Jazz in the South Loop, market mornings in the West Loop, art along the river and a free spooky Saturday at Navy Pier.

Venue image: Jazz Showcase. General music imagery, not the scheduled performers.

Give the week before Halloween a little range. From Friday, October 23, through Thursday, October 29, downtown Chicago offers a mix of music, movies, market shopping and museum time. Our neighborhood guide includes both weekend outings and reasons to leave the house after Monday.

South Loop: make it a jazz night

The Lenard Simpson Quartet plays Jazz Showcase, 806 S. Plymouth Court, during a run that includes October 23–25. The venue lists Friday and Saturday sets at 8 and 10 p.m., plus Sunday performances at 4 and 8 p.m. General admission for Friday through Sunday is listed at $30; VIP preferred seating is $45. Choose the specific performance when booking. Performance details and tickets →

The music continues during the workweek: the calendar lists the Bob Lark Septet on Monday, October 26, at 8 p.m.; a WDCB fundraising concert with the Isaiah Spencer Quartet paying tribute to John Coltrane on Tuesday, October 27, at 8 p.m.; and Sabertooth Organ Quartet on Wednesday, October 28, at 8 p.m. Check each event’s ticket page for admission and seating. Browse the week’s calendar →

On Thursday, October 29, the Mike Stern Quintet begins its engagement, with the venue listing Thursday sets at 8 and 10 p.m. Thursday admission is $35 general or $50 VIP. The engagement continues beyond this roundup’s dates; select October 29 when purchasing. Mike Stern tickets →

Image: Green City Market. Archival September 2020 photograph; venue context.

West Loop: start Saturday at the market

Green City Market returns to Mary Bartelme Park, 900 W. Monroe Street, on Saturday, October 24, from 8 a.m. to 1 p.m. The market’s seasonal offerings include apples, pears, winter squash, greens, breads and prepared foods. Make it a relaxed morning: bring a shopping bag and leave room for something to eat along the way. Vendor attendance can change. October 24 calendar listing → Location and visitor information →

Streeterville: a little spooky, a lot to do

Navy Pier’s Slightly Spooky October brings free activities to Crystal Gardens on Saturday, October 24. Science demonstrations, crafts and other activities run 1–5 p.m.; short films begin at 5 p.m., followed by WALL-E at 5:30 p.m. and Scream at 7:30 p.m. Choose the film appropriate for your group—the evening horror selection differs sharply from the earlier family option.

Bring a blanket or chair, as the organizer suggests. The Pier is at 600 E. Grand Avenue. Food, parking and separately ticketed attractions are additional expenses. See the official schedule →

River North: sculpture, then the river

The Driehaus Museum’s Emma Stebbins: Carving Out History examines the nineteenth-century sculptor’s career through marble works, paintings and archives. Visit at 50 E. Erie Street on October 23–25 or 28–29. Regular hours are 11 a.m.–5 p.m., with Wednesday extended to 7 p.m.; the museum closes Mondays and Tuesdays.

Adult admission is $23. Wednesday, October 28, offers Pay What You Wish from 4–7 p.m., with last entry at 6 p.m. Explore the exhibition → Hours and admission →

ART on THE MART adds an outdoor option at the River North/Loop edge. Projections run 7:30–8 p.m. on October 23, 24, 25 and 29, following the organizer’s Thursday-through-Sunday fall schedule. View from the Riverwalk between Wells and Franklin streets; the display lights up THE MART across the river. Viewing details →

The Loop: catch the festival on Friday

The Gene Siskel Film Center’s Chicago International Film Festival screenings conclude Friday, October 23. Options listed include While We Are Here at 5:15 p.m. and Elephants in the Fog at 8:15 p.m. Book through the festival’s links and check availability and price before making plans. Friday’s screenings and booking links →

All times are Chicago local time. Listings and displayed prices were checked October 21; ticket fees may apply. Recheck the organizer’s page for schedule changes, availability and weather-related updates.