31 of the Best Things to Do in Chicago This October

As the leaves change and the weather turns crisp, Chicago turns into the quintessential Midwestern town with enough pumpkin, apple pie, and craft beer to carry you into November. And for those who are not into the pumpkin spice hype, October is also a month of creativity and consciousness with events such as Chicago Ideas Week and the Chicago Humanities Festival.


Oct. 3 to Nov. 3: Jack’s Pumpkin Pop-Up

With a corn maze, carnival games, pumpkin carving, and three full-service bars, Jack’s Pumpkin Pop-Up has pumpkin fun for all ages. The entire pop-up is outdoors, and visitors must purchase tickets beforehand. 1465 N. Elston Ave., Chicago

Oct. 5: Chicago Rare and Wild Beer Fest

Hosted at the Field Museum, this second annual event will feature more than 60 breweries pouring their rare, barrel-aged, funky, sour, and one-of-a-kind brews during a beer fest for yeast’s biggest fans. 1400 S. Lake Shore Drive, Chicago

Oct. 5-6: Lincoln Square Ravenswood Apple Fest

Join in this Lincoln Square community tradition for all things apple. Enjoy candy apples, apple pie, apple cider, and more from local vendors, as well as live music and entertainment for kids. The perfect way to celebrate fall as a family! Lincoln Avenue between Lawrence and Eastwood, Chicago 

Oct. 7: Pints for Pets

Held in the Lagunitas Taproom, join the Anti-Cruelty Society in a night of animal trivia and pints to raise money for animals in need. Have a drink for a purpose! 2607 W. 17th St., Chicago

Oct. 11-13: Highwood Pumpkin Fest

Highwood Pumpkin Fest
Photo by Rick Roshto.

Come kick off the fall season at the Highwood Pumpkin Fest, benefiting the Make-A-Wish Foundation. Carve and light pumpkins, listen to live music, do some early trick or treating, drink hot apple cider, and more. 17 Highwood Ave., Highwood

Oct. 12: Bacon and Beer Classic

For the fifth year, the Bacon and Beer Classic will bring together over 100 craft beers from local breweries and endless bacon-inspired dishes, for a weekend that is sure to leave you full. There will also be music, games, and giveaways — and you won’t want to miss the Hormel Bacon Eating Contest. Soldier Field, 1410 S. Museum Campus Drive, Chicago

Oct. 12-17: Chicago Ideas Week

This week-long festival features, well, ideas from a variety of thinkers. Presenting more than 200 speakers and innovators speaking on a variety of topics, from leadership and life’s lessons, to science and technology, to issues of the day and insights in entertainment, Chicago Ideas Week is a chance to expand your normal consciousness. Various

Oct. 12-27: Boo! at the Zoo

Brookfield Zoo's Boo! at the Zoo
Guests can dress up in their favorite Halloween attire and show it off in Brookfield Zoo’s Costume Parade during its annual Boo! at the Zoo. (Photo courtesy of Chicago Zoological Society.)

Join Brookfield Zoo for this year’s Boo! At the Zoo. With candy stations, a corn maze, giant pumpkin carving demos, and more, this event has something for everyone. 8400 31st St., Brookfield

Oct. 16-20, 23-27: Night of 1,000 Jack-o’-Lanterns

Chicago Botanic Garden Night of 1,000 Jack-o'-Lanterns
Photo courtesy of Chicago Botanic Garden.

More than 1,000 jack o’ lanterns light up Chicago Botanic Garden for this unforgettable night featuring hand-carved, intricately designed pumpkins. Artists from the New York-based company RISE of the Jack O’Lanterns spend up to 15 hours on a single pumpkin. The event also features seasonal fare and spiked cider and ale. 1000 Lake Cook Road, Glencoe

Oct. 18: Fleurotica

Don’t miss the flowery fashion event of the season, hosted by Garfield Park Conservatory. You’ll want a front row seat so you can take in the exquisite clothes made entirely from plants, flowers, and natural materials, created by some of Chicago’s best floral designers, fashion designers, landscape artists, and students. Proceeds from the fashion show directly benefit the Garfield Park Conservatory Alliance. 300 N. Central Park Ave., Chicago

Oct. 19: Susan Orlean

The Wilmette Public Library will sponsor this discussion with New York Times bestselling author of “The Library Book,” Susan Orlean. Wilmette Junior High School, 620 Locust Road, Wilmette

Oct. 19: Cider and Ale Festival

Morton Arboretum Cider and Ale Festival
Photo courtesy of The Morton Arboretum.

What could be better than sipping on some brews while surrounded by nature? Enjoy an afternoon of ciders and ales at The Morton Arboretum, and don’t forget your lawn chair! 41 Illinois Route 43, Lisle

Oct. 19: Arts in the Dark

An evening parade that celebrates Halloween as an “Artist’s Holiday,” Arts in the Dark draws together institutions like The Art Institute of Chicago and Lookingglass Theatre Company and programs like After School Matters for a night of magic and creativity. Expect floats, puppets, and one-of-a-kind performances set amongst an October night in Chicago. State Street moving south from Lake to Van Buren, Chicago

Oct. 19-20: Open House Chicago

Step inside some of the most architecturally spectacular buildings in Chicago during Open House. This is a free public festival that offers behind-the-scenes access to more than 250 buildings across the Chicago area, including private offices, businesses, and theaters. Various

Oct. 26 to Nov. 10: Chicago Humanities Festival

It’s the 30th year of the Chicago Humanities Festival, and this promises to be just as thought-provoking as the years before. You’ll hear from your favorite artists, activists, journalists, policy makers, and many others. Some well-known names include George R.R. Martin, Rachel Maddow, and Julia Louis-Dreyfus. Various

Through Nov. 2: Pier Pumpkin Lights

Pier Pumpkin Lights at Navy Pier
Photo courtesy of Navy Pier.

Explore pumpkin-themed pop-ups and fall deals at Navy Pier’s first-ever Pier Pumpkin Lights. All month long, visitors will be able to celebrate fall with jack-o’-lantern towers and light displays. 600 E. Grand Ave., Chicago


Oct. 18: Stars, Stories, and S’mores

Head out to Erickson Woods and look through telescopes into the great beyond — and enjoy cool stories and tasty treats. This fun and free event from Adler Planetarium is the perfect opportunity to spark the interest of a budding astronomer. 1651 Willow Road, Winnetka

Oct. 20 to Jan. 26: Andy Warhol—From A to B and Back Again

Experience the wild and wonderful world of Warhol at The Art Institute of Chicago. This major retrospective features more than 350 works by the artist, including soup cans, celebrity portraits, electric chairs, album covers, and more. Hot tip: Members can preview the exhibition early, Oct. 17-19. 111 S. Michigan Ave., Chicago


Oct. 3 to Nov. 22: Latino Music Festival

Chicago Latino Music Festival — Kaia String Quartet
Kaia String Quartet (Photo courtesy of The Silverman Group, Inc.)

Don’t miss Chicago’s only Latin classical music festival. See performers from both Latin America and Spain, from the colonial period to the 21st century. Various

Oct. 5: Fields Jam

Listen to five Chicago-area bands and enjoy food and drink during this fundraiser for the Winnetka Youth Organization. Fields Chrysler Jeep Dodge RAM Glenview, 2800 Patriot Blvd., Glenview

Oct. 11: Hugh Jackman

See the Academy Award nominee and Golden Globe and Tony Award winner perform songs from “Les Misérables” and “The Greatest Showman” accompanied by a live orchestra with special guest Keala Settle. United Center, 1901 W. Madison St., Chicago

Oct. 14: The Galaxy’s Greatest Hits!

Join the Melbourne Symphony Orchestra for a one-night special event celebrating the moon landing. The concert will feature popular works from “2001: A Space Odyssey,” “Star Trek,” “E.T.,” and “Star Wars.” Symphony Center, 220 S. Michigan Ave., Chicago

Oct. 30: Postmodern Jukebox

Postmodern Jukebox features a rotating cast of musicians who play popular music from today in a variety of vintage styles. Intrigued? Join them on their “Welcome to the Twenties 2.0 Tour,” and find out what they’re all about. North Shore Center for the Performing Arts, 9501 Skokie Blvd., Skokie

Oct. 31 to Nov. 1: Disney in Concert: Tim Burton’s “The Nightmare Before Christmas”

"The Nightmare Before Christmas" at Auditorium Theatre
Photo by Kelly A. Swift.

The Chicago Philharmonic Orchestra is here to make Tim Burton’s beloved Halloween/Christmas mashup film “The Nightmare Before Christmas” even more magical. Catch their live-to-film performance of this modern classic starring Jack Skellington and the residents of Halloweentown, plus enjoy trick-or-treating and a costume contest before the show. Auditorium Theatre, 50 E. Ida B. Wells Drive, Chicago


Oct. 16-27: The Joffrey Ballet’s “Jane Eyre”

The Joffrey Ballet's "Jane Eyre"
Joseph Taylor as Mr Rochester and Hannah Bateman as Jane in “Jane Eyre.” (Photo by Emma Kauldhar.)

This balletic adaptation of Bronte’s groundbreaking novel will have you falling in love all over again. The gorgeous Victorian tale was practically begging to be set to a romantic score with vivid choreography that brings the entire cast of characters to life. Auditorium Theatre, 50 E. Ida B. Wells Drive, Chicago

Media Sponsorships

Better is a proud media sponsor of these events:

Oct. 11: Connections for the Homeless — INSPIRE

Dr. Jennifer Eberhardt, a Stanford University professor and author of “Biased: Uncovering the Hidden Prejudice That Shapes What We See, Think, and Do,” will serve as keynote speaker at Connections’ annual fall luncheon. The Woman’s Club of Evanston, 1702 Chicago Ave., Evanston

Oct. 24: Children’s Place International — Place the Hope Celebration

The Place the Hope Campaign, which supports Children’s Place International’s partners in Africa and the Caribbean working to help children in extreme poverty, annually ends with this celebration. Architectural Artifacts, 4325 N. Ravenswood Ave., Chicago

Oct. 24: YMCA of Metropolitan Chicago — Recognition Dinner

This event supports the Y’s youth and family development programs. Morgan Manufacturing, 401 N. Morgan St., Chicago

Oct. 26: Alzheimer’s Association — Walk to End Alzheimer’s

Walk to support the work of the Alzheimer’s Association. Soldier Field, 1410 Museum Campus Drive, Chicago

Additional events Better is proud to support:

  • Oct. 5: Evanston Rebuilding Warehouse — Wrecking Ball, Jewish Reconstructionist Congregation, 303 Dodge Ave., Evanston
  • Oct. 12: The Harbour — Havana Nights, Mini Cooper of Glencoe, 2100 Frontage Road, Glencoe