What’s the best thing about the weather turning and summer arriving in Chicago?  The opening of the beaches?  The re-emergence of skirts and halter tops on the female faction of our populace?  The bleachers at Wrigley?  Well, yes, technically all of those trump this, but another highlight is the opening of the festival season in our fair city.  For those not in the know, Chicago consists of the big, downtown Loop with the skyline and skyscrapers you have seen in the movies, but more importantly it is a net of smaller communities and neighborhoods that go by clever names such as Lakeview, Bucktown, Old Town, etc.  These neighborhoods provide unique identities within our collective identity and thus each feels the need to throw its own soirée to establish just how much fun their niche adds to our culture.  So as the calendar turned to June a few days back, the shroud was lifted and outdoor party season began. 

For a full listing of all activities that you could be partaking in I would point you in this direction:


Now mind you there are events mixed in here that sound better than they actually turn out – I submit exhibits A-G in the form of SlutWalk Chicago, which based on these pictures was not nearly as cool as one might be led to believe – but generally speaking the Chicago festival scene is fantastic.  If you enjoy live music, over priced drinks, crowded bars, and small samples of food for healthy prices, boy did you come to the right place.  I say this in jest because while true, I don’t mean to dissuade you from attending the event of your choice by any means. 

To serve as a primer for the uninitiated, here are some of my favorite memories of past festivals that I’ve attended and I would encourage you to dive right in and make some for yourself:

Old Town Art Fair – This was held last weekend and is a personal favorite.  I prefer the Old Town Triangle portion of it rather than the section of Wells St. that gets blocked off as it was in this neighborhood that I had my first apartment in the city, moving in just a few days prior, and we had someone with a booth give us $20 a day to run an extension cord through our window for power.  Can you say ‘free beer for the weekend’?  Since then I moved away but return most every year (this year I passed as I was in the ‘burbs with my family and attended the St. Charles Pride of the Fox festival.  When was the last time you were on a Zero Gravity or The Zipper?  We came very close to needing the services of the pixie dust spreader on staff).  I own multiple pieces of art from the Old Town Art Fair and am a regular at the Adobo Grill guacamole stand – can’t recommend it highly enough.    

 Taste of Randolph Street (June 17-19) – There are a lot of good restaurants on Randolph St.  Take advantage.  The bar Lumen used to be named Fulton Market Lounge and was a notorious cougar den.  All the more reason to go.

Chicago Pride Fest (June 24-25) – Actually a very good time.  It’s the only place I’ve ever been where I’ve seen emotional boys crying over being dumped and girls getting into full blown fisticuffs in the same parking lot.  Apparently the Chicago police don’t know what to make of this group either as a very liberal stance is taken on girls being topless for these few days in public.

Taste of Chicago (June 24-July 3) – Completely overrated, save your money.  It goes against everything cool about neighborhood identity and all the food is a rip-off.  The turkey legs they sell that let you feel like Fred Flintstone are full of tendons and are not enjoyable.  The fireworks are nice but not even the best the city has to offer (Venitian Night take them to the cleaners).  The best part of Taste of Chicago is getting drunk on Metra on the way to and from the suburbs.

Chicago Folk & Roots Festival (July 9-10) – I have a very vague recollection of attending this one year and seeing Ziggy Marley play.  There was a general haze about the concert that keeps my memory fuzzy

West Fest (July 9-10) – Free dog baths are a nice touch.  They also have a petting zoo.  Much more of a daytime stroll than a night full of fun.

Old St. Pat’s World Largest Block Party (July 15-16) – Reportedly the best place to meet your future spouse.  Given the omnipresence of The Wife I don’t know that I’ll ever have an opportunity to attend.

Pitchfork Music Festival (July 15-16) – Lollapalooza for the hipsters and hippies.  Great line up this year however.  I hear very good things about the Fleet Foxes.

Sheffield Garden Walk & Festival (July 23-24) – I have had some absolutely outstanding times at this little get together (or so I’ve been told the following morning).  My favorite experience was when a friend of mine that worked at Kelly’s Pub felt the need to be bringing a table of our friends whole bottles of vodka at a time which we promptly consumed.  I’ll remember this evening because I threw a full drink towards a garbage can out in the beer garden and it hit a young lady who stepped in the way.  Rather than equating me to a gigantic asshole that throws drinks (unintentionally mind you) she thought it was funny, pulled up a chair, and hung out with us for the next few hours.  The Garden Walks draws a special breed.  That same night I was headed over to the next festival via taxi and saw some kids I didn’t know doing keg stands on their porch.  I got my taxi driver to stop the car so I could run out and do a standing 20 count off the keg, return to the car, and continue on our merry way.  Good times.

Wicker Park Fest (July 23-24) – That cab driver ended up dropping me at the corner of North and Damen for Wicker Park Fest where I had told The Wife – back when she was barely The Girlfriend, we’re talking third date at best here – to meet me earlier in the day.  To her credit she hung with my friends and I as we got kicked out of a string of bars along Damen due to our general inebriation.  I knew she was a keeper from that point forward and Wicker Park Fest will always hold a special place in my heart.

Lollapalooza (August 5-7) – A true marathon of an event if you do it right.  Inevitably this will be the hottest weekend of the year and like wildebeests on the Serengeti, the concert-goers flock to the shade as the sun beats down.  Perry Farrell throws a good bash however and I would highly recommend at least trying a Day Pass if you’ve never been.  The hard core will take Friday off and try to pull the entire three day event off.  I recommend lots of water and you pretty much have to live in the city with L train access to get to and from the grounds every day to make it feasible.  I will guarantee you will walk away with three new bands that will carry your iPod through the rest of the summer.

Chicago Air & Water Show (August 20-21) – Your goal this summer is to make friends with people who live in high rises downtown that have rooftop pools and make sure you get invited to a party there this weekend.  It’s by far the best way to take in a couple fly-bys.  I’m always amazed at the human race’s fascination with loud noises and bright lights.  I’m convinced it’s why NASCAR is so popular.  We’re basically hairless raccoons.

Taste of Greece (August 27-28) – I have a very weak spot in me for Greek food.  Give me some dolmades and a little saganaki and you’ll have a very happy little boy on your hands.  The Wife loves the fortune tellers who will happily take your money and tell you things like, “I see you on a journey” or “your hard work will be rewarded.”  Some people just have a gift.

Chicago Jazz Festival (September 2-4) – I like jazz music just fine and actually celebrate a nice collection myself, but this festival will always be associated in my mind by my dad dragging the whole family down to Grant Park each summer to take in the vibe.  What six year old doesn’t want to be confined to a 4’x4’ blanket listening to acid jazz?  These were not happy memories.

Windy City Wine Festival (September 9-10) – Quite possibly my favorite festival of the year.  Now I’m going to sound like an old codger but it used to be a whole lot better than it is.  That first summer I moved to Chicago from Madison a friend and I stumbled upon this little gem on Wells St. and much to our delight found out that for $10 we could get a commemorative wine glass and all the refills we could handle.  Within 45 minutes we had purple teeth, stained shirts, and had ripped through our entire phone book calling everyone we could think of to come to this land of milk and honey we had discovered.  Another memorable year, that same friend, The Wife (who by this point we had let in on our secret), and I spent a lovely day drinking wine and smoking cigars (purchased at Up Down Cigar).  For some reason we had to leave by 4pm so at 3:30p we decided to have a race to see who could drink the most in the next half hour.  We went to another party that evening that I have no recollection of, and people have told The Wife since that she was speaking in tongues throughout the event.  Awesome.  Since then however they have implemented a ticket based system where for an absurd amount of money you can buy X tickets which get you X sips of wine.  Another example of the man trying to hold us down.  I do take some solace in thinking that I played a small role in forcing the policy change.

While by no means is this a complete list of all the fun that is to be had, I encourage you Chicagoans to embrace the city festivals and walk away with your own stories.  And remember the best ones are those that need to be pieced together the next morning over a Bloody Mary (Stanley’s has an outstanding Bloody Mary bar if you’re into that sort of thing), a quick check of your outbound texts and phone calls, and a bunch of laughs with your friends.  The weather is warm, be merry.