30 of the Best Things to Do in Chicago This September

A new season is here, and with it comes a variety of can’t-miss events, including Kohl Children’s Museum’s Fall Family Festival, Chicago Bourbon & Barbecue Festival, the American Craft Exposition, Chicago Gourmet, and World Dumpling Fest.


Sept. 8: Fall Family Festival

Say hello to fall at Kohl Children’s Museum with kiddie train rides, a petting farm, wagon rides, hair styling and coloring with KidSnips, an apple cider press that kids can use, and more. 2100 Patriot Blvd., Glenview

Sept. 8: 2019 Evanston Streets Alive & Green Living Festival

Evanston Streets Alive and Green Living Festival
Photo courtesy of the Evanston Environmental Association.

Main Street in Evanston becomes a public park where you can walk, bike, and play for this one day. Local businesses and organizations also share their best green products and services. Main Street, Evanston

Sept. 8: Mushroom Hikes & Bites

Go on a guided trail hike through The Grove and learn about mushrooms before dining on some mushroom snacks. 1421 Milwaukee Ave., Glenview

Sept. 14-15: Chicago Bourbon & Barbecue Festival

Head out to Roscoe Village for a weekend of bourbon tastings, barbecue, and live music. 2000 W. Roscoe St., Chicago

Sept. 20-22: American Craft Exposition

The North Shore Auxiliary is hosting its 35th American Craft Exposition, featuring emerging and entrenched artists and a variety of products, from basketry to leather and jewelry, at Chicago Botanic Garden. Proceeds go to improve mental health resources at NorthShore University HealthSystem. 1000 Lake Cook Road, Glencoe

Sept. 21-22: Lakeview Taco Fest

Enjoy the fall weather and as many tacos as your heart desires at the Lakeview Taco Fest. Sponsored by Sam Adams (because, obviously, you need a beer with your taco), this fun weekend event will feature tons of award-winning tacos from all over the city. 3500 N. Southport Ave., Chicago

Sept. 24-29: Chicago Gourmet

Chicago Gourmet
Photo by Neil John Burger.

Sponsored by Bon Appetit, the Chicago Gourmet festival is your opportunity to become part of the rarified crowd of high-powered foodies. Watch celebrity chefs cook their favorite dishes as they answer questions and take selfies, or head to the Great Lawn, where you can sample food, wine, spirits, and beer. Keep an eye out for stars! Millennium Park, 201 E. Randolph St., Chicago

Sept. 26-29: Plein Air Painting Festival

Watch more than 50 artists from around the Midwest paint throughout Northbrook during this festival, now in its third year. Northbrook

Sept. 27-29: Monster Jam Triple Threat Series

Monster Jam Triple Threat Series
Photo courtesy of Feld Entertainment.

Do you want to see giant Monster Trucks race around a dirt track and soar through the air? Of course you do. Watch racing and freestyle events that will leave you on the edge of your seat. Allstate Arena, 6920 N. Mannheim Road, Rosemont

Sept. 28: Walk a Mile in Her Shoes

The Northwest Center Against Sexual Assault is hosting its 6th Annual Walk a Mile in Her Shoes event to create awareness of the millions of women who are subjected to sexual violence every year. Funds will go to Northwest CASA, which provides support to those affected by sexual assault and abuse. Arrington Lakefront Lagoon Shelter, 1631 Sheridan Road, Evanston

Sept. 28-29: Harvest Weekend

Chicago Botanic Garden Harvest Weekend
Photo courtesy of Chicago Botanic Garden.

Learn about preserving and storing produce from your garden or most recent trip to the farmers market during this weekend-long event that also features shopping, kids activities, and a cookbook swap. Chicago Botanic Garden, 1000 Lake Cook Road, Glencoe

Sept. 29: World Dumpling Fest

Yes, you read that right: an entire festival dedicated to dumplings, those tiny pockets of deliciousness adored the world over. Taste dumplings from around the world and enjoy live music from the World Music Festival at Navy Pier. 600 E. Grand Ave., Chicago

Sept. 29: Evanston Oktoberfest

Back for its fifth year, this fall fest features live music, traditional German dancers, a stein holding contest, tricycle racing, and more. Plus, sample from more than 40 craft beers and hard ciders. University Place and Oak Avenue, Evanston


Opens Sept. 6: The Way the Mystic Sees

Weinberg/Newton Gallery: The Way the Mystic Sees
Christopher Meerdo, Eigengrau, 2019 archival digital prints, dichroic film, 48×48 in (Photo courtesy of Carol Fox and Associates.)

Weinberg/Newton Gallery presents this exhibit that “surveys contemporary perspectives and historical approaches to technology and surveillance” in collaboration with Human Rights Watch. 688 N. Milwaukee Ave., Chicago

Sept. 7: Flora, Fauna & Fascination Opening Reception

Ice House Gallery’s newest main show includes pieces inspired by life and nature from more than 40 local artists. Celebrate the show’s opening with refreshments and live music. 609 South Blvd., Evanston


Opens Sept. 21: Pop América

Experience the world of pop art through the lens of artists from North, Central, and South America, the United States, and the Caribbean. Enjoy the explosive and colorful style through nearly 100 artworks that will help reframe an entire hemisphere’s worth of art. Block Museum of Art, 40 Arts Circle Drive, Evanston

Opens Sept. 22: Memory Unearthed

This photojournalistic exhibit offers a rare look inside the Lodz Ghetto between 1940 and 1944. Jewish photojournalist Henryk Ross trained his lens on daily life to recount a moving and memorable narrative that includes physical artifacts from Ross’ own life. Illinois Holocaust Museum & Education Center, 9603 Woods Drive, Skokie

Ongoing: Nature Cat: Backyard and Beyond

Nature Cat exhibit at Kohl Children's Museum
Photo courtesy of Kohl Children’s Museum.

Tally Ho! Join PBS Kids’ animated hero Nature Cat and his friends as they explore the marsh, the cave, and the forest while learning important lessons about the great outdoors! Exhibit created by Kohl Children’s Museum in partnership with WTTW Chicago and Spiffy Pictures. Kohl Children’s Museum, 2100 Patriot Blvd., Glenview

Ongoing: Fantastic Bug Encounters

Fantastic Bug Encounters at Field Museum, Chicago
Photo © Te Papa 2016

Nature’s tiniest creatures are some of the most important — come find out why these creepy crawlies make the world go ‘round. Observe bugs’ special skills, see specimens, and even hold some live ones! Obviously not for those afraid of spiders. Field Museum, 1400 S. Lake Shore Drive, Chicago


Sept. 6: Stars of Lyric Opera at Millennium Park

Enjoy the best of the Lyric Opera of Chicago for free during this outdoor concert. Pack a picnic and bring a blanket or lawn chairs to complete the experience. 201 E. Randolph St., Chicago

Sept. 8: Kesha

Ravinia Festival
Photo courtesy of Ravinia Festival.

Kesha is performing for the first time at Ravinia this month, and you can make the most of the evening with a Girls Night Out package that includes dinner, service staff, dedicated lawn space, and a gift for each member of your group. 418 Sheridan Road, Highland Park

Sept. 11: Lucy Roche

The daughter of folk queen Suzzy Roche (and musician Loudon Wainwright III) is a folk rocker in her own right. Catch her at SPACE in an intimate setting. 1245 Chicago Ave., Evanston


Opens Sept. 6: Tiny Beautiful Things

Tiny Beautiful Things at Victory Gardens Theater
Janet Ulrich Brooks in “Tiny Beautiful Things” (Photo by Todd Rosenthal.)

Making its Chicago premiere, this play is based on the book by Cheryl Strayed and was adapted for the stage by Nia Vardalos. Victory Gardens Theater, 2433 N. Lincoln Ave., Chicago

Opens Sept. 26: Murder on the Nile

Agatha Christie fans can’t miss this theatrical adaptation of “Murder on the Nile” at Oil Lamp Theater. It has a romantic honeymoon voyage turned disastrous, conspiracies, a lush setting, and, obviously, murder. 1725 Glenview Road, Glenview

Opens Sept. 28: The Barber of Seville

Rossini’s classic tale of a marriage gone awry is back at the Lyric Opera of Chicago. One of the most beloved operatic comedies of all time, watch as Figaro, the crafty and hysterical barber of Seville, wreaks havoc as two men attempt to win the fair Rosina’s hand. 20 N. Wacker Drive, Chicago

Through Jan. 5: Hamilton

If you still haven’t seen “Hamilton,” don’t worry — there’s still time to jam out to Lin Manuel-Miranda’s runaway hit. Make sure to snag tickets so you can watch America’s history unfold to some of the catchiest Broadway tunes in recent memory. See it at the CIBC Theatre downtown before it leaves Chicago. 18 W. Monroe St., Chicago

Media Sponsorships

Better is a proud media sponsor of these events:

Sept. 15: Selah Freedom – Rock the Boat Against Sex Trafficking

Selah Freedom, a Philanthropy Award winner working to end sex trafficking, will host an afternoon on the Spirit of Chicago. Support this organization’s work as you enjoy live music, food, an open bar, live and silent auctions, and more. Board at Navy Pier, 600 E. Grand Ave., Chicago

Sept. 26: The People’s Music School – South Side Expansion Launch

Join this Philanthropy Award winner as they announce a major expansion of pilot programs on the South Side. TPMS provides free music programs to underserved youth across Chicago. Bronzeville Classical School, 8 W. Root St., Chicago

Sept. 29, Oct. 6: JDRF Illinois – One Walk

Walk to support JDRF’s work to find a cure for Type 1 diabetes. Walks will take place in Chicago and Libertyville on Sept. 29 and in Schaumburg, Warrenville, and Orland Park on Oct. 6.

Additional event Better is proud to support: