Music & Concerts in Chicago
LE SSERAFIM — PUREFLOW Tour
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| Who / What | LE SSERAFIM at United Center — 2026 LE SSERAFIM “PUREFLOW” Tour |
| When (Date) | October 2, 2026 |
| Where (Venue/ Location) | United Center, 1901 W Madison St, Chicago, IL 60612 |
| Start Time | 7:30 PM |
| Duration | Approx. 3 hours |
| How Many Days | 1 day |
| From | October 2, 2026 |
| To | October 2, 2026 |
| Price | Varies by seat/package |
| Website | United Center |
Doja Cat — Tour Ma Vie World Tour
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| Who / What | Doja Cat at United Center — Tour Ma Vie World Tour, with Latto |
| When (Date) | October 3, 2026 |
| Where (Venue/ Location) | United Center, 1901 W Madison St, Chicago, IL 60612 |
| Start Time | 7:30 PM |
| Duration | Approx. 3 hours |
| How Many Days | 1 day |
| From | October 3, 2026 |
| To | October 3, 2026 |
| Price | Varies by seat/package |
| Website | United Center event page |
Journey — Final Frontier Tour
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| Who / What | Journey at United Center — Journey: Final Frontier Tour |
| When (Date) | October 5, 2026 |
| Where (Venue/ Location) | United Center, 1901 W Madison St, Chicago, IL 60612 |
| Start Time | 7:30 PM |
| Duration | Approx. 3 hours |
| How Many Days | 1 day |
| From | October 5, 2026 |
| To | October 5, 2026 |
| Price | Varies by seat/package |
| Website | United Center event page |
Gorillaz — The Mountain Tour
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| Who / What | Gorillaz — The Mountain Tour, with Little Simz and Deltron 3030 |
| When (Date) | October 8, 2026 |
| Where (Venue/ Location) | United Center, 1901 W Madison St, Chicago, IL 60612 |
| Start Time | 7:30 PM |
| Duration | Approx. 3 hours |
| How Many Days | 1 day |
| From | October 8, 2026 |
| To | October 8, 2026 |
| Price | Varies by seat/package |
| Website | United Center |
Olivia Rodrigo — The Unraveled Tour
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| Who / What | Olivia Rodrigo — The Unraveled Tour, with Wolf Alice |
| When (Date) | October 11–12, 2026 |
| Where (Venue/ Location) | United Center, 1901 W Madison St, Chicago, IL 60612 |
| Start Time | 7:00 PM each night |
| Duration | Approx. 3 hours |
| How Many Days | 2 days |
| From | October 11, 2026 |
| To | October 12, 2026 |
| Price | Varies by seat/package |
| Website | United Center event page |
The Smashing Pumpkins — Rats in a Cage Tour
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| Who / What | The Smashing Pumpkins — Rats in a Cage Tour |
| When (Date) | October 14, 2026 |
| Where (Venue/ Location) | United Center, 1901 W Madison St, Chicago, IL 60612 |
| Start Time | 8:00 PM |
| Duration | Approx. 3 hours |
| How Many Days | 1 day |
| From | October 14, 2026 |
| To | October 14, 2026 |
| Price | Varies by seat/package |
| Website | United Center event page |
Food & Drink in Chicago
Oktoberfest Nation Chicago
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| Who / What | Oktoberfest Nation Chicago — German beer, Bavarian food, live music, carnival games and Devil’s Wheel |
| When (Date) | Oct. 1–24, 2026 — multiple ticketed sessions |
| Where (Venue / Location) | 171 N. Peoria St., Fulton Market, Chicago, IL 60607 |
| Start Time | Various — sessions begin from about 11:00 AM on weekends and 4:00–5:00 PM on weekdays |
| Duration | Varies; ticket is an arrival window and guests may stay during the event |
| How Many Days | 24 calendar days in the requested Oct. 1–24 window |
| From | Oct. 1, 2026 |
| To | Oct. 24, 2026 |
| Price | Varies by date/package |
| Website | Oktoberfest Nation Chicago |
SPIN Oktoberfest Celebration
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| Who / What | SPIN Oktoberfest Celebration — beer, bites, ping-pong, DJ, contests and Oktoberfest specials |
| When (Date) | Friday, Oct. 2, 2026 |
| Where (Venue / Location) | SPIN Chicago, 344 N. State St., Chicago, IL 60654 |
| Start Time | 8:00 PM |
| Duration | 3 hours |
| How Many Days | 1 day |
| From | 8:00 PM |
| To | 11:00 PM |
| Price | $10 |
| Website | SPIN Chicago official website |
Iconic Foods of Chicago Food Tour
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| Who / What | Iconic Foods of Chicago Food Tour — deep dish, Italian beef, Chicago popcorn, Chicago hot dog and a Chicago-style dessert |
| When (Date) | Oct. 3, 2026; recurring Saturdays through Jan. 10, 2027 |
| Where (Venue / Location) | Starts at Lou Malnati’s, 439 N. Wells St., Chicago |
| Start Time | 12:00 PM |
| Duration | 3 hours |
| How Many Days | 1 day per tour |
| From | 12:00 PM |
| To | 3:00 PM |
| Price | $85 ages 11+; $69 ages 6–10; under 5 free |
| Website | Chicago Food & City Tours |
Yes, Chef! Chicago — A Bear-Inspired Food Tour
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| Who / What | Yes, Chef! Chicago — food tour visiting restaurants and locations associated with The Bear, including Italian beef and Chicago culinary stops |
| When (Date) | Oct. 17, 2026; recurring Saturdays |
| Where (Venue / Location) | Ground Up Coffee & Bites, 363 W. Erie St., Chicago |
| Start Time | 11:00 AM |
| Duration | 3.5 hours |
| How Many Days | 1 day per tour |
| From | 11:00 AM |
| To | 2:30 PM |
| Price | $139 ages 6+; under 5 free |
| Website | Chicago Food & City Tours |
The Chinatown Adventure Food Tour
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| Who / What | Chinatown Adventure Food Tour — dim sum, Szechuan dishes, milk egg tarts and Chinese culinary/history experience |
| When (Date) | Oct. 10, 2026; recurring Saturdays |
| Where (Venue / Location) | Starts at Triple Crown, 2217 S. Wentworth Ave., Chicago |
| Start Time | 11:00 AM |
| Duration | 3 hours |
| How Many Days | 1 day per tour |
| From | 11:00 AM |
| To | 2:00 PM |
| Price | $99 ages 11+; $79 ages 6–10; under 5 free |
| Website | Chicago Food & City Tours |
Gateway to the West Loop Food Tour
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| Who / What | Gateway to the West Loop Food Tour — restaurants, craft breweries, food tastings and West Loop bars |
| When (Date) | Oct. 4, 2026; recurring Sundays |
| Where (Venue / Location) | Starts at Formento’s, 925 W. Randolph St., Chicago |
| Start Time | 1:00 PM |
| Duration | 3 hours |
| How Many Days | 1 day per tour |
| From | 1:00 PM |
| To | 4:00 PM |
| Price | $129 ages 21+; $99 ages 11–20; $79 ages 6–10 |
| Website | Chicago Food & City Tours |
Festivals & Cultural Events in Chicago
62nd Chicago International Film Festival
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| Who / What | 62nd Chicago International Film Festival — international competitive film festival with 150+ films, premieres, filmmaker Q&As and special events. |
| When (Date) | Oct. 14–25, 2026 |
| Where (Venue / Location) | Multiple Chicago venues |
| Start Time | Varies by screening |
| Duration | 12 days |
| How Many Days | 12 days |
| From | Oct. 14, 2026 |
| To | Oct. 25, 2026 |
| Price | Individual tickets generally $18; special events vary. Festival passes also available. |
| Website | Chicago International Film Festival |
Black Alphabet Film Festival – Chicago
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| Who / What | Black Alphabet Film Festival – Chicago — Black LGBTQ+ film festival featuring features, shorts, artist talkbacks and closing-night programming. (Black Alphabet) |
| When (Date) | Oct. 16–18, 2026 |
| Where (Venue / Location) | AMC Roosevelt Collection 16, 1011 S. Delano Ct. E.; Jamii Center, 3850 S. Indiana Ave. |
| Start Time | Varies by screening |
| Duration | 3 days |
| How Many Days | 3 days |
| From | Oct. 16, 2026 |
| To | Oct. 18, 2026 |
| Price | Ticket price varies by screening; reservations are required. |
| Website | Black Alphabet Film Festival |
Black Harvest Film Festival
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| Who / What | 32nd Black Harvest Film Festival — Chicago showcase of Black cinema from across the diaspora, with feature films, shorts, special programs and filmmaker events. |
| When (Date) | Nov. 6–15, 2026 |
| Where (Venue / Location) | Gene Siskel Film Center, 164 N. State St., Chicago |
| Start Time | Varies by film/program |
| Duration | 10 days |
| How Many Days | 10 days |
| From | Nov. 6, 2026 |
| To | Nov. 15, 2026 |
| Price | Varies by screening/special event; current programs are individually ticketed. |
| Website | Black Harvest Film Festival |
Arts, Exhibitions & Shows in Chicago
Bill Burr Live — stand-up comedy
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| Who / What | Bill Burr Live — stand-up comedy |
| When (Date) | Oct. 2–3, 2026 |
| Where (Venue / Location) | The Chicago Theatre, 175 N State St, Chicago, IL 60601 |
| Start Time | Oct. 2: 7:30 PM; Oct. 3: 7:00 PM & 10:00 PM |
| Duration | Not specified on current listing |
| How Many Days | 2 days |
| From | Oct. 2, 2026 |
| To | Oct. 3, 2026 |
| Price | Varies by seat |
| Website | The Chicago Theatre |
Operation Mincemeat: A New Musical
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| Who / What | Operation Mincemeat: A New Musical — award-winning musical comedy based on the WWII deception operation |
| When (Date) | Sep. 29–Oct. 11, 2026; performances after Oct. 1 qualify |
| Where (Venue / Location) | CIBC Theatre, 18 W Monroe St, Chicago, IL 60603 |
| Start Time | Multiple performances; e.g. 7:00 PM Oct. 2, 2:00 & 7:30 PM Oct. 3 |
| Duration | 2 hr 35 min, including intermission |
| How Many Days | 13-day run |
| From | Sep. 29, 2026 |
| To | Oct. 11, 2026 |
| Price | Varies by performance/seat |
| Website | Broadway In Chicago |
Jerry Seinfeld — live stand-up comedy
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| Who / What | Jerry Seinfeld — live stand-up comedy |
| When (Date) | Oct. 9–10, 2026 |
| Where (Venue / Location) | The Chicago Theatre, 175 N State St |
| Start Time | Oct. 9: 7:00 PM; Oct. 10: 5:00 PM & 8:00 PM |
| Duration | Not specified on current listing |
| How Many Days | 2 days |
| From | Oct. 9, 2026 |
| To | Oct. 10, 2026 |
| Price | Varies by seat |
| Website | The Chicago Theatre |
The Winter’s Tale
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| Who / What | The Winter’s Tale — Shakespeare theatrical production |
| When (Date) | Oct. 13–Dec. 12, 2026 |
| Where (Venue / Location) | Chicago Shakespeare Theater, Navy Pier, 800 E Grand Ave, Chicago |
| Start Time | Multiple performances; generally 7:00 PM evenings and 1:00/2:00 PM matinees |
| Duration | Check performance listing; varies by production schedule |
| How Many Days | 61 calendar days in the run; performed in repertory |
| From | Oct. 13, 2026 |
| To | Dec. 12, 2026 |
| Price | Varies by seat/date; packages also available |
| Website | Chicago Shakespeare Theater |
The Book of Mormon
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| Who / What | The Book of Mormon — Tony Award-winning musical comedy |
| When (Date) | Oct. 23–Nov. 1, 2026 |
| Where (Venue / Location) | Cadillac Palace Theatre, 151 W Randolph St, Chicago |
| Start Time | Multiple performances; evenings generally 7:00–7:30 PM, matinees 1:00–2:00 PM |
| Duration | 2 hr 35 min, including intermission |
| How Many Days | 10 days |
| From | Oct. 23, 2026 |
| To | Nov. 1, 2026 |
| Price | Varies by seat |
| Website | Broadway In Chicago |
Nikki Glaser: The Stunning Tour
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| Who / What | Nikki Glaser: The Stunning Tour — live stand-up comedy |
| When (Date) | Nov. 13–14, 2026 |
| Where (Venue / Location) | The Chicago Theatre, 175 N State St, Chicago |
| Start Time | 7:00 PM both dates |
| Duration | Not specified on current listing |
| How Many Days | 2 days |
| From | Nov. 13, 2026 |
| To | Nov. 14, 2026 |
| Price | Varies by seat |
| Website | The Chicago Theatre |
Sports in Chicago
Chicago Bears vs. New York Jets
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| Who / What | Chicago Bears vs. New York Jets — NFL regular-season game |
| When (Date) | Sunday, October 4, 2026 |
| Where (Venue / Location) | Soldier Field, 1410 Special Olympics Dr., Chicago, IL 60605 |
| Start Time | 12:00 PM CDT |
| Duration | Approx. 3–3.5 hours |
| How Many Days | 1 day |
| From | 12:00 PM |
| To | Approx. 3:15–3:30 PM |
| Price | Varies by seat/market |
| Website | Chicago Bears official website |
Chicago Blackhawks vs. St. Louis Blues
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| Who / What | Chicago Blackhawks vs. St. Louis Blues — NHL regular-season home opener |
| When (Date) | Tuesday, October 6, 2026 |
| Where (Venue / Location) | United Center, 1901 W. Madison St., Chicago, IL 60612 |
| Start Time | 7:00 PM CDT |
| Duration | Approx. 2.5–3 hours |
| How Many Days | 1 day |
| From | 7:00 PM |
| To | Approx. 9:30–10:00 PM |
| Price | Varies by seat |
| Website | Chicago Blackhawks official website |
Chicago Fire FC vs. Vancouver Whitecaps FC
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| Who / What | Chicago Fire FC vs. Vancouver Whitecaps FC — MLS soccer |
| When (Date) | Tuesday, October 6, 2026 |
| Where (Venue / Location) | Soldier Field, Chicago |
| Start Time | 7:30 PM CDT |
| Duration | Approx. 2 hours |
| How Many Days | 1 day |
| From | 7:30 PM |
| To | Approx. 9:30 PM |
| Price | Varies by seat |
| Website | Chicago Fire FC official website |
Chicago Bulls vs. Phoenix Suns
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| Who / What | Chicago Bulls vs. Phoenix Suns — 2026 NBA preseason |
| When (Date) | Wednesday, October 7, 2026 |
| Where (Venue / Location) | United Center, 1901 W. Madison St., Chicago |
| Start Time | 7:00 PM CDT |
| Duration | Approx. 2.5–3 hours |
| How Many Days | 1 day |
| From | 7:00 PM |
| To | Approx. 9:30–10:00 PM |
| Price | Varies by seat |
| Website | Chicago Bulls official website |
Chicago Fire FC vs. New York City FC
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| Who / What | Chicago Fire FC vs. New York City FC — MLS soccer; Anime Day/Naruto-themed match |
| When (Date) | Saturday, October 10, 2026 |
| Where (Venue / Location) | Soldier Field, Chicago |
| Start Time | 1:30 PM CDT |
| Duration | Approx. 2 hours |
| How Many Days | 1 day |
| From | 1:30 PM |
| To | Approx. 3:30 PM |
| Price | Varies by seat |
| Website | Chicago Fire FC official website |
Chicago Blackhawks vs. Carolina Hurricanes
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| Who / What | Chicago Blackhawks vs. Carolina Hurricanes — NHL regular-season game |
| When (Date) | Saturday, October 10, 2026 |
| Where (Venue / Location) | United Center, 1901 W. Madison St., Chicago |
| Start Time | 6:00 PM CDT |
| Duration | Approx. 2.5–3 hours |
| How Many Days | 1 day |
| From | 6:00 PM |
| To | Approx. 8:30–9:00 PM |
| Price | Varies by seat |
| Website | Chicago Blackhawks official website |