Samara Joy & the CSO & 4 More Chicago Plans This Week

A Grammy winner at the CSO, a free Tuesday variety show, Rodrigo y Gabriela's 20th anniversary stop, a riot grrrl festival in Avondale, and the Renegade Craft Fair takes over Andersonville.

By Raj Singh · Published May 12, 2026.

Drizzly Tuesday in Chicago — 80F high but a 35% chance of getting your jacket damp, which is the universe nudging you toward something indoors with great acoustics. Wednesday clears to a cool 59F and overcast, basically perfect walking-to-the-Loop weather. And the weekend is shaping up to be the first proper spring-festival Saturday of the year. Here's where we'd be.

TUESDAY, MAY 12

Samara Joy & the CSO @ Chicago Symphony Orchestra

Samara Joy is having one of those careers that feels both inevitable and slightly miraculous. She swept the 2023 Grammys with Best New Artist while still in her early twenties, and she's been quietly becoming one of the most important young voices in American jazz ever since. Tonight she shares Orchestra Hall with the Chicago Symphony — full orchestra behind her, doing what jazz singers used to do with big bands, but at a different scale of richness. The kind of show that becomes an 'I was there' memory.

Symphony Center at 220 S. Michigan is one of the great rooms in this city — gold leaf, acoustic perfection, every seat in the house actually good. Dressy-casual works (no one's looking at your shoes). For dinner, walk a block south to Cafecito for a cubano on the way in, or after the show grab a martini at the Berghoff bar around the corner on Adams — wood-paneled, old-school Chicago, exactly the energy you want post-Samara.

7:30PM downbeat. Tickets at the box office and online — Tuesday night with a Grammy winner means you might luck into the door, but don't gamble. Drizzly 35% rain forecast tonight, but you're walking from a CTA station or garage straight into the lobby — no weather concern unless you're trying to street-park.

Tuesday Good Show @ The Gallery Cabaret (FREE)

Every Tuesday, Nick Bonsignore and Keller Paulson commandeer a Bucktown dive and turn it into a rotating showcase of comedy, music, and whatever-else-the-week-brought. The bill changes weekly — that's the point. You don't go because of who's on, you go because the curators have taste, and a free Tuesday night spent watching working Chicago performers test new material is one of the more underrated pleasures in this city.

The Gallery Cabaret at 2020 N. Oakley is the kind of bar Chicago doesn't make anymore — neighborhood spot at a quiet Bucktown intersection, low ceilings, low cover (none, tonight), beer-and-shot menu that doesn't pretend to be anything else. Eat first: walk over to Mott Street on Damen for the cheeseburger, or stay closer and grab Honey Butter Fried Chicken on California. Both are quick.

Doors around 7PM, show 7-8:30PM. Free — but bring cash for tip-the-performer hats. Indoor, so the drizzle doesn't matter. If you're driving, Oakley has decent street parking after 6PM; otherwise the 56 Milwaukee bus drops you two blocks away.

WEDNESDAY, MAY 13

Rodrigo y Gabriela — 20th Anniversary Tour @ The Chicago Theatre

Rodrigo Sánchez and Gabriela Quintero met in a Mexico City thrash metal scene in the 90s, decamped to Dublin to busk on Grafton Street, and figured out how to translate metal aggression and flamenco rhythm into two acoustic guitars sitting cross-legged on stage. Twenty years later, that translation has earned them Grammy wins, a James Bond theme, and one of the most physically thrilling live shows in modern music. The 20th Anniversary Tour is the kind of milestone these two don't take lightly — expect deep cuts alongside the songs that made them.

The Chicago Theatre at 175 N. State is the showpiece of the Loop — gilded marquee, that vertical 'CHICAGO' sign that ends up in every establishing shot in every movie set here, 3,600 seats and not a bad sightline. Pre-show, walk a block to Pizano's on Madison for tavern-style thin crust, or hit the Walnut Room at Macy's State Street if you want pre-theater old-Chicago energy. The Marquee Lounge inside the theatre has signature cocktails if you want to skip dinner.

8PM downbeat. Wednesday means the Loop empties out after rush hour — Brown/Orange/Purple Line to State/Lake puts you right at the doors. Wednesday's forecast is 59F and overcast, basically perfect walking weather. Tickets still available across price tiers; Rodrigo y Gabriela usually pull a tour-veteran crowd that shows up on time, so don't roll in at 8:15.

THIS SATURDAY

Ragbagalia Festival w/ ESG @ Sleeping Village (Avondale)

ESG — three sisters from the South Bronx who, in 1981, made 'UFO,' a song so funky and weird it ended up sampled on something like 500 hip-hop records — are headlining the inaugural Ragbagalia festival in Avondale on Saturday. That alone would be a destination show. The bill stacks under them with local riot grrrl spirit: Em Grace & the Undercuts and Beastie Boys tribute band She's Crafty among the all-day lineup. Inaugural year is the year to go — these things either grow into landmark Chicago festivals or quietly disappear, and either way you want to say you were there.

Sleeping Village is the move-room a city like Chicago needs — patio, indoor stage, beer garden energy, the kind of place where you can drift between bands without feeling like you're at 'an event.' Avondale's eating game is underrated: Honey Butter Fried Chicken on California is the obvious move, Parachute on Diversey is the Korean-influenced tasting menu, and Pequod's pan pizza on Clybourn is the move if you're walking in starving. Hopewell Brewing on Milwaukee is two stops north on the Blue Line for a pre-show beer.

All-day means showing up at doors is optional but smart — the early local sets are part of the value proposition. Saturday isn't in the 3-day window yet, but plan for spring-Chicago variability: layers, comfortable shoes, water bottle. Tickets still moving, but inaugural festivals with a name headliner have a way of selling out the day-of.

Renegade Craft Fair @ Andersonville (FREE)

Renegade has been doing this since 2003 — they essentially invented the modern 'good' craft fair model, the one where the vendors are working independent artists making things you actually want, not Etsy-cosplay glassware and bad scented candles. The Andersonville edition takes over Clark Street with more than 100 booths selling screenprints, ceramics, jewelry, candles, leather, zines — the spectrum of independent-maker Chicago, all in walking distance.

Andersonville is one of the great strolling neighborhoods in this city, and Renegade gives you the excuse to make a day of it. Coffee at Sip & Savor, lunch at Hopleaf (the mussels and frites, please), a stop at Middle East Bakery on Foster for a loaf on the way home. Bring a tote — actually bring two. The good vendors sell out by mid-afternoon, so morning is for browsing and afternoon is for committing.

Free to enter. Bring cash and a working credit card — Square readers go down all the time in dense Wi-Fi areas. Saturday morning Clark Street parking is hopeless; take the Red Line to Berwyn and walk west. Saturday's forecast isn't locked in yet, so a layer in the bag in case the lake breeze kicks up.