Chicago Like a Local Blog

With fall foliage and the cool breeze comes the spookiest month of the year—October! Besides Halloween festivities, Chicagoans have several things to look forward to, including fall festivals, book expos, art walks and food fairs. Movie fans won't run out of things to watch with several free screenings and the International Film Festival coming up, while history buffs will enjoy free admission to several of Chicago’s best landmarks. Without further ado, here are the top 10 free things to do in Chicago this October.

The weather is cooler, but the #ChicagoLeafPeeping is prime. As autumn wraps the city in reds and golds, it's the perfect time to check out the harvest festivals and Oktoberfests that are popping up around town. As we cruise into a new month, take a moment to check out the biggest events happening in October, and make some time for these weekend picks (that is, if you don't stay out too late at these bars that keep the party going past last call). 

The biggest international art event of the fall season kicks off with the sixth annual Expo Chicago, the international exposition of contemporary and modern art at Navy Pier, on September 14–17. An array of 135 galleries that hail from 58 cities and 25 countries will transform the Navy Pier festival hall into a colorful, global showcase. Art lovers can browse an exciting display of contemporary art works as well as attend panel discussions, view curated film and video and participate in special daily events.

Another Labor Day rolls around, but Chicago holds on to summer as long as it possibly can. We’ve written a guide to most of the festivals happening around town this weekend, such as the African Festival of the Arts, Taste of Polonia, the North Coast Music Festival and more. Of course, don’t miss out on the fireworks at Navy Pier. Here's our roundup of things to do in Chicago this weekend!

Celebrate the end of summer by biting into an iconic Chicago summer treat! Here are three sweet summery treats that you'll only find in Chicago. 

The Chicago Air & Water Show, one of the summer's most thrilling spectacles, is coming up on August 19–20 (10 a.m.–3 p.m.). The U.S. Navy Blue Angels, the U.S. Army Parachute Team Golden Knights and many more experts in speed will hit the skies over our fair city in this, the largest free air-and-water-focused show in the U.S. While you can always catch the Air & Water Show from pretty much anywhere on the lakefront between Fullerton Avenue and Oak Street, here are four ways to view the show in comfort and style:

It’s time for the weekend once again, Chicago. Summer is winding down, but the things to do in Chicago aren’t! Explore Chicago’s breweries using the craft beer trail itineraries built around six neighborhoods of the city. For sports fans, the MLS All-Star game is coming to Chicago hosted by Soldier Field. There are multiple events leading up to the big match beginning this Sunday. For more on the weekend happenings, we curated a list of things to do in Chicago this weekend below.

As we head into the final stretch of summer, it's time to pack in everything on your bucket list. Spend a long day building sandcastles on Oak Street Beach, hit up the museums you've missed, and enjoy dinner al fresco with a scenic view. While you're at it, why not run away and join the circus? Or hang out with your animal pals from Madagascar... wait—what?!

Here are two whimsical, family-friendly shows you won't want to miss this summer in Chicago: Cirque du Soleil's Luzia and Chicago Shakespeare Theater's Madagascar – A Musical Adventure.

A trip to Navy Pier always promises a day of fun; but this summer, Chicago's No.1 tourist attraction ups the ante with a brand-new, 13-acre green outdoor space that's packed with amazing (and free!) programming. Polk Bros Park will now serve as the Pier’s gateway and the city’s unofficial front yard. Two performance and picnic-friendly lawns, located at the south end of the park, will offer free arts and cultural programming throughout the summer and beyond.

Happy weekend, Chicago! I hope the Taste didn't keep you too full, because there are a handful of events this weekend ready to fill your belly. There are plenty of things to do in Chicago this weekend, whether you're looking for a craft brew festival, a BBQ feast, a nationally acclaimed music festival, family friendly entertainment, or a special birthday celebration for our very own Navy Pier. Don't forget to check out our July festivals list so you don't miss anything. And if you're a big planner, we also have our August schedule ready!