While New England may get the most attention when it comes to experiencing the changing colors and activities of the fall season, I believe Chicago and the South Loop offer some of the most amazing spots to not only appreciate the incredible multitude of colors, but also enjoy some autumn activities.  Let’s face it – we’ve only got a few more weeks of pleasant weather. Now’s the time to get out and savor every extra minute before the cold sweeps in and day light savings puts an end to our long, sultry evenings. You don’t need to leave the South Loop or downtown to experience the best of fall. Check out our list of activities in urban neighborhoods bustling with changing colors and events during October!


Best Things about Autumn in the South Loop and Chicago Downtown Area

Fall Foliage  

The South Loop is a hidden treasure of parks, gardens, and tree lined streets. Plan a day walking through Printer’s Row, Dearborn Park I and II, Central Station, and the Prairie District. All along the way you’ll see vibrant hues of yellow, red, and orange in the parks and canopy-lined streets. You can also extend your walk to nearby Grant Park, Millennium Park, and the Riverwalk, home to many varieties of trees including elms, hawthorns and maples that show off their colors at the peak of the season.  

The Chicago Marathon (Oct. 13) is a great opportunity to get into the autumn spirit and explore fall foliage.  Join South Loop residents along the route to cheer on the runners!

Keep your eyes open on your walk for open houses! Better yet,  schedule a tour It’s the perfect time to check out the neighborhood and look for a new home.


Fall Activities   

Nothing says fall more than crisp, sweet apples, pumpkin patches, and autumn festivals! Sure, you can drive an hour or so to go hunting for pumpkins and apple picking, but why do it if you don’t have to? Get the best of both worlds at Applepalooza! Held at the Chicago Women’s Park and Gardens (1801 S. Indiana Ave.), Sat., Oct. 5, 11:00 a.m. – 2:00 p.m., this annual apple fest includes games, an apple food court, hayrides, storytelling and more! The fee is $5 per child.  

Pier Pumpkin Lights, Navy Pier, Oct. 1 – Nov. 2, Find nearly 1,000 glowing pumpkins spread across Navy Pier at the attraction’s month-long Pier Pumpkin Lights event. Stop by Polk Bros Park to visit the Juggernaut of Jack-O-Lanterns installation then head to the pier to take in five more pop-up experiences, all of which will be illuminated after dusk each evening. 

House of Beetle (Beetlejuice Inspired Pop Up Bar), Bassline (2239 S. Michigan Ave.), – Oct. 17 – Nov. 2.  Enjoy music, ghoulishly good music, and epic vibes inspired by “Beetlejuice,” the hit 1988 Tim Burton film. Tickets available online. 21+. 

Fall Festival at Maggie Daley Park (337 E. Randolph St.), Sat, Oct .19, 12:00 – 5:00 p.m. This fun, family fest is filled with fall activities, crafts, and much more. Best of all it is free!  


Spooky Happenings 

Campfire Horrors at Northerly IslandGet your Friday night fright fix with scary movies in the park. Cozy up to a crackling campfire, roast marshmallows, enjoy horror classics under the October sky. Campfires begin at 6:30 Marshmallows provided! Bring your own blankets and chairs! In case of rain, the event will be moved inside.

Fri, Oct 4, 7:00 p.m.  – Hocus Pocus (PG) 

Fri, Oct 4, 8:45 p.m.- Frankenstein (1931) (NR)  

Fri, Oct 11, 7:00 p.m. – Misery (R) 

Fri, Oct 18, 7:00 p.m. – Shaun of the Dead (R) 

Fri, Oct 18, 8:45 p.m. – I Know What You Did Last Summer (R) 

Fri, Oct 25, 7:00 p.m. – Interview With the Vampire (R)  

Stargazing at Northerly Island (1521 S. Linn White Dr.), Fri, Oct. 4, 6:30 – 8:30 p.m.  Join the Chicago Astronomer at Northerly Island for an out of this world adventure! Learn how to read a star map, identify major constellations, bright stars, and other planets. Telescopes provided. 

Aliens vs. Monsters,Adler Planetarium, Oct. 17, 6:00 p.m. Get in the spooky spirit and celebrate your favorite cinematic aliens and monsters at Adler After Dark! Enjoy scenes from your favorite classic sci-fi and horror movies in a special improv performance: It Came From Space! Channel your inner extraterrestrial (or monster) in the “Creatures Features Scavenger Hunt” and “Mask Making Workshop.” Dance the night away to Thriller and other spooky hits. Chicago’s own self-described retro-futurist dance band Terrible Spaceship, will perform sections from their albums, ZontarThe Thing from Venus and Invaders 1938 in the Johnson Family Star Theater.  Costumes encouraged—check out their Cosplay and Costuming Weapons Policy. Purchase tickets online.

Haunted Maze at Navy Pier, Oct. 18 – 27 & Oct. 31 beginning at 5:00 p.m. Enjoy a scary good time through the haunted twists and turns of the Funhouse Maze on Navy Pier. Encounter some of Chicago’s most notorious ghosts. Travel through notable centuries of Chicago history-such as the Union Stockyards, and the Capone era. Guests under the age of 18 will not be permitted to enter without a paying adult chaperone. The haunted maze is not recommended for guests under the age of 10. This is designed to be a much scarier visit through the maze, as additional effects and costumed characters will be inside. $15 

Shadows on the Street: Haunted Tours of Historic Prairie Avenue, Glessner House (1800 S. Prairie Ave.) Fri, Oct. 25, and Sat., Oct. 26, 7:00 – 9:15 p.m. Explore Prairie Avenue after dark! Hear tales of strange sounds, unexplained sightings, and untimely endings during this 60-minute walking tour through the Prairie Avenue Historic District. Learn about the mystery surrounding the death of Marshall Field Jr., the tragic events that plagued the Philander Hanford house, the lingering ghost of Edson Keith, and more! Pre-paid reservations required. The tour takes place rain or shine. Dress appropriately. Not recommended for children. $15 per person / $12 for members 

33rd Annual Edgar Allan Poe ReadingsGlessner House (1800 S. Prairie Ave.), Sat., Oct. 26, 5:00 – 9:15 p.m. (Two readings: 5:00 – 6:15 p.m., 8:00 – 9:15 p.m.) Squirm in your seats as actors from Lifeline Theatre present staged readings of Poe’s terrifying stories and poetry. A Glessner House tradition for three decades, it’s an evening not to be missed. Not recommended for children. Pre-paid reservations required.

Halloween Festivities  

Arts in the Dark Halloween Parade, Sat., Oct. 19, 6:00 – 8:00 p.m. This magical night time parade takes place on State St. from Lake St. to Van Buren St. World-renowned institutions, celebrated Chicago organizations, and aspiring artists in every field come together to delight audiences with unique floats, legions of lanterns, costumes, music, dance, dramatic lighting, spectacle puppets, and creative performances!

Halloween Bash at Maggie Daley Park – Fri, Oct. 25, 5:30 – 7:30 p.m. This family fun event, for children 2-10 years, is filled with activities, crafts, and much more. The fee is $5 per child.

Haunted Halloween Ball – Congress Plaza Hotel, Sat., Oct. 26, 9:00 pm – 3:00 a.m. Join hundreds of costumed party goers for a night of thrills in the 122-year-old hotel classified as one of the most haunted hotels in the world by USA Today!  Transformed into an abandoned hotel run by zombies, entertainment includes world renowned DJs and recording artists, as well as encounters with vampire bellmen, zombie cocktail servers, and theatrical performances by costumed go-go dancers. Come in costume to compete in the virtual costume contest. This event is 21+, ID required. Purchase tickets online.

Prairie District Neighborhood Alliance – Children’s Halloween Party – Glessner House Museum (1800 S. Prairie Ave.), Sun., Oct. 27, 3:00-5:00 p.m. Come in costume to PDNA’s annual, not-so-scary Halloween party. Enjoy games, prizes, pumpkin decorating, cookie decorating, a petting zoo, family photo booth, candy, snacks, refreshments, music, and more. Rain or shine. Purchase tickets online (children 1-12 years – $15; 13 years and older – $8; infants free).

Navy Pier Trick or TreatingDress up in your best costumes for Trick-or-Treating at Navy Pier. Walk throughout the Pier and collect candy from participating establishments.  October 26, 27 & 31, 2:00 – 6:00 p.m.

Prairie District Neighborhood Alliance Family Costume Parade/Walk, Halloween, Oct. 31, 4:30 – 5:00 p.m. Join neighbors for a festive family Halloween costume walk! Dress up the whole family – kids, adults, pets, and strollers! Parade begins on Historic Prairie Ave. at 18th St. Neighborhood Trick or Treating runs from 5:00 -7:00 p.m. All welcome. Free! For more info email pdna.chicago@gmail.com.

Shedd After Hours – Halloween, Shedd Aquarium, Oct. 31, 6:00 -10:00 p.m. Come face to face with predators of land, sky, and the deep blue sea! Enjoy surprising pop-up animal encounters and a hair-raising shark chat with facts stranger than fiction. Wear your most imaginative Halloween attire for a chance to win prizes in the costume contest. Haunt the aquarium, devour festive bites, and sip a spooky spirit as you visit the science pub to learn how spooky the deep ocean can be! Purchase tickets online. Photo ID required for entry.

Get Your Costume On!

Check out these additional fun events and make sure to come in costume!

Jazz Age Party, Glessner House (1800 S. Prairie Ave.), Thurs., Oct. 10, 6:00 – 9:00 p.m. October marks the 100th anniversary of the passing of Prohibition. It’s 1919 and Prohibition has just been signed into law. Get your flapper on and come drink and party before it’s enforced! Enjoy music, dancing, entertainment, open bar and food. Celebrate with actors from Stockyards Theatre Project. Meet some characters of the time with different views on the ills of drinking. Tickets are $50 per person. Purchase tickets online.

Shedd After Hours: 80’s Night, Shedd Aquarium, Oct. 17, 6:00 -10:00 p.m., Rock your totally awesome 80’s look with leg warmers and big hair. Dance the night away with live music from the Jolly Ringwalds. Reminisce about the origin of Shark Week or play some rad games with the Chicago Public Library. Nosh on nostalgic bites or sip a specialty cocktail (available for purchase). ’80s attire encouraged. Online ticket sales only. Photo ID required for entry.


Happy Fall & Halloween

There’s no doubt about it.  Fall is one of the most beautiful seasons in Chicago. So, get out and enjoy that crisp, inviting, weather and the beautiful autumn in the South Loop and downtown Chicago! Share your favorite fall happenings and photos on my Facebook page.

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