The TL;DR:
- The Big Weekend: Chicago's calendar for September 25 to 27 is stacked with neighborhood festivals and fall pop-ups.
- Festival Lineup: The 20th Annual Hyde Park Jazz Festival, an Oktoberfest in West Lakeview, and a pumpkin patch pop-up in Goose Island all run this weekend.
- What's New: The Art Institute is showing the first Norman Rockwell painting ever added to its collection, and it features the Chicago Cubs.
Chicago is easing into fall this weekend, and the city is not slowing down to do it. From September 25 to 27, neighborhoods across town are hosting everything from a 20-year-old jazz festival to a pumpkin patch with three full bars.
Whether you want live music on a lawn blanket, a stein of cold beer, or a quiet afternoon with a new piece of Cubs history, there is a version of this weekend built for every kind of local.
🎷 Music and Neighborhood Festivals
Hyde Park hosts its 20th Annual Jazz Festival on Saturday, September 26 and Sunday, September 27 at the Midway Plaisance.
The lineup includes Joshua Redman, Alfredo Rodriguez, Emmett Cohen, and Tomeka Reid, and the vibe is soulful and community-centric. Bring a lawn blanket and a picnic.
Over in West Lakeview, Oktoberfest at Historic St. Alphonsus Church runs Friday, September 25 through Sunday, September 27, with bratwurst, live music, and steins of German beer.
Admission is free, though a $5 to $10 donation is encouraged. Meanwhile, Union Park in the West Loop kicks off the International Festival of Life & JSVFest on Friday.
🎃 Fall Shopping and Pumpkin Season
If shopping is more your speed, Randolph Street Market in the West Loop runs Saturday, September 26 and Sunday, September 27 at 1341 W. Randolph Street.
Expect dozens of curated stalls of antiques, vintage clothing, and artisan goods, plus food and drink vendors scattered throughout. General entry starts at $14.
For something more autumnal, Jack's Pumpkin Pop-Up at 1265 West Le Moyne Street in Goose Island is open all weekend. It bills itself as Chicago's largest pumpkin patch pop-up, complete with a corn maze, axe throwing, fall treats, and three full bars on the property.
🎠Art, Theater, and More to Add to the List
The Harris Theater for Music and Dance hosts a bolero concert on Friday, September 25 at 8:00 PM, its second annual series celebrating the genre, featuring Grammy-winning Chicana artist Martha Gonzalez alongside pianist Marco Antonio Godoy and a performance by Voz Bohemia.
At the Art Institute of Chicago, the American Wing is now showing the very first Norman Rockwell painting ever added to the museum's collection, and it depicts the Chicago Cubs. It's on view all weekend, and the Drawing Room lounge inside the Chicago Athletic Association across the street is a good spot to unwind afterward.
There is plenty more if you're still looking. Chicago Gourmet's Grand Cru brings a rooftop tasting with chefs Stephanie Izard, Sarah Grueneberg, and Art Smith, while Gallagher Way near Wrigley Field hosts Wing Out with live R&B and soul.
Pilsen's Sabor Fest adds a new Rave Edition blending regional Mexican music with EDM, and the Beverly Art Walk brings over 150 artists across 43 venues for its 13th year. Friday night alone also brings Teddy Swims at the United Center, SOFI TUKKER at Northerly Island, and Martin Lawrence at the Arie Crown Theater.
The Local’s Guide
- Price Range: $5 to $10 donation suggested at Oktoberfest, general entry starts at $14 at Randolph Street Market.
- Insider Tip: For the Hyde Park Jazz Festival, bring a lawn blanket and a picnic.
Which one is making your weekend list, the jazz fest, the pumpkin patch, or the Rockwell painting? Tell us over on the HeyChicago social pages!
