Skip to main content

Things to do in Fall in Chicago 2021

With a host of activities on offer throughout the season in a pleasant climate, fall in Chicago is a great time to explore the city. With favorite American holidays such as Halloween and Thanksgiving alongside many other exciting festivals, it truly is a great season to be out and about in the Windy City.

Get Spooked

The highlight of fall for many is October 31st when ghost stories, creatively carved pumpkins, and outrageous costumes combine to create a fun and frightful night. In the lead-up to Halloween, there are many events in and around Chicago that will get you in the mood for the big celebration at the end of October. 

On Saturday 30th October, the Haunted Halloween Ball takes place at the Congress Plaza Hotel on Michigan Avenue. It is an event for adults (21+) and promises a surreal experience with partygoers encouraged to dress in their most crazy, bizarre, and risque outfits for the event. The best-dressed winners will take home prizes at this spooky event hosted in a ballroom that has been transformed into an abandoned hotel run by zombies, some of which are dressed as French maids serving you cocktails. So dance the night away at this ball that according to their website “combines elements of a lavish VIP nightclub and lounge experience, with the exclusiveness of a luxury hotel gala, and the terror and chills of a haunted house.” 

Another adults-only (21+) event is The Great Pumpkin Glow at Lincoln Park Zoo. The Pumpkin Glow encourages partygoers to dress up in their best Halloween costumes for the occasion. Activities include live music from DJ Marcus Carter, animal chats, free rides on the AT&T Endangered, a haunted trail, and a host of other fun games. 

If you want to do something more family-oriented then we suggest heading to a pumpkin patch to pick your very own pumpkin! Some of the best pumpkin patches near Chicago are only 30 miles from the city including Bengtson’s Pumpkin Farm and Odyssey Fun Farm which both have plenty of things to do and see on the farm and its surroundings. You can also find a pumpkin patch in the city by the Chicago Riverwalk at the Island Party Hut Fall Fest, but after 5 pm access is limited to people over the age of 21. The Island Party Hut also has various activities for all the family before then and shouldn’t be missed. 

Among the many visual delights that Halloween in Chicago has to offer, one of the best shows is at the Pier Pumpkin Lights at Navy Pier. It is a truly wonderful spectacle throughout October with approximately 1000 pumpkins carved, lit up, and spread out across Navy Pier – it’s a jack-o’lantern display you won’t forget! There are many other seasonal activities for all the family and visitors can also explore the many bars and restaurants in the area as well as taking advantage of many great family photo opportunities around the pier.

Get Arty

As well as the Halloween festivities, you will also find many other events taking place in Chicago this time of year. The Chicago International Film Festival is in its 57th year and runs from the 13th October to 24th October and, as the name suggests, it showcases cinema from around the world. The organizers boast that “this year’s Festival features screenings in theaters, at the drive-in, and streaming virtually to your home. We’re thrilled to screen over 80 films and more than 60 shorts films from around the world, ranging from heart-wrenching dramas to eye-opening documentaries to midnight shockers!”

Fall is also a great time to take a cruise along the Chicago River and gaze upon the brilliant architecture that Chicago has to offer. Be sure to check Chicago’s best 90-minute architecture boat tour from Tours and Boats. You will get to see Chicago from the water and learn about the city’s buildings and admire the extraordinary vistas while you cruise. 

A Walk In The Park

There’s always a plethora of activities to do in and around the parks of the city. Fall is an amazing time of year to take a stroll in Grant Park or Lincoln Park as you enjoy the sound of leaves crunching underfoot. Grant Park is especially popular as it is also home to various museums including the Art Institute of Chicago and the Field Museum. Also in the area is the Buckingham Memorial Fountain, which is a sought-after landmark to snap photos at with its impressive water display giving you a perfect backdrop for your shots. 

You’ll find plenty of fallen red and gold leaves in Lincoln Park which also houses the aforementioned Lincoln Park Zoo as well as the Lincoln Park Conservatory. However, for many, Chicago Botanic Garden steals the show with its incredible displays of fall color and has over 2 million plants in its landscaped gardens. Non-members must pre-register for timed entry as this is a popular spot with the unique chance to see a variety of trees with changing leaf colors.

Things To Do On The Chicago Riverwalk Previous Article