Activities & Events in Chicago: Set a Fun and Memorable Fall Calendar

Summer is almost ending, but it doesn’t mean the fun has to end or be put on hold until next summer! The fall is quite pleasant in many cities across the US, including Chicago. There are many upcoming events and activities in Chicago year-round. Continue reading to learn more about exciting concerts, exhibitions and festivals and to make the most of this fall in Chicago. 

➤ Experience Cool September Winds in Chicago

Traveling is a time to relax. If you are into boats and want to make your trip more enjoyable, consider putting your feet up and relaxing on a boat down the Chicago River. If you want a private experience, book a private luxury sailboat or a private pontoon. If you are feeling a little more independent, consider renting a Jet Ski on Lake Michigan.

➤Visit the Blockbuster Ear Taxi Festival 

September is the month of festivals in Chicago. Visit to find out about upcoming festivals this fall and to purchase tickets. The Ear Taxi Festival, held in early October is a multi-day celebration with many show options for lovers of experimental, improvised, and contemporary music. Here, you will get to attend everything from miniature operas to dance performances and artist workshops. Over 600 Chicago artists perform in over 100 venues in the Chicago area.

➤Shop Unique Art Pieces at Pilsen Art House 

If you are fond of classic jewels, artistic home decors, and handmade goods, Pilsen Art House hosts indoor and outdoor markets featuring a variety of artistic pieces.  

➤Go to One of the Many Art Exhibitions

It’s impossible to go back and experience the Classic Era in person. But what is possible in Chicago is to visit some of the Classic Era’s Art Exhibitions which are an important part of the city. Every weekend local’s, along with their kids, visit Art Exhibitions to see vintage paintings and frescoes. Tours are held in the exhibitions to give visitors a glimpse into what the Classic Era was like.  

In addition, Chicago welcomes millions of tourists each year to explore their famous museums showcasing ancient cultures, sculptures, and more. 

➤ Hit One of the City’s Comedy Clubs 

There are plenty of comedy shows in Chicago just waiting to make audiences laugh. Year round you can find top stand-up comedy shows across the city in various venues. You will see the famous comedians at Beats and Bits, Verified Laughs, The Nasty Show, and many other events. Make your trip memorable and full of laughter by booking a comedy show at

➤Ride Through the Town on a Bike

If you are seeking adventure, renting a bike to tour the city might be just what you are looking for. You can tour the city independently, or hire a bike tour guide and explore the city with an experienced local.  Lakefront trail is the city’s staple and shouldn’t be missed!  

➤See Chicago from the Willis Tower Skydeck

Take an elevator up to the 103rd floor of the Willis Tower Skydeck to get an amazing view of Chicago. This is not an activity for those who have agoraphobia but for those who enjoy heights and want the feeling of climbing a mountain or being on top of the world. You can get some instagrammable pics from the view on top!  

➤Dance the Night Away at One of Chicago’s Nightclubs

Chicago is filled with nightclubs. There is a nightclub for everyone. To experience a high-profile club, get yourself to Green Mill Cocktail Lounge. Do you love listening to house and electro beats? The Underground is an ideal destination. Visit to see upcoming events at nightclubs in Chicago.

Wrapping Up

Events and activities in Chicago for the fall and year-round are unlimited. For an upcoming live experience and one that is sure to be memorable visit our website and find out about famous festivals, concerts, comedy shows, and more.