presidential Center for Free
Chicago and the rest of the world are poised to visit the country's newest and most innovative presidential library. The Obama Presidential Center stands on 19.3 acres within Jackson Park on the South Side of the city, ready to welcome visitors and tell the riveting political and personal story … [Read more...] about Visit the Obama Presidential Center for Free
New Greektown Public Art Exhibit
Chicago's historic Greektown neighborhood will introduce a new public art exhibit, "We The People," on June 9, 2026, along Halsted Street between Madison and Van Buren Streets. Celebrating the 250th anniversary of the Declaration of Independence, 'We The People: Life, Liberty and the … [Read more...] about New Greektown Public Art Exhibit
Free Chicago Cultural Center Tours
Explore the neoclassical beauty of the historic Chicago Cultural Center during free tours every Thursday and Friday. Discover the fascinating history and landmark status of one of Chicago's most beloved architectural treasures. Nicknamed the "People's Palace," the building … [Read more...] about Free Chicago Cultural Center Tours
Free Instagreeter Downtown Tours
Explore Chicago with a knowledgeable local as your guide. This free service matches visitors with enthusiastic, city-wise volunteers for one-hour guided walks around downtown. Instagreeter Loop Walks are available all year round. Let a friendly local give you an insider’s perspective of … [Read more...] about Free Instagreeter Downtown Tours
2026 Free Chicago Museum Days
Chicago boasts an impressive number of acclaimed museums and cultural institutions. All across the city, there are museums to document the history and culture of various people, topics, and interests. Most of these public institutions feature free days at certain times of the year. Check out our … [Read more...] about 2026 Free Chicago Museum Days
