Chicago Summer Bucket List

August 20, 2020

2020 Chicago Summer Bucket list


There is truly nothing better than summertime in Chicago! The city is filled with locals and tourists alike out exploring all the city has to offer. Whether you’ve lived here your whole life or you’re just here for a weekend getaway there are a lot of things to experience this summer. I know it can be hard to narrow down what to do so here’s my 2020 Chicago summer bucket list for some ideas.

Millennium Park Film Series

Every Tuesday between June 5 and August 21, the Department of Cultural Affairs and Special Events hosts a film screening in Millenium Park. Guests are invited to attend the free event and sit in either the Jay Pavilion or lay out on the Great Lawn. See the full movie schedule here.

Chicago Blues Festival

The Chicago Blues Festival is the largest free blues festival in the world and remains the largest of Chicago’s Music Festivals. During three days on four stages, blues fans enjoy free live music in the “Blues Capital of the World.”

Taste of Randolph

Located in the heart of restaurant row in the West Loop, the Taste of Randolph takes over 6 city blocks to bring guests some of the best local food along with great live music.

Taste of Chicago

Taste of Chicago is the nation’s premier outdoor food festival showcasing the diversity of Chicago’s dining community. Every summer since 1980, Chicago’s beautiful Grant Park on the city’s magnificent lakefront has been home to the world’s largest food festival.

Windy City Smokeout

If you love BBQ, bands, and beer then Windy City Smokeout is for you. The event feature 20 of the world’s best pitmasters along with live music from some of the biggest names in Country music.

Go to a Market

One of my favorite things about Chicago are all of the outdoor markets during the summer. Everyday of the week from May through October, there is nearly always a market open. Two of my absolute favorite markets are the City Market at Daley Plaza (go and get the crepes) and the Green City Market in Lincoln Park.

Sheffield Music Festival and Garden Walk

The “Summer’s Best Festival” features self-guided tours of more than 80 Gardens, guided Architectural Tours, live entertainment by some of Chicago’s and North America’s finest bands, food and drink, and activities for children at the Kids’ Corner.

Cubs Game at Wrigley

Watch the Cubs play and enjoy the newly renovated grounds this summer out at Wrigley. See their full schedule here

Watch the Air and Water Show

Featuring military and civilian flight aerobatics, historic aircraft, simulated water rescues and parachute teams, the Chicago Air and Water Show is one of the largest and longest-running free admission events of its kind.

Navy Pier Fireworks

Navy Pier is the destination for spectacular fireworks in Chicago, perfectly synchronized to music on Lake Michigan. The biweekly Aon Summer Fireworks shows occur on Wednesdays and Saturdays

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