Essential Chicago Summer Festivals: September 2015 Edition

September in Chicago

September in Chicago

Sad, but true: another Chicago summer, albeit a short one, has flown by. September is typically a gorgeous month in Chicago, one of my favorites. But alas, September signals the end of street festival season and tends to arrive with a bit of melancholy as autumn is ushered in, ultimately giving way to that inevitable Chicago winter. So, for now, we can focus on reveling in the warmth of every last sun-soaked day, in true Chicago-fashion. Below is a guide to September festival fun (aside from the ever-popular music festivals, North Coast Music Festival & Riot Fest) and road map to assist you in making your weekends count.

Chicago Jazz Festival

Who: Jazz appreciators. Music lovers.

What: A Chicago Labor Day tradition of jazz with a remarkable lineup of jazz performances. Food vendors.

Where: The Chicago Cultural Center, 78 E. Washington Street & Millennium Park.

When: Thurs., September 3rd {noon- 4:30p @ the Cultural Center, 6:30p- 9:00p @ Millennium Park}; Fri., September 4th- Sun., September 6th {noon- 9:30p @ Millennium Park}.

Why: It’s a truly impressive showcase of jazzy talent from the Chicago scene and around the globe and the largest, gratis jazz festival in the world.

How Much: FREE!

Pro-Tip: If you can’t make the Chicago Jazz Festival, or are just a jazz junkie, don’t miss the Hyde Park Jazz Festival on Saturday, September 26th and Sunday, September 27th at Midway Plaisance Park.

Taste of Polonia

Taste of Polonia, Chicago, IL

Taste of Polonia, Chicago, IL (photo by R_A_L at

Who: Polish people. Sausage devotees. Polka fiends.

What: Polish food & drink. Nonstop music w/ 4 stages featuring a wide range of genres. Cultural events. Family events. Polka dancing. The largest Polish festival in the US of A.

Where: Copernicus Center, 5216 W. Lawrence Avenue in Chicago’s Jefferson Park neighborhood.

When: Fri., September 4th {5:00p- 10:30p}; Sat., September 5th & Sun., September 6th {noon- 10:30p}; Mon., September 7th {noon- 10:00p}.

Why: Because what better way to immerse yourself in the Polish culture than via pierogies, kielbasa, and polka in a city that is home to one of the largest Polish populations in the world?

How Much: $7.

German American Fest

Who: Those that value the finer aspects of the German culture (read: sausage and beer).

What: German food and drink. Traditional German song and dance. Bands. German hospitality. Carnival games. A parade on Saturday (at 2:00p).

Where: Lincoln Avenue & Leland Avenue in Chicago’s Lincoln Square neighborhood.

When: Fri., September 11th {5:00p- 11:00p}; Sat., September 12th {noon- 11:00p}; Sun., September 13th {noon- 10:00p}.

Why: To embrace your inner-German and affinity for encased meat and steins of beer.

How Much: Free admission.

Shock Top Oyster Fest

Shock Top Oyster Festival

Shock Top Oyster Festival (photo by Tony at

Who: Bivalve aficionados. Roscoe Village neighborhoodies.

What: Oysters (East Coast Delaware Blue Bay Points & West Coast Purple Mountain). Beer (formerly Guinness, now Shock Top). Live music. Local eats. Arts and crafts vendors.

Where: Damen Avenue & Roscoe Street in Chicago’s Roscoe Village neighborhood.

When: Fri., September 11th {5:00p- 10:00p} & Sat., September 12th {11:00a- 10:00p}.

Why: It is as good an excuse as any to eat oysters, oh, and drink in the street while the weather still permits.

How Much: $7 suggested donation.

Lakeview East Festival of the Arts

Lakeview East Festival of the Arts

Lakeview East Festival of the Arts (photo by Katie Kullen at

Who: Art enthusiasts. East Lakeview neighborhoodies. Yuppies.

What: Over 150 juried artists showcasing artwork from paintings and sculptures to photography and jewelry. Two stages featuring live music. Children’s activities. Food and drink.

Where: Broadway Avenue between Belmont Avenue & Hawthorne Place in Chicago’s Lakeview East neighborhood.

When: Sat., September 12th {10:00a- 7:00p w/ music until 10:00p} & Sun., September 13th {10:00a- 6:00p w/ music until 7:00p}.

Why: Because wandering around and checking out art in a cool neighborhood can be fun.

How Much: $5.

Windy City Wine Festival

Buckingham Fountain, Chicago, IL

Buckingham Fountain, Chicago, IL (photo by Grant at

Who: Oenophiles. Oenophiles-in-training.

What: Wine tastings. Over 300 wines to sample from all over the world and closer to home. Wine seminars & cooking demos. Tasty food from local Chicago favorites. Live music.

Where: Buckingham Fountain, 500 S. Columbus Drive.

When: Fri., September 11th {4:30p- 10:00p} & Sat., September 12th {2:30p- 8:00p}.

Why: Because WINE.

How Much: Tickets are $35 in advance, $45 at the door (includes a souvenir wine glass, 12 wine tastings, one pint of beer, discounted prices on wine sold).

Renegade Craft Fair

Who: A hip crowd. Artsy types. Creative folks.

Renegade Craft Fair, Chicago, IL

Renegade Craft Fair, Chicago (photo by Nate Burgos at

What: Local vendors and artists. Lots of etsy-esque art. Delicious local food and beverage (hello, Dia de los TamalesDönerMenBlack Dog Gelato, Revolution Brewing).

Where: Division Street between Paulina Street and Damen Avenue in Chicago’s Wicker Park neighborhood.

When: Sat., September 19th & Sun., September 20th {11:00a- 6:00p}.

Why: This is one of the trendiest, coolest craft fairs around and is filled with glorious, artsy gift ideas.

How Much: Free.

Oktoberfest Chicago

Oktoberfest, Chicago

Oktoberfest, Chicago (photo by heyrocc,

Who: Oktoberfest devotees. Beer buffs. Lakeviewers.

What: All-things German with a heavy emphasis on beer, brats and pretzels. A craft beer tasting evening on Friday. Bands. German entertainment. Activities for youngsters.

Where: St. Alphonsus Church at Southport Avenue & Lincoln Avenue in Chicago’s Lakeview neighborhood.

When: Fri., September 25th {5:00p- 10:00p}; Sat., September 26th {11:00a- 10:00p}; Sun., September 27th {11:00a- 7:00p}.

Why: Autumn has officially arrived (signaling the conclusion of festival season), so you may as well embrace it with the Oktoberfest tradition of beer, pretzels, sausage, and merriment.

Berghoff Oktoberfest, Chicago, Illinois

Berghoff Oktoberfest, Chicago (photo by John W. Iwanski at

How Much: $5 suggested donation, $40 for the craft beer tasting night.

Pro-Tip: If you can’t get enough Oktoberfesting, be sure to check out Berghoff Oktoberfest, Wed., September 16th- Fri., September 18th {11:00a- 9:00p} at the John C. Kluczynski Federal Plaza at 230 S. Dearborn St. For a listing of other Illinois Oktoberfests, click here.

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