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Chicago in the summer is the best place in the world. (I haven’t been everywhere, but I’ve been enough places to be pretty convinced.) One of the best things is our seemingly unlimited supply of free street festivals – there’s something going on every weekend, and even during the week. Music festivals are super popular and run all summer, from Do Division the first weekend in June through the end of October, so check out these cheap and free Chicago music festivals!
Bookmark this post and come back all summer to find activities to check out!
Navy Pier Beer Garden: The Miller Lite Beer Garden at the end of the Pier features performances almost every day of the week. Beer here is also super reasonably priced, and the gorgeous views of the city as the sun sets is totally worth the schlep out to the shore from whatever neighborhood you’re in. Check out their calendar for music events, plus other great free things to do while you’re in Chicago.
Haymarket Brewery: On Thursdays, Haymarket Brewery has an Americana music series featuring a lot of my faves and friends from Nashville. This is actually a year-round series happening every week, so pop over for some great brews and tunes, even in the dead of winter!
Grant Park Music Festival: Grant Park is home to the largest outdoor classical music festival, which is pretty cool. Events here feature the option to purchase tickets, otherwise, GA seating is always free on the back of the great lawn. Special guest conductors and performers and performances of classical greats is an excellent way to add some culture to your Chicago trip, without adding a big price tag.
Do Division Fest: Do Division is sort of the symbolic start of summer for me. It’s the first weekend after Memorial Day on one of the coolest stretches of West Town. This year’s headliners include Ted Leo and the Pharmacists, Deerhoof, and Bear Vs. Shark – not bad for a free street fest! In addition to eight(ish) hours of music at two stages per day, there’s also a sidewalk sale with local artists and vendors, a family fun festival with activities for the kiddos, the shops on Division set up their sales outside, and restaurants expand their patio seating.
Andersonville Midsommarfest: Andersonville on the north side is a really fun and diverse area, and from June 8-10, they present a great street festival. A $10 donation goes to the neighborhood chamber, and you can take part in yoga, check out music, shop the vendors and sidewalk sales, and eat until you can’t eat anymore. Andersonville has a heavily Swedish heritage, so partake in some traditions like dancing around the Maypole and eating Swedish food (it’s more than just meatballs.)
Chicago Blues Festival: This free festival in Millennium Park is also June 8-10, so if you’d like to stay closer to downtown, stop in for a set here. I love picnicking at Millennium Park, and there’s a Mariano’s nearby – pick up some snacks and a bottle of wine for a cheap, romantic date downtown. The incomparable Mavis Staples caps this year’s festival on Sunday night at the Pritzker!
Taste of Randolph: Three stages in the West Loop along Restaurant Row? Sign me up, please! This festival is pretty long-running, and this year will take over Randolph Street from June 15-17. The lineup is insane – I can’t wait to see Mayer Hawthorne and the amazing MONAKR again – for a $10 entry donation. Taste of Randolph is definitely a can’t-miss event for your weekend in Chicago!
West Fest: Another festival that shuts down along a stretch of great restaurant options, West Fest is July 6-7 this year. The first time I met Craig Finn was at this festival, so it holds a dear place in my heart. It’s on the smaller scale, so if you get overwhelmed by the big crowds at Grant Park or Taste of Randolph, this is a great one to head over to. A small kids area is far away from the stage to protect their hearing, food trucks park at the end of the street, and vendors line the road. (My suggestion? Grab dinner at Roots Pizza. Soooo good.)
Square Roots Festival: This festival in Lincoln Square gets some pretty heavy hitters every year – the first year I went, it was my first solo Dessa show, and I was just delighted. (I heard her sound check start, thought I was running late to the show, and ran in on crutches… only to realize it hadn’t yet started.) This year Square Roots is from July 13-15, featuring Nashville favorite Pokey LaFarge and Chicago locals Get Up With the Get Downs among (many) others. A $10 donation gets you through the gates for the full weekend (and benefits the Old Town School of Folk Music), and like many other festivals, there are lots of vendors and family-friendly activities. I remember this festival as one of the best food spots – it felt like the food and beer options went on for miles!
Wicker Park Fest: Wicker Park/Bucktown is still my favorite part of Chicago, and Wicker Park Fest is July 29 and 30 this year. It’s a $10 suggested donation for admission, but they shut down part of Milwaukee Ave., put up three stages for music, and fill the street with vendors and Goose Island beer. There’s also a kids festival here. Headliners should be announced in a few weeks, and after Doomtree and Guided By Voices last summer, I’m not sure how they can top it this year!
Big Evanston Block Party: I’m really excited for this first-year block party. SPACE in Evanston is one of my favorite venues here, and from August 25-26, they’re celebrating ten years of concerts. Two of my favorites are headliing – The Old 97’s and Guided by Voices – so I can’t wait! It’s a free festival with options to purchase VIP upgrades, but it looks like early registration is required, so grab your August 25 and August 26 tickets early.
Chicago Jazz Festival: This festival is where I lost my keys last year, but I’ll try not to hold that against them. Sitting on the lawn here, sipping bottles of wine picked up at Mariano’s nearby, and watching the sun set over the city skyline is such a nice, relaxing way to say goodbye to summer.
312 Block Party: This Goose Island party represents the end of summer to me. 2018 dates haven’t been posted yet, but it’s typically the third weekend in September. Last year, Ted Leo and the Pharmacists headlined, and in 2016, Beach Slang was my favorite set. Word on the street is that this year, the Empty Bottle is bringing in the best lineup yet, and another bonus (besides the beers and excellent brews?) Grab Hot Doug’s from the food area here, which is a Chicago classic.