CHICAGO — This weekend, Chicago is set to be buzzing with excitement as the highly anticipated Air and Water Show makes its return to the lakefront.
From high-flying aerial performances to ground-level festivities, there’s something for everyone to enjoy.
If the jet fighter displays and water stunts aren’t your scene, fear not! The city is brimming with cultural events that cater to diverse tastes, including the Taylor Street Little Italy Festa, the Chicago Vintage Festival, and the Stay High Trinket Fest.
Additionally, art enthusiasts can look forward to the Glenwood Avenue Arts Fest, while health-conscious individuals may want to check out M.A.P. Your Health Chicago.
For a night of theater, catch the tribute play inspired by the beloved film “Waiting to Exhale,” or head to Pilsen for a special concert event.
For those looking to expand their weekend plans, here’s your guide to 28 fantastic activities happening in Chicago this weekend:
Starting with events occurring throughout the weekend, we have the Taylor Street Little Italy Festa taking place from 5-10 p.m. on Thursday and Friday, and then from noon to 10 p.m. on Saturday and Sunday.
Located at 1431 W. Taylor St., this festival, hosted by Onesti Entertainment, is a celebration of Italian culture and cuisine.
Expect live performances, a variety of food vendors, Italian merchandise, and fun for kids, including a “Bambini Corner” and “Nona’s Cooking Stage.”
The Glenwood Avenue Arts Fest will follow the Festa hours on Friday from 6-10 p.m. and on Saturday from 11 a.m.-9 p.m. and Sunday from 11 a.m.-7 p.m.
This immersive event features over 100 artist booths, open studio hours at local galleries, and live entertainment across multiple outdoor stages.
Admission is free, making it an excellent opportunity for art lovers to explore Rogers Park’s vibrant artistic community.
For aerial and aquatic thrill-seekers, the Chicago Air and Water Show takes place Saturday and Sunday from 10:30 a.m. to 3 p.m.
The event promises spectacular aerial displays from the U.S. Air Force Thunderbirds, U.S. Army Parachute Team Golden Knights, and various other extraordinary performances along the lakefront, highlighted by North Avenue Beach.
Another exciting event is the SAUCED Summer Night Market from 5-10 p.m. at the WNDR Museum located at 1130 W. Monroe St.
Indulge in a delightful mix of food and drinks while enjoying live entertainment, including custom cake designs from Crappy Cake Art and unique demonstrations from Ignite Glass Studio.
If you want a more exclusive viewing of the Air and Water Show, head to the 2025 Air & Water Show Viewing Party at the Lakefront Green at Theater on the Lake from 11 a.m. to 4 p.m.
Tickets include food from Smoque BBQ, an open bar, ample seating, and restrooms on-site. Prices start at $129.89 for adults and $55.20 for children aged 6-12, while kids under five get in for free.
Vintage lovers should not miss the Chicago Vintage Festival on Saturday and Sunday from noon to 6 p.m. at Village Bucktown Dispensary, where over 50 vendors will showcase the best in vintage shopping.
Admission is free, ensuring you can find that unique piece for your collection.
Additionally, if you’re interested in theater, don’t miss “When Boys Exhale,” a play that pays tribute to the film “Waiting to Exhale.”
Held at Definition Theatre from 7-10 p.m. on Friday and 2-5 p.m. and 7-10 p.m. on Saturday, you can witness how the story resonates with the experiences of Black gay men today.
General admission starts at $39.19, with VIP options available for those looking for a premium experience.
Now, let’s dive into Friday’s events! The Stay High Wear Trinket Fest kicks off from noon to 6 p.m. at Village Bucktown Dispensary.
This pop-up festival is your last chance for summer shopping, featuring over 40 vendors offering accessories, clothing, and more. Admission is free with RSVP, though it will be $5 at the door.
Engage with the arts at the opening reception of “Cuckoo – I’m Not Crazy You Are” from 6-9 p.m. at Jackson Junge Gallery, showcasing Laura Lee Junge’s newest exhibition.
Entry is free, and the event promises an intimate look into the artist’s work.
Art aficionados can join the 19th Bronzeville Art District Trolley Tour from 6-9 p.m., starting at Gallery Guichard, where attendees can hop on a double-decker bus to explore art galleries and cultural venues showcasing local and national artists.
This artistic journey is completely free to the public.
On Saturday, the Summer Brunch Saturdays at Miyagi Records runs from 10 a.m. to 3 p.m., pairing delectable Korean brunch with the laid-back vibe of a record store.
In addition, M.A.P. Your Health Chicago will take place from 10 a.m. to 3 p.m. at the Humboldt Park Health Wellness Center.
This free health fair will feature discussions on crucial health topics like obesity and diabetes and offer interactive activities for attendees.
Music lovers won’t want to miss the Drop The Needle: Vinyl Crawl Vol. 1 from 11 a.m. to 3 p.m. at Miyagi Records.
Join other vinyl collectors for a day of exploring record stores, complete with complimentary lunch and discounts at participating shops.
For pet lovers, the Nonnina Dog Dayz Summer Paw-ty is a must-attend event from noon to 4 p.m. at Nonnina, featuring fun for furry friends and discounted drinks for their humans.
Handmakers Pop Up, located at So Happy You’re Here from noon to 7 p.m., invites attendees to shop handcrafted goods and delicious food options.
Don’t miss the Taste of Africa 2025, happening at Ohio Street Beach from noon to 8 p.m., promising an immersive cultural experience filled with traditional African cuisine.
Dog owners can let their pets splash around and enjoy a Summer Splash Fest at Pup Social from 2-4 p.m., complete with water features and fun activities for both canines and their companions.
The Plant and Clothing Swap at Gallery Cafe occurs between 2-5 p.m., allowing attendees to trade items and plants they no longer need for something new.
The Sunny Collective Vol. 3 at 1706 S. Halsted St. wraps up the summer with a day of local art, shopping, and music.
Meanwhile, Ponyboy and the Idiots will perform live at the Chicago Danztheatre Ensemble Auditorium from 5-10 p.m., providing a fun evening of music along with art vendors present.
For music enthusiasts, Gloria y Dolores with La Cassandra is presenting a one-night-only concert at Hoste Cocktails, featuring a mix of music and tasty bites from Chef Manny Mendoza from 7-11 p.m.
As the weekend winds down, take part in the Hyde Park Handmade Bazaar on Sunday from 11 a.m. to 3 p.m. at The Promontory, showcasing craftmakers and unique items.
Matcha lovers can indulge in Matcha Craze Pt. 2 at Amber Agave from noon to 6 p.m. featuring a variety of matcha-based drinks and desserts.
The Yah Yah Collective will unveil their new exhibit, Switching Costs, at the Chicago Cultural Center on Sunday from noon to 4 p.m. with live refreshments and performances, all free to the public.
Additionally, Petterino’s is hosting its inaugural Dog Dayz Bash from 1-3 p.m. with activities for pets and $6 drinks for dog parents.
Wrap up the Sunday festivities at Soul & Smoke in Avondale from 5-8 p.m. with live music and BBQ.
After that, enjoy the album release listening party for Apres Pompeii at Dorothy from 7-9 p.m.
Conclude the weekend with live music at Urban Luxe Cafe from 7-10 p.m. where attendees can enjoy some tasty food and drink options during the event.
With so many activities planned across Chicago, you’ll find events to suit any interest in the city this weekend!
image source from：blockclubchicago
