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Discover the Best Things to Do in the Windy City during Summer

Updated: Mar 12

Are you looking for something to do in the Windy City this summer? Look no further than Chicago’s countless attractions, events, and activities. From sailing on Lake Michigan to exploring the city’s vibrant culture and history, there is something for everyone in the Windy City. If you’re looking for an unforgettable experience, why not try Windy City Sailing to see the city from a unique perspective? In this blog post, we’ll explore the best things to do in Chicago during summer.


Visit the Beach

Chicago is known for its beautiful lakefront beaches, making it the perfect destination for a summer getaway. Whether you want to soak up the sun, dip in the cool water, or get active with some water sports, there’s a beach for everyone. Here are some of the best beaches to visit during your trip to the Windy City:


Foster Beach: Located in the northern part of the city, Foster Beach is a popular destination for families and beachgoers alike. Its clean sand, clear water, and beautiful views make it the perfect spot for a fun day in the sun. There are also plenty of picnic areas, volleyball courts, and playgrounds to keep you entertained.


North Avenue Beach: This beach is known for its iconic beach house, which offers stunning views of Lake Michigan. North Avenue Beach is also one of the most popular beaches in the city, so be prepared for crowds. If you’re looking for a more luxurious experience, book a daybed or cabana at the trendy Shore Club Chicago.


Rainbow Beach: If you want a quieter, more secluded beach experience, head to Rainbow Beach. Located on the city’s South Side, it offers stunning skyline views and plenty of space to relax and unwind.


If you’re feeling adventurous, rent a jet ski, kayak, paddleboard, or flyboard at Chicago Water Sport Rentals at 31st Street Harbor. Or, join a kayak tour or paddleboard class with Urban Kayaks at Monroe Harbor.


Happy beaching!


Eat at a Rooftop Restaurant

One of the best things about Chicago in the summer is the city’s selection of rooftop restaurants. Whether you’re looking for a fancy spot for a romantic dinner or a more casual hangout for drinks and appetizers with friends, there’s no shortage of options with breathtaking views.


One of our top picks is LH Rooftop, which is located in the heart of the Loop and boasts stunning views of the Chicago River. This tri-level lounge is the only rooftop bar in the city to offer such a unique vantage point, and its craft cocktails and seasonal menu make it a must-visit spot.


Another great choice is VU Rooftop, located in the South Loop. This restaurant has a more upscale vibe, chic decor, and a menu heavy on seafood and steak. But the view steals the show here: VU Rooftop offers an unobstructed look at the Chicago skyline that you won’t forget.


For a more laid-back atmosphere, head to Cabana Club in Wicker Park. This hip hangout has a small pool, plenty of seating for sunbathing, and a cocktail menu that changes with the seasons. It’s the perfect spot for a low-key day of lounging in the sun with friends.

Of course, these are just a few of the rooftop restaurants that Chicago has to offer.


Attend a Festival

One of the best things to do in Chicago during the summer is attend one of the many festivals around the city. Chicago is known for its music festivals, but there are also plenty of other events to enjoy.


Lollapalooza is one of the most well-known festivals in Chicago. The festival in Grant Park features big-name musical acts from all genres. It’s a four-day event usually held in late July or early August.


Pride in the Park is another must-attend event for Chicagoans and visitors alike. Held in June, this festival celebrates the LGBTQ+ community with music, food, and entertainment. It’s a great way to show your support for the community and have fun while doing it.

If you’re a fan of gospel music, then the Chicago Gospel Music Experience is a must-see event. This festival takes place in July and features some of the best gospel performers from around the country.


The Chicago Blues Festival is an event for blues music fans. It’s the largest free blues festival in the world and features top-notch performers from the blues world. The festival takes place in June and is held in Millennium Park.


If you’re a foodie, then the Taste of Chicago pop-ups are your event. It’s a smaller version of the annual Taste of Chicago festival in various neighborhoods around the city. You can try delicious food from local restaurants and food trucks.


For fans of country music and BBQ, the Windy City Smokeout is the festival to attend. Held in July, this festival features some of the best BBQs, and top-notch country music acts from around the country.


These are just a few of the festivals happening in Chicago this summer!


Get Out on The Water

If you’re looking for a way to beat the heat and take in the breathtaking Chicago skyline, getting out on the water is the perfect solution. Chicago is known for its stunning waterfronts and offers visitors a wide range of water activities. There’s something for everyone, from renting jet skis and paddleboards to sailing on Lake Michigan.


Lake Michigan offers miles of sandy shoreline and crystal-clear waters for a perfect summer getaway. One of the best ways to explore the lake is by renting a bareboat charter. Sailing on Lake Michigan provides a peaceful, relaxing atmosphere, where you can take in the views of the city skyline and enjoy a refreshing breeze. If you’re an experienced sailor, then renting a bareboat charter is the way to go. But even if you’ve never sailed before, plenty of charters offer captain and crew to guide you through your adventure.  Read More About Bareboat Chartering.


For a more immersive experience, take a kayaking tour on the Chicago River. Paddle through the heart of the city and get a unique perspective on the architecture and history of the Windy City. You’ll see stunning skyscrapers, historic bridges, and wildlife along the way.

If you’re feeling more adventurous, try renting a jet ski or paddleboard. Jet skiing on Lake Michigan is a thrilling experience that will pump your adrenaline. You can explore the lake and see the city from a different angle. Paddleboarding is another great option for a more relaxed water activity. The calm waters of Lake Michigan are perfect for paddleboarding, and it’s a great workout, too!


In summary, getting out on the water in Chicago is a must-do activity for anyone visiting during the summer. From sailing on Lake Michigan to kayaking on the Chicago River, there’s a water activity for everyone. So, grab your swimsuit, sunscreen, and sense of adventure, and head to the water for a fun-filled day in the Windy City.


Navy Pier

Navy Pier Centennial Wheel
Copyright © Adam Romanowicz. All Rights Reserved.

Located on the historic lakefront of Chicago, the Navy Pier is a must-visit spot during the summer months. With so much to see and do, it’s the perfect place for a fun-filled day out. Whether you’re looking for thrilling activities, amazing sights, or just some relaxation by the water, Navy Pier has it all.


One of the most popular attractions at the pier is the Centennial Wheel. This giant Ferris wheel takes you on a scenic ride above the city skyline. You’ll get amazing views of the lakefront and the Chicago skyline from the top. If you’re feeling brave, try riding in one of the glass-enclosed gondolas for an even more thrilling experience.


The Navy Pier is also great for free live music, movies, dance performances, and other entertainment. With so many events happening throughout the summer, there’s always something new to see and experience.


If you’re a fan of craft beer, make sure to check out the waterfront beer garden. It’s the perfect spot to enjoy a cold brew and delicious food while soaking up the sun.

For those who love water sports, plenty of options are available at Navy Pier. Rent a bike or take a bike tour, hop on a lakefront cruise, or even charter a yacht to see the incredible fireworks display during the summer nights.


And if you’re looking for a great spot to enjoy dinner with a view, check out the country’s largest rooftop bar on the pier. With amazing food and drinks and stunning city views, it’s the perfect place to relax and unwind after a day of fun and adventure.



Whether traveling solo or with your family and friends, Navy Pier is essential to any Chicago summer to-do list. So be sure to put it on your list and make the most of your summer in the Windy City!

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