Riverwalk Lights, Rogers Park Arts & a Warm Rain

Arts fests, free park movies, and a rainy-Sunday game plan for Chicago.

By Raj Singh · Published August 16, 2026.

Sunday lands warm and unsettled — 83 degrees with about a coin-flip chance of rain, so today rewards a flexible plan and a packable poncho. Monday cools into the 70s and dries out, which makes the back half of this guide the easy outdoor bet. Here's where to point yourself, from a 25-year-old street arts fest up in Rogers Park to a free jazz quintet on the Northwest Side.

SUNDAY, AUGUST 16

Glenwood Avenue Arts Festival @ Rogers Park

The Glenwood Avenue Arts Festival hits its 25th year this weekend, and it has grown into one of the North Side's anchor street fests. More than 130 local and visiting artists set up along Glenwood Avenue in Rogers Park, joined by two dozen music and dance performances, live art demonstrations, a kids' activities area, and open studios where you can watch people actually work.

Rogers Park is the city's far-northeast corner — diverse, walkable, lakefront-adjacent — and the fest runs right through the neighborhood's artist community near the Morse stop. Wandering the stalls costs nothing; bring cash if you want to take a piece home. The Red Line drops you at Morse, a short walk from the action.

It runs 11am to 7pm today. Weather's the wildcard: 83 and muggy with roughly a 49% chance of rain, so pack a poncho and check the radar before you commit — outdoor fests push through drizzle, but a real downpour thins the crowd fast.

Chicago Fire FC vs. Portland Timbers @ Soldier Field

The Fire host the Portland Timbers at Soldier Field tonight, a cross-conference matchup that carries a little edge — Portland travels well and brings noise. Kickoff is 5:30pm, wrapping around 7.

Soldier Field sits on the Museum Campus in the South Loop, right on the lake, so you're pairing a match with some of the best skyline-and-water views in the city. Tickets are mobile-only this season — no printing, no will call — so load them onto your phone before you leave. The Roosevelt stop (Red, Green, and Orange lines) puts you a walk east of the stadium.

It's an open-air stadium, so tonight's rain risk is worth watching — 83 and humid with a 49% chance of showers. Bring a light layer for after sunset and a clear bag that meets the stadium's policy.

CHI ON TAP TOUR @ Pilot Project Brewing

CHI ON TAP is a walk-around tasting at Pilot Project Brewing on Milwaukee Avenue, pouring from nine breweries alongside bites from five local restaurants — and it's a benefit, with proceeds going to Meals on Wheels Chicago. It runs noon to 3pm today.

Tickets are $45, but the event's own promo code DO312 gets you two for the price of one, which turns this into one of the better afternoon values in town. Pilot Project is a brewing incubator, so the pour list skews toward small, experimental labels you won't find on every tap wall.

This one's largely indoors, which makes it a smart rainy-Sunday pick. Go in with a plan to pace yourself across nine breweries, and eat something before the samples run out.

Buffalo Nichols & Al Scorch @ The Hideout

Buffalo Nichols brings his stark, modern take on the blues to The Hideout tonight, with Chicago's own Al Scorch opening — a pairing of national touring act and homegrown folk-punk energy. The show starts at 7:30pm; tickets are $26.

The Hideout is a tiny wood-paneled roadhouse tucked into an industrial pocket off Elston in Bucktown, and it's the right room for this kind of show — close, warm, and loud in the good way. There's no bad sightline because there's barely any distance to the stage.

It's tucked away with little street life around it, so plan on driving or a rideshare; parking is usually easy nearby. The room's indoors, so tonight's rain is a non-issue.

MONDAY, AUGUST 17

Movies in the Parks: The Dark Knight @ Bartelme Park

Monday's Movies in the Parks screening is The Dark Knight — Christopher Nolan's 2008 Batman, Heath Ledger's Joker and all — projected under the sky at Bartelme Park on the Near West Side. It's free, it's all ages, and it starts around 8:30pm once it's dark.

Bartelme is a compact, modern park at 115 S. Sangamon, an easy hop from the West Loop's restaurant row. Bring a blanket or a low chair and get there before dusk to stake out a spot on the lawn. The Green and Pink lines both stop at Morgan, a few blocks north.

Monday is the weather sweet spot this week: 74 and overcast with only a 5% chance of rain, close to ideal for lying on the grass through a 152-minute movie. Layer up once the sun's down.

Emily Kuhn Quintet @ Jefferson Memorial Park

Trumpeter Emily Kuhn brings her quintet to Jefferson Memorial Park on Monday evening — a free, all-ages set from the Park District's Night Out in the Parks series. Expect material from her album Feathered Things, with Meghan Stagl on piano and voice, Erik Skov on guitar, Kitt Lyles on bass, and Gustavo Cortiñas on drums.

This is easygoing neighborhood jazz that rewards showing up early with a blanket. Jefferson Park sits on the Northwest Side and is one of the city's true transit hubs — the Blue Line stops right at Jefferson Park, so it's an easy ride in from downtown.

Music runs 5:30 to 7pm. Monday's forecast — 74 and overcast, 5% rain — is about as good as August park weather gets, so this and the Bartelme movie make a tidy free double-header if you're ambitious.

ON THE HORIZON

ART on THE MART @ Chicago Riverwalk

If you're planning past the weekend, ART on THE MART is worth catching before it goes dark for the season. The installation turns the 25-story river face of THE MART into the largest permanent digital art projection in the world — a genuinely only-in-Chicago sight, and completely free to watch.

The projections light up in the evening (around 7:30pm), and you view them from the Chicago Riverwalk on the south bank, between Wells and Franklin. The Merchandise Mart stop on the Brown and Purple lines lets out practically underneath it. Grab a spot along the rail; the Riverwalk's cafes and wine bars are right there if you want a drink in hand.

The current run is on view through August 30, so you have a couple of weeks — but it only shows a few evenings a week, so check the schedule before you make the trip. No ticket, no reservation, just show up at dusk.