Summer time is coming to a close, but Chicago’s event calendar isn’t showing signs of slowing down anytime soon. Looking for things to do near downtown Chicago this weekend? Check out some of these events!
Air & Water Show
Saturday and Sunday, August 17th-18 at 9am
The Chicago Air and Water Show showcases aerial maneuvers and rescue simulations from the U.S. Navy and Airforce as well as Chicago police department. The U.S. Leapfrogs (active duty SEALs and Special Forces crew members) will be doing a parachute freefall and the Chicago Fire Department Air and Water Rescue Unit will perform demonstrations as well.
This year will also feature a guest performance from the U.K.’s Royal Airforce Red Arrows. The headline attraction will be the U.S. Navy Blue Angels, featuring over 100 enlisted members of the Navy and Marines.
You can watch the Air and Water Show from one of many places this weekend, including for free at North Avenue Beach or aboard the Anita Dee II boat cruise for $60, which boards at Dusable Harbor.
Saturday Night Standup Comedy at Laugh Factory
Saturday, August 17that 7:15, 9:15, and 11:30pm
Laugh Factory is located in the new Belmont Theatre District in Lakeview. Seasoned comedians as well as brand new faces have graced the stage at Laugh Factory. Featured guests have included Das Chapelle, Bob Hope, Tim Allen, Jim Carrey, George Carlin, Adam Sandler, Wanda Sykes, Eddie Murphy, and many more. Stop by for one of three comedy sets for free with registration prior to the show, or $10 at the door.
Chicago Westside Music Festival
Saturday, August 17that 2pm
Check out the Westside Music Festival this weekend in Douglas Park! The headliner will be Faith Evans and the event will feature a collection of local artists. The Westside Music Festival is sponsored by the West Side Cultural Foundation and is free to attend.
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‘Summer time Chicago’ is one of the best times of the year to be downtown on the lakeshore. With endless possibilities of exciting adventures, be sure to check out some of the cities favorites!
Enjoy a beautiful summer day or evening paddling down the shores of Lake Michigan in a kayak! Kayak Chicago offers multiple locations at North Ave Beach, Montrose Beach and the Chicago River to set off on your great adventure. Enjoy multiple tours including sunset rides, firework shows, day time skyline tours and city light night paddles down the Chicago River. They also offer stand-up paddleboards as well! Grab your friends and hit the water this summer with these exciting tours.
Don’t forget about your furry friends, they want to enjoy the summer weather as well! Bring them by the Montrose Dog Beach for a great day splashing in the water and digging in the sand. As one of the only dog-friendly, off-leash beaches in the city, your dog will love interacting with all the others as well as making new friends! Open till around 9 pm during summer hours, stop by and check this place out, your dog will surely thank you.
For a full day of fun in the sun, check out Oak Street Beach located just minutes from Michigan Ave. In the heart of the city, Oak Street Beach has a ton to offer to those looking to catch some rays and take a break from the bustling downtown area. Sunbathing and swimming aren’t the only options– take your workout outside and exercise along the paved path lining the beach. Grab a bite to eat at the Oak Street Beachstro, located at the Southern end of the beach. Enjoy options from their breakfast buffet, full lunch and dinner menu or their full bar. Beachgoers can take in the views while diving into delicious cuisine.
For an exciting day on the water, many Chicagoans flock to the playpen for an amazing boating day and plenty of nautical things to do. Don’t worry – if you don’t have your own boat rentals are available through through many companies, including Chicago Boat Rentals. Experience the thrill of boating by renting sailboats or power boats. Head over to Jet Ski Chicago at North Ave beach to rent jet skis for some more fun in the sun if you don’t want the hassle of a boat!
Located within walking distance from Navy Pier is the well known Ohio Street Beach. With its sheltered curve of the shoreline, the calm waters are great for all swimmers. Enjoy the conveniences of being centrally located near the city while taking in the beauty of lake
Michigan and the sand between your toes. Bike rentals on-site offer additional things to do to make the most of your beach days! Also along the lakefront trail, many go for jogs or walks parallel to the water!
Don’t miss all the fun happening on the shores of the lake this summer and be sure to check out some of these amazing beaches and some of the great activities they have to offer to everyone!
Downtown Chicago has a reputation for being home to a wealth of events and activities. From music and food festivals to summer rooftops and outdoor activities, there is something for everyone!
If there’s one thing Chicagoans enjoy most about summer – it’s enjoying some cocktails at the city’s best rooftop bars. These sky-high bars offer unparalleled views combined with tasty bites and divine cocktails. Some of the favorites include Cindy’s, Raised, and London House!
Cindy’s is located in downtown Chicago’s Loop directly across from Millennium Park, offering unbeatable views and outdoor fire pits if it gets a little chilly. Raised is an indoor/outdoor garden lounge located on top of the Renaissance Hotel. Serving craft beers, exquisite cocktails, small plates and stunning views there’s no doubt why it’s a local favorite. Located in the Loop along the Chicago River is the ever-popular London House.
Another renowned Chicagoan summer activity is the Taste of Chicago hosted in Grant Park. It’s the nations premier outdoor food festival displaying the diversity of Chicago’s cuisine. Dishes range from classic local dishes to specialty cuisines from the array of eclectic neighborhood restaurants! The festival is complemented by outstanding music and exciting activities perfect for the whole family. Foodies, be sure to check out this extravagant, massive food festival!
If you’re a fan of BBQ and country music – stop by the Windy City Smokeout! With 20 of the world’s best pitmasters, there isn’t a dish here that won’t leave you lickin’ your fingers clean! Enjoy exquisite brisket, ribs, chicken, and more! Award-winning country music stars mixed with great up-and-coming artists create a spectacular show all day long! Some of the main headliners this year include Brett Young, Midland and Brett Eldredge. While eating the BBQ, refresh with some craft brews for the perfect downtown Chicago summer day.
Every year, the annual Chicago Air & Water Show has remained one of downtown Chicago’s most popular festivals. The show is a free event that takes place at North Avenue Beach that showcases daredevil pilots, parachute teams, and jets flying in formations. The water show displays incredible water-skiing and boat-jumping. Viewers can enjoy from the beach or head to Castaways to dine while enjoying this spectacular summer show! The U.S. Army Golden Knights participate each year while the U.S. Navy Blue Angles and the U.S. Air Force Thunderbirds alternate each year as the headliner. Be sure to check out this amazing show!