What To Do In Chicago This October

Fall in the Chicago area; you gotta love it! It’s not super hot, but you don’t need an Arctic-level winter coat in Rogers Park just yet. The tourist hordes and the heat have subsided, but there’s still so much to do. Plus, things are finally opening back up again after all the COVID madness. Here are a few great picks of things to do as fall kicks off.

Fall Foliage In The City

Who says you have to head up to the UP or out to the Kankakee River to leaf-peep? Not us. The first spot might be Lincoln Park, a place that has not only some of the oldest trees in the city but also a lot of other great attractions. It’s the largest park in CHI, so give it a shot before you try anything else. Also check out LaBagh Woods, the Chicago Botanic Garden, and Winnemac Park over near Lincoln Square for some other in-town foliage picks that will be Instagram-worthy this October.


Lincoln Square Ravenswood Apple Fest

Yes, October is a month where pumpkins get a lot of press (and more on that later) but we’d be silly if we didn’t mention Apple Fest. On Sat October 2nd, Lincoln Square becomes singularly devoted to all things apple. Pro tip: the apple-stuffed grilled cheese is an incredible treat! Also, don’t forget to check out their fall market; lots of the vendors are small, local businesses that sell things no one else has.

Art on the MART/Art Institute of Chicago

Maybe you’ve heard of Supreme, the New York skateboard brand that took over the world with its iconic red-and-white ‘box logo’ style. What you might not know (unless you’re an art fan) is that their style and graphics are a direct lift from the famous artist Barbara Kruger. Long before skaters and hypebeasts were lining up for Supreme hoodies, Barbara Kruger was making waves with her provocative installations and street art pieces. This month, her art installation entitled ‘Questions’ will be projected onto the whole of the Merchandise Mart in full, 25-story glory. Check it, then go see her exhibition at the Art Institute of Chicago.


Pilsen Vendor Market

Fall means some of the last bit of time we all get to enjoy being outside without freezing our faces off! Make the most of that time by heading out to the Pilsen Vendor Market this October. If you’re looking for some local art to decorate your home (and if you’re on this blog, there’s a good chance you might be!) this is one of the best spots in Chicago to check out. Hosted by the Pilsen Art House.


Visit A Pumpkin Patch

Yes, it’s October, thus it’s logical to visit a pumpkin patch. Grab one to carve up for Halloween, or just pick some up to make a pumpkin pie or authentic pumpkin-spiced anything! Plus most pumpkin patches offer things like hayrides, cider, and snacks to get anyone in the fall mood. Check out spots like Didier Farms, Sonny Acres Farms, Bengtsons Pumpkin Farm, or County Line Orchard, all about 30 or 45min away from Chicago by car.


Open House Chicago

Ever been walking around the CHI and seen a crazy or super cool-looking building? They’re all over the city. Open House Chicago is an architectural tour and celebration that lets eventgoers behind the scenes and inside some of the most interesting structures and homes in the area! After putting the event on pause due to COVID, it’s finally back on October 16th and 17th. Over 100 venues in the city will be open to the public. See more at Open House Chicago.


Chicago Haunted Houses/Ghost Tours

For many people, the best holiday is not Christmas or a birthday, but Halloween. Besides costume parties and trick-or-treating on the big day, you can extend the spooky holiday spirit in Chicago by checking out a haunted house or ghost tour! One of the best haunted houses is Basement Of The Dead, and the Free Tours By Foot Ghost Tour is great!



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