My Chicago Summer Festival Challenge


When I first moved to Chicago in 2001, my summer plans consisted of working, studying for the bar exam and occasionally going out for a beer to break the monotony of studying for the bar exam. My circle of friends consisted of law school classmates and colleagues with whom I had worked the previous summer at a large law firm and we were almost all new to Chicago. Somehow, we missed the memo that you are supposed to spend every weekend in Chicago at a street festival. I’m not sure I made it to even one that summer.

Indeed, it took me a while to catch on to the fact that summer in Chicago is really street festival season. I probably hit my peak in street fest attendance the summer of 2007 when, in an attempt to get over a breakup, I was determined to go out every single Friday and Saturday night of the entire summer. This almost necessarily involved a lot of festival-going.

After a while, though, my festival attendance dropped off. I started feeling a bit too old for the Taste of Lincoln Avenue and my newly diagnosed gluten intolerance took away the excitement of trying everything under the sun at Taste of Randolph or noshing on German pretzels and drinking beer at German-American Fest. And once I returned from my career break, it seemed not nearly as many of my friends were up for hitting any festivals. I think I made it to two all of last summer.

This summer will be different.

This summer will the summer of street festivals.

German American Fest

But not just any street festivals – I want to check out the ones that I ignored in the past. While I will probably still go to some favorites like Retro on Roscoe and the Old Town Art Fair, I am challenging myself to visit a new street festival every weekend this summer – one that I have never been to before.

Here’s a weekend-by-weekend preview:

May 3-4: Yes, street festival season is already kicking off, with Cinco de Mayo Fest in Little Village, Cinco de Mayo Festival and Parade in Douglas Park and Polishfest in Jefferson Park.

May 10-11: Not much going on this weekend – since I can’t drink beer, the American Beer Classic at Soldier Field really doesn’t make sense.

May 17-18: This is when the season “officially” kicks off, with Mayfest in Lakeview. I think I’ve attended once before, but as the only fest this weekend, this is where you’ll find me.

May 24-25: No festivals this weekend as I’ll be hiking in the Grand Canyon!

May 31-June 1: Now that we’re post-Memorial Day, it will hopefully start feeling like summer! My favorite Maifest (note the spelling difference) will be taking place in Lincoln Square, as well as Do-Division Fest in Wicker Park, the Millennium Arts Festival in the Loop and the brand new Festival del Taco in Little Village. I think tacos are calling my name!

June 7-8: This is one busy festival weekend with Ribfest in North Center, Midsommarfest in Andersonville, 57th Street Art Festival in Hyde Park, Belmont-Sheffield Music Festival in Lakeview and the Printers’ Row Lit Festival. I’ve been to all of the north side ones in the past, so I will head south for the 57th Street Art Festival in Hyde Park.

June 14-15: Another busy weekend, with the Chicago Blues Festival in Millennium and Grant Parks, the Old Town Art Fair and Wells Street Art Festival in Old Town, the Puerto Rican Festival in Humboldt Park, the Taste of Randolph Street in the West Loop and the 6 Corners BBQ Fest in Portage Park. The winner for this weekend? I’m thinking the Puerto Rican Festival.

June 21-22: Things start to slow down a bit, with only the Green Music Festival in Wicker Park, Pride Fest in Lakeview, and the Tap Beer Festival in Wicker Park. Sounds like Wicker Park is the place to be this weekend, so the Green Music Festival it will be!

June 28-29: My favorite street fest, Old St Pat’s World’s Largest Block Party, is this weekend so I will be there for sure. My other choices are the Milwaukee Avenue Arts Fest in Logan Square, Chicago Summerfest in Lincoln Park and the Gospel Music Festival in Bronzeville. I’ve never really been to Bronzeville before (aside from this walking tour), so I’m thinking I should head there for some gospel music.

July 4-6: Assuming I’m in town this weekend, I can check out the Windy City Ribfest in Uptown (which was quite the good time last year!), the Taste of Lakeview, Rock Around the Block, also in Lakeview, or the African/Caribbean International Festival of Life Carnival of Nations in Union Park. The latter is definitely the most intriguing for me!

July 12-13: Things pick up again with the Taste of Chicago (why does this not coincide with the 4th of July this year?), the Windy City Smokeout in River North, the Square Roots Music Festival in Lincoln Square, West Fest in West Town, Summer on Southport in Lakeview, the Roscoe Village Burger Fest in Roscoe Village and the Irish American Heritage Festival in Jefferson Park. So many choices, but I think West Fest will be the way I go, with Square Roots a close second.

July 19-20: No festivals this weekend – I’ll be in Minnesota for my high school reunion!

July 26-27: I’ll definitely be skipping the Taste of Lincoln Avenue, but am thinking either Jeff Fest in Jefferson Park or Wicker Park Fest would be good options.

August 2-3: This is Lollapalooza weekend but instead of sweating away with thousands at Lolla, I’ll be checking out the Taste of Latin America in Logan Square, Fiesta del Sol in Pilsen, Edge Fest in Edgewater or Wrigleyville Summerfest in yes, Wrigleyville.

August 9-10: This may be the last festival-filled weekend of the summer, with the Ginza Festival in Old Town (I have no clue what that is), the Bud Billiken Parade and Picnic in Washington Park, Northalsted Market Days in Lakeview and Retro on Roscoe in Roscoe Village. Since I don’t often get to the south side, I think Bud Billiken will be worth the trip down there.

August 16-17: While the rest of Chicago is at the Air & Water Show, I’ll be checking out either the Festa Italiana in Little Italy, the Festival Cubano in Riis Park, the Glenwood Avenue Arts Fest in Rogers Park or the Albany Park World Festival.

August 23-24: I apparently am never around this weekend in Chicago because I have never been to any of the festivals taking place this weekend – New Orleans Festival in Wicker Park, Taste of Greece in Greektown, Bash on Wabash in the South Loop and the Bucktown Arts Fest in Bucktown.

As of right now, I plan to be out of town the next two weekends, so this will mostly wrap up my summer festival challenge.

If you’re in Chicago and want to join me for any of these festivals, let me know! Additional recommendations are welcome as well – according to one source, there are more than 400 neighborhood festivals in Chicago each summer, so the ones mentioned above are just a fraction of what’s available!


4 thoughts on “My Chicago Summer Festival Challenge”

  1. The summer events are my favorite thing about Chicago. I try to go to every festival that has a decent band. The evening concerts in Millennium Park are always great too. I’ll see you out there!

  2. That’s a lot of festival-going! 🙂 Looks like so much fun though. Have a blast. Here in Toronto we have loads of festivals also but I have to admit that I get exhausted going to too many. Please being vegan limits some of the foods I can eat (no rib fests for me). Enjoy the summer.

  3. Chicago seems to know how to do summer right … one of my former homes in Canada is really good with summer festivals, so I know how fun they can be. Enjoy yourself!

Comments are closed.

Scroll to Top