Chicago Festivals May 2018

It might be hard to believe this (it’s currently snowing as I write this on April 18th) – but summer will be here soon. And that means festival season here in Chicago. Also means that rooftop bars are going to open!

Chicago has fests for just about anyone and anything. Some have said Chicago is the festival capital of the US. I don’t know if that’s true or not, but whatever – there is plenty of fests to check out and here are our favorite Chicago Festivals taking place in May 2018.

Chicago Kids and Kites Festival

Kids & Kite Free Chicago Walking Tours

Photo Source: City of Chicago

May 5, 2018 (10AM-4PM), Montrose Harbor,  Admission: FREE

Here’s one the kids will really enjoy, and the adults will like it too. This marks the 20th year of the Chicago Kids and Kites Festival, and they are bringing out some big stuff. There will be professional kite flyers with oversized, gigantic crafted kites in all different forms. Come out with the whole family and sit on top of Cricket Hill while you marvel at the sea of kites flying before you. Oh and guess what? Attending this event won’t cost you a penny.

Chicago Kids and Kites Festival Website

Lincoln Park Wine Festival – May 19-20, 2018 – Jonquil Park

wine fest free Chicago walking tours

May 18, 19 & 20, 2018, Jonquil Park, Admission: From $20

Although it’s a relatively new festival, having only begun 4 years ago, the Lincoln Park Wine Festival is already a huge hit amongst fermented grape lovers. Hosted at a 2-acre park, this fest features an array of live music, food-wine pairing, and exquisite crafts from local artists and vendors. 90 separate wine tastings are offered, though each general admission ticket only comes with 12 tastings. While sipping wine and eating delicacies, there will also be wine connoisseurs present providing interesting information the featured wine, and wine in general.

Lincoln Park Wine Festival Website

Chicago House Music Festival

House music Free Chicago Walking Tours

Photo Source: City of Chicago

May 26, 2018, Logan Square, Admission: FREE!

If you like house music, this is one of the granddaddy places to go for a true house experience. Featuring 10+ different house artists, the annual show strives to educate and commemorate the origins of the house movement, and its growth thus far. In addition to listening to diverse styles of house music and browsing different stages, the festival will also feature some of the best-rated food trucks in all of Chicago. Believe it or not, this festival does not charge anything for admission.

Chicago House Music Festival