Bears, Bareilles, and a Crisp Fall Monday

Your daily guide to what's popping in Chicago

By Raj Singh · Published September 28, 2026.

MONDAY, SEPTEMBER 28

Sara Bareilles: The Good Grief Tour @ The Chicago Theatre

Sara Bareilles brings her Good Grief Tour to the Chicago Theatre tonight — an 8 p.m. show in the Loop. If catching her live has been on your list, this is the downtown marquee of the evening; check the listing for tickets before you head over.

Chicago Bears vs. Philadelphia Eagles @ Soldier Field

It isn't every week the Bears play under the lights. Chicago hosts the Philadelphia Eagles at Soldier Field tonight, a 7:15 p.m. kickoff on the Museum Campus in the South Loop. Monday Night Football at the lakefront doesn't come around often — the wildcard of the night.

$10 Improv Night @ iO Theater

Ten bucks, nine o'clock, and a rotating cast of brand-new improv teams: iO Theater's Monday incubator hands the stage to comedy's rising talent for a short, fast set. Doors are at 8:45 (right after Armando), the show's at 9, and it's $10 flat — the cheap, easy call for a school-night laugh.

The Bewitching Hour @ Chicago Magic Lounge

Happy hour, remixed. Every Monday through Wednesday from 8 to 10 p.m., the Performance Bar at Chicago Magic Lounge pours specially priced cocktails, a rotating seasonal drink and featured wines while a magician works close-up magic at the bar. No reservations, no tickets — just walk into the Performance Bar and grab a seat. It's free to sit down; you only pay for what you drink.

TUESDAY, SEPTEMBER 29

Illinois Resident Free Evening @ Shedd Aquarium

Tuesday is a free night at the Shedd. From 5 to 9 p.m., Illinois residents get in free for Free Hours — all exhibits plus the seasonal Stingray Touch. The catch is demand: the Shedd says to reserve ahead because walk-up spots sell out fast. Online reservations carry a $5 convenience fee per order; reserve by phone at 312-939-2438 (9 a.m.–4 p.m.) and there's no fee. Bring proof of Illinois residency.

Silent Reading Club at Barrel Cheese & Wine

If a screen-free Tuesday sounds better, the Silent Reading Club meets at Barrel Cheese & Wine in Lakeview at 7 p.m. The format is simple: about 30 minutes to chat with fellow readers, then an hour of quiet reading in the upstairs seating area. Bring whatever you're currently reading. No sign-up required, and it's free — unless you order a drink.

THIS WEEK

Kitt Lyles' Arabic Jazz Project @ Douglass Park

Circle Friday: a free park concert worth the trip. Kitt Lyles' Arabic Jazz Project plays Douglass Park at 6 p.m. Oct. 2, weaving Arabic and Turkish maqam through contemporary jazz. The band runs deep — Kitt Lyles on bass, Ronnie Malley on oud and percussion, Bryan Pardo on clarinet, Joaquin Garcia on piano and Yuri Hevia on drums — and the evening opens with short sets from student musicians. It's all ages and free.