These Are All of Your Chicago Weekend Plans for August
These are all your local must-hit music and food festivals, events, movies, markets, deals, and concerts to help you make the most of your weekend.
The sun is shining. The air is warm, sweet, and sharp with the smell of sunshine and freshly cut grass. It’s the summer, and after Chicago’s three requisite nice-weather-false-starts, our fair city has finally come out of its hibernation and there’s plenty to do, whether you want to check out the city’s best restaurants, browse at a local farmer’s market, or have a romantic night out with your partner.
Chicago has something to offer everyone, from state parks to thrift shops to pop-ups. And if that’s not enough for you, it’s also well within driving distance of some wonderful day trip spots. Whether you want to hit the trails, relax at a spa, or test your friendship at one of our city’s escape rooms, the City of Broad Shoulders has you more than covered.
Knowing all this, it should come as no surprise that there are plenty of weekend outings that are worth your time this August. Here are some of our can’t-miss favorites.
Festival Events in Chicago
August 3 - 6
Grant Park, $135+ for a one-day pass and $385+ for a four-day pass
Listen, we know you know about Lolla already, but it is Chicago’s biggest summer party. This year, the lineup is jam-packed with acts like Billie Eilish, Carly Rae Jepsen, Kendrick Lamar, The Red Hot Chili Peppers, and ODESZA. Tickets are pricey, but it should be worth it. If you’re looking to save some cash on Lolla’s best acts, though, scroll down a bit.
August 5
Bronzeville, Free
Celebrate Bronzeville’s rich jazz and blues history with a day full of food, fun, and incredible music. The fest will feature live music all day courtesy of Buddy Fambro, Marqueal Jordan, Joan Collaso, and the Willie Fultz Band feat. Skinny Williams, alongside local vendors, a kid’s play zone, and a fully-stocked cigar truck for the adults.
August 12 - 13
Harrison Park, Weekend passes start at $79
Chicago is the birthplace of house music, so why not spend a weekend paying tribute alongside legends of the genre like Armand Van Helden, Derrick Carter, and Joeski? The festival will also feature local artists and vendors, as well as bites provided by neighborhood-favorite eateries. Stay hydrated.
August 12 - 13
Northalsted, $20 suggested donation
Bust out your best crop top and head over to Boystown for Market Days, one of Chicago’s best and longest-running festivals, having been held in the neighborhood since 1982. This year’s fest will feature international superstars like Shea Coulee, Pussy Riot, and Betty Who, alongside drag shows, DJ sets, and cover bands. August Hotel’s Saturday afternoon set is not to be missed.
August 11 - 13
Roscoe Village, $15 suggested donation
Half blast-from-the-past-cover-band-music-festival, half retro-fashion-swap-meet, Retro on Roscoe will feature dozens of musical acts including tributes to ABBA, Amy Winehouse, and Santana, alongside Chicago’s favorite cover act Rod Tuffcurls and the Benchpress, but don’t miss the local vendors shilling awesome vintage clothes, art, and other treasures. Oh, there will be an antique car show featuring over $2 million in classic cars.
Food & Drink Events in Chicago
August 5
6743 South Kedzie Avenue, Free
Taste of Chicago’s neighborhood tour continues through August, bringing live local music, free dance classes, and, of course, delicious local food to Marquette Park. Over two dozen food vendors including favorites like Badou Senegalese Cuisine and Los Mangos will be on site to satisfy even the heartiest appetites.
August 19 - 20
Humboldt Park, $20+
What could be better than two days in sunny Humboldt park soaking up the rays alongside some irresponsible pours of sangria? Sangria Festival Chicago will feature a variety of local chefs, mixologists, musicians, and artists, all celebrating the food and wine of Latin America.
August 26 - 27
The Salt Shed, $95+
Celebrate the best pizza city in the world (take that, New York City and also Naples) with dozens of the city’s best pizza spots, all stuffed into the Morton Salt Shed. Not only will Steve Dolinsky’s pet pizza project stuff you with the city’s best pie, but it’ll also feature a variety of panels, as well as a lab showcasing unique, one-off pizza collaborations.
August 26 - 27
Lakeview, $10 suggested donation
Close out August in Lakeview alongside neighborhood taco favorites like Tuco & Blondie, Tikka Masala Taco House, and Cabos Tacos. The festival not only features live music across two stages, but comes complete with a “best taco” contest, activities for kids, and honest-to-goodness lucha libre wrestling.
August 18 - 20
North Center
$10 suggested donation
The premier food fest for carnivores in the know, Ribfest will descend on Chicago’s North Center neighborhood for the 23rd time. The three-day event will feature national rib royalty like Mrs. Murphy’s, Robinson’s, and Blazin’ Bronco, as well as refreshments, games, and live music (including an ABBA cover band).
Art & Entertainment Events in Chicago
August 3 - 6
Multiple locations, Ticket prices vary
If you don’t want to pay $400 for a Lollapalooza ticket, it’s time to support one of Chicago’s many incredible local venues and catch an official Lolla aftershow. Venues like Lincoln Hall (Suki Waterhouse), Metro (Carly Rae Jepsen), House of Blues (Yung Gravy), Schubas (The Happy Fits), and many, many more are hosting Lollapalooza’s best acts at a budget-friendly price.
August 19 - 20
North Avenue Beach, Free
The largest free event of its kind in the USA, the Chicago Air and Water Show returns to North Avenue Beach, complete with acrobatic performances from a variety of stunt performers and highlighted by the Air Force Thunderbirds.
August 19 - 20
Morton Arboretum, $17 admission price
As if the Morton Arboretum couldn’t get any more beautiful. This juried art exhibit in the middle of the arboretum features artists from across the midwest, showing off jewelry, photography, ceramics, woodturning, fused glass, and all sorts of other captivating art. Grab a glass of wine, stroll through the picturesque greenery, and bask in the art. What could be better?
Through September 4
The Art Institute of Chicago, $14 for Chicago residents
The Art Institute always seems to be exhibiting the most iconic artists in the history of the world, but this Van Gogh exhibit in particular is not to be missed. Featuring landscapes painted during Van Gogh’s time in the suburbs to the northwest of Paris, the exhibit is a study in a time at which the French countryside was changing rapidly. Van Gogh found inspiration in how the bustle of an industrializing region interacted with the placid, relaxed countryside, and it’s fascinating to see that inspiration play out on the canvas.
Through September 4
The Museum of Science and Industry, Museum admission $25.95, plus $18 for exhibit
The exhibit features full-body casts of some of the catastrophic volcano eruption’s victims, for an incredible-if-morbid look into the daily lives of the folks who lived in the shadow of Mount Vesuvius. And there’s also a holographic gladiator display and the immersive 4D simulation of the Vesuvius eruption. You’re guaranteed to leave with a new appreciation of Chicago’s overwhelming lack of active volcanoes—or mountains at all, for that matter.