10 events to visit in Chicago this Fall


Fall is a busy time in Chicago, with the city’s atmospheric Autumnal colours providing a scenic backdrop to a number of popular events that draw visitors from far and wide. Many of these event have a long and distinguished history, but none of them could be accused of resting on their laurels, with each edition presenting a fresh take featuring new performers, exhibits and programmes, all serving to ensure that originality prevails.

Street lights in Chicago wrapped in foliage (Photo: Brad Hagan via Flickr / CC BY 2.0)

If you’re planning a visit to Chicago this Fall and would like to attend one of the myriad of events taking place, we’ve helped you out by selecting 10 of the best events scheduled for Autumn 2020. You should note that due to ongoing restrictions, several of these events have gone partly or fully online this year, so be sure to check on the official websites for full details.

Open House Chicago

Cherished architecture festival Open House Chicago is back with a reimagined event for 2020. Hosted by the Chicago Architecture Center, the annual festival will now span 10 days and more than 20 of Chicago’s unique neighbourhoods, inviting visitors to explore a number of interesting buildings that are typically closed off to the public. This year’s event includes both online and outdoor events that combine to showcase the fascinating history, architecture, and culture of the city’s diverse districts.

LOCATION Venues across Chicago DATES 16-25 October

The entrance to one of the venues at a previous edition of Open House Chicago (Photo: Open House Chicago)

Reeling: The Chicago LGBTQ+ International Film Festival

This acclaimed festival, said to be the second-oldest LGBTQ+ film festival in the world, celebrates its 38th anniversary in 2020 with a new streaming virtual edition. Showing 32 features and 54 shorts from 21 countries, the event will offer home viewers access to new films not currently available on commercial streaming platforms. From dramas to comedies to international documentaries and short films, the festival offers something for every movie lover! And no film festival would be complete without Q&As, so this year Reeling will feature more interviews with filmmakers and other movie talent than ever before. Patrons can binge watch the entire festival with an all-access members passport.

LOCATION Online only for 2020 DATES 24 September – 4 October


A still from a movie screened at a previous edition of Reeling Festival (Photo: Reeling Festival)

Lincoln Square Ravenswood Apple Fest

In a normal year Apple Fest attracts over 35,000 apple-loving attendees to Lincoln Square to support local businesses and strengthen community ties. Alas, this year circumstances will deny them the chance to attend in such numbers, but fear not, as for 2020 the festival has been pulled, tweaked and refashioned into a smaller, but no less exciting celebration of all things pomme. The event will take place partly as an online market and partly in the form of a weekend-long, in-the-flesh Farmers Market featuring locally produced food, craft cider and artisan goods. All proceeds will go to participating businesses.

LOCATION Lincoln Square Ravenswood DATES 21 September – 3 October (Online Market) October 3-4 (Farmers Market)

Chicago Palestine Film Festival

Since its inaugural edition in 2002, the Chicago Palestine Film Festival has grown to become one of the most important events in the US for providing a platform for Palestinian filmmakers to showcase their talents. Organised in collaboration with the Gene Siskel Film Center of the School of the Art Institute of Chicago, the 19th edition of the festival takes place this year as a drive-in and online event, and promises to be as exciting as ever. Presenting a diverse mix of films, documentaries, dramas and comedies — in both long and short formats and all reflective of Palestinian culture and the unique vision of a number of gifted filmmakers – each Drive-in and online showing will include one feature and one short film.

LOCATION Pilsen’s ChiTown Futbol Drive-In, 2343 South Throop Street DATES 26 September – 16 October


A talk during the Chicago Palestine Film Festival (Photo: Chicago Palestine Film Festival)

Night of 1,000 Jack-o’-Lanterns

Come and marvel at more than 1,000 amazingly intricate hand-carved pumpkins at this hugely popular Halloween event in the picturesque surroundings of Chicago Botanic Garden. Some of the array of pumpkins on display are even LED-lit, helping them illuminate the night sky. In addition to the visual feast on offer, there are also seasonal drinks and snacks such as spiked cider and ale to help keep visitors warm and cosy and stave off those Autumnal breezes.

LOCATION Chicago Botanic Garden DATES 14-18 & 21-25 October

Night of 1,000 Jack-o’-Lanterns

Visitors admire a glowing lantern at the Night of 1,000 Jack-o’-Lanterns (Photo: Chicago Botanic Garden)

Chicago South Side Film Festival

A not-for-profit arts organisation, Chicago South Side Film Festival holds its first virtual edition this year, with a renewed focus on providing a platform for local South Side filmmakers while broadening diversifying and improving the quality of entertainment options for local residents Indeed, all films screened this year are made by filmmakers from the South Side or explore ideas and issues at the heart of the neighbourhood’s cultural and social life. As well as a wide number of movie screenings, there’ll also be a busy programme of online talks and panel discussions throughout the festival.

LOCATION Online only for 2020 DATES 27 September – 4 October

Chicago South Side Film Festival

Attendees at the Chicago South Side Film Festival pose for a photo (Photo: Chicago South Side Film Festival)

Adults Night Out: The Great Pumpkin Glow

Not every Halloween-themed event requires you to drag the kids along. Thanks to Lincoln Park Zoo, parents have the chance to indulge in some well-earned time without the little ones by attending an ‘adult nights out’ while leaving the kids at home (with a responsible adult, if their ages require it). The Great Pumpkin Glow welcomes liberated grown-ups enjoying some fleeting freedom to a unique after-hours experience featuring seasonal activities such as a corn maze, a pumpkin walk, a haunted trail, themed food, and heart-warming cocktails.

LOCATION Lincoln Park Zoo DATES 29 October

Music Box of Horrors

Usually taking place over 24-hours, this year the Music Box of Horrors will instead morph into a month-long marathon of spine-tingling movies. Taking place at Chicago’s drive-in theatre, the event will feature late-night screenings and double features throughout October, as well as specially curated content such as filmmaker Q&As. The scary screenings will range from classics like A Nightmare of Elm Street and Carrie through to lesser known flicks.

LOCATION ChiTown Movies Drive-In, 2343 South Throop Street DATES 1-31 October

Chicago Gourmet In-Person Dinner Series

Immerse yourself in Chicago’s rich and diverse culinary scene and enjoy a fun and intimate night out while supporting local Chicago restaurants by booking yourself onto this in-person dinner series. Many of Chicago’s most acclaimed restaurants are opening their doors for a one-of-a-kind dining experience, which invites hungry patrons to sample specially-devised tasting menus, meet distinguished chefs, discover wine and cocktail pairings, and plenty more.

LOCATION Venues across Chicago DATES 14-30 September

Chicago Gourmet In-Person Dinner Series

A delectable dish of the type served up during the Chicago Gourmet In-Person Dinner Series (Photo: Chicago Gourmet)

Septemberfest at Eataly

The fifth edition of Septemberfest returns with a significant twist this year, inviting the most beloved restaurants and eateries in Chicago to a virtual foodie extravaganza throughout the entire month of September. Those wanting to participate can order a cookery kit from an assortment of distinguished guest chefs to then concoct their own multi-course dining experience from the comfort of their home, then connect with the chefs and ask them questions on Instagram Live.

LOCATION Online only for 2020 DATES 1-30 September

By Paul Joseph