Summer in the City: Chicago-style

Bluesfest, Pritzker Pavilion, Millennium Park Chicago

Now that summer is in full swing, it’s time to soak in some sun and enjoy Summer in Chicago. It’s why we hibernate all winter long! Whether you’re a local or a visitor, there are a plethora of activities from the beach to parks and bike riding around the city – learn everything Chicago has to offer…

Explore Millennium Park

Pritzker Pavilion in Millennium Park

Start your summer adventure at Millennium Park, one of Chicago’s most iconic spots. Snap a selfie with the famous Cloud Gate (aka “The Bean”), an incredible reflective sculpture that’s perfect for unique photos. 

Enjoy a free outdoor concert or movie at the Jay Pritzker Pavilion, where you can spread out a blanket and listen to a variety of musical performances or films under the stars. 

Take a leisurely walk through the Lurie Garden, a beautiful oasis filled with colorful flowers and native plants. 

Don’t forget to splash around in the Crown Fountain to cool off, especially if you’re visiting with kids—they’ll love it!

Hit the Beach

Who doesn’t love the beach to cool off on a warm sunny day? Chicago’s lakefront is home to some amazing beaches that provide the perfect escape…

  • North Avenue Beach: A popular spot where you can sunbathe, swim, or play beach volleyball. It features a unique beach house shaped like a ship, offering food, drinks, and stunning lake views.
  • Ohio Street Beach: A smaller, more secluded beach located close to Navy Pier, perfect for a quiet afternoon by the water.
  • Oak Street Beach: Located near the Gold Coast, this beach is a favorite with the skyline as your backdrop.
  • Montrose Beach: Known for its expansive sandy area it includes the Montrose Point Bird Sanctuary. This beach is great for picnics, swimming, paddleboarding and has a pretty large dog beach.

Explore more quieter beaches north & south of these more popular ones since they can get very crowded. Click here for locations.

If you’re feeling adventurous, rent a paddleboard or kayak and explore the Chicago River & Lake Michigan. It’s a fantastic way to enjoy a summer day and get a bit of exercise.

Visit Navy Pier 

Rainbow Cone

Navy Pier is a summer must-visit destination that has something for everyone. Ride the Centennial Wheel for breathtaking views of the city and Lake Michigan. The pier is also home to the Chicago Children’s Museum, where kids can engage in interactive exhibits and activities. 

Enjoy a show at the Chicago Shakespeare Theater, which offers top-notch performances in a beautiful setting. Stroll through the shops, grab a bite to eat at one of the many restaurants or hear some live music at the beer garden. Enjoy the lively atmosphere & spectacular views, and don’t forget to get a Rainbow Cone!

There are fireworks every Wednesday & Saturday evenings during the summer season. It’s a magical way to end your day at the pier. 

Explore everything Chicago has to offer this summer from parks, beaches, concerts, festivals, and more!

Explore the Chicago Lakefront Trail 

Chicago's Lakefront Trail

For those who love outdoor activities, the Chicago Lakefront Trail is a fantastic way to explore part of the city’s 26 mile shoreline. This 18-mile-long path stretches from Hollywood to the South Shore neighborhood and is perfect for biking, running, or a leisurely walk. 

Along the way, you’ll pass by parks, beaches, and some of the city’s most iconic landmarks. The trail offers stunning views of Lake Michigan and the city skyline, making it a scenic route for exercise or a peaceful stroll.

Experience Chicago’s Festivals 

Bluesfest, Pritzker Pavilion, Millennium Park Chicago
Bluesfest, Pritzker Pavilion, Millennium Park Chicago

It’s festival time in Chicago, and there’s something for everyone. From music to food to art, you’ll find a festival that suits your interests. Here are some well-known downtown festivals.

  • Chicago Blues Festival: June 7th-9th – A celebration of the city’s rich blues heritage, featuring performances by renowned blues musicians.
  • Lollapalooza: August 1st-4th – One of the world’s biggest music festivals, featuring a lineup of international artists and drawing huge crowds to Grant Park. 
  • Chicago Air and Water Show: August 17th-18th – An exhilarating event featuring breathtaking aerial acrobatics and stunning water stunts along the lakefront.
  • Chicago Jazz Festival: August 29th – September 1st – An annual event that brings jazz enthusiasts together for four days of exceptional jazz performances in Millennium Park. 
  • Taste of Chicago: September 6th-8th – A culinary extravaganza showcasing the city’s diverse food scene for over 40 years has various food vendors offering delicious samples and concerts featuring an array of musical talents as well. Click here for a few neighborhood Taste of Chicago pop-ups happening earlier in the summer.  

To experience festivals like a local, check out the many smaller, additional neighborhood festivals happening all summer long in the city and suburbs. Click here for more information.

Stroll the Riverwalk

Starting at the confluence of the Chicago River you can meander the 1.25 miles from Franklin Street all the way to the Lake along the south bank. Take note of the different sections of the Riverwalk which include fountains, gardens, amphitheater seating, a Vietnam Veterans Memorial, dining and boat or kayak rentals. Grab a seat and relax while you enjoy watching life on the Chicago River. Don’t forget to check out the illuminating public art, the Art on the Mart show that happens nightly throughout the summer.

Enjoy a Picnic in Grant Park 

Known as “Chicago’s Front Yard,” Grant Park offers a vast green space for picnicking, relaxing, and enjoying the outdoors. The park is home to Buckingham Fountain, one of the largest fountains in the world, which features a spectacular nightly light show.

Pack a picnic and enjoy a leisurely afternoon in this urban oasis. It’s a perfect spot to unwind and take in the beauty of the city.

Take a Bike Ride with Divvy Bikes 

Explore the city on two wheels with Divvy, Chicago’s bike-sharing system.

With hundreds of stations throughout the city, it’s easy to rent a bike and ride along the lakefront, through busy neighborhoods, or to the many parks and attractions. Please use caution & share the lakefront paths!

Biking is a great way to see the city at your own pace while enjoying the summer weather.

It’s an eco-friendly and fun way to explore Chicago’s diverse and vibrant neighborhoods.

Book a tour with a Local Expert

If you’re interested in exploring all the best Chicago has to offer, hire a local expert with Tours by City Girl. We offer a variety of tours including half-day tours by foot, bike, boat, or car and offer many specialized experiences. Each tour gives you an insider’s view of the city’s top attractions and hidden gems. Interested in a custom tour? Contact me at mimi@toursbycitygirl.com.

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