Chicago's Best Events, Festivals, & Things To Do This October

Posted by Leo Clark. on Friday, October 4th, 2019 at 11:21am.

Even though summer is officially over, October is one the most festive months of the year in Chicago with plenty to do all over the city. Here’s our updated list of events, festivals, and fun things to do this year..

Fall Fest at Lincoln Park Zoo - Now to October 27th

This year marks the 5th year for the Fall Fest at Lincoln Park Zoo. As a family-friendly celebration of autumn, the festival features a corn maze, Ferris wheel, an inflatable obstacle course, live professional pumpkin carving, and so much more!

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Jack’s Pumpkin Pop-Up - Now to November 3rd

Presented by Samuel Adams, this BOO-zy outdoor experience includes the city’s largest outdoor corn maze, axe throwing, 4 full-service bars, and plenty of carnival games, food trucks, and Instagram-able stops along the way.

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Pier Pumpkin Lights - Now to November 2nd

The first ever Pier Pumpkin Lights will feature a number of pop-up installations throughout Navy Pier, including amazing jack o’lantern towers to spectacular light displays.

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St. Benedict’s Oktoberfest - October 4th - 6th

One of Chicago’s most authentic Oktoberfest celebrations, St. Benedict’s version will include live music, yummy food, plenty of beverages, and even carnival rides and games that are fun for the whole family.

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Chicago Rare and Wild Beer Fest - October 5th

If you’re a beer lover, this one is a can’t miss event. Returning to The Field Museum this fall, the Rare and Wild Beer Fest will feature over 60 breweries, not to mention some of the rarest and funkiest brews you’ll ever try.

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Lincoln Square Apple Fest - October 5th & 6th

Nothing says fall like the Lincoln Square Apple Fest. Dozens of vendors will be on hand selling fresh apple pie, candy apples, hot apple cider, and even hats, scarves, and fall clothing!

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Bacon and Beer Classic - October 12th

If you can’t make it to a Bears game this year, you can still swing by Soldier Field for the 5th annual Bacon and Beer Classic. More than 100 craft beers will be available, as well as plenty of bacon-inspired dishes from some of the city’s top local restaurants.

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Spooky Pooch Parade - October 13th

The only time dogs are permitted into the Chicago Botanic Garden, the Spooky Pooch Parade features cleverly costumed canines and their owners, and of course the fun also includes a costume contest, judging, and an awards ceremony!

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Bank of America Chicago Marathon - October 13th

Every October is the Chicago Marathon, which along with Boston, New York, London, Berlin, and Tokyo, is one of the six World Marathon Majors.

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Chicago International Film Festival - October 16th - 27th

Having started back in 1964, the Chicago International Film Festival is the longest running competitive film festival in all of North America. Like most years, the 2019 line-up shouldn't disappoint.

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Arts in the Dark - October 19th

Now in its 5th year, Arts in the Dark is a magical evening parade that celebrates Halloween as the “artist’s holiday.” Included is a powerful procession filled with costumes, performances, dancing, lighted lanterns, and more!

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Music Box of Horrors - October 19th

The annual 24-hour horror movie marathon at the Music Box returns. This year’s lineup includes Demons 2, Halloween II, Buffy the Vampire Slayer, Dog Soldiers, and many more!

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