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doing Chicago: cheap and free music festivals

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free festivals in chicago

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!

Weekly Events

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.

Annual Events

June

do division

Photo via Do Division Facebook

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!

Logan Square Arts Festival: This is a small music, arts, and family festival in Logan Square. One of my favorite bands, Priests, is playing this year, and I’m excited to pick up some enamel pins from local seller Jini & Tonic!

July

craig finn at west fest

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.)

dessa at square roots festival

Dessa at Square Roots Festival 2016

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!

doomtree at wicker park fest

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!

August

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.

September

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.

goose island 312 block party

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.

Did I miss any other free Chicago music festivals? Let me know what your can’t-miss picks are!

May 23, 2018
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monthly roundup no. 8, april 2018

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The end of April has to mean that this long slog of winter and cold weather has to be on it’s way out. Right? RIGHT?!?! As we ease into yet another weekend that’s too cold to leave the house, here’s some reading from the past month.

Confession: I like wrestling. It’s goofy, it’s funny, it’s storytelling – and wrestlers are real, complex people. Jervis Cottonbelly, my favorite indie wrestler, is often vocal and open about his history with depression and anxiety. Earlier this month, his suicidal ideation led to a hospitalization. His blog post, On Sweetness and Suicide, is a great read for insight into not only what the hospitalization process is like, but also how it feels to have these thoughts you don’t want.

I’ve used Evernote for quite a few years, and I really like this post on how their CEO uses it and stays organized. The idea of assigning a theme for each workday is something I started doing recently, and it’s really helped my productivity to be able to think (and tell co-workers) when something isn’t on the docket for that day.

It’s little secret that Maybe in Another Life by Taylor Jenkins Reid is my favorite book, and it tripped me out thinking about the hundreds of different lives we could have depending on the choices we make. Turns out this is an actual physics concept, and I’ve been reading a lot about the multiverse and many-worlds theories of quantum physics. Just some casual reading for your Friday. 

6 Apps That Will Streamline Your Investments Starting Now: I’m really focusing on getting my finances in order this year, and that includes setting up an investment or 401k account. I’m relying on breakdowns and reviews like this from blogs I trust to help cut out some services to help put me on the right track while I research the best option for me. 

My Boston BFF and I are OB-SESSED with these money diaries. They really hearken back to when I first started getting into blogging and almost exclusively read personal finance blogs. Man Repeller has them too – the comments on theirs are often much less toxic or judgey – they definitely make me feel behind on my savings for where I am in my life now, but tracking my spending as though it’s a diary is making it a lot easier to to consistently track. (Today is day 23 – consistency!)

For the last several years, I’ve been feeling the crush of what it’s like to be an only child. This post from The Everygirl puts many of my concerns together – specifically the first and last points. My built-in support system is very limited, and I think a lot about what will happen if my parents die (and now that my mom is sick, I feel a lot of the responsibility on that,) but that kind of freedom can also be a real blessing.

I don’t know why this is sponsored content from Taco Bell, but we’ll go with it. The Muse posted an article with scientifically-backed tips on creativity, and I will admit that I wish it was a little more informational – I don’t need any more encouragement to grab a beer – but it’s a nice reminder sometimes that you could be too “into” your ideas and need to take a step back into your daily tasks, or even reset with a nap or shower.

I’ve really been enjoying the Girlboss blog lately (and the new layout took some getting used to, but now I’m really into it. I hope it was built by women.) They recently featured an article about guitar badass Sister Rosetta Tharpe – she was a killer on electric guitar and probably the first rock ‘n roll woman. She gets overlooked far too often, so do yourself a favor and read their great primer on her.

April 27, 2018
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music monday: record store day ready

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music monday

Record Store Day is one of the most wonderful times of the year for music fans – it’s a time to line up outside your favorite store and hope you’ll get to pounce on all the limited releases and deluxe editions the retailers are sent. I’ve had some remarkable Record Store Days, from the time I got a black eye in competition for a Dave Matthews Band release (I wish I was kidding) to the time I got my favorite Hold Steady record on vinyl. It’s a day that’s always been close to my heart because in college I got to sit in on a few roundtables about planning the next year’s national event, which was really cool. The 2017 edition is this Saturday, so download your list, get ready to line up, head to the store, and be sure to check out the bands that are playing! These are the bands with releases this year I’m excited to check out. If you have a minute before diving in to the jams, please take my reader survey!

Mayer Hawthorne, Someone Like You

Jason Isbell & the 400 UnitHope the High Road

Sunny Day Real EstateRain Song

TotoAfrica

Goo Goo Dolls‘Cuz You’re Gone

Are you a vinyl fan? What releases are you excited for this year?

April 17, 2017
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tune tuesday: insomnia edition

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tune tuesday

I haven’t been sleeping well lately, so Counting Crows’ “Up All Night (Frankie Miller Goes to Hollywood)” has been running through my head a lot. While I try not to listen to music or turn on any lights while I flop around trying to fall asleep, there are a lot of songs by people who’ve suffered a similar plight. Here’s a playlist inspired by the sleepless – plus a few other songs I’m just digging a lot lately!

Dave Hause, The Flinch

The Staves, Tired as Fuck

Sorority Noise, No Halo

Wussy, Airborne

Counting Crows, Up All Night (Frankie Miller Goes To Hollywood)

What’s on your sleep playlist? If you have trouble sleeping as well, what are your tips to drift back off?

February 28, 2017
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gift guide: 2016 last minute

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Last week I shared a week of posts with great gift ideas, but there are always those procrastinators – no time to go shopping, can’t find Tickle Me Elmo (if you’re in the market, there’s one in the basement at my parents house), or whatever. Shipping deadline to arrive by December 24 for a lot of websites is TODAY (sure, there’s a lot of great stuff on Amazon Prime yet, but small shops are so much more unique.) Here are some last minute ideas if you still have some outstanding shopping to do!

This Is Fine Dog: 2016 is (mercifully) coming to a rapid end, but I still find myself in frequent need that everything is fine. The dog from the Gunshow comic is being made into a plush animal, and he’s on preorder. It will look like you planned ahead, and they even have a card you can print out for your giftee to open in the meantime. Read more…

December 15, 2016
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