Summertime in Chicago marks the beginning of festival season. Whether you’re into food, music, art, or all three; there’s something for you. Festivals run throughout the months of May to September and take place in various neighborhoods across Chicago. Take a pick of your favorite festival and bring a friend or family member along!

Belmont-Sheffield Music Fest

This Lakeview festival takes place over Memorial Day weekend. Featuring local tribute bands, artisans, and food, this festival has been in the neighborhood for over 30 years. Jam out, eat out, and check out some local vendors.


Located in Lincoln Square, Mayfest takes place in late May or early June. Mayfest (Maifest in German) is the traditional German celebration for the arrival of spring. If you like German food & beer, live music, and want to experience German traditions, this festival is the perfect fit for you.

Old Town Art Fair

The Old Town Art Fair takes place in early June with 250 nationally acclaimed artists. Not only will you get your art fix in the Old Town Triangle, but live music, a food court, and a Children’s Corner are also featured. The perfect family outing.

Grant Park Music Festival

Located inside the famous Millennium Park, the Jay Pritzker Pavilion hosts free musical performances from June – August 18. Each performance is a different form of classical music, ranging from piano to violins. Grab your blanket and enjoy your evening under the stars.

Taste of Chicago

The world’s largest food festival is located right in Grant Park in July. Taste delicious native eats while enjoying the views of the Chicago skyline and musical talents of local musicians


One of the biggest Chicago music festivals, Lollapalooza takes place the first weekend in August. Located in Grant Park, the festival always features some incredible acts as well as some of Chicago’s top eats for the ultimate festival experience.

Chicago Air and Water Show

The Chicago Air and Water Show is the largest free show of its kind. From August 17 – 18, North Avenue Beach will be the host of amazing sites of famous air planes as they soar over you. Grab a picnic basket and towel, and enjoy the sun in the sky and the rumble of the planes.

Chicago is booming with festivals every weekend throughout the summer months. Book your stay and come check out summer and festival season in the city.

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