An Overcast Weekend Worth Leaving Home For

Your daily guide to what's popping in Chicago

By Raj Singh · Published November 7, 2026.

SATURDAY, NOVEMBER 7

The Naked Comedy Show @ The Crib Comedy Playspace

Six comics take the stage with nothing but a microphone. The Naked Comedy Show is exactly what the name promises: a 21+ stand-up night where the performers drop the armor and everything else. Time Out flagged it, and after launching in New York the show is back in Chicago for a night of, in its own words, probably the most revealing sets of their lives.

It's an 8 p.m. show at The Crib Comedy Playspace on West Madison, strictly 21-and-up. Tickets run $39 in advance and $49 the day of, so this is one to lock in before you head out.

Friends of Budlong Woods Library Book Sale @ Budlong Woods Library

The Friends of the Budlong Woods Library are throwing their fall book sale, and it's a straight-up treasure hunt: tables of fiction, nonfiction, puzzles and games to stock up on before the long reading season sets in. Proceeds go right back into the Budlong Woods branch's materials and programming, so you're padding your winter shelf and funding the library in one trip.

It runs 9:30 a.m. to 4:30 p.m. Saturday at the branch on North Lincoln Avenue, and it's open to all ages.

Black Harvest Film Festival: Where Do We Go From Here? @ Gene Siskel Film Center

Now in its 32nd year, the Black Harvest Film Festival is Chicago's annual showcase for Black film across the diaspora, and this program, WHERE DO WE GO FROM HERE?, gathers stories of lives in transition: family obligation, migration, coming of age, reproductive choice, and the moments of reckoning that reshape a future.

The screening is at the Gene Siskel Film Center on North State Street, 5:15 p.m. Saturday, $15.50 a ticket. It screens again on November 11 if Saturday doesn't work.

Dancing on the Spot: Artist(s) Statement! @ Berger Park Coach House Theater

Dancing on the Spot Presents Artist(s) Statement! is an improvised dance show built from an unusual source. The ensemble visited Material Studios and Gallery in Milwaukee, interviewed the artists working there, and turned those conversations into a performance. The soundscape stitches together the interview answers, found poems pulled from them, and original poetry: a show about art, made out of talking to artists. As the company puts it, if you've ever made art, seen art, or just been curious about it, this one's aimed at you.

It's at the Berger Park Coach House Theater on North Sheridan Road, 2 p.m. Saturday, and it's an adult show. Admission is $15 general, $10 for students and seniors, as part of the Park District's Night Out in the Parks.

SUNDAY, NOVEMBER 8

Peter Pan @ The Theatre School at DePaul

The Theatre School at DePaul takes a dark turn on a childhood staple: this Peter Pan peels back Neverland's whimsy to sit with the real cost of never growing up. As the Darling children move through pirates, testy fairies and an ever-so-cocky Peter, the line between playing pretend and genuine danger starts to thin. A hauntingly playful adaptation, in the company's words.

It plays a 2 p.m. matinee on Sunday, November 8 at the school's Racine Avenue theatre in Lincoln Park, with tickets scaled from $5 to $30. There's a post-show discussion that Sunday, too, if you like to stick around and talk it out.

Chicago By Night River & Lake @ Chicago's First Lady Cruises

If Sunday calls for something slower, Chicago's First Lady runs its Chicago By Night cruise along the river and out onto the lakefront, with the skyline lit up and lively commentary along the way. It's the postcard version of the city, seen from the water after dark.

Boats board at 112 East Wacker Drive, and tickets start at $50. It's sailing nightly through November 14; check the operator for exact departure times.

ON THE HORIZON

Randolph Street Market Festival @ Plumbers Union Hall

The Randolph Street Market Festival is back for its indoor winter run: two days of European-style vintage and antique hunting with hundreds of vendors under one roof, plus cocktails, bites from local restaurants and live music while you dig. A proper treasure-hunt if you like your shopping with some digging involved.

The November dates are Saturday the 14th and Sunday the 15th at the Beaux Arts Plumbers Union Hall building on West Washington in the West Loop. Admission is $14, and the Green or Pink Line stops at Ashland/Lake nearby.