Celebrate Polish culture at the largest Polish festival in the country, Taste of Polonia, scheduled for September 4-7- 2026. The 44th-anniversary festival brings four days of traditional Polish food, music and crafts. The Taste of Polonia festival serves up live music on four stages, art … [Read more...] about Taste of Polonia
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World Dumpling Fest
Explore Chicago's diverse cultures with music, dance and samples of all the variations of ethnic dumplings during the annual World Dumpling Fest on September 19-20, 2026, in the Lincoln Park neighborhood. The Chicago Cultural Alliance hosts the sixth annual World Dumpling Fest to support and … [Read more...] about World Dumpling 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
Get $7 Meal Deal (includes sundae!) at Dairy Queen
For those who enjoy their meal with a cool treat, Dairy Queen has the perfect option to satisfy their craving for something a little sweet. Even sweeter, it’s at a bargain price! Bundled meal deals usually only include an entrée, side and drink — never any dessert. That’s what makes this meal … [Read more...] about Get $7 Meal Deal (includes sundae!) at Dairy Queen
Free and cheap things to do this weekend in Chicago
Looking for something fun to do this weekend in Chicago? There are tons of free and cheap events in the city. Here’s our list of the top free events, discounts, and deals to have fun around town on your Friday, Saturday, and Sunday. There are many diverse events, so choose your favorite. … [Read more...] about Free and cheap things to do this weekend in Chicago
Randolph Street Market Festival
One of the most beloved events of the fall season is Chicago's signature open-air market, the Randolph Street Market Festival. Filled with vintage treasures, live bands, food and fun, the market opens on September 26- 27, 2026, in the West Loop. Celebrating 23 years, the Randolph Street … [Read more...] about Randolph Street Market Festival
Free Chicago World Music Festival
The 26th annual World Music Festival Chicago is a city-wide, multi-venue festival presenting over 30 artists and ensembles from 22 countries around the globe, presented for free over 10 days from September 25 to October 4, 2026. Dance to the rhythms and melodies of musicians from all … [Read more...] about Free Chicago World Music Festival
Renegade Craft Fair Chicago
The iconic Renegade Craft Fair celebrates 23 years with a fall market featuring over 400 artists, designers and creatives on September 12-13, 2026, in the Wicker Park neighborhood. Support local and national small businesses with a visit to the fair, which showcases a big … [Read more...] about Renegade Craft Fair Chicago
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
Englewood Jazz Fest
The 27th annual Englewood Jazz Festival presents an exciting line-up of established and emerging Chicago musicians for three days in the Englewood community on September 17-19, 2026. Live the Spirit Residency at Hamilton Cultural Center educates and mentors the next generation of jazz … [Read more...] about Englewood Jazz Fest
Retro on Roscoe Festival
Go back in time and enjoy oldies and throwback fashion at the 29th annual Retro on Roscoe festival on September 18-20, 2026, in the Roscoe Village neighborhood. Groove to music on three stages, including a family stage, within a six-block stretch of Roscoe Village. Enjoy music from … [Read more...] about Retro on Roscoe Festival
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
Enjoy daily Blizzard buy-one-get-one special at Dairy Queen in August
What’s the forecast for bargain hunters and DQ fans? There’s a blizzard of savings at Dairy Queen this month! It’s just not summer without enjoying one of the ice cream shop’s signature (and iconic) menu items — the Blizzard Treat. Image: Dairy Queen And fans have just a few more … [Read more...] about Enjoy daily Blizzard buy-one-get-one special at Dairy Queen in August
Edgewater Music Fest
Visit the vibrant Edgewater community to experience a free, three-day festival of live music, food and elite vibes, during the annual Edgewater Music Fest from August 28-30, 2026. Enjoy two stages featuring over 35 local music acts, 100 vendors selling art, crafts, jewelry, and clothes and an … [Read more...] about Edgewater Music Fest
Free Chicago Jazz Festival
Since 1974, jazz fans from all over the globe have flocked to Chicago for the annual Chicago Jazz Festival, which showcases jazz legends as well as up-and-coming musicians. This year's four-day festival will run from September 3-6 2026. Celebrate jazz in all its forms in Millennium Park and … [Read more...] about Free Chicago Jazz Festival
