Top 10 Things to Do in Chicago and DuPage This Weekend: August 14-16, 2026

CHICAGO—Another busy summer weekend is approaching, with one of Chicago’s biggest lakefront traditions, neighborhood festivals, professional baseball, live music, art fairs, and family-friendly events scheduled across Chicago and DuPage County.

From the Chicago Air and Water Show and Taylor Street Little Italy Festa to concerts in Naperville, art at The Morton Arboretum, and vintage baseball in Wheaton, here are 10 of the best things to do Friday, August 14 through Sunday, August 16, 2026.

1. Chicago Air and Water Show

Saturday, August 15 and Sunday, August 16 | 10:30 a.m.-3 p.m. | North Avenue Beach | Free

Chicago’s signature lakefront spectacle returns with the U.S. Air Force Thunderbirds headlining two days of aerial demonstrations over Lake Michigan.

The show can be viewed along the lakefront from Fullerton Avenue to Oak Street, with North Avenue Beach serving as the focal point. The lineup also includes the U.S. Army Golden Knights, military demonstrations, civilian aerobatic performers, and more.

Want an early look? The official rehearsal takes place Friday, August 14. Public parking is not available at North Avenue Beach, so CTA and other public transportation are strongly recommended.

2. Taylor Street Little Italy Festa

Thursday, August 13 through Sunday, August 16 | Taylor Street | Little Italy

One of Chicago’s classic neighborhood festivals takes over Taylor Street between Ashland Avenue and Throop Street with Italian food, live entertainment, carnival attractions, cultural programming, and family activities.

The four-day festival features five live music stages, more than 40 food and merchandise vendors, cooking demonstrations, artisan goods, and performances from acts including The Bronx Wanderers and Hugo: The Ultimate Journey Tribute.

Admission is free, with a $10 suggested donation at the entrance.

3. Glenwood Avenue Arts Fest

Friday, August 14 through Sunday, August 16 | Rogers Park | Free

The 25th annual Glenwood Avenue Arts Fest transforms the cobblestone streets around Morse and Glenwood avenues in Rogers Park into a neighborhood-wide celebration of independent art.

The festival features more than 100 artist booths, open studios, art demonstrations, local food, craft beer, and multiple stages of live performances.

Friday’s Cobblestone Jam runs from 6 to 10 p.m., followed by the main artists market from 11 a.m. to 9 p.m. Saturday and 11 a.m. to 7 p.m. Sunday. Scheduled performers include Funkadesi, Son Monarcas, Nicholas Barron, and other Chicago artists.

4. Printer’s Row Art Fest

Saturday, August 15 and Sunday, August 16 | 10 a.m.-5 p.m. | South Loop

Historic Printer’s Row becomes an open-air gallery this weekend as approximately 100 artists from across the country display work along South Dearborn Street.

Visitors can browse paintings, photography, sculpture, jewelry, woodworking, street art, and other original pieces while enjoying live music and personalized poetry.

The festival runs from 10 a.m. to 5 p.m. both Saturday and Sunday near 728 S. Dearborn St., making it an easy stop for anyone spending the weekend in the South Loop.

5. Chicago Cubs vs. St. Louis Cardinals

Friday, August 14 through Sunday, August 16 | Wrigley Field

One of the National League’s most recognizable rivalries returns to Wrigley Field as the Chicago Cubs host the St. Louis Cardinals for three games.

Friday and Saturday games begin at 1:20 p.m., with Sunday’s matchup scheduled for 2:15 p.m.

Friday is also a Bud Fridays promotion, with a Cubs 1980s Replica Jersey available to up to the first 5,000 eligible early-arriving fans age 21 and older in the Budweiser Bleachers, while supplies last.

6. Ritmo del Mar at Shedd Aquarium

Saturday, August 15 | 7-11 p.m. | Shedd Aquarium | Ages 21+

Shedd Aquarium stays open after hours Saturday for Ritmo del Mar, an evening combining aquatic exhibits with salsa, cumbia, merengue, bachata, Latin jazz, and dancing.

The August event features Chicago Latin Groove Band, DJ Mala Vida, salsa and bachata lessons from Mayambo Dance Co., bilingual animal chats, and Lotería.

Admission includes aquarium exhibits and entertainment. Tickets are listed at $29.95 for adults and $19.95 for members, with food and beverages available separately. Guests must be 21 or older and bring photo identification.

7. Naper Nights Concert Series

Friday, August 14 and Saturday, August 15 | Gates open at 5 p.m. | Naper Settlement

Naper Nights delivers two completely different evenings of tribute music across the 13-acre Naper Settlement campus in Downtown Naperville.

Friday features the Dan Peters Band performing classic rock from 6 to 7:30 p.m., followed by JUMP: America’s Van Halen Experience from 8 to 10 p.m.

Saturday shifts to a Taylor Swift tribute by Sparks Fly from 6 to 7:30 p.m., followed by Made in America’s Toby Keith tribute from 8 to 10 p.m., featuring special guest Rich Eckhardt, Keith’s longtime lead guitarist.

Tickets are $25 for adults, $15 for children ages 4-12, and free for children 3 and younger.

8. Wine and Art Walk at The Morton Arboretum

Saturday, August 15 and Sunday, August 16 | 10 a.m.-5 p.m. | Lisle

Art meets nature at The Morton Arboretum, where visitors can stroll around Meadow Lake while viewing and purchasing nature-inspired artwork.

The juried Wine and Art Walk includes 67 artists working in photography, painting, ceramics, jewelry, fiber arts, glass, woodturning, sculpture, and other mediums.

Artist booths are located around the paved 0.6-mile Meadow Lake Trail and nearby Tram Road. The event is included with regular Arboretum admission.

Members can also attend an early-access event on Friday, August 14 from 5 to 7:30 p.m.

9. Park Palooza in Elmhurst

Saturday, August 15 | 4-8 p.m. | Berens Park

Elmhurst Park District is closing out summer with Park Palooza at Berens Park, 493 N. Oaklawn Ave.

The afternoon includes live music from School of Rock from 4 to 5:30 p.m. and Bon Journeyed from 6 to 8 p.m.

Families can also find an inflatable slide and obstacle course, carnival games, balloon twisting, airbrush tattoos, food trucks, a beer garden, and access to Hub attractions including mini golf, the spray ground, and batting cages.

10. Vintage Baseball at Cantigny

Sunday, August 16 | Noon-3 p.m. | Cantigny Park, Wheaton

Baseball looks very different when the rules come from the 1850s.

At Cantigny Park, the hometown DuPage Plowboys face the Creston Regulators in a vintage game played without gloves, overhand pitching, called balls and strikes, stealing bases, sliding, or leading off.

The game runs from noon to 3 p.m. and is free with paid parking. Visitors are encouraged to bring a lawn chair.

And if you want to stay longer, Cicada Summer performs bluegrass, Irish, folk, and acoustic music in Cantigny’s Beer Garden beginning at 3:30 p.m., making this an easy full Sunday afternoon outing.

Plan Ahead for a Very Busy Chicago Weekend

The Chicago Air and Water Show will bring especially large crowds to the lakefront Saturday and Sunday, while festivals in Little Italy, Rogers Park, and the South Loop will create additional traffic and parking demand around their respective neighborhoods. City officials are encouraging Air and Water Show attendees to use public transportation.

For DuPage events, advance tickets are worth considering for Naper Nights and general admission to The Morton Arboretum, particularly if you have a preferred day or arrival time.

Event schedules, ticket availability, outdoor programming, and weather-related plans can change. Use the official event page linked in each event name above before heading out.

Exploring Chicago or DuPage County?

Summer weekends offer a great way to experience what different Chicago neighborhoods and DuPage County communities are actually like beyond the real estate listings. Festivals, parks, restaurants, entertainment, transportation, and everyday neighborhood amenities can all help shape where you want to live.

Connect with The Cory Tanzer Group at Option Premier for personalized guidance when comparing homes, condos, rentals, commute options, and lifestyles across Chicago, Downtown neighborhoods, DuPage County, and the Western Suburbs.

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