Cool Things to Do in Chicago: Music Edition

If there’s one thing we like to do in Chicago, it’s brag about our hometown. (In fact, that’s how this place originally earned its nickname, “The Windy City.” But that’s another story for another time.)

As a Chicago resident, and as someone who once lived in Manhattan for nearly five years, I can honestly say that outside of a handful of music hubs like New Orleans, Nashville, and Austin, I’m not sure any city in America has as much affordable, eclectic and easily accessible live music as my adopted hometown.

Given that, if you’re coming in the weekend before the Show, as I know many of you are, I urge you to sample just a fraction of the incredible — and affordable — music Chicago has to offer.

Here are just five of the many suggestions I would have for you:

Blues Fest

As luck would have it, one of the finest (and most manageable) of all the city’s summer music festivals will be taking place the weekend before the National Show. From June 10-12, some of the biggest names in blues will appear at venues throughout town. The highlight promises to be the closing night event at the Petrillo Music Shell in Grant Park (just a stone’s throw from McCormick Place) in which guitar virtuoso Lonnie Brooks will headline a 40th Birthday Party for iconic Chicago blues label, Alligator Records.

Date: June 10-12
Time: 11:00 AM to 9:00 PM
Place: Grant Park
Admission: Free

FitzGerald’s Pub

Just west of the city in the bedroom community of Berwyn is a classic live music venue called FitzGerald’s Pub, a place which, much like, say, Antone’s in Austin, you simply trust in their potential to wow you on any given night of the week. On Saturday, Fitzgerald’s will play host to the Honey Island Swamp Band, a New Orleans-based group that plays what one gushing critic called “Bayou Americana.” I don’t know them, but I know Fitzgerald’s. And I’m betting the Honey Island Swamp Band will prove to be well worth a $28 cab ride to Berwyn.

Date: June 11
Time: 9:00 PM
Place: FitzGerald’s Pub, Berwyn
Admission: $12 in advance; $15 night of show

The Whistler

Recently named by GQ magazine as one of the “Best 25 Cocktail Bars in America,” the Whistler on Chicago’s North Side fancies itself a jazz venue. But what it really is, is a place to hear terrific music of all shapes and sizes. That, of course, and to drink some of the most exotic and unlikeliest cocktails you’d ever want to taste (some created by Paul McGee, one of the quirkiest and most unique bartenders in town). On Monday, the Whistler will host what they’re calling a “listening party” for local band Color Radio’s new CD, Architects. The band will be there, as will guest DJ, Kid Color. Just a hunch, but as good as these guys are, someday you’ll be proud to say you knew them when.

Date: June 13
Time: 8:00 PM
Place: The Whistler, 2421 North Milwaukee Ave.
Admission: Free

Millennium Park

Image captured by Jeremy Farmer.

The Decemberists Perform At Millennium Park

Former Mayor Richard M. Daleywanted his legacy to be the 2016 Summer Olympics. However, even if he’d been able to land the Olympics, his greatest legacy is, was and will always remain the most remarkable and imaginative use of urban public space deployed in this country in 100 years. Millennium Park, a former railroad switching yard, is a cultural wonderland, from the Frank Geary-designed Pritzger Pavilion to the dozens of pieces of commissioned art; not to mention the vast amount of free, live music. During the summer, the Chicago Parks Department sponsors what they call their Edible, Audible Picnics. The music is as eclectic as the people you’ll see wandering through the park, and usually a lot more cutting-edge. But don’t worry. It’s not really about the music anyway. It’s all about the venue… and the vibe.

Date: Weekdays
Time: Noon
Place: Pritzger Pavilion, Millennium Park
Admission: Free

The Green Mill

I first developed my personal crush on Chicago-based jazz singer Patricia Barber when I was living in New York and heard WFUV play her icy cool version of one of the hottest songs known to man, “Light My Fire.” The Monday before The Cable Show, Barber and her equally cool quartet will be playing their regular Monday gig at what amounts to my hometown’s version of Birdland, the legendary Green Mill Tavern, a club from another era; and a place that since 1907 has somehow survived shifting musical tastes, the decay of its neighborhood and subsequent (and far more life-threatening) gentrification. Trust me — if you’re a jazz buff, or just a lover of history — you owe it to yourself to check out the Green Mill.

Date: June 13
Time: 9:00 PM
Place: The Green Mill, 4802 North Broadway
Admission: $7


To read more from M.C. Antil, visit his blog at


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