10 Best Things to Do in Chicago and DuPage This Weekend: August 21-23, 2026
CHICAGO—Another busy summer weekend is approaching, with food festivals, outdoor art, live music, professional baseball, lakefront competition, and family events filling the calendar across Chicago and DuPage County.
This weekend has some especially strong neighborhood events. Southport Avenue turns into a three-day taco festival, Fulton Market becomes an outdoor art gallery, classical music takes over a Ravenswood street, and thousands of athletes head to Chicago's lakefront for Supertri Chicago.
In DuPage County, visitors can choose between a downtown food festival in West Chicago, a major 40th anniversary celebration at College of DuPage, Latin American cultural programming at The Morton Arboretum, and a special Gabby's Dollhouse weekend in Naperville.
Here are 10 of the best things to do Friday, August 21 through Sunday, August 23, 2026.
1. Lakeview Taco Fest
Friday, August 21 through Sunday, August 23 | Southport Avenue between Addison and Roscoe | Lakeview
Come hungry. The 13th annual Lakeview Taco Fest takes over the Southport Corridor with more than 10 Chicago-area food vendors competing for taco bragging rights.
The lineup goes beyond traditional steak, chicken and chorizo tacos. Vendors include Cafe Tola, Beat Kitchen, Taqueria Arceo, Taqueria Teotihuacan, Tuco & Blondie and others, while visitors can vote for their favorite taco throughout the weekend.
There will also be two live music stages, beer and taco pairings, children's activities, and one of the festival's more unusual attractions: live lucha libre wrestling at Southport and Cornelia at 5 p.m. each evening.
Festival hours are 4 to 10 p.m. Friday, 11 a.m. to 10 p.m. Saturday, and 11 a.m. to 9 p.m. Sunday. Entry carries a $10 suggested donation benefiting Friends of Lakeview.
2. West Loop Art Fest
Saturday, August 22 and Sunday, August 23 | 10 a.m.-7 p.m. | Fulton Market
Fulton Street becomes an open-air gallery this weekend for the West Loop Art Fest, which stretches across roughly four blocks in Fulton Market.
The two-day event brings together emerging artists, established creators, makers and small businesses with work ranging from painting and photography to ceramics, jewelry, textiles, mixed media and home décor.
This year's festival is being produced by Bash Creates in partnership with the West Central Association, with interactive art, demonstrations, food and other programming woven through the event.
Admission is free, making it an easy addition to a Saturday or Sunday spent exploring the restaurants and shops around Fulton Market and West Loop.
3. Thirsty Ears Festival
Saturday, August 22 and Sunday, August 23 | Wilson Avenue between Hermitage and Ravenswood | Ravenswood
This is not a typical Chicago street festival.
The Thirsty Ears Festival closes Wilson Avenue to traffic and replaces the usual rock and cover-band format with two full days of classical and contemporary music performed outdoors.
Saturday's program runs 2 to 11 p.m. with performances from the Chicago Chamber Music Festival, Bach + Beethoven Experience, Olea Ensemble, PlayOUT! and others. At 9:30 p.m., the festival presents a miniature version of its Sound of Silent Film Festival, pairing modern silent films with newly composed scores performed live.
Sunday runs 1 to 9 p.m. and includes Lakeshore Rush, Emily Mwila, Wurtz-Berger Duo, Origin of Animal and additional performers.
Food trucks, beer, wine, children's programming and face painting are also available. Entry is free with a $10 suggested donation.
4. Villapalooza
Saturday, August 22 | Little Village
Villapalooza returns to Little Village as a free grassroots celebration built around music, art, neighborhood culture and local young creatives.
Unlike many larger commercial festivals, Villapalooza has a strong community focus. The nonprofit event was created to provide a platform for local talent and youth entrepreneurship while creating accessible cultural programming within Little Village.
The festival has grown into an annual neighborhood tradition and is one of the standout events on Chicago's August festival calendar.
5. Supertri Chicago
Saturday, August 22 and Sunday, August 23 | Chicago Lakefront
Chicago's lakefront becomes a racecourse this weekend as Supertri Chicago, formerly widely known as the Chicago Triathlon, brings swimming, cycling and running to some of the city's most recognizable scenery.
Saturday focuses on younger athletes and shorter-distance events at Foster Beach. Kids races begin at 7 a.m., followed by the SuperSprint at 10 a.m.
The major races shift downtown Sunday. The Olympic-distance race begins at 6 a.m., while the Sprint starts at 8 a.m. Athletes swim through Monroe Harbor, cycle along closed portions of the lakefront roadway and run through the downtown lakefront area.
For spectators, this is one of the more unusual ways to experience Chicago's shoreline, particularly early Sunday morning when competitors move through the city with the skyline as the backdrop.
6. New York Mets vs. Chicago White Sox
Friday, August 21 through Sunday, August 23 | Rate Field
The White Sox host the New York Mets for a full three-game series on the South Side this weekend.
First pitch is scheduled for:
Friday: 6:40 p.m.
Saturday: 6:10 p.m.
Sunday: 1:10 p.m.
Sunday's afternoon game can be an especially easy fit for anyone looking to pair baseball with lunch or dinner in Bridgeport, Armour Square, Chinatown or the South Loop.
Check the official White Sox schedule before leaving for any changes to start times, promotions or ticket availability.
7. West Chicago Food Festival
Saturday, August 22 | 4-8 p.m. | Downtown West Chicago | Free
More than 15 area food vendors are expected in Downtown West Chicago Saturday for an evening built around food, live entertainment and community activities.
The West Chicago Food Festival runs from 4 to 8 p.m. and offers free admission. Guests can bring lawn chairs or blankets, although outside food, drinks and coolers are not permitted.
Drivers should pay attention to temporary street closures. Galena Street between Main and High streets and Main Street from Turner Street to West Washington Street are scheduled to close beginning at 10 a.m. Saturday.
Several public parking areas around downtown are listed by the city for festival visitors.
8. McAninch Arts Center 40th Anniversary Festival
Sunday, August 23 | Noon-5 p.m. | College of DuPage, Glen Ellyn | Free
The McAninch Arts Center at College of DuPage is turning 40, and instead of limiting the celebration to a formal performance, the MAC is throwing a free outdoor festival.
The afternoon at the Lakeside Pavilion includes live music, art activities, dance, theater and family programming.
The schedule includes the COD Student & Alumni Jazz Ensemble, dance lessons, a New Philharmonic trombone trio, selections from College Theater's production of Footloose, and a 2 p.m. concert by Sixteen Candles celebrating the music of the 1980s.
Visitors can also find face painting, mural painting, woodblock printing, a scavenger hunt and other activities around the grounds.
The festival runs from noon to 5 p.m. and admission is free.
9. Noche de Familia at The Morton Arboretum
Sunday, August 23 | 5-7:30 p.m. | The Morton Arboretum, Lisle
The Morton Arboretum is celebrating the cultures of Latin America Sunday evening while summer flowers are still blooming and monarch butterflies are moving through the gardens.
Noche de Familia includes children's activities, lawn games, crafts, face painting, bilingual nature bingo, community organizations and food concessions in and around the Children's Garden.
A separate Spanish-language tram tour departs at 4 p.m., taking guests through the Arboretum's woodlands, wetlands and prairies while connecting the landscape with cultural and natural-history stories.
The evening event is included with regular Arboretum admission, or visitors can purchase special $5 evening admission for guests age 4 and older beginning at 5 p.m. Children 3 and younger are free.
10. Gabby's Dollhouse MEOWseum Discovery Days
Friday, August 21 through Sunday, August 23 | DuPage Children's Museum, Naperville
Families with younger children have a particularly good reason to visit DuPage Children's Museum this weekend.
For three days, the museum is hosting Gabby's Dollhouse MEOWseum Discovery Days in partnership with DreamWorks Animation and the Association of Children's Museums.
Programming includes story times, dance-alongs, an instrument makerspace, crafts, scavenger hunts, sensory activities, racetrack design and other hands-on projects inspired by characters from the series.
There are also opportunities to meet and take a photo with a Gabby costumed character, but those meet-and-greet sessions require a timed reservation, including for museum members.
The museum is open 9 a.m. to 4 p.m. Friday and 9 a.m. to 5 p.m. Saturday and Sunday. The themed activities are included with museum admission or membership.
Turn a Weekend Favorite Into Your Next Neighborhood
A weekend spent at a street festival, park, downtown district or neighborhood event can reveal things a real estate listing cannot: how walkable an area feels, where residents gather, what businesses are nearby, how easy transportation is, and what the community is actually like when people are out enjoying it.
If a weekend in West Loop, Lakeview, Little Village, Naperville, Glen Ellyn, Lisle or another Chicagoland community has you thinking about your next move, connect with The Cory Tanzer Group at Option Premier to compare homes, condos, neighborhoods, commute options and local market conditions with a strategy tailored to what you want from everyday life.
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