Searching for what to do this weekend in Chicago? Below are the best things to do in Chicago this weekend (August 14-16, 2026) including the best events and activities.
You can find more things to do in Chicago this week here.
(If you are planning ahead, you can also find the best things to do next weekend here.)
I suggest bookmarking this blog post as it is updated regularly with new events and activities.
Disclosure: This article contains affiliate links. I may make a small commission if you make a booking using my links at no extra cost to you.
Best Weekend Events in Chicago
Below are the best weekend events in Chicago:
Chicago Air & Water Show – August 15 & 16, 2026 (Rehearsal on August 14, 2026) | Free (see below for private watch parties, events and cruises)
Printer’s Row Art Fest – August 15-16, 2026, 10am-5pm | Free
Sangria Festival (Humboldt Park) – August 15-16, 2026
Glenwood Avenue Arts Festival (Rogers Park) – August 14-16, 2026 | Free
Taylor Street Little Italy Festival – August 13-16, 2026 | Free (suggested donation)
Fan Expo – August 14-16, 2026
F1® Arcade Opening Day – Opening Friday, August 14, 2026
Sonido Fest at the National Museum of Mexican Art – Saturday, August 15, 2026, 2pm | Free
Summer Slow Jams & RnB Party – Saturday, August 15, 2026, 4pm
Ritmo del Mar at the Shedd Aquarium (21+) – Saturday, August 15, 2026, 7-11pm
South Shore Summer Fest – Sunday, August 16, 2026, 12-8pm | Free
Sinatra Under The Stars at AIRE Rooftop – Sunday, August 16, 2026, 5pm & 8pm
More Weekend Events in Chicago
Below are more events taking place this weekend in Chicago:
Rise Pilates Club Summer Series at Oak Street Beach – Friday, August 14, 2026, 6-8am | Free
Chi Food Truck Fest – Friday, August 14, 2026, 11am-3pm
BAPA Porch Concert Series – Friday, August 14, 2026, 6-8pm | Free
Mike Reed’s Common Good Dance Band w/ Katie Ernst (solo) and DJ Joe Bryl – Friday, August 14, 2026, 6-9pm | Free
4th Annual Summer Traffic Light Party w/Music by Tall Girl & The Bangers (Ages 21+) – Friday, August 14, 2026, 7pm
Tori Amos In Times of Dragons Tour – Friday, August 14, 2026, 8pm
Millennium Park Free Summer Workout – Saturday, August 15, 2026, 8-11:45am | Free Admission
Romancing Roscoe – Saturday, August 15, 2026, 10am-6pm | Free – One-day sidewalk block party taking place in Roscoe Village, celebrating all things romance, books, and community.
Zhu on the Move at East End Plaza at Navy Pier – Saturday, August 15, 2026, 4pm
Retro Party at Swedish American Museum (21+) – Saturday, August 15, 2026, 6-10pm – Celebrate their 50th Anniversary with a 1970s dance party.
Mat Kearney at The Auditorium Theatre – Saturday, August 15, 2026, 8pm
BonFest at North Park Village Nature Center – Saturday, August 15, 2026, 7:30-9pm | Free
Free Day at the American Writers Museum – Sunday, August 16, 2026, 10am-5pm | Free
Summer Sunday at Navy Pier – Sunday, August 16, 2026, 12-5pm | Free – New summer series filled with free live music, interactive workshops, games and activities for all ages.
Rockefeller Chapel 60th Bells of Summer Concert Season – Sunday, August 16, 2026, 5pm – Final concert this summer.
Grant Park Music Festival: Beethoven Symphony No. 9 at Jay Pritzker Pavilion – August 14, 2026, 6:30pm & August 15, 2026, 7:30pm – Final concert for the summer.
Summerdance: Spirit of Music Garden in Grant Park – August 14 & 15, 2025, 6-9pm | Free
Vintage House $10 and Under Sale (Avondale) – August 15 & 16, 2026, 12-5pm | Free
Marvel’s Spider-Man: Beyond Amazing – The Exhibition at The Griffin Museum of Science and Industry – Through August 16, 2026
The Notebook: The Musical at the James M. Nederlander Theatre – Through August 16, 2026
Iceboy! at the Goodman Theatre – Through August 16, 2026
SAW The Musical: The Unauthorized Parody of SAW – Through September 6, 2026
See the Chicago Air & Water Show
While you can see the Air & Water Show for free from the beach, you can also avoid the crowds by joining one of the following cruises or watch parties:
Air & Water Show Preview at Shore Club – Friday, August 14, 11am-2pm
Air & Water Show Watch Party at Caffe Oliva on Ohio Street Beach – August 15 & 16, 2025, 10am
Air & Water Show Viewing Party at The Lakefront Green at Theater on the Lake – Saturday, August 15, 11am-4pm
Air & Water Show Saturday Lake Cruise (21+) – Saturday, August 15, 12-3pm
Flight Deck: Air Show Rooftop Party at Offshore Rooftop – Sunday, August 16, 11am-4pm
Air & Water Show Viewing Party at The Lakefront Green at Theater on the Lake – Sunday, August 16, 11am-4pm
Air & Water Show Sunday Lake Cruise (21+) – Sunday, August 16, 12-3pm
More Things to Do in Chicago This Weekend
Take an Architecture River Cruise
An architecture river cruise is a must do Chicago experience.
Take a Lake Cruise
Enjoy a cool lake breeze and admire the Chicago skyline from a lake cruise.
If your time is short, you can do a combination river and lake cruise.
Watch Fireworks
Watch fireworks at Navy Pier every Saturday at 10pm in the summer. The fireworks can be seen from various spots along the Lakefront including North Avenue Beach, Oak Street Beach and the Adler Planetarium Skyline Walk.
The best and most relaxing way to see the Navy Pier fireworks show is on a fireworks lake or river cruise.
If you enjoy guided tours, you can also see the fireworks and other attractions on this fireworks segway tour.
Kayak in the River or Lake
A fun way to explore the city is to go kayaking in the Chicago River or Lake Michigan. You can rent a kayak in the Chicago River here and Ohio Street Beach here.
You can also join a guided kayaking tour in the downtown portion of the Chicago River including this history and architecture kayak tour and this sunset kayak tour.
Please note that you will get a little wet when kayaking so bring a waterproof case for your phone and water-resistant or quick-drying clothing.
Attend a Candlelight Concert
Chicago’s Candlelight Concerts is a series of special classical music concerts that take place in beautiful venues bathed in candlelight. Some of the concerts taking place this weekend include:
Tribute to Queen
A Tribute to Drake
Tribute to the Beatles (Oak Park)
You can find the full list of candlelight concerts in Chicago here.
Titanic: A Voyage Through Time
Step into history at Titanic: A Voyage Through Time an extraordinary virtual reality (VR) journey into history’s most famous ship. Dive to the wreckage as it rests today, then travel back to 1912 to experience the Titanic as a passenger. Walk the Grand Staircase, meet the people who shaped its story, and witness history firsthand in this immersive adventure.
When: Through September 27, 2026
Where: 108 West Germania Place, Chicago, IL 60610
Cost: Prices vary. Click here to purchase tickets.
Minecraft Experience: Villager Rescue
Minecraft Experience: Villager Rescue is an immersive adventure that lets you and your friends become heroes, fighting spiders, creepers, and skeletons on your quest to rescue villagers from a zombie attack. Explore eight interactive Minecraft rooms and gather resources for your quest in these interactive biomes. Practice your Minecrafting skills with a handheld Orb to chop down trees, collect resources, and fight mobs.
Where: 9900 Berwyn Ave, in the Pearl District, Rosemont, IL 60018
Cost: Prices vary. Click here to purchase tickets.
AirOtic Soirée
AirOtic Soirée is a bold, sensual and provocative cabaret-circus experience blending high-level acrobatics, seductive choreography and visual artistry. After sold-out runs across the U.S. and Europe, it is returning to Chicago for a full summer run. 21+ with valid ID.
When: Through August 29, 2026
Where: Experience 868, 868 North Franklin Street, Chicago, IL 60610
Cost: Prices vary. Click here to purchase tickets.
Watch a Drunk Shakespeare Play
Join The Drunk Shakespeare Society for an unforgettable evening of Shakespearean revelry. Set within a speakeasy, five actors attempt to perform a Shakespearean play after one of them downs multiple shots of various alcohols. Every show is different depending on who is drinking and what they’re drinking. Must be 21+ with valid ID.
Where: The Lounge At The Lion, 182 North Wabash Avenue
Cost: Prices start at $29 per person. Click here to purchase tickets.
Wondra: Immerse yourself in the magic of nature
Looking for a fun activity for kids? Head to the suburbs for Wondra, where each space invites curious minds to discover hidden details, dazzling colors, and natural awe-scapes that spark imagination and evoke wonder. Experience nature’s wonders in a whole new light with this immersive journey.
Where: 5 Woodfield Mall, Schaumburg, IL 60173
Cost: Prices vary. Click here to see prices and purchase tickets.
As you can see there are many things to do in Chicago this weekend. If you are looking for things to do during the week, you can find more things to do in Chicago in August.
