If you’re looking for exciting activities to do this summer in the Windy City, you won’t be disappointed. 

Chicago hosts countless annual events throughout the year as it is a hub for entertainment, culture, and the arts. 

With a booming industry of artists and different forms of excitement alike, it’s no surprise that you’ll find the summer months in Chicago absolutely brimming with things to do. 

We’ve listed just 5 of some of the most beloved Chicago attractions in the summer you simply cannot miss, so get together with some friends and family and fall in love with what the city has to offer. 

Chicago Blues Festival

A staple in Chicago’s annual big festival lineup, the Chicago Blues Festival is a beloved event held for 3 days in June celebrating the history and future of blues music. 

Incredible, atmospheric, and brimming with Chicago residents simply looking to appreciate the culture of blues, Chicago Blues Festival is an amazing experience for any music lover, not just those who are a fan of blues. 

The events used to always take place around Petrillo Music Shell in Grant Park, east of the Loop in Chicago, however was moved to nearby Millenium Park in 2017. 

With a history that goes hand in hand with blues itself, Chicago time and time again plays tribute to great names in blues, especially “the father of Chicago blues” - McKinley Morganfield, better known as Muddy Waters. 


A world renowned, annual four-day giant music festival held in Grant Park in Chicago - Lollapalooza brings visitors from all over the world to visit every year. 

Originally starting as a touring event in 1991, Lollapalooza made its way to become a permanent location in Chicago, with performing music genres such as alternative rock, hop hop, electronic dance music, heavy metal, and many more. 

One of the largest, iconic, and most globally recognized festivals in the world, Lollapalooza is an incredible Chicago event you simply cannot miss this summer. 

Chicago Air And Water Show 

Chicago’s second most popular festival, the Chicago Air and Water Show is the largest free show of its kind in the entire country. 

With stunning aerial waterfront shows right above Lake Michigan, get ready to be completely immersed in the performances of formation jet flyers, parachute teams, daredevil pilots, and even water-skiing and boat-jumping shows. 

The show is visible from nearly anywhere along the Chicago lakefront, with both military and civilian pilots having onlookers in absolute disbelief over the incredible shows.

Flavors of Albany Park 

A loved, local “restaurant crawl” showing off the neighborhood’s incredible diversity and mixture of delicious cuisine from all around the world, Flavors of Albany Park is simply an event that cannot be missed by food lovers everywhere. 

An annual, one day event that celebrates one of Chicago’s most diverse neighborhoods, this restaurant crawl is usually held in August and tends to host around 50 different restaurants along separate routes and sample food from all over. 

From Mexican cuisine to Italian, Korean to Peruvian, Japanese to Michoacan, and much more, the Flavors of Albany Park is an absolute treat for those looking to satiate their taste buds. 

Chicago Summerdance 

One of the city’s most popular and loved dance festivals, stop on by a multi-month event that spans every weekend it's held offering incredible open-air dancing, live music, and even dance lessons.

With a large group of bands and dancers sweeping through the Music Garden in Grant Park’s dance floor, you can learn various styles of dance ranging from salsa to tango, swing, steppin, polka, flamenco, and more. 

Posted by Michael Clendenning on
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