Location: Jack's Pumpkin Pop-up, West Le Moyne Street, Chicago, IL, USA See map: Google Maps Jack's Pumpkin Pop-UpDates: 10/03/202610/04/202610/05/2026Show more datesHide these dates10/06/202610/07/202610/08/202610/09/202610/10/202610/11/202610/12/202610/13/202610/14/202610/15/202610/16/202610/17/202610/18/202610/19/202610/20/202610/21/202610/22/202610/23/202610/24/202610/25/202610/26/202610/27/202610/28/202610/29/202610/30/202610/31/202611/01/2026Time: Timed Tickets from 5 - 9 pm weekdays; 12 - 9 pm weekends Location: Jerry Smith Pumpkin Farm, 7150 18th Street, Kenosha, WI 53144, United States See map: Google Maps Fall Fun at Jerry Smith Farm!Dates: 10/03/202610/04/202610/05/2026Show more datesHide these dates10/06/202610/07/202610/08/202610/09/202610/10/202610/11/202610/12/202610/13/202610/14/202610/15/202610/16/202610/17/202610/18/202610/19/202610/20/202610/21/202610/22/202610/23/202610/24/202610/25/202610/26/202610/27/202610/28/202610/29/202610/30/202610/31/202611/01/2026Time: See website for details. Location: Konow's Corn Maze, 16849 S Cedar Rd, Homer Glen, IL 60491, United States See map: Google Maps Fall Fest at Konow’sDates: 10/03/202610/04/202610/05/2026Show more datesHide these dates10/06/202610/07/202610/08/202610/09/202610/10/202610/11/202610/12/202610/13/202610/14/202610/15/202610/16/202610/17/202610/18/202610/19/202610/20/202610/21/202610/22/202610/23/202610/24/202610/25/202610/26/202610/27/202610/28/202610/29/202610/30/202610/31/2026Time: 10 am - 8 pm usually, but see below for exceptions Location: All Seasons Orchard, 14510 IL-176, Woodstock, IL 60098, United States See map: Google Maps Weekends at All Seasons Orchard: Entertainment, Apple Picking, Corn Maze, Barn Yard, and More!Dates: 10/03/202610/04/202610/10/2026Show more datesHide these dates10/11/202610/12/202610/17/202610/18/202610/24/202610/25/2026Time: 10 am - 5 pm Location: N. Lincoln Avenue between W. Lawrence and W. Sunnyside Avenues See map: Google Maps Lincoln Square Ravenswood 2026 Apple FestDates: 10/03/202610/04/2026Time: Friday, 3–7 PM | Saturday, 9 AM–6 PM | Sunday, 9 AM–6 PM Location: All Seasons Orchard, 14510 IL-176, Woodstock, IL 60098, United States See map: Google Maps Weekdays at All Seasons Orchard: Apple Picking, Corn Maze, and Barn Yard, and More!Dates: 10/05/202610/06/202610/07/2026Show more datesHide these dates10/08/202610/09/202610/12/202610/13/202610/14/202610/15/202610/16/202610/19/202610/20/202610/21/202610/22/202610/23/202610/26/202610/27/202610/28/202610/29/202610/30/2026Time: 10 am - 5 pm Location: Children's Museum in Oak Lawn, Museum Drive, Oak Lawn, IL, USA See map: Google Maps Fall Fun FestDates: 10/11/2026Time: 10:00 am - 3:00 pm Location: Chicago Architecture Center, 111 East Wacker Drive, Chicago, IL 60601, United States See map: Google Maps Open House Chicago 2026Dates: 10/17/202610/18/2026Time: See website for details. Location: Magnificent Mile, Chicago, IL, USA See map: Google Maps The Wintrust Magnificent Mile Lights Festival 2026Dates: 11/21/2026Time: all day - check the website for the full schedule
