Weekend 101: 11 Things to Do Around Chicago Oct. 18-20

This weekend, get a behind-the-scenes look at some of Chicago’s most historic buildings, sample chocolate and wine, explore Chicago Botanic Garden while it’s decorated for Halloween, and more.

“Jane Eyre”

Oct. 16-27

Watch Charlotte Brontë’s novel come to life with choreography by Cathy Marston and music by Philip Feeney in this Chicago premiere from The Joffrey Ballet.

Night of 1,000 Jack-o’-Lanterns

Oct. 16-20, 23-27

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

This Chicago Botanic Garden event begins this weekend with more than 1,000 hand-carved pumpkins lighting the grounds. As you explore the garden, enjoy food and drinks available for purchase, watch live pumpkin carving, and more.

Chocolate, Wine & Spirits Expo

Oct. 18-19

Photo by Michele Blackwell on Unsplash.

Sample chocolate and other treats from more than 40 vendors, sample wine and spirits during a tasting to benefit Chicago Canine Rescue, and more.

Meet the Author: Susan Orlean

Oct. 19

Susan Orlean
Photo courtesy of Wilmette Public Library.

Hear from Susan Orlean as she discusses her New York Times bestseller, “The Library Book.” The event also includes a book signing.

Open House Chicago

Oct. 19-20

The Second City for Open House Chicago
The Second City (Photo by Eric Allix Rogers.)

This architecture festival, one of the largest in the world, returns with access to more than 350 of Chicagoland’s coolest buildings. Go behind the scenes of Broadway in Chicago’s James M. Nederlander Theatre, the Bahá’í House of Worship, Garfield Park Conservatory, The Second City, Metropolis Coffee Roasterie, Park No. 571 Boathouse, Wild Blossom Meadery & Winery, and much more.

Bloody Mary Fest

Oct. 20

Bloody Mary
Photo by Johann Trasch on Unsplash.

Theater on the Lake hosts this day-long celebration of Bloody Marys and brunch featuring past winners from their Bloody Mary Competition, as well as yoga, a fun run, lawn games, and more. A portion of proceeds will be donated to K9 4 Keeps.

More Can’t-Miss Events:

  • Love pinball? The 35th Annual Pinball Expo in Wheeling Oct. 16-19 features games, vendors, a tournament, and more. The Expo is also partnering with Project Pinball, which puts pinball machines in children’s hospitals, and Make-A-Wish Illinois this year.
  • Decorate a pumpkin, show off your best costume, enjoy carnival games, and more during Winnetka’s Pumpkins in the Woods event on Oct. 18.
  • Don’t miss the inaugural Pilsen Arts & Craft Beer Tasting Oct. 19-20. On Saturday and Sunday, discover works by 15 Pilsen artists, and on Sunday sample craft beers from local breweries.
  • Keep the fall fun going at River Trail Nature Center’s Fall Festival in Northbrook on Oct. 20. Listen to stories, watch beekeeping demonstrations, paint pumpkins, go on a hayride, and more.
  • Meet Olympian, “Dancing With the Stars” champion, and author of new memoir “Beautiful on the Outside” Adam Rippon during an author event with The Book Stall on Oct. 20 at The Music Box Theatre in Chicago.