Introduction to Chicago’s Weekend Events
It feels like fall outside in the Chicago area, but there’s still plenty to do as residents look to enjoy the sunshine outdoors.
Taste of Chicago
Event Overview
WHAT: Since 1980, Taste of Chicago has been highlighting the city’s impressive array of eateries, along with plenty of entertainment.
WHERE: Grant Park, 331 E. Randolph St
WHEN: 11a.m. – 9p.m. on Sept. 5 – Sept. 7
German-American Oktoberfest
Event Details
WHAT: Chicago’s German-American Oktoberfest, hosted by the United German-American Societies of Greater Chicago, features tons of German music, food and drinks.
WHERE: 4521 Lincoln Ave (in the parking lot)
WHEN: 5p.m. – 10pm on Sept. 5; noon – 10p.m. on Sept. 6 & Sept. 7
Festival: Retro on Roscoe
Event Information
WHAT: The 30th annual Retro on Roscoe features live music across three stages, local restaurant food and drink a classic car show, and tons of fun for the kids.
WHERE: 2000 W. Roscoe Street, Chicago (Roscoe Village)
WHEN: 5p.m. – 10p.m. on Sept. 5; Noon – 8p.m. on Sept. 6; Noon – 8p.m. on Sept. 7
Printers Row Lit Fest
Event Description
WHAT: The 40th Annual Printers Row Lit Fest is billed as the largest free outdoor literary event in the Midwest.
WHERE: 620 S. Dearborn Street, Chicago (Printers Row)
WHEN: 10a.m. – 6p.m. on Sept. 6 & Sept. 7
Lyric Opera of Chicago: Sunday in the Park with Lyric
Event Details
WHAT: Sunday in the Park with Lyric, features performers from the Patrick G. and Shirley W. Ryan Opera Center are in concert with the Lyric Opera Orchestra.
WHERE: Millennium Park, 201 E Randolph St, Chicago
WHEN: 7p.m. on Sept. 7
Sundays on State
Event Overview
WHAT: Chicago Loop Alliance presents Sundays on State, a series of events designed to uplift the city’s iconic arts and culture, supports the Loop’s vital commerce and fosters community with Chicago’s 77 neighborhoods and beyond.
WHERE: On State Street, between Jackson and Randolph
WHEN: 11a.m. to 6p.m. on Sept. 7 & Oct. 5
Festival: The Miracle in Mundelein
Event Information
WHAT: Green Thumb Industries presents the return of The Miracle in Mundelein, a two-day music festival that features legal, on-site cannabis consumption.
WHERE: RISE MUNDELEIN, 1255 Armour Blvd, Mundelein IL
WHEN: 2p.m. – 10p.m. on Sept. 6; 12noon – 9p.m. on Sept. 7
Great American Dog Show
Event Details
WHAT: The Great American Dog Show brings together professional trainers and dog owners of 200 different dog breeds come to compete for the coveted title of Best In Show.
WHERE: Cantigny Park, 1S151 Winfield Road, Wheaton, IL
WHEN: 8a.m. to 6p.m. on Sept. 5 – Sept. 7
Escape the Museum
Event Description
WHAT: Griffin MSI is hosting 12 nights of "The Wandering Alchemist." This giant escape game asks you to find clues and solve puzzles as you explore the Museum after hours.
WHERE: Griffin Museum of Science and Industry, 5700 S. DuSable Lake Shore Drive, Chicago
WHEN: Select dates through October 2025 with entry times between 5:30–8:30 p.m.
Comedy: Wanda Sykes
Event Overview
WHO: Wanda Sykes, is an Emmy winning stand-up comic, writer, actress and producer who has been entertaining audiences for over twenty years.
WHERE: Hard Rock Northern Indiana, 5400 W 29th Ave, Gary, IN
WHEN: 7p.m. on Sept. 6
Concert: 10cc
Event Information
WHO: The 1970’s English pop rock band 10cc is an one of the UK’s most innovative and influential bands.
WHERE: Park West , 322 W Armitage Ave, Chicago
WHEN: 7:30p.m. on Sept. 5
Concert: Uncle Charlies R & B Cookout
Event Details
WHO: Charlie Wilson, Babyface, K-Ci Hayley and El DeBarge join forces for a concert, called Uncle Charlie’s R & B Cookout.
WHERE: Huntington Bank Pavilion at Northerly Island, 1300 S Linn White Dr, Chicago,
WHEN: 7:15p.m. on Sept. 6
Concert: Shemekia Copeland
Event Description
WHO: Shemekia Copeland, acclaimed American blues and soul vocalist, and known for her electrifying performances, and carries on the legacy of her father, Johnny Copeland.
WHERE: Old Town School of Folk Music, 4544 N Lincoln Avenue, Chicago
WHEN: 8p.m. on Sept. 5
Concert: Duo Lipa
Event Overview
WHO: Albanian singer songwriter Dua Lipa rose to fame with her dance pop hits, and brings her Radical Optimism Tour to Chicago
WHERE: United Center, 1901 West Madison Street, Chicago
WHEN: 7:30p.m. on Sept. 5 & Sept. 6
Concert: The Who
Event Information
WHO: Considered one of the greatest bands in rock history, The Who, brings their North American Farewell Tour to Chicago.
WHERE: United Center, 1901 West Madison Street, Chicago
WHEN: 7:30p.m. on Sept. 7
Conclusion
This weekend in Chicago offers a wide range of events and activities for all interests, from food and music festivals to concerts, dog shows, and literary events. Whether you’re a local or just visiting, there’s something for everyone to enjoy in this vibrant city.
FAQs
What events are happening in Chicago this weekend?
This weekend in Chicago features events such as Taste of Chicago, German-American Oktoberfest, Retro on Roscoe, Printers Row Lit Fest, and many more concerts and festivals.
Where can I find more information about these events?
For more information about the events mentioned, you can visit the official websites of the event organizers or check local listings for details on dates, times, and locations.
Are there any free events happening in Chicago this weekend?
Yes, some of the events mentioned are free, such as the Printers Row Lit Fest and Sundays on State. However, some events may require tickets or have a cover charge, so it’s best to check ahead of time.
