Drizzle, Distortion & Deep-Dish Done Right

Your daily guide to what's popping in Chicago

By Raj Singh · Published June 22, 2026.

It's a gray, dripping Monday in Chicago — 64F and an 86 percent chance of rain — so today's picks all keep you under a roof: a rock show, a pizza class, a free gallery, and a comedy set. The good news is tomorrow clears up (65F, overcast, barely any rain), so we've stacked the going-out plans for Tuesday and pointed you toward a free Pride kickoff this weekend. Here's where to be.

MONDAY, JUNE 22

Brian Fallon & The Painkillers, Emily Wolfe @ Reggies

The Gaslight Anthem's Brian Fallon brings his solo band, The Painkillers, to Reggies tonight, with Austin guitar-slinger Emily Wolfe opening. Fallon — the New Jersey lifer who fronted one of the 2000s' most beloved heartland-punk bands — has spent the last decade carving out a rootsier, more confessional solo lane, and this is the rare chance to catch that catalog in a room small enough to see the setlist taped to the floor.

Reggies is a no-frills South Loop rock club: standing-room floor, loud PA, 17-and-up crowd that's there for the songs. It's an indoor night, which matters — today is 64F and a heavy drizzle, so this is a good place to be dry and a little sweaty instead. Reggies runs its own kitchen if you want to eat where you stand; otherwise the South Loop and Chinatown are a quick hop down the Red Line.

Doors and music at 7:00PM, 17+, tickets through Do312. Take the Red Line to Cermak-Chinatown and walk a few blocks, or grab the usually-easy street parking along State.

Hands-On: Pizza Napoletana with Rossopomodoro @ Eataly

Eataly's pizzaiuolo walks you through real Pizza Napoletana tonight — stretching the dough, dressing it, and getting your hands genuinely messy in a hands-on class built around Rossopomodoro's Naples-style method. It's a 90-minute session aimed at people who'd rather build the pie than just order it.

The vibe is exactly as advertised: flour on your forearms, a working counter, and the smell of a hot oven in Eataly's River North marketplace. It's an indoor, hands-busy way to spend a soggy Monday evening. If you'd rather have someone else cook afterward, Siena Tavern is a short walk away in River North for a sit-down Italian nightcap.

Class runs 6:00PM to 7:30PM, $120 per person, tickets via Do312 — the splurge slot of the night. Take the Red Line to Grand; Eataly is a couple of blocks east.

NoMI Gallery: Everything is Bright @ NoMI

Up on the seventh floor of the Park Hyatt, NoMI is showing a quietly remarkable exhibit by contemporary artist Dwight Hwang, built on gyotaku — the traditional Japanese art of inking and printing fish, originally used by 1800s fishermen to document their catch before refrigeration. Hwang's work turns that utilitarian craft into studies of nature, movement, and preservation.

The gallery is free to walk through and overlooks the Magnificent Mile, which makes it a close-to-perfect rainy-day refuge on an 86-percent-drizzle afternoon. NoMI itself is a restaurant and lounge, so you can pair the art with a drink without ever going back outside.

On view now off Michigan Avenue. Take the Red Line to Chicago and walk a block east — no ticket needed, just head up to the seventh floor.

Bridget McGuire – Ballet Flats For Dinner @ Zanies

Bridget McGuire is a New York-based storyteller and stand-up who somehow kept her hot Chicago accent, and tonight she brings her touring solo show, Ballet Flats for Dinner, to Zanies. Her material runs through anxiety, family, dating, and living with OCD — self-deprecating and conversational, the kind of set that feels like a friend telling you the truth over drinks.

Zanies is the intimate, low-ceilinged Old Town comedy room where the front rows are close enough to make eye contact you might regret. It's 21+ and indoor — a good call on a drizzly Monday. The Vig is right across the block on Wells if you want a pre-show drink in Old Town.

7:00PM, $32.25, 21+, tickets through Do312. Take the Brown or Purple Line to Sedgwick; Zanies is a short walk down Wells.

TUESDAY, JUNE 23

Free Museum Day at the MCA @ Museum of Contemporary Art

Every Tuesday, the Museum of Contemporary Art is free for Illinois residents — bring a valid ID and walk right in. The MCA is where Chicago goes for the bold, the strange, and the right-now: rotating contemporary shows, big installations, and a permanent collection that rewards an unhurried afternoon.

It sits just off the Magnificent Mile in Streeterville, with a stepped terrace out back. Tomorrow's forecast is the good one this week — 65F and overcast with just a 1 percent chance of rain — so it's an easy day to walk over without getting soaked. The museum has its own cafe if you want to linger; the Mag Mile is a block west for everything else.

Free with Illinois ID on Tuesday. Take the Red Line to Chicago and walk two blocks east. Worth checking the MCA site for which exhibitions are up before you go.

Kim Gordon @ Metro

Kim Gordon — Sonic Youth co-founder, art-world fixture, and at this point a genuine elder statesperson of noise — headlines Metro tomorrow on her first-ever solo headlining tour. She's touring behind a restless new record, PLAY ME, that pushes her sound toward melodic beats and the motorik drive of krautrock; it follows 2024's two-time Grammy-nominated The Collective. She gave the music keynote at SXSW this spring, which tells you the reputation precedes the gig.

Metro is the longtime Wrigleyville rock room — steep, loud, and close, with sightlines that make even a packed floor feel personal. It's 18+. Murphy's Bleachers is right nearby in Wrigleyville for a pre-show beer if you're making a night of it. Tomorrow's weather cooperates: 65F, overcast, basically no rain.

Doors 7:00PM, show at 8:00PM, $35 advance / $40 day-of, 18+, tickets through Do312. Take the Red Line to Addison — Metro is right by the stop.

THIS WEEKEND

OUT at Gallagher Way @ Gallagher Way

Pride weekend lands this Saturday, and Gallagher Way — the open plaza outside Wrigley Field — throws its free, all-day OUT celebration to kick it off. The Chicago Gay Men's Chorus performs, the Rock and Roll Playhouse plays, and the plaza fills with face painting, balloon artists, bracelet-making, and Voguing classes. It's the daytime, everyone's-welcome counterpart to the weekend's bigger parties, and it costs nothing to walk into.

The vibe is open-air and easygoing: families, dogs, first-timers, and regulars all sharing the same lawn. Because it's outdoor and runs 11am to 5pm, keep an eye on the forecast as the weekend gets closer — this week's pattern has been wet, and Saturday is past the current three-day window. Murphy's Bleachers is right there in Wrigleyville if you want food or a drink mid-afternoon.

Free, Saturday June 27, 11am-5pm. Take the Red Line to Addison; the plaza is steps from the stop. With the Pride Parade the next day, this is the free, low-key way to start the weekend early.