This weekend, we’re soaking up the Chicago summertime one festival at a time. Whether you like to gape at marvels in the sky or observe the street-level around you, here are some of our top picks for things to do in Chicago this weekend. 

59th Annual Chicago Air and Water Show Presented by Shell Oil
August 18-19 // Free

Watch the skies this weekend as the 59th Annual Chicago Air and Water Show takes flight across Lake Michigan. About two million spectators are expected to observe the aerial acrobatics, and expect to see daring formations by headlines the U.S. Navy Blue Angels and the U.S. Army Parachute Team Golden Knights. Although food will be available along the lakeshore from Oak Street Beach to Fullerton, you’re welcome to pack your own coolers and blankets for the day. Learn more at


Festa Italiana
August 17-19 // Free

Taylor Street Festa Italiana

For all things Italian, make your way to Festa Italiana, a three-day affair that will have you dancing, singing, learning and (of course) eating.


Comedy Sportz 30th Anniversary
August 17-19 // $25

We all know that improv is an art, but ComedySportz is celebrating 30 years of making it an interactive game. A great time for all ages, watch teams battle for the audience’s applause through sketches created with your on-the-fly suggestions.

Need another excuse to laugh? The Second City is closing out some big-name shows this weekend, so get tickets while they’re available. Poke fun at online dating encounters as #DateMe: An OKCupid Experiment performs the finale of its three-year run or edge in some late-night laughs during Improv All-Stars: After Midnight.


Sangria Fest
August 20 // $35-55

Sangria Fest Chicago

If Sangria is your drink of the summer, it’s your day to shine at the Sangria Fest in Humboldt Park. Sample your way through some of the most creative sangria flavors in Chicago, and enjoy the flamenco, samba, Latin jazz and other entertainment as the day progresses. Come ready to try tapas, tacos and elotes for an all-around authentic experience.


Glenwood Avenue Arts Fest
August 18-20 // Free

Head up to Rogers Park for an exploration of all art forms. More than 50 music and performance groups will entertain across three stages this weekend, and the art that is admitted into the fair must be personally made by the exhibiting artist. 



If you’re taking time off Monday for the solar eclipse, make sure you have your plans in place! Here are three ways to observe the event in Chicago, including a day-long block party.


Can’t believe August is already half-way through? Neither can we. That’s why we’re already looking at events in Chicago this September. Highlights include the Chicago Jazz Festival, Chicago Gourmet, EXPO Chicago and the Chicago Architecture Biennial.