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7 Do Not Miss Things To Do in Chicago in the Summer

Updated: Mar 12

Nothing beats coming to Chicago in the summer. There are so many fun-filled activities to choose from those persons of all ages are guaranteed to enjoy their visit. You can go on a tour, dance at festivals, or soak up the sun on the beach. Whatever floats your boat, something will surely pique your interest.


All of the summer happenings in Windy City provide a unique experience. With so many options, you might wonder which activities to choose when your time in the Windy City is limited.


Here are the top 7 do not miss things to do when you visit Chicago in the summer.


1. Visit Local Farmers Markets in Chicago

If you want to get to know the city you are visiting, explore its local farmer’s markets. Not only will you gain access to the freshest produce in the area, but local farmers’ markets are also an excellent venue where you can mingle with the locals and learn more about the Windy City. They are also excellent food trip destinations as they allow you to discover and sample food that may be unique to the place. If you’re into souvenirs and vintage goods, you might be lucky enough to find some on your visit to the local farmers market.


When you visit Chicago from May through October, you will surely stumble upon one of the many local fresh markets in the area. Do not pass up the chance to explore it.


2. Catch A Movie Under The Stars

Have you ever tried watching a movie under the stars? If you haven’t, then do not pass up the chance to catch a movie at Millennium Park’s Jay Pritzker Pavilion this summer. Guests can take their friends and family to the pavilion to relax and have a picnic while watching old or new movies shown on the 40-foot LED screen.


The annual Millennium Park Summer Film Series takes place on Tuesday evenings at 6:30 p.m., and admission is entirely free.


3. Attend A Summer Festival

One of the reasons Chicago is a popular tourist destination is its many festivals, especially in the summer. There are different festivals, from neighborhood parties to local food and music and dance festivals.


If you’re a foodie, here are just a few of the many food festivals that you would enjoy:

  • Taste of Chicago is the largest free-admission outdoor food festival in the world. Because dozens of Chicago’s best restaurants participate, the event is a great way to sample their food without buying entire portions.

  • Chicago Gourmet is one of the country’s most distinguished festivals as it is participated in by the city’s top chefs. This 3-day event happens at the Harris Theater Rooftop in Millennium Park.

  • Chinatown Summer Fair, which happens annually in July, includes a showcase of Chinese cuisine and a dragon and lion dance procession.

For music lovers and enthusiasts, here are a few music festivals to check out this summer:

  • Lollapalooza is one of the world’s largest and most iconic music festivals, visited by thousands of people yearly.

  • Pride in the Park is an outdoor music festival held in Grant Park to celebrate Pride Month. It features LGBTQ+ performers, artists, vendors, and more.

  • The Chicago Blues Festival, which happens in early June in Millennium Park, is one of the world’s biggest music festivals. It highlights the genre’s contributions to the soul, R&B, gospel, rock, hip-hop, and more.

Check out Choosechicago.com for the complete list of festivals. If you missed them this year, catch them next year.


4. Savor A Day At The Beach

No summer vacation is complete without a trip to the beach. Luckily, Chicago has been blessed with miles of sandy shoreline lined with public parks and beaches.


The most famous beach in the city is North Avenue Beach in Lincoln Park. It is conveniently located near tourist attractions and has a one-of-a-kind beach house with over 22,000 square feet that offer activities for all ages. Guests can go kayaking, rent a bike, participate in beachfront yoga classes, or join a beach volleyball game. There are also beachfront bars where one can dine or enjoy refreshments while soaking up the sun and some of the best views in Chicago.


The largest beach in the city is Leone Beach Park, located in the Rogers Park Community. This is the best beach if you enjoy laid-back activities such as picnics, yoga, meditation, or an afternoon nap while soaking in the sun.


Another beach where you could enjoy picnics and other family activities is Foster Beach. This beach is the venue for the Chicago Full Moon Jam, which happens once a month in the summer.


Aside from these beaches, there are over 20 more along the waterfront maintained by the Chicago Park District. Check the list and their swim conditions here.


5. Get Out On The Water

Chicago has two waterfronts: along the Chicago River and the 26-mile-long sandy shoreline along Lake Michigan. Both offer plenty of activities to entice people to get out on the water.

Tourists may explore the river and lake by renting kayaks, while jet skis and paddle boards may be used on the lakefront. Another great option, especially for families or large groups who want to spend more time on the water, is to rent a boat or yacht.


Windy City Sailing, Inc. in Belmont Harbor has a 40-foot sloop-rig yacht, the Nebula, which may be rented for private charters and bareboat sailing. Sailing is an extraordinary way to get on the water and explore Chicago. A must-try!


6. Check Out The Navy Pier

The Navy Pier was built in 1916. It is a year-round historic lakefront tourist attraction. In the summer, Navy Pier comes alive with the scheduled fireworks displays and fun-filled activities. Here are a few of the many things to see and do there during the summer:

  • Rent a bike

  • Watch the summer fireworks display

  • Check out free live music, movies, dance, and more

  • Take a spin on the Centennial Wheel

  • Enjoy the waterfront beer garden

  • Check out the country’s most extensive rooftop bar

7. Take A Boat Cruise

To make your trip to the Windy City extraordinary, you should take a boat cruise. Cruise on Lake Michigan and the Chicago River and enjoy everything from relaxed sightseeing and elegant dining to adrenaline-pumping thrill rides and private charters.


Sailing is one of the best ways to enjoy the summer in Chicago. Drifting along the deep blue waters of Lake Michigan with a clear view of Chicago skyscrapers gives you an amazing perspective of the Chicago skyline.


Windy City Sailing, owner of the yacht – Nebula, is one of the best sailing companies in Chicago. They have been offering different cruise options for over 20 years.

Windy City Sailing offers the following charters:


  • Special Events Charter These are sailing charters for spectacular events that the City of Chicago looks forward to. There’s the 4th of July Charter, Air & Water Show Charter, and the Navy Pier Firework Charter. Guests can take advantage of the spectacular view from the yacht, away from the throngs of tourists. Windy City Sailing can also charter a yacht, so guests have more convenient access to the Huntington Bank Pavilion Special Events & Concerts, the Jazz Festival Special Event, the Blues Fest, the Taste of Chicago, and the Chicago Yacht Club Race to Mackinac.

  • Anniversary Charter Windy City Sailing’s crew guarantees to make any anniversary memorable, whether it’s watching the sunset over Chicago’s magnificent skyline, watching the fireworks from the Navy Pier from the lake, or simply enjoying each other’s company as they sail and relax.

  • Bachelorette Sailing Charter The Nebula, Windy City Sailing’s yacht, is fully equipped to make your bachelorette or bachelor party fun and memorable.

  • Birthday Sailing Charter Windy City Sailing’s birthday charter brings an exciting flair to your party. Regardless of your setting, whether in front of a Chicago sunset or during a fireworks show, the crew will ensure the birthday charter is smooth and enjoyable.

  • Client Charter Windy City Sailing’s client charter would undoubtedly do the trick if you want to impress your clients. You and your guests avoid noisy, crowded eateries and sporting events. As a result, your clients will know that you mean business and value their time. It’s simple, charming, and highly memorable.

  • Proposal Charter Windy City Sailing makes your engagement proposal memorable. Sailing on a private proposal charter in the comfort of one of our exquisite yachts with the beautiful Chicago skyline or the bursting fireworks as your backdrop as you pop the question is so unique and romantic!

  • Bareboat Charter Do you have a group of more than six people and want to sail on a private yacht? You can set sail using a process known as “Bareboat Charter” or “Demise Charter.” It’s the ultimate way to experience Chicago and its stunning skyline. You and your group of up to ten (10) people supply your own food and beverages and have complete control over your itinerary. For the duration of the charter, the Nebula is all yours.


For the ultimate sailing experience with Windy City Sailing, feel free to call or email Edwina with any questions at 773.868.0096 or edwina@windycitysailing.com.


Final Thoughts

If you’re visiting the City of Chicago this summer, keep in mind the seven do not miss things to do we recommended. If you missed them this year, start planning your visit for next year. Make the Windy City your ultimate summer destination.

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