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30+ Best Things To Do This Fall In & Around Chicago

30+ Best Things To Do This Fall In & Around Chicago

30+ Best Things To Do This Fall In & Around Chicago-chicago bean cloud gate

After a trying 2020 into the better half of 2021 that saw  some of us cautious on covid mostly cooped up at home venturing out for essential things and outdoor walks, really not much in the fun department its nice to get back outside and do things that were normal to many of us pre-covid. After summer, fall is my favorite season because you get a colorful landscape as the leaves turn, the weather chills but still lucky enough to get some very warm and sunny days and its still nice enough to get outside and do things; Fall is technically from September 22 until December 21. With that in mind, we’ve scoured for all the things happening in Chicago, and boy there a lot but we’ve curated a list of over 30 things that we think you our SociaLifeChicago readers will enjoy. Some are free, some are virtual, some hybrid, regardless of what you pick we hope it will entertain, inform or educate you. Please scroll down for all the details, if you do end up going to one or many of these, do tag us when you take your social media pics. Have fun and please continue to practice safety measures.


Lincoln Square Apple Fest

DATE: Saturday October 2 & Sunday October 3
TIME: 9am-6pm
COST: Free to attend

LOCATION: Lincoln Avenue between Lawrence and Wilson
INFO: A long standing tradition in Lincoln Square, bringing city dwellers and visitors alike together to usher in the beginning of autumn. The Lincoln Square Ravenswood Chamber of Commerce’s 34th Annual Apple Fest is back with over 50 vendors, entertainment, a menu of ciders and apple inspired dishes and so much more! Money raised from apple fest event supports beautification projects in Lincoln Square Ravenswood, as well as contributes financially to several community non-profits each year. Click here for more info.


StarChefs Rising Stars Restaurant Week

StarChefs magazine is celebrating the city of Chicago’s most talented up-and-coming food and beverage professionals with a restaurant week promotion from Tuesday, September 21 — Tuesday, October 5, for their newest class of 24 Chicago Rising Stars. Rising Stars Restaurant Week is a two-week promotion showcasing the 2021 Chicago Rising Stars restaurants, dishes, pastries, wine pairings, and cocktails that best represents the future of American dining. Chicago Rising Stars Restaurant Week menu includes dishes from these restaurants: Dear Margaret, Virtue Restaurant, Lao Peng You, Smyth, North Pond, Monteverde Restaurant & Pastificio plus pastries, wine paired meals and more. Click here for more info.

Chicago Humanities Festival

The Chicago Humanities Festival has an exciting lineup of in-person and virtual events for their fall session and it couldn’t come at a better time as I slowly make my way outside to more in-person events held indoors. Some of the highlights include a conversation between brothers, Academy award winning director Ron and Clint Howard with Chaz Ebert; Younger‘s Sutton Foster shares all the moments where crafting saved her life; Pulitzer Prize-winning journalist Nikole Hannah-Jones of the 1619 Project is on the lineup, a gala celebration honoring Jeanne Gang with the Vision Award and so many more wide ranging events from September 25–December 9. Tickets and full event calendar can be found here. TICKETS@CHICAGOHUMANITIES.ORG

57th Chicago International Film Festival

North America’s longest-running competitive film festival, is coming in hot for its 57th year. The Chicago International Film Festival will take place from Wednesday October 13 through Sunday October 24 with 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. Dune, Any Given Day, Love, Charlie: The Rise and Fall of Chef Charlie Trotter, Oscar Micheaux – The Superhero of Black Filmmaking, The French Dispatch, The Harder They Fall, The Last Duel, Julia, King Richard, Shorts 7: Illuminating Gazes (Black Perspectives) are some of the films on this year’s list that look great to watch. Screenings will be held in theaters, at the drive-in, and streaming virtually to your home so you have many opportunities to catch a flick or 5. Click here for passes and tickets and more info.

Neon Light Museum Pop-Up

When I think of neon, my mind immediately races to Las Vegas and then artist Tracey Emin. Not sure how they both relate but I do know neon lights have come such a long way from the ubiquitous OPEN signs and its been having such a moment lately that does not look to be fading off. The Neon light museum pop-up located 325 W. Huron in what used to house Nacional 27, features sculptures and interactive light shows both kitschy and nostalgic, ironic and literal. Tickets cost $25 and as of now, its set to run through Oct. 31.

Gene Siskel Film Center 2021 Black Harvest Film Festival

The pandemic ravaged 2020 had forced a somewhat scaled back, hybrid form of the long running Black Harvest Film Festival presented by the Gene Siskel Film Center at the School of the Art Institute Chicago. This year’s Black Harvest Film Festival running from Friday November 5 through Thursday December 2, though will be a CELEBRATION! The inspiring documentary “Dionne Warwick: Don’t Make Me Over” chronicling the iconic singer’s fascinating six-decade career in both music and Black and LGBTQ activism is set to kick off the festival with other programming including 25 feature narrative and documentaries, six short film programs and tributes to both Gordon Parks and Melvin Van Peebles who recently passed away, and more. Black Harvest Film Festival is Chicago’s annual showcase for films that celebrate, explore and share the Black, African American and African Diaspora experience. The Festival curates both short and feature length films, proudly presenting influential auteurs and emerging filmmakers of color side by side. Festival passes, tickets and more info can be found here.

Poetry Foundation 2021 Pegasus Awards Ceremony

The Poetry Foundation’s celebration of contemporary poets in living lineage with one another will be a special one this year. Not only will the 2021 Pegasus Awards and the Ruth Lilly & Dorothy Sargent Rosenberg Poetry Fellowships Winners be honored together at one ceremony, a first in many years, the awards ceremony is also to be held virtually on October 21 so many can be a part of it from all over the country, the world. Chicago’s Patricia Smith will receive the Ruth Lilly Poetry Prize with an award of $100,000. Susan Briante will recive the Pegasus award for poetry criticism. Natasha Rao, Noor Hindi, Bryan Byrdlong, Steven Espada Dawson, and Simon Shieh are the 2021 Ruth Lilly & Dorothy Sargent Rosenberg Poetry Fellows.

Lightscape at Chicago Botanic Garden

You won’t want to hear how amazing the Lightscape experience was from a friend or simply vibe to it via a video from someone you follow on social media. It sold out the first 2 years since its debut at the Chicago Botanic Garden and we expect it to be another sold out year. Lightscape will run from November 12 through January 2 on select dates. Bask in the glow of thousands of twinkling lights in favorites like the Winter Cathedral and new delights you’ve never seen before. Ticket prices vary based on the date you choose to attend. Chicago Botanic Garden is located at 1000 Lake Cook Road Glencoe, IL 60022; (847) 835-5440.

Museum of Science and Industry Marvel: Universe of Super Heroes

Missing your summer dose of Marvel Universe blockbuster? Fall into this blockbuster museum exhibit around the Marvel Universe right here in Chicago. The Museum of Science and Industry (5700 S Lake Shore Drive Chicago, IL 60637) is presenting the largest exhibition celebrating the Marvel Universe history with more than 300 artifacts including original comic book pages from the first Marvel comic published in 1939, sculptures, interactive displays, and costumes and props from Marvel’s blockbuster films. Guests will have the chance to “examine the origins of iconic characters such as Spider-Man, Black Panther, Hulk, and Captain Marvel and see how they have evolved alongside society over the past 80 years, making these characters a pop culture mainstay.” A separate, timed-entry ticket must be added to your order after you select your visit date and number of guests. This runs through October 24.

Andrea Bowers at Museum of Contemporary Art Chicago

The Museum of Contemporary Art Chicago (MCA) will present the first major retrospective for Los Angeles based artist Andrea Bowers from November 20, 2021 – March 26, 2022 housed in the museum’s Griffin Galleries of Contemporary Art on fourth floor. This exhibition, co-produced by former MCA Chief Curator Michael Darling with Hammer Museum Chief Curator Connie Butler is very apt for the times. Bowers who focuses on the people leading and participating in public discourse as a chronicler of contemporary history, documents activism as it unfolds and collects research on the frontlines of protest. Her artwork touches on issues like immigration, labor, abortion rights, LGBTQ activism and transgender advocacy,feminist causes. This exhibition also ushers a new model being trialed MCA by working with Chicago-based organizations A Long Walk Home and Centro Sin Fronteras to present their work in dedicated galleries in the exhibition and in public programs. The artist herself Andrea Bowers will kickoff the opening of the exhibition at an in-person event in a conversation with exhibition curators Michael Darling and Connie Butler. The program will also be streamed on Facebook Live.

Chicago Council on Global Affairs Presents Prioritizing a Gender Inclusive Economic Recovery

A virtual panel discussion that includes the first woman and the first African to serve as director-general of the World Trade Organization (WTO) Dr. Ngozi Okonjo-Iweala who will deliver the spotlight remarks, sign us up please. The Chicago Council on Global Affairs on Wednesday Oct 13 from 10:00 – 11:15 am CST, will host a discussion on “what infrastructure, investments, and partnerships are necessary to catalyze action and fuel a globally inclusive economic recovery?” Registration is FREE.

Immersive Van Gogh Exhibit Chicago

Pieces of art hanging in a gallery or a vaunted museum this exhibit is not but its one-of-a-kind way of showing the audience a vast portfolio of works by the illustrious Vincent Van Gogh might have you saying, “why didn’t I think of that?!” Immersive Van Gogh Chicago displays some of Van Gogh’s iconic works (more than 400 Van Gogh paintings) via projections in the Lighthouse ArtSpace inside the historic Germania building (108 W. Germania Pl, Chicago 60011) in the Gold Coast. The experience ticket prices start at $39.99 and it runs through Thursday Nov. 18.


Conversations at the Edge at Siskel Film Center

The School of the Art Instute of Chicago’s Department of Film, Video, New Media, and Animation in collaboration with the Gene Siskel Film Center and the Video Data Bank presents this dynamic weekly series of screenings, performances, and talks by groundbreaking media artists. Each week features a different artist through November 4. The theatrical screenings are held at the Gene Siskel Film Center (164 N. State Street) and virtual screenings can be seen via the Gene Siskel Film Center Virtual Cinema. 312-846-2600

Night of 1,000 Jack-o’-Lanterns

More than 1,000 hand-carved pumpkins—some as large as 150 pounds—will light up the night at the Chicago Botanic Garden’s Halloween event from October 13 – 17 and 20 – 24. Guests in attendance will see costumed entertainers, live carving demos, along with seasonal light fare and drinks for purchase. Timed Tickets are $16 for adults (Tickets purchased the day of the event are an additional $2 per ticket). If you’re not a member, you must purchase parking online before your visit. Parking will not be sold on-site.

Dusable Museum Kara Walker Exhibition

Kara Walker: Presenting Negro Scenes Drawn Upon My Passage through the South and Reconfigured for the Benefit of Enlightened Audiences Wherever Such May Be Found, By Myself, Missus K.E.B. Walker, Colored is a must see exhibition. The exhibit which runs through October 16,  is an initiative of Toward Common Cause, which features new and recontextualized work by 29 visual artists who have been named MacArthur Fellows; Walker was named a MacArthur Fellow for 1997. The installation on view, was first presented in 1997 at the nearby Renaissance Society is now making a historic return to Chicago’s South Side at the DuSable museum. Kara Walker: Presenting Negro Scenes Drawn Upon My Passage through the South and Reconfigured for the Benefit of Enlightened Audiences Wherever Such May Be Found, By Myself, Missus K.E.B. Walker, Colored is a collaboration between the Smart Museum of Art at the University of Chicago and the DuSable Museum of African American History. Tickets can be reserved online.

Pumpkin Lights Pop-Up at Navy Pier

Starting on Friday October 1 and lasting throughout the month, Navy Pier is being transformed into an experiential fall spectacle with nearly 1,000 pumpkins for Pier Pumpkin Lights. Navy Pier has partnered with the eAtlas mobile adventure app to create a Pier Pumpkin Lights Scavenger Hunt. Guests can follow the clues in the eAtlas app and learn facts about the Pier, Chicago history, local ghost stories, and Lake Michigan shipwrecks while enjoying the Pier Pumpkin Lights installations and earning deals and discounts for specials at several on-site restaurant partners throughout the Pier and for the Centennial Wheel. Full details of all the activities plus other activations from Pier partners can he found here.

Chicago Athletic Hotel Skate Night at the Track

Skating on the CAA track is back just in time for fall fun. The Chicago Athletic Hotel welcomes guests back to Stagg Court for the two nights (Friday October 15 & Saturday October 16) of Skate Night at The Track in October. Guests can resave a two hour time block but in order to enter for the event, proof of vaccination or a negative Covid-19 PCR test result within 72 hours of the event will be required for entry. Skate rental is available on a first come, first served basis for $5.

Brushes With Cancer Benefit in the Midwest

Brushes with Cancer is a benefit fundraising program of Twist Out Cancer, that strategically matches artists with individuals touched by cancer (inspirations). Twist Out Cancer, an organization that provides psychosocial support to cancer survivors and their loved ones through creative arts programming will host the Midwest region benefit on Sunday November 14 both in-person and virtual. @proerties co-founder Thad Wong and his wife Emily Sachs Wong will be honored. The in-person portion of the celebration taking place at the Floating World Gallery is a culmination of the unique artworks created by the artists matched to an individual that’s been touched by cancer. Tickets for the virtual events starts at $75 and the in-person portion is only available to current program participants (Inspirations, Artists, and Mentors).

Black Ensemble Theater’s 37th Annual Gala

This year’s Black Ensemble Theater’s 37th Annual Gala “The Legacy Continues – Together We Are the Change: A Musical Celebration of Hope and Faith” is set to take place virtually this year on October 15 from 6:30-7:30pm. Actor/Singer Chester Gregory will serve as the events honorary National Chair. Registration to the B.E.T Gala is complimentary though donations are highly welcomed. Click here to register and donate.

Taste of Fulton Market

The hot hot on the real estate market and dining scene neighborhood Fulton Market with many of our fave restaurants and drink spots will host its first Taste of Fulton Market celebrating “the past and present of Chicago’s hottest neighborhood” at Morgan’s on Fulton (950 West Fulton Street Chicago 60607) on November 4. Lineup of events includes exhibition featuring historical photography and primary source materials from Fulton Market’s past century; charity auction and raffle. Tickets priced at $55, from 5-9pm.

Lincoln Park Zoo Adults Night Out: The Great Pumpkin Glow

No kids allowed on this night, sorry. Lincoln Park Zoo’s Adults Night Out: The Great Pumpkin Glow will take place on Thursday October 28 and on this night its all treats and maybe a lil tricking as you stroll amongst the wildlife with a beer, cider, hard seltzer or glass of wine (cash bar) in hand. Guests will enjoy unique animal chats, educational entertainment, a live DJ, and multiple bars throughout the zoo at this after-hours event. Costumes are encouraged and super early bird discounted tickets start at $15.

Young, Gifted, and Black at UIC

An art exhibit, showcasing works from different mediums by black artists, curated from the highly regarded private collection of Bernard I. Lumpkin and Carmine D. Boccuzzi, oh yes lets go! “Young, Gifted, and Black: The Lumpkin-Boccuzzi Family Collection of Contemporary Art,” at Gallery 400 (400 S. Peoria Street Chicago, IL 60607) at the University of Illinois Chicago is a cutting-edge exhibition of works by Black artists co-curated by writer and curator Antwaun Sargent,and artist Matt Wycoff. Some of the artists whose works will be on display as part of “Young, Gifted, and Black” are Chicagoan Kerry James Marshall; Chicago-born artists Caitlin Cherry, Rashid Johnson, and Chiffon Thomas; and artists pushing the boundaries of figurative painting, such as Jennifer Packer, Christina Quarles and Lynette Yiadom-Boakye, to name a few. The catalogue for Young, Gifted and Black can be purchased via Semicolon bookstore. The exhibit runs through Dec. 11.


Cider and Ale Festival

Morton Arboretum hosts a Cider and Ale Festival on Saturday October 23. Guests will enjoy 80+ beers, ciders, and meads from over 30 local breweries and cideries. Breathe in the fresh autumn air and stroll among the trees while you sip. VIP tickets are $65/members; $75 non-members; General Admission prices are $55 Members/$65 Guests. This is a 21+ event.

See Also


Chicago Children’s Choir’s Red Jacket Optional

Chicago Children’s Choir’s largest annual fundraiser Red Jacket Optional is back in-person following a year of virtual celebration in 2020. The event set to be held on Saturday October 16 at The Geraghty (2520 S. Hoyne Ave.) is co-chaired by Monica Carney, Renee & John Salomon, and Rahul Sekhar & Lauren Johnson Sekhar, and will honor local philanthropic leaders Mridu & Chandra Sekhar. Red Jacket Optional secures critical funds that deliver empowering music education programs to schools and neighborhoods for young people from every zip code in Chicago—regardless of socioeconomic circumstance. Red Jacket Optional 2021 will feature performances by select CCC ensembles alongside a slate of high profile artists that includes Grammy Award-winner Kurt Elling, Chicago native singer-songwriter Natalie Bergman, Eurovision’s Vasil Garvanliev, and acclaimed opera singer Jonathan Green with free livestream beginning at 8:30 p.m.


GROOMED x BLESSWELL Pop-up at Kimpton Gray Hotel Chicago

GRAMMY® Award-winning artist DJ Khaled is bringing his CBD-infused skincare GROOMED x BLESSWELL to Chicago for its first ever pop-up store at the Kimpton Gray Hotel (126 W. Monroe Street) from September 29 through October 23. Guests of the hotel and visitors will experience the keys to wellness by indulging in a range of offerings including cuts, shaves, and facials. Award-winning barber JC Tha Barber, alongside some of the best groomers in Chicago courtesy of the Anti Broke Barbers Club including resident Jesse Elite, providing their services and sharing tips and trends as it relates to the CBD-enhanced line. The full collection of BLESSWELL products, a brand co-founded by Chicago native Ryan Stender, will also be available to purchase on-site. Appointments will be available Wednesday through Friday from 2 p.m. to 9 p.m. and Saturday from 12 p.m. to 5 p.m.


Lynn Sage Breast Cancer Foundation Virtual Benefit

October is Breast Cancer Awareness month and to honor, celebrate and raise funds, the Lynn Sage Cancer Foundation will be hosting their annual Lynn Sage Breast Cancer Foundation benefit. This year’s event, set to be held virtually on Thursday October 21 hosted by Val Warner and Ryan Chiaverini with Keynote speaker, Glennon Doyle. Lynn Sage Breast Cancer foundation board member Dr. Kate Nash who is a breast cancer survivor will also be featured.

Chicago Public Library Foundation Awards

The Chicago Public Library and the Chicago Public Library Foundation on Tuesday, November 9 will present the Chicago Public Library Foundation Awards formerly known as the Carl Sandburg Literary Awards Dinner. Acclaimed New York Times bestselling author Amy Tan will receive the 2021 Carl Sandburg Literary Award, making her the first Asian American author to be presented with this honor. Artist and social innovator Theaster Gates will receive the Arts Award and actor, author, director, playwright and educator J. Nicole Brooks will receive the 21st Century Award.YoThis year the awards ceremony will also be held virtually, Legendary Chicago news anchor Bill Kurtis will host the event and NPR’s Scott Simon will lead an intimate conversation with Tan.

Union League Boys & Girls Clubs 44th Gala 

The Union League Boys & Girls Clubs, a foundation of the Union League Club of Chicago founded in 1919, which serves the after-school needs of over 15,000 youth from neighborhoods with the highest hardship index in Chicago is hosting a fundraising benefit gala. On November 6 at the private Union League Club of Chicago, Union League Boys & Girls Clubs will host Leaders in the Making Gala, its 44th annual benefit, at the Union League Club of Chicago (65 W. Jackson Blvd.). As organizations slowly start hosting in person events once again, it’s time to don your fave black-tie attire and enjoy an evening of cocktails, auctions, dinner, a program and paddle raise to honor the accomplishments of its youth membership, followed by dancing and dessert. Tickets start at $350/per person.

Día de los Muertos: Love Never Dies Ball

National Museum of Mexican Art’s Auxiliary Board cordially invites you to Día de los Muertos: Love Never Dies Ball on November 6, a special celebration that honors life and the spirits of los muertos. Indulge in delicious culinary treats from some of Chicago’s best restaurants; sip on specialty cocktails and craft beer; and dance the night away to live music by Esso Afrojam Funkbeat and DJ Mo Mami. Attire is Creative Cocktail. Tickets are $125/person in advance.

Frontera Farmer Foundation Dinner Like No Other 2021

Good food, good company for a good cause with a possible Rick Bayless sighting? Lets gooooo! The annual blowout dinner party benefitting the Frontera Farmer Foundation is back and set to take place Sunday, Oct. 17 at Frontera Grill and Topolobampo. This year, our chef team is reaching back into their childhood memories to create a once-in-a-lifetime menu, complete with expertly matched wine pairings and special cocktails. You can upgrade to VIP tickets and you’ll be treated to Rick Bayless’ test kitchen and cookbook library for a welcome cocktail from Spirits Director Julianna Arquilla, special bite from our kitchen and a private cooking demo from Rick.

Gene Siskel Film Center x Chicago International Film Festival

The Chicago International Film Festival (CIFF), North America’s longest-running competitive film festival, now in its 57th year will kick off on Wednesday October 13 and run through October 24. Streaming, drive-in and various theaters around the city including the Gene Siskel Film Center will be hosting select screenings. As part of their partnership with Chicago International Film Festival, the Film Center will be presenting a total of five films in their theaters. Siskel Film Center members get special discount rate for tickets.

Apparel Industry Board, Inc’s Rev Up Chicago 2021

 The Apparel Industry Board, Inc. (AIBI), an organization specifically dedicated to the needs of the sewn products industry here in our great city will host a hybrid of their annual RevUP Chicago event on Thursday October 21. The evening will feature Fashion Vignettes showcasing 10 emerging and established designers and their latest collections and the presentation of our AIFI Scholarships. AIBI will broadcast the event to a virtual audience for free, but will also be hosting a private watch party at Bentley Gold Coast for VIP ticket holders.

I|O Godfrey Rooftop Asylum Halloween Party

The I|O Godfrey at the Godfrey Hotel Chicago’s annual Halloween party is back in person and will be held on Saturday, October 30. The party is taking place on the 4th floor rooftop ONLYT this year. I|O will be decked out with nine haunted igloos – eight regular sized and one large – decorated in spooky décor. Each igloo will have a theme, such as Children of the Corn, creepy baby doll, torture, and more. I|O (127 W. Huron St.) will be decorated in a demented hospital/medical/asylum theme. A limited number of tables and general admission tickets are available. Periodic performances throughout the night will include fire performers, a contortionist, stilt walker, and more. All attendees must show proof of full vaccination, or a negative COVID-19 test from the previous three days and masks must be worn indoors at all times when not actively eating or drinking. This is a 21+ event.

Chicago Urban League Golden Fellowship weekend

For six decades, The Chicago Urban League’s Golden Fellowship Dinner has brought our partners and friends together to celebrate progress and raise additional support for our mission. On Friday November 5 and Saturday 6, we will again gather for a Golden Fellowship Weekend. Themed 60 Years and Onward: Meeting the Moment with the Movement, this two-day event will examine current issues that underscore why the Urban League movement is more important than ever and, of course, celebrate 60 years of fellowship with our partners, friends and supporters. Friday will host Golden Fellowship Exchange with the presentation of the Edwin C. “Bill” Berry Civil Rights Award to Attorney Benjamin Crump. Saturday guests in black tie attire will turn out at the Hyatt Regency Chicago for the 60th Annual Golden Fellowship Dinner with honorees including Northern Trust’s EVP and Head of Corporate Social Responsibility Connie Lindsey and United airlines President Brett J. Hart.

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