Chicago Live at Navy Pier

Chicago Live returns to Navy Pier on Saturday, September 19 and Sunday, September 20, 2026, from noon to 6pm each day. Navy Pier bills it as the Midwest’s largest free performing arts festival, with live music, dance, theater and multidisciplinary performances along the lakefront. No ticket is required. Listing compiled by Stumblday, an independent city event guide. Photo of Navy Pier by Moses8910

Also in Downtown, the Loop & West Loop

Chicago Bears vs. Minnesota VikingsSun, Sep 20, 2026 · 12:00pmSoldier Field, Museum Campus, Downtown, the Loop & West LoopOne Day Only

Dirty Dancing (Chicago)Sep 9–20, 2026; closes Sun, Sep 20, 2026James M. Nederlander Theatre, 24 W Randolph, Downtown, the Loop & West LoopLimited Run

Atsuko Okatsuka – The Big Bowl TourFriday, September 18, 2026, 8:00 p.m.The Chicago Theatre, The Loop, Downtown, the Loop & West LoopOne Weekend Only

Fall Magnificent Mile Art FestivalSaturday, September 19 and Sunday, September 20, 2026, 10:00 AM–5:00 PM both days875 North Michigan Avenue plaza, Magnificent Mile, Downtown, the Loop & West LoopFree admissionOne Weekend Only

Chicago White Sox vs. Detroit Tigers – Cole Swindell Postgame ConcertFri, Sep 18, 2026 · 6:40pmRate Field, Downtown, the Loop & West LoopOne Weekend Only

More festivals this weekend

Riot Fest 2026 - SaturdaySat, Sep 19, 2026 · 11:00amDouglass Park, 1401 S Sacramento Dr., Pilsen, West Town & the West SideOne Day Only

Riot Fest 2026 - FridayFriday, September 18, 2026, 11:00 a.m.Douglass Park, North Lawndale, Pilsen, West Town & the West SideOne Day Only

The 27th Anniversary Englewood Jazz FestivalSeptember 17–19, 2026; Thursday and Friday sets from 5:30 p.m. indoors, Saturday noon–6 p.m. outdoorsHamilton Park and Cultural Center, Hyde Park, Bronzeville & the South SideFreeOne Weekend Only

Annual Lakeview East Festival of the ArtsSeptember 19–20, 2026; Saturday 11 a.m.–7 p.m. (music, food and drink through 10 p.m.); Sunday 11 a.m.–7 p.m.North Broadway, Lincoln Park, Lakeview & Wrigleyville$5 suggested donationFree

Old Town Oktoberfest on Wells StreetSep 18–20, 2026; Fri 5–10 p.m., Sat 11 a.m.–10 p.m., Sun 11 a.m.–8 p.m.1360 N Wells St – Wells Street between Schiller and Evergreen, Downtown, the Loop & West LoopOne Weekend Only

See the full ranked weekend board →