Concerts, festivals, food, art, and more happening soon.
Explore upcoming events and local discoveries in Chicago, across every kind of experience. Check each listing for confirmed dates, times, and its official source.
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5:00pm - 7:00pm
Weekly
Picnic Wine & Provisions · Rogers Park
Taste four small pours at this Thursday wine night. The $10 tasting fee is credited toward a bottle purchased that evening; Wine Club members taste free.
12:00pm - 4:00pm
Weekly
Vin Chicago · Bucktown
Explore a changing selection of wines at the Chicago shop’s Saturday tasting, held from noon to 4pm.
5:00pm
October 9, 2026
Jonquil Park · Lincoln Park
Choose a ticketed two-hour wine tasting session at Jonquil Park. Friday sessions run 5–7pm and 8–10pm. Tickets are specific to the day and session; ages 21 and over with valid ID.
11:00am
October 10, 2026
Jonquil Park · Lincoln Park
Choose a ticketed two-hour wine tasting session at Jonquil Park. Saturday sessions run 11am–1pm, 2–4pm, 5–7pm, and 8–10pm. Tickets are specific to the day and session; ages 21 and over with valid ID.
11:00am
October 11, 2026
Jonquil Park · Lincoln Park
Choose a ticketed two-hour wine tasting session at Jonquil Park. Sunday sessions run 11am–1pm, 2–4pm, and 5–7pm. Tickets are specific to the day and session; ages 21 and over with valid ID.
6:00pm - 8:00pm
October 24, 2026
Columbus Dr. & Balbo Dr. · The Loop
Chicago’s nighttime Halloween parade returns to Columbus Drive with illuminated floats, spectacle puppets, creative costumes, music, dance, food trucks, and family-friendly performance. The free procession steps off at Balbo Drive and travels north toward Jackson Boulevard.
9:00am
October 13, 2026
mHUB · Fulton Market
Chicago Fashion Week’s one-day Fashion Summit brings designer and entrepreneur Elie Tahari to mHUB for a keynote plus sessions, showcases, and networking focused on the Midwest fashion ecosystem. Check-in begins at 7:30am and programming starts at 9am.
Oct 7 5:00pm; Oct 8-9 11:00am; Oct 10 11:00am
October 7-10, 2026
THE MART · River North
The inaugural Chicago Art Fair brings contemporary and modern galleries to THE MART for a four-day run. The event listing confirms October 7 through 10 sessions with daily hours and THE MART as the venue.
10:00am - 5:00pm
October 17-18, 2026
Chicago Architecture Center · Citywide
Open House Chicago returns with free behind-the-scenes access to more than 200 architecture, culture, and community sites. The 2026 program is scheduled for October 17 and 18, with participating sites and neighborhood itineraries listed by the Chicago Architecture Center.
7:00pm
October 18, 2026
Zhou B Art Center · Bridgeport
Close out Chicago Fashion Week with this ticketed runway experience blending designer collections, live entertainment, and visual production. Doors and lounge access begin at 5pm, with showtime at 7pm at Zhou B Art Center.
8:00am
October 9-November 1, 2026
Lincoln Park Zoo · Lincoln Park
Lincoln Park Zoo brings back its free family Fall Fest with harvest-season activities, seasonal displays, and daytime festival programming. The Choose Chicago series lists Friday through Monday opening weekend and Friday-to-Sunday dates through November 1, all from 8am to 5pm.
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