Best Chicago Festivals in September

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September 4, 2017

While September has become synonymous with back to school shopping, the return of the cold and the end of summer, there’s still some hope! Here in Chicago, we don’t let those things get in the way of our fun. So we have compiled a list of our favorite festivals all throughout September. Mark your calendars because these are some you’ll definitely want to check out!


Chicago Jazz Festival

August 31September 3, 2017

Free Admission

[Image: Chicago Jazz Festival]

Since 1979, The Chicago Jazz Festival has showcased some of the greatest jazz artists from Chicago and around the world. Happening over the busy Labor Day weekend, this festival is the perfect way to close out your summer. With shows in Millennium Park and all over the city, wherever you are in Chicago, you’re never far from world-class jazz. For more information about locations, times and headliners, click HERE.

Fiesta Patrias (Little Village Festival)

September 8 – 10, 2017

Free Admission

[Image: Special Events Management]

As one of the largest celebrations of Mexican culture and history in the Midwest, Fiesta Patrias is a must see! Held in the Little Village neighborhood, this feast celebrates Mexico’s independence from Spanish rule in September 1810. For 28 years, it has offered something for the whole family including: local music, entertainment, food carnival rides and much more! For more information on events, parking and directions, click HERE.

Chicago Gourmet

September 19-24, 2017

Admission: Buy HERE

[Image: Chicago Gourmet]

This is a food festival unlike any other.  Celebrating its 10th year, this fest combines star chefs, amazing dishes and food lovers alike to a feast for the ages. With 10 events all over the city, there is something for every palate to enjoy. This year, over 150 of the finest restaurants, chefs, vintners, spirit makers and breweries from all over the world descend on Chicago for 6 days. Must be 21+ for all events. Tickets may be purchased to any or all of the events throughout the week.

Oktoberfest- St. Alphonsus

September 29- October 1, 2017

Admission: $5 before 5pm, $10 after 5pm

Free for Active Military and Veterans with ID

[Image: Special Events Management]

September always means the kick off to Oktoberfest. While there are celebrations all over the city, we had to pick this one because for 17 years, they have done it right. USA Today even voted them one of the 10 Best Oktoberfests in America! Located in the South Lakeview neighborhood, it takes place outside of St. Alphonsus church, which was founded by German immigrants in 1882. While you’re here, feast on homemade bratwurst and German beer while listening to authentic music. The fest even features “Kinderfest” which is a kid friendly version of the main festival! Grab your favorite stein and get yourself over to Oktoberfest at St. Alphonsus! For more information, click HERE.


Which festivals are you excited to go to this month? Remember, if you need a private trolley for your day of festivities, contact us and we’ll get you to where you need to go stress-free!