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Unique Chicago Summer Experiences


Chicago is a great city to explore all year round, but it gets even better in the summer! With so many things to do, you’re sure to find something that interests you. There are many great ways to enjoy this vibrant city with its amazing architecture and natural beauty. You can explore local parks, hang out on the riverwalk, or watch an outdoor concert under the stars at night. This list has everything from fireworks displays to air shows – an experience you can make more special by watching from the vantage point of your own chartered yacht!

If you’re planning your summer outing in 2023, check out our recommendations for some unique experiences you must not miss on your visit to the Windy City.


Hang Out On The Riverwalk

The Riverwalk is a network of parks, gardens, trails, and bridges along the Chicago River. It is the only urban riverwalk in America and stretches over ten miles. The best part is that most parts of the riverwalk are free to visit!

There are two ways to access the riverwalk:

  • Bus or train – take public transportation if you can

  • Bike – biking has recently increased in popularity, so renting a bike at Navy Pier or Millennium Park would be ideal.

There are many things you can do on the Riverwalk:

  • See architecture like Wrigley Building and Tribune Tower;

  • Watch boats sail by;

  • Walk along Lake Michigan, where you’ll find beaches with pristine water

Watch a Fireworks Display on Navy Pier

With its impressive architecture, Navy Pier is a must-see Chicago attraction. It’s located at the end of Lake Shore Drive and provides magnificent views of the city skyline. You can enjoy great shopping opportunities and exciting entertainment on this famous pier.


The pier is open year-round, with summer hours between Memorial Day Weekend in May through Labor Day in September. Hours vary during other parts of the year, so check their website before visiting to be safe!


The best time of year to visit Navy Pier depends on what activities interest you most; however, many people like coming here during summer because there are fireworks displays every Wednesday & Saturday night! These shows begin around 9:30 p.m. If this sounds appealing, catch them while they’re happening – they’re worth seeing!


Enjoy an Outdoor Candlelight Concert

Do you want to enjoy an outdoor concert but hate dealing with the hassle of traffic and parking? No problem! Chicago has plenty of concerts happening during the summer months, both big and small. You can find a concert for just about any musical taste or interest, from rock to jazz to classical. Here are some options:

  • If you’re looking for something classic, try Ravinia in Highland Park. This is one of the biggest outdoor music venues in Chicago and hosts local bands and more well-known acts like Hall & Oates and The Who.

  • Want something more family-friendly? How about Millennium Park? Several different concerts take place in Millennium park throughout the summer season. There are free Friday Night Jazz recitals and free Saturday morning concerts where kids play instruments. At the same time, parents get their exercise by walking around listening to live music instead of driving back home after work, and our personal favorite: The Grant Park Music Festival, which happens every July 4th weekend!

Explore Local Parks

In Chicago, summer is a time for exploration. You can take advantage of the city’s many parks, museums, and other attractions to get away from it all and explore what makes this great city so unique.

  • Park yourself on the green lawns of Lincoln Park or Burnham Park. Read a book under a tree, grab some friends, and kick around an old soccer ball until twilight.

  • Take an early evening stroll along the Lakefront Trail or Millennium Park; watch boats sail by, listen to live music from street performers, and take in some spectacular views of downtown Chicago at nightfall.

  • Visit one of the many museums offering free admission during certain hours (including The Art Institute of Chicago), where you can explore exhibits ranging from Native American artifacts to Asian art to contemporary photography without spending a dime!

Watch The Ducky Derby

The Ducky Derby is a Chicago summer experience that has been around since the 1930s and is still strong today. The main attraction of this event is the ducks themselves! You can buy a ticket or adopt one from another person who cannot attend, then place your duck into the race from an oversized bathtub turned into a starting gate. If you win (which you won’t), you’ll get two free tickets to Shedd Aquarium for each entry purchased. Otherwise, watching hundreds of squeaky yellow rubber ducks race down Lincoln Park Lake for hours until someone claims victory by crossing over their finish line first is fun.


The Duck Derby is not only a fun event to watch, but it’s also a fundraising activity held yearly to support Special Olympics Illinois. Special Olympics is “a not-for-profit organization offering year-round training and competition in 18 sports for more than 21,000 athletes with intellectual disabilities and over 9,000 Young Athletes ages 2-7 with and without intellectual disabilities.”


Chicago Air and Water Show

In August, the Chicago skies are brought to life by the annual Chicago Air and Water Display. This is the largest and longest-running free-air show in the United States. The event features exhibitions from daredevil pilots, formation jet flyers, and parachute teams. It is participated by both civilian and military pilots. Many performers use the Gary/Chicago International Airport for ground support. Aside from the air exhibitions, there are also water stunts such as boat jumping and water-skiing demonstrations.


The Chicago Air and Water Show is a great way to spend the day with friends and family. The show is visible almost anywhere, but watching it from Windy City Sailing, Inc. yacht, The Nebula, gives you a 360-degree view of the show.


The Chicago Air and Water Show is one of those experiences that reminds us why we love Chicago so much!


Discover Chicagohenge

The phrase “Chicagohenge” refers to the setting sun between buildings at the vernal and autumnal equinoxes. It is a rare occurrence that happens twice a year, during the summer and winter solstice.


For two weeks every summer, the sun rises and sets in perfect alignment with the street grid of Chicago’s major east-west thoroughfares. This phenomenon is connected to Stonehenge and has been getting more attention recently. It’s believed that Stonehenge existed as early as 3000 BC to mark certain agriculture-related events (such as eclipses), but they aren’t sure when it was built or who started it all!


You can experience Chicagohenge as you watch the sunset over the city or attend one of the many festivals that take place during this time. The Vernal Equinox (Spring) happens on March 20, 2023, at 4:24 p.m., while the Summer Solstice will be on June 21, 2023, at 9:58 a.m.

This astronomical event happens twice a year—so mark your calendars!


Bareboat Charter in Chicago

Renting a yacht to explore Chicago is one of the best ways to see the city. Whether you are looking for a day, weekend, or longer rental, boats of different sizes are available throughout the city.


If you are traveling with a party of six to ten people and would love an extra extraordinary sailboat adventure, renting a boat via a bareboat charter would be great! During a bareboat charter, you dictate where the yacht sails and when to drop anchor and go swimming, as long as it’s within Lake Michigan, Illinois waters.


Bareboating a sailing yacht on the Chicago Lakefront is the ultimate way to enjoy the city’s stunning Skyline, watch evening fireworks, or witness the excellent Chicago Air and Water Show. Contact Windy City Sailing, Inc., Chicago’s best and most trusted sailboat charter, to book a bareboat charter.


Final Thoughts

There is so much to do in Chicago in the summer. It’s a city with so many things to offer, whether you’re looking for culture or want some time off from work. You could spend days exploring Chicago’s museums and galleries while enjoying food and drink at local restaurants. If you are looking for some outdoor activities, there is no shortage of parks where you can go hiking or biking on your own time! And remember all those beaches nearby too!


For an unforgettable summer adventure, you should try bareboat sailing with us! Windy City Sailing, Inc. offers Chicago’s best sailing and yacht charters. Windy City Sailing, Inc. will provide the ultimate sailing experience for your and your party. For inquiries or bookings, feel free to call or email Edwina at 773.868.0096 or edwina@windycitysailing.com.


Let’s make your 2023 summer in Chicago unique and unforgettable; come sail with Windy City Sailing, Inc. See you soon!

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