
Summer in Chicago isn’t complete without attending at least one street festival. It’s one of the best things about living in Chicago and one of the reasons why I endure the brutal winters.
Whether you live in Chicago or plan to visit Chicago in the summer, be sure to check out a street festival.



A few weeks ago, we attended our first street fest of the season in Old Town at the Old Town Art Fair. It was a wet morning but we managed to walk around and look at all the beautiful art work from the vendors. I didn’t take any pictures of the vendors’ art work out of respect for their work as they were selling them. We also found time to do a little garden walk, which is a part of the fair. And…we got to take some pictures in front of this beautiful blue door!
What is a street festival like in Chicago?
Well, that depends on what neighborhood and street festival you are attending. There are street fests featuring the restaurants in the neighborhood (i.e., food) like the Taste of Randolph or art like the Old Town Art Fair. Some neighborhoods like Andersonville, with the Swedish influence has the Midsommarfest. But a few things are the same…food and music. Streets are closed down to traffic for these fests and there’s normally a small donation to enter (about $5 or $10).
What do you do at a Chicago street festival?
Well, that also depends on you and how old you are. Before kids, I would attend a street fest later in the day (or at night) to drink, hang out with friends, and listen to live music by the stage. But now, we go during the day and take a peek at some vendors, eat some food, and check out the kids area.
What street festivals should I check out?
I know it’s late June and some of my picks on street fests in Chicago has already passed but here is my list of the street fests that I have attended in the past and have enjoyed!
June
- Old Town Art Fair – Old Town
- Taste of Randolph – West Loop
- Do Division Street Festival – West Town
- Midsommarfest – Andersonville
July
- West Fest – West Town
- Square Roots Festival – Lincoln Square
August
- Retro in Roscoe – Roscoe Village
- NorthHalsted Market Days – Boystown/Lakeview