From Bud Billiken to Jerry Garcia's Days Between

Your daily guide to what's popping in Chicago

By Raj Singh · Published August 6, 2026.

It's a grey, sticky stretch in Chicago — overcast and 73 today, with heavier air and passing showers rolling in for the weekend. That's no reason to stay in. Tonight leans indoor-friendly: a Grateful Dead tribute residency and an SNL comic in a tiny Old Town club, with a free park movie for the optimists and a downtown market for the daylight hours. Then the weekend opens up — a West Town art crawl, free music on the lake, and the granddaddy of them all, the 97th Bud Billiken Parade, on Saturday. Here's the plan.

THURSDAY, AUGUST 6

Terrapin Flyer — Days Between @ Martyrs'

Terrapin Flyer has been Chicago's house band for the Grateful Dead songbook since 1999, and every August they run their "Days Between" residency at Martyrs' — the stretch of calendar Deadheads reserve to mourn and celebrate Jerry Garcia, who was born August 1 and died August 9. Tonight is Night 3 of a five-show run, and the band's history of pulling in actual Dead alumni (keyboardists Tom Constanten, Bob Bralove, and the late Vince Welnick have all sat in over the years) is why it plays less like a bar cover band and more like a proper keeper-of-the-flame gig.

Martyrs' is a mid-size North Center rock room on Lincoln Ave with a big painted mural out front and sightlines that stay good even when the floor fills with tie-dye. Expect a loose, danceable crowd that skews graybeard-Deadhead but welcomes anyone who wants to twirl. The surrounding stretch of Lincoln Ave is thick with taquerias and old-school taverns if you want a bite before the show.

Tickets are $20 via do312, all general admission, 7PM. Parking on Lincoln is metered and tight on a show night, so the Brown Line to Irving Park is the easy move — and since it's an indoor room, tonight's overcast forecast never enters the equation.

Andrew Dismukes @ Zanies Comedy Club

Andrew Dismukes is the baby-faced SNL utility player who's quietly become one of the show's sharpest sketch writers, and he's bringing his stand-up to Zanies tonight. He came up doing open mics in Austin while at UT before landing at 30 Rock in Season 43, and he's got an Amazon animated series ("The Hospital," alongside Maya Rudolph and Natasha Lyonne) on the way — worth catching in a 100-seat club now, because rooms this size don't stay on a touring schedule long once the specials hit.

Zanies is the cramped, brick-walled Old Town institution where a two-drink minimum and elbow-to-elbow seating are the whole point — you're close enough to heckle (don't), and the intimacy makes even a testing-material set feel like an event. It's on Wells St in the heart of Old Town's bar strip; The Vig, right across the street at 1527 N Wells, is a solid pre-show stop for a cocktail and a burger.

The show is 7PM, tickets via do312, with the usual two-drink minimum on top of the ticket. The Brown or Purple Line to Sedgwick drops you two blocks away; street parking in Old Town is a circling nightmare, so take the train.

Movies in the Parks: Wicked: For Good @ Mayfair Park

The Chicago Park District's Movies in the Parks series is the best free thing the city does all summer, and tonight Mayfair Park screens "Wicked: For Good" — the second half of the Ozian blockbuster — on a giant inflatable screen under the (cloudy) stars. Bring a blanket, a lawn chair, and snacks; there's no admission, no ticket, and no bad seat once the sun drops.

Mayfair Park is a tidy neighborhood green on the Northwest Side, the kind of low-key spot where families spread out early and kids run the field until the projector fires up around 8:30. It's a come-as-you-are crowd. Pack your own dinner — this is a residential pocket without a restaurant row — or grab something on Lawrence or Elston on the way.

It's free, all ages, PG, and runs about 138 minutes starting at dusk (around 8:30PM). Tonight's forecast is 73 and overcast with roughly a 31% chance of a passing shower, so throw a poncho or a tarp in the bag — an evening this mild is worth the small gamble, but you'll want a backup if the clouds open. Street parking is easy this far out.

Daley Plaza Farmers Market @ Daley Plaza

Chicago's longest-running farmers market sets up every Thursday on Daley Plaza, right under the Picasso, and it's the easy midweek move for anyone working or wandering downtown. Seasonal produce is peaking in early August — sweet corn, the first tomatoes worth eating, peaches — alongside cut flowers, prepared foods, and Chicago-made pantry goods.

This is a lunch-break market more than a leisurely-Saturday one: quick, busy, and dead center in the Loop. Grab a bag of produce to take home and eat lunch from one of the prepared-food stands right there on the plaza. If you want a sit-down afterward, The Berghoff — the 1898 German institution a few blocks south on Adams — is a Loop classic for a schnitzel and a house beer.

It's free to browse, 7AM to 2PM, with cash and cards both fine at most stands. As an open-air plaza, today's overcast 73 is close to ideal market weather — no umbrella needed unless the 31% shower chance cashes in. Any Loop L stop puts you within a couple blocks; it doesn't get more central.

FRIDAY, AUGUST 7

West Town First Fridays @ West Town

On the first Friday of every month, West Town's galleries and arts-driven storefronts throw their doors open late — until 8pm — for a self-guided art crawl through one of the city's most quietly creative neighborhoods. Tomorrow (Friday, Aug 7) is the August edition: wander from gallery to studio, meet the makers, and see work that never makes it to the museum circuit.

West Town sits just east of Wicker Park, a mix of old Polish and Ukrainian bones with a new layer of design shops, tattoo studios, and gallery spaces. First Fridays is free and low-pressure — no ticket, no RSVP, just pop into whatever storefront has its lights on along Chicago Avenue and the side streets off it. It draws an easygoing, art-curious crowd, more neighborhood than scene.

Galleries stay open until 8pm Friday. The #66 Chicago Avenue bus runs straight through the district if you don't want to hunt for parking. Tomorrow's forecast is a warm, humid 80 with a small chance of passing showers — but this is mostly a duck-in-and-out-of-storefronts evening, so a little drizzle won't derail it.

THIS WEEKEND

Ravenswood Feel Good Fest @ Sunnyside Avenue

The inaugural Ravenswood Feel Good Fest takes over Sunnyside Avenue on Saturday (Aug 8) with music, food, art, and a stated mission of "feeling good, doing good, and fostering meaningful community." First-year street fests are their own kind of fun — smaller and scrappier than the big Northalsted-scale blowouts, with the whole neighborhood clearly invested in getting it right.

Ravenswood is the leafy, low-key North Side pocket just west of Andersonville — all brick two-flats, breweries tucked into old warehouses, and a walkable main-street feel. Expect a family-friendly daytime crowd, local vendors and makers, and a couple of stages of neighborhood music rather than national headliners: the kind of block party where you actually talk to the people running the booths.

It's a free, come-and-go afternoon on Sunnyside Ave. Saturday's forecast is a warm, humid 84 with a small chance of drizzle (around 16%), so dress light and bring water. The Brown Line to Damen or Montrose puts you within a short walk, and the Metra UP-N Ravenswood stop is right in the neighborhood if you're coming from downtown.

Bud Billiken Parade @ King Drive

Two days out, the horizon belongs to the Bud Billiken Parade — the 97th edition of the largest and oldest African-American parade in the country, stepping off Saturday morning (Aug 8) down King Drive from 39th Street. Since 1929 it's been Chicago's back-to-school rite, a marching-band-and-drill-team spectacle that draws hundreds of thousands to the boulevards of Bronzeville and Washington Park.

This is a full-day, family-anchored street celebration — drill teams, floats, dance squads, local dignitaries, and block after block of cookouts spilling off King Drive into the parks. The energy is joyful and deeply local; find a curb spot early, because prime shade goes fast on an August morning. Vendors line the route, but many families make a cooler-and-grill day of it in the surrounding parks.

The parade steps off Saturday morning and runs into the early afternoon — get there early to claim a spot along King Drive. Saturday's forecast is a hot, sticky 84 with a chance of drizzle (around 16%), so bring water, sunscreen, and a hat regardless. The Green Line to 43rd or Indiana drops you a block or two off the route; driving and parking near King Drive on parade morning is a headache best avoided.