Vintage Finds, Latin Jazz & Mulaney at Wrigley

Your daily guide to what's popping in Chicago

By Raj Singh · Published July 11, 2026.

It's a soft, overcast Saturday in Chicago — high around 77, barely a whiff of rain — and the city is loaded. Tonight alone you can watch a hometown comic make Wrigley Field history, catch free salsa on a Humboldt Park lawn, or let the lake breeze carry Jack Johnson across Northerly Island. Then the sky clears for a bright, 80s-degree Sunday. Here's where we'd point you.

SATURDAY, JULY 11

John Mulaney: Mister Whatever Tour @ Wrigley Field

Wrigley Field has hosted a lot of things in 110 years, but never a stand-up set — until tonight. John Mulaney, the Chicago-raised, three-time Emmy winner behind Baby J and the live Netflix show Everybody's Live, brings his Mister Whatever Tour to the Friendly Confines for the first comedy show the ballpark has ever staged. A hometown kid doing an hour out on the outfield grass is a real one-off, and the 8PM start means the sky's going dark over the bleachers while he works.

Wrigleyville on a Saturday night runs on its own energy — Clark Street packed, marquee lit, crowd loud before anyone says a word. The Red Line drops you at Addison right at the gate, which beats parking anywhere near the park; grab a pre-show beer at Murphy's Bleachers across from the marquee. It's overcast with a high near 77 sinking to the mid-60s after dark, and a stadium bowl feels cooler than the street, so bring a layer. This is a first-ever, so walk-ups are a long shot — sort your ticket before you go.

Chicago Latin Jazz Festival @ Humboldt Park

Two Chicago bands, three hours, zero dollars. The Jazz Institute of Chicago and the Park District bring their Jazz City series to Humboldt Park tonight with a Latin jazz double bill. Raices (Roots), the quintet led by vibraphonist Joe Sonnefeldt and modeled on the classic Cal Tjader group, opens at 5PM — they packed a standing-room set across town last year and fold Afro-Cuban rhythms into original tunes. At 6:30 the stage turns over to Trabuco, a Chicago salsa institution first assembled in Humboldt Park barrios in 1969 and reformed in 2022 by bandleader Jose E. Reyes Jr. It's the block-party salsa the neighborhood invented.

This is a bring-a-blanket, all-ages show at 1440 N Humboldt Blvd, right on the boulevard, running 5 to 8PM. Weather cooperates: overcast, high near 77 easing to the mid-60s by the last set, only a 2% chance of rain. There's no L stop close by, so plan on a bus or a rideshare — and the boulevard and nearby Division Street have taquerias and paleta carts if you want to eat before the horns start.

Jack Johnson: SURFILMUSIC Tour @ Northerly Island

Jack Johnson playing an open-air amphitheater on a peninsula in Lake Michigan is about as on-brand as it gets. The surf-folk fixture brings his SURFILMUSIC Tour to Huntington Bank Pavilion at Northerly Island tonight at 7:30, with Swiss instrumental duo Hermanos Gutierrez opening — their dusty, reverb-soaked guitar sets a perfect sundown mood before Johnson's mellow catalog. Two dollars from every ticket goes to environmental work through REVERB and Johnson's own Ohana Foundation, which is very much the vibe.

The Pavilion sits on Northerly Island just south of the Loop, on the Museum Campus. It's a hike from the nearest train, so most people drive to the Soldier Field or Adler lots or take a rideshare — budget extra time getting out. Right on the water, the lakefront runs cooler and breezier than the forecast high of 77 suggests and drops toward the mid-60s after dark, so pack a light jacket even with rain odds near zero. Eat before you come; on-site options are limited.

Craft With Me: Tote Bag & Card w/ Cricut @ Da Book Joint

For a low-key, hands-on afternoon on the South Side: a 3PM craft session at Da Book Joint, the Black-owned bookstore on Stony Island in South Shore, where you design and press your own tote bag and greeting card on a Cricut cutter. No experience required — you leave with two things you actually made, and your $27.24 ticket puts money into a neighborhood small business. A gray Saturday is exactly when an indoor make-something session earns its keep.

Da Book Joint is on Stony Island Avenue in South Shore, easy to pair with a neighborhood wander or a lakefront stop. There's no L close by, so drive, bus, or take the Metra Electric down. Bring a friend — the tables are more fun with two.

SUNDAY, JULY 12

Slice of Chicago Pizza 5K @ Museum Campus

A 5K where the finish-line reward is a slice — this is Chicago running culture distilled. The first-ever Slice of Chicago Pizza 5K goes off Sunday at 8AM from the Museum Campus by Soldier Field, and everyone who runs or walks the course collects a medal, a T-shirt, and pizza from a stacked vendor lineup: Angelo's Stuffed Pizza, Bob's Pizza, Connie's Pizza, and Rosati's. DJs Flipside, Maddjazz, and Metro spin the pre- and post-race party, so it leans block party over grind.

The course hugs the South Loop lakefront, one of the prettiest stretches in the city for a slow 5K. Sunday's forecast is about ideal: clear skies, low near 69 at the gun climbing toward 83, so go early and bring water. The 146 bus runs to the Museum Campus and parking fills fast on event mornings. Registration is $60 for a single, $49 a head with a 10-plus bib pack — come hungry.

Andersonville Vintage Market @ St Gregory the Great

Andersonville does vintage as well as any neighborhood in the city, and Sunday it turns the St Gregory the Great lot into a 30-plus vendor treasure hunt. From 11AM to 5PM you dig through antiques, home decor, jewelry, and clothing from sellers like Antiqueandmod, Scal's Vintage, J-Bird Clay, and The Paper Archive. It's a $5 suggested donation, and it's one of six summer dates — no rush, but the good stuff moves early, so come at open if you're hunting something specific.

The market's at 5535 N Paulina St, a short walk off the Clark Street drag and a few blocks from the Red Line's Berwyn stop. Make an afternoon of it: browse, then walk over to Clark for mussels and a Belgian beer at Hopleaf, the Andersonville standby. Sunday's clear and warm near 83 — dress light and bring a tote for your finds.

ON THE HORIZON

West Fest Chicago @ Chicago Ave, West Town (Jul 17-19)

Mark the calendar now: West Town's rollicking street festival takes over Chicago Avenue between Wood and Damen next weekend, July 17-19, for three days of music, food, and shopping. What sets it apart from the dozen other summer street fests is the music curation — Empty Bottle Presents books the lineup, so the bands run a cut above the usual circuit, and there's a Bass By the Pound DJ stage spinning vinyl on the side. Bring the dog: the Pet Fest area has a dog obstacle course and pet painting.

It's a $10 suggested donation at the gate, with local vendors and food the length of the strip. The 66 Chicago bus runs right down the middle of the footprint, making it an easy one to reach without a car. Full lineup details post on West Fest's site as the weekend nears — worth a look before you plan Saturday, since the bigger Empty Bottle acts tend to land in the evening slots.