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Insider’s Guide to Chicago Summer 2023 Activities

Updated: Mar 12

Chicago is a city that comes alive during the summer months, with plenty of exciting things to do and see. As a local, I have explored this beautiful city and discovered some of the best activities it offers during the summer season. There is no shortage of entertainment, from the beautiful beaches to the iconic museums and parks. In this insider’s guide, I will share my top picks for the best things to do in Chicago during the summer of 2023. Whether you are a tourist or a long-time resident, you won’t want to miss out on these fun-filled experiences.



The Art Institute of Chicago

As one of the most well-known museums in the country, the Art Institute of Chicago is a must-visit destination during your Chicago summer vacation. Located in the heart of downtown Chicago, this impressive museum is home to over 300,000 works of art, including masterpieces by iconic artists like Van Gogh, Monet, and Picasso.


Aside from the vast collection of artwork, the Art Institute also boasts impressive architecture and design. The museum’s historic Beaux-Arts building, completed in 1893, features intricate details and a grand entrance. Visitors can marvel at the stunning modern wing, which opened in 2009 and was designed by renowned architect Renzo Piano.

Take advantage of the museum’s audio guides and guided tours to make the most of your visit. You can also explore the museum on your own, taking your time to wander through the galleries and appreciate the incredible works of art on display.


Whether you’re a seasoned art enthusiast or enjoy appreciating beautiful things, the Art Institute of Chicago is a must-see destination during your Chicago summer vacation. So, be sure to add it to your itinerary and prepare to be wowed by the stunning collection of art and architecture.


Buckingham Fountain Water Display

One of the most iconic landmarks in Chicago, Buckingham Fountain is a must-see for anyone visiting the Windy City during the summer. Located in Grant Park, this massive fountain is one of the largest in the world, boasting 133 jets and a central jet that can shoot water up to 150 feet high.


Every hour on the hour, the fountain produces a major water display that lasts for 20 minutes. During this time, visitors can marvel at the stunning choreography of the jets, which dance in time to the music. And if you’re lucky enough to catch the fountain at nightfall, you’ll be treated to a spectacular light and music display that adds an extra layer of enchantment to the already stunning water show.


Whether you’re visiting Buckingham Fountain for the first time or you’re a seasoned Chicago local, this magnificent landmark is not to be missed. So, make sure to set aside some time to see this spectacular display of water, light, and music in action!


Take a Lake Cruise or Explore the Lake Front

If you want to experience Chicago’s breathtaking skyline and refreshing breeze, a lake cruise or a stroll along the Lakefront Trail is necessary. The Lakefront Trail is a paved path along Lake Michigan that is 18 miles long and provides a scenic and active route for walking, running, and biking.


For a unique experience, take a lake cruise to enjoy the magnificent view of the city from a different perspective. The cool breeze and scenic view will take your breath away. You can enjoy a daytime or evening cruise while exploring the city’s breathtaking architecture and skyline views. Lake cruises depart from Navy Pier or the Michigan Avenue bridge so that you can choose the most convenient.



Whether you take a lake cruise or explore the Lakefront Trail, bring your camera to capture the city’s stunning beauty. A map of the Lakefront Trail and its access points is easily accessible online and at the tourist center so that you can plan accordingly. With its refreshing lakefront breeze and unbeatable skyline views, this is one of the best things to do in Chicago during the summer of 2023.


Navy Pier

Navy Pier is one of Chicago’s most famous and well-loved destinations, especially in the summertime. It’s not hard to see why – with attractions for people of all ages, there’s never a dull moment here. One of the highlights of Navy Pier is the free fireworks show every Wednesday and Saturday night from Memorial Day weekend through Labor Day weekend. You can watch the show from Navy Pier itself or various spots along the lakefront, as well as some restaurants and bars. For an even more memorable experience, consider taking a fireworks lake or river cruise to watch the show from the water.


Navy Pier is a must-visit if you’re traveling with toddlers or kids. The attractions include a large Ferris Wheel, rides and games, restaurants, shops, and the Chicago Children’s Museum. Until September 10, 2023, there’s also Pixar Putt, a pop-up, open-air, 18-hole mini-golf course featuring characters from some of Pixar’s most beloved films. Even if you’re traveling without kids, Navy Pier is a fun place to explore. There’s always something happening here, from concerts and performances to festivals and art exhibitions.


Wrigley Field – Is it summer without a baseball game?

Chicago is known for its love of sports teams, with fans passionate about supporting their favorite teams throughout the year. And when it comes to baseball, there’s no place like Wrigley Field – the home of one of Chicago’s most beloved baseball teams, the Cubs.

Wrigley Field is a 100-year-old ballpark located on the North Side of Chicago and is a must-visit spot for locals and tourists alike during the summer months. Even if you don’t particularly enjoy baseball, there’s just something about the atmosphere and energy of a Cubs game that’s hard to resist.


With an enthusiastic fan base and stunning city skyline views, Wrigley Field is more than just a ballpark – it’s an experience. From the moment you step inside the gates, you’re transported into a world of hot dogs, peanuts, and beer, with the sounds of cheers and the crack of the bat filling the air.


So why not grab some friends, don your favorite Cubs gear, and spend an afternoon or evening at the ballpark this summer? Whether you’re a die-hard baseball fan or just looking for a fun way to spend a day in the city, Wrigley Field is a must-visit spot.


If you’re interested in checking out a Cubs game during your visit to Chicago this summer, be sure to check out their schedule here. Trust us, you won’t regret it!


Millennium Park – FREE Music!

One of the highlights of summer in Chicago is the amazing outdoor concerts at the Jay Pritzker Pavilion in Millennium Park. And the best part? They’re completely free! Whether you’re into classical music or something more eclectic, you’ll find plenty to enjoy at the park.


First up, there’s the Grant Park Music Festival. This is the only free outdoor classical music concert series in the US, and it’s an absolute must-see for anyone who loves great music. Featuring the Grant Park Symphony Orchestra and Grant Park Chorus, along with guest performers and conductors, the festival runs from June 14 – August 19, 2023. With a wide variety of pieces, you’ll surely find something to love.


If classical music isn’t your thing, don’t worry. The Millennium Park Summer Music Series is a great alternative, and it’s just as free and just as fantastic on Mondays and Thursdays from June 22–August 21, 2023. There’s something for everyone here, from jazz to blues to indie rock.


So, Millennium Park has you covered whether you’re looking to chill out to some beautiful classical music or dance the night away to something a little more upbeat. And with so many great concerts, you might spend every free night at the pavilion!


Hang Out on the Riverwalk

The Chicago Riverwalk is a must-visit spot for any visitor to the Windy City. Not only is it a great place to watch the boats go by, but it’s also a great spot for people watching too. Take a stroll along the river and soak in the atmosphere of this vibrant and lively area.

The Riverwalk has amenities and activities, making it a perfect destination for a lazy afternoon or a fun night out. There are various restaurants and bars along the river, where you can sit outside and enjoy the view. Additionally, plenty of shops and other activities are available for you to check out.


One of the most exciting things about the Riverwalk is catching a water taxi from there. Water taxis are a fun and unique way to explore the city, and they’ll give you an amazing view of Chicago’s skyline as you float down the river.


We recommend taking a self-guided walking tour to get the most out of your Riverwalk experience. This will allow you to explore the area at your own pace, taking in all the sights and sounds this bustling area offers.


Overall, if you’re looking for a great way to spend an afternoon or evening in Chicago during the summer, the Riverwalk should be at the top of your list. It’s a must-visit spot for anyone who loves food, drink, and beautiful scenery.

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