Savor summer in Chicago, like an insider

For those of us who live in places where winter is a burden, August signals the beginning of the end of glorious summer days and warm weather outdoor activities.

Chicago, of course, is a place where summer always seems to rush right by. So here are some delights to savor in this city before the seasons turn. And this isn’t just for Chicagoans. Summer is a great time to visit this most American of American cities.

Chicago MP aerial shot
Millennium Park is a playground on the water and in the heart of the city. Photo by Terri Colby

Chicago is defined by its location on Lake Michigan, with miles of parkland and beaches the legacy of Daniel Burnham who wrote that the lakefront “belongs to the people.”

Few other cities around the world offer such an expanse of easily accessible free beaches in such close proximity to world-class attractions. With 26 beaches on 26 miles of shoreline, you’re sure to find one that suits your style. And there’s an 18-mile bike path along the water as well.

CC_SUNRISE skyline
The Chicago lakefront at sunrise. Photo courtesy of Choose Chicago.

From Oak Street and North Avenue beaches, you are just a stone’s throw from the Magnificent Mile and its high-end restaurants and boutique shopping. It’s only a few blocks further to the Loop and its theaters and Millennium Park and its free evening events. From 12th Street Beach, you’re surrounded by three world-class museums:  The Field Museum of Natural History, the Shedd Aquarium and the Adler Planetarium.

But one of the best parts of summer on the lakeshore is being able to sit outside for a cup of coffee, a cocktail or a meal, with a view of the lake and maybe even the city skyline.

Lakefront dining
Dining on the shores of Lake Michigan is almost always a pleasure, like here at the Lakefront Restaurant at Fullerton. Photo by Terri Colby

Check out the Lakefront Restaurant at 2401 N. Lakeshore Dr.,  the Shore Club and Castaways at North Avenue Beach, the Oak Street Beach restaurant at you guessed it, Oak Street Beach, and Pier 31 at the 31st Street Beach.


Chicago’s Millennium Park is a center of summer activities, many of which are free. Opened in 2004, the 24.5- acre park fronts Michigan Avenue and is perhaps most famous for its Cloud Gate sculpture by Anish Kapoor. It seems nearly every tourist who visits the city, not to mention locals, needs a picture taken at the reflective sculpture, which is known to Chicagoans as The Bean.

But on hot summer days, the Crown Fountain designed by Jaume Plensa is a big draw. Showcasing giant moving images of Chicagoans appearing to spit water onto the plaza, it’s a playground for children in bathing suits, and even some older folks.

Don’t miss the free movies at 6:30 p.m. Tuesday nights at the park’s Jay Pritzker Pavilion. Upcoming are “Coco” on August 14 and “Slumdog Millionaire” on August 21.

The Pritzker Pavilion also hosts concerts throughout the summer.  Upcoming performances include Whitney and NE-HI on Aug. 12 and The Sea and Cake and Moonrise Nation on Aug. 16.

Check out this website for the latest details on what is happening at the park.


Just a little bit down the street from Millennium Park, at 601 S. Michigan Ave., in the Spirit of Music Garden, Chicago Summerdance continues into August. The free events Thursday through Sunday begin with dance lessons followed by music and dancing. Check out the schedule at to see what is coming up, including Country two-step and Bomba.


Chicago’s Riverwalk, a 1.25-mile pedestrian walkway along the South bank of the Chicago River.  has been expanding over the past several years and now includes an outdoor wine garden, fishing, kayaking and live music. You can even rent a cycleboat for you and a dozen of your closest friends to maneuver.


One of the city’s most popular tourist attractions, Navy Pier has gone from boom to bust and back again in its first 100 years. Now, this 34-acre pier jutting 3,000 feet into Lake Michigan is an entertainment space offering concerts, theater, boat rides, restaurants, a children’s theater and a 196-foot-tall Ferris wheel.


If you want to see where President Obama lived before he headed to the White House, you can take a walk down the street where he lived in Chicago when he was a U.S. Senator and before. You won’t get into the house, but you can take photos from outside. The address is 5046 S. Greenwood. But you’ll know you’ve got the right place when you see the Secret Service signs on the posts in front of the house. The Kenwood neighborhood is adjacent to the University of Chicago and it’s worth a stroll around the neighborhood to walk in Obama’s steps and along tree-lined streets filled with  stately homes.


Rainbow MollyYou can get good ice cream in lots of places in the city and Chicago is known for its pizza. But for a different take on both, consider a trip to the Southwest Side and a two-fer that includes Vito & Nick’s pizza and Rainbow Cone, both long-time family businesses.

Vito & Nick’s signature thin-crust pizza pies have been the contrarian answer to Chicago’s iconic deep dish since the 1940s.  At 8433 S. Pulaski Rd., this retro spot with turquoise vinyl seating is kitschy but authentic.

The pizza has a thin, crispy crust, well-seasoned sausage and the perfect mix of tomato sauce and cheese. For about $30 you can get a large sausage and pitcher of Old Style. But make sure to bring cash. They don’t take plastic, or checks.Vito pizza

After your pie, head a few miles south and east to Rainbow Cone at 9233 S. Western, where you can get the traditional cone with five flavors of ice cream piled atop a cake cone. In business since 1926, and still run by the same family, the cone is indeed a rainbow of flavors and colors. Chocolate is on the bottom, topped with strawberry, then Palmer House (vanilla with cherries and walnuts), pistachio, and orange sherbet atop it all.


The city is always abuzz for the Air and Water show, this year on Aug. 18 and 19. You have to show up early to get a spot at North Avenue Beach to view the performances in the sky.

The Museum of Contemporary Art’s “Tuesdays on the Terrace” are free outdoor jazz concerts from 5:30 p.m. to 8 p.m. on the same day that museum admission is free to Illinois residents. Up this month is the Charles Heath Quartet on August 14 and Ernest Dawkins on Aug. 21.

The 606 is an elevated, nearly 3-mile long path through some of the hippest neighborhoods in the city. You can rent a bike or just have a nice stroll through the path in Wicker Park/Bucktown, Logan Square and Humboldt Park.

The Adler Planetarium will have astronomers on hand on Aug. 24  between 8:30 and 10:30 so visitors can get a look at Saturn and Mars.

The 40th annual Chicago Jazz Festival at Millennium Park and the Chicago Cultural Center begins Aug. 30.

Now that I have my summer fun to-do list, I’m wondering how I’ll fit all of it into one month.


Leave a Reply

Fill in your details below or click an icon to log in: Logo

You are commenting using your account. Log Out /  Change )

Facebook photo

You are commenting using your Facebook account. Log Out /  Change )

Connecting to %s