Gray-Sky Picks: Comedy, Hockey and a Design Graveyard

Your daily guide to what's popping in Chicago

By Raj Singh · Published November 2, 2026.

It's a gray, drizzly stretch in Chicago — Monday opens under light drizzle in the low 60s, with heavier showers rolling in midweek — which makes it a perfect week to duck indoors for something good. Tonight alone you can catch the city's longest-running improv show, a Blackhawks home game, a free exhibition of designs that never got built, and a free night of new solo theater. Looking ahead, the Uptown Farmers Market closes out its season Wednesday, Garfield Park cooks up a harvest demo Thursday, and the Black Harvest Film Festival opens Friday. Here's where to point yourself.

MONDAY, NOVEMBER 2

The Armando Diaz @ iO Theater

Chicago more or less invented modern improv, and The Armando Diaz is the city's longest-running comedy show — created in 1995 by iO alum Armando Diaz and still running every Monday at iO Theater. The format is the whole draw: a guest monologist tells true stories from their own life, and the cast improvises a run of interconnected scenes out of them on the spot. New players rotate through each week and surprise guests turn up, so no two nights are the same.

Doors are at 6:30, the show starts at 7, and it's $17 — about as cheap as a reliably funny Monday gets. The theater is at 1501 N. Kingsbury in River West, and if you miss it tonight it runs again next Monday.

Chicago Blackhawks vs. Colorado Avalanche @ United Center

The Blackhawks are home Monday night at the United Center (1901 W. Madison), hosting the Colorado Avalanche with a 7 p.m. puck drop. If a weeknight game is your idea of a cure for a gray Monday, this is the hockey fix — our listing doesn't name a price, so check the team's ticketing for seats before you head over.

Design Graveyard: An Exhibition of Unbuilt Chicago Design @ The Field Building

Every finished building or logo started as a pile of ideas that didn't make it, and Design Graveyard is a free exhibition devoted entirely to that pile. It collects abandoned concepts, rejected pitches, unbuilt proposals and scrapped projects from Chicago designers working in architecture, graphics, interiors and exhibition design. Each piece hangs on a 17-by-17-inch canvas alongside a short note on what it was meant to be and why it never happened — and visitors get to take a canvas home once the show closes.

It's presented by SEGD Chicago and curated by Ryan Odom and Katie Osborne, and it runs through November 9 inside the Field Building at 135 S. LaSalle. Tonight's hours are 5:30 to 9:30 p.m., it's free, and no registration is required — a genuinely interesting indoor stop in the LaSalle Street canyon on a wet night.

Monday Night PlayGround @ The Den Theatre

PlayGround-Chicago's Monday Night series opens its fifth season at a new home, The Den Theatre, with a program built around America 250: The Dreamers, The Builders & The Leaders. Expect new first-person solo pieces inspired by historical figures who shaped the country, written and selected through the company's monthly process — the specific playwrights are announced close to showtime. Admission is free (suggested donation $10–30), the readings are also simulcast online if you'd rather stay dry, and it starts at 7 p.m. at 1331 N. Milwaukee.

THIS WEEK

Uptown Farmers Market — final Wednesday of the season @ Sunnyside Mall

Wednesday is the last Uptown Farmers Market of 2026. The independent market on Sunnyside Mall wraps its May-through-November run on November 4, so this is your final crack at the season's farmed goods and local foods until spring. It runs 2:30 to 7 p.m. along the pedestrian stretch of Sunnyside between Magnolia and Beacon (1250 W. Sunnyside), it's free, SNAP and Link Match are accepted by all eligible vendors, and well-behaved dogs are welcome. It's outdoors and the vendors go rain or shine — and with showers in Wednesday's forecast, bring a jacket and don't let the gray talk you out of the last one.

Harvest Fest: Cooking Demonstrations @ Garfield Park (Thursday)

Thursday evening, Garfield Park hosts a free Harvest Fest cooking demonstration — a chef walking through jams and jellies, presented with the Garfield Park Advisory Council as part of the Park District's Night Out in the Parks series. It's all ages and free, 6 to 8 p.m. at 100 N. Central Park Ave. A small, seasonal midweek outing on the West Side if you want to pick up a kitchen trick for the fall.

ON THE HORIZON

Black Harvest Film Festival Opening Night @ Gene Siskel Film Center

The Black Harvest Film Festival — Chicago's annual showcase for Black film across the diaspora, now in its 32nd year — opens Friday night at the Gene Siskel Film Center. Opening night pairs four standout short films with the presentation of the Richard and Ellen Sandor Family Prize and a post-screening reception for the filmmakers. It's 7 p.m. Friday, November 6, at 164 N. State in the Loop; general admission is $40, with $35 student tickets and $25 for Siskel members and SAIC students, staff and faculty. Opening night sets the tone for the whole festival, so it's the one to catch if you only pick a single screening.