20 Fall Haunts & Happenings

Last week marked the first of fall. Naturally, Fulton Grace Realty gathered some of the city’s best ways to usher in the season. From beer guzzling and pumpkin picking to horror screening and outdoor adventuring, the leaf-obsessed and less thrilled can all partake. 

Old Town
Now | The Rabbit Hole


First up on your autumn itinerary: madness, spice and maybe something on ice. Pop down to The Rabbit Hole for the most lively in Old Town spirits. You might even get this new Alice in Wonderland themed bar to slip you something pumpkin infused.

Now-Dec 11 | Día de los Muertos: Journey of the Soul 


Roam a collection of art, offerings, and elaborate skulls for the 30th annual Day of the Dead exhibition. The National Museum of Mexican Art hosts this cultural and soul celebration.

West Town
Sept 30-Oct 1 | West Town Art Walk & Food Truck Social


Need a reprieve from stringing ghoulish light strands or depleting your candy stash? West Town provides “art through every door”. Explore the multimedia frenzy, or follow your nose to over 15 food trucks.

Lincoln Park
Sept 30-Oct 30 (Fridays-Sundays) | Fall Fest

Lincoln Park Zoo

Delight your “basic” half with corn mazes, hay mountains, pumpkin carving, and beast greetings. The Lincoln Park Zoo (and all its creatures) look forward to you and your family. Trick-or-treat a few days early with Spooky Zoo Spectacular.

Logan Square
Sept 30-Oct 31 | Horror Movie Madness


Classic horrors return to Logan Square Theatre every eve in October. Pick your poison at the bar, and stay for late night showings of Psycho, The Exorcist, Night of the Living Dead, Beetlejuice, Rosemary’s Baby, and of course, Halloween.

Oct 1 | Logan Square Beer Festival


Too old for apple bobbing? How about ale-induced nodding? Check out 20 breweries and over 50 beers at this 4th annual festival. Logan Square Auditorium to house.

Lincoln Square/Ravenswood
Oct 1-2 | Apple Fest


Speaking of the forbidden fruit…tune into all apple everything. Wander through a world of autumn favorites–caramel apples, pie, cider, you name it. Even grab non-edible treats like scarves and hats. The Kids Zone offers extra fun for every age.

West Loop
Oct 2 | Fulton Market Harvest Fest


Expand your yield this fall with live music, local beer makers and cooking demonstrations by Fulton Market District’s leading restaurants. Spend the first Sunday of October with Goose Island drafts, Girl & the Goat provisions, and top chefs.

Oct 25 | Expecto! A Harry Potter Wine Dinner


Feast like a Gryffindor, Hufflepuff, Slytherin or Ravenclaw with a 4-course wine & dine experience. Wannabe wizards now have an opportunity to secure tickets (with or without the summoning charm) for day 2 of City Winery’s event. Sort yourself a spot before they vanish! Tickets go on sale today at NOON.

Steeterville, Navy Pier
Oct 7 | Shoreline Sightseeing Oktoberfest Cruise

A Shoreline Architectual Boat Tour heads south.

Get goosebumps from the cool splash of lake waves or an ice cold “bier”. Oktoberfest takes to the water. Expand your horizons, and indulge in some sausage on Lake Michigan.

Grant Park, Millenium Park
Oct 9 | Chicago Marathon


Embrace the season by supporting runners at designated viewing areas throughout the 26.2 mile stretch. Maybe the marathon will inspire a repeat city or cardio expedition.

Oct 14 | The Head and The Heart @ Aragon


Embrace the mellow with this American indie folk band. Hear them resurrect hits and play newly crafted music at one of Chicago’s favorite venues.

More ‘Hoods Than You Can Handle (Downtown; Bridgeport; Bronzeville; Edgewater; Englewood; Evanston; Garfield Park; Gold Coast; Hyde Park; Jefferson Park; Lakeview; Lincoln Park; Near West Side; Oak Park; Rogers Park; South Loop; South Shore; Ukrainian Village; Uptown; Westown)
Oct 15-16 | Open House Chicago


Paralyzing fear of the unknown may keep you from haunted houses, but don’t let that stop you from 200 of Chicago’s most exclusive sites. The Chicago Architecture Foundation exposes looming structures, hallowed halls, elite headquarters and storied spaces. Sneak into the Sky-Line Club, Ernest Hemingway’s Birth Home, The Wheeler Mansion, Holy Name Cathedral and more without selling your soul.

Northerly Island
Oct 17 | Fall Adventure Day


If you’re over the sweltering heat but still identify with outdoor activities, this day is for you! Pedal a new path; embark on a woodsy hike; catch a fish; spy a flying something; put your craft pants on. Autumn (and self) exploration starts at Northerly Island Park.

Wicker Park
Oct 18 | Drink n Draw An Evening of Terror!


Your drawing abilities may be frightening, but that just might work in this case. Emporium and Mistress Bones Portrait Playhouse will showcase hauntingly dressed models for your sketching or photographing pleasure plus BOOze.

University Village
Oct 22 | Pumpkin Patch @ Sheridan Park


Skip picking fights with wind-blown hair and tackle the perfect pumpkin instead. Sheridan Park welcomes children of the gourds (and chaperones) to select one for free. 1st come, 1st served!

River North
Oct 22-23 | Chili Fest Chicago


Comfort foodies, football enthusiasts and tailgate newbies welcome. Cozy up to the finest chili, craft beer and game selection outdoors. Kickoff is 10:30AM Saturday and 11:30 Sunday.

The Loop
Oct 28 | Halloween Masquerade @ Civic Opera House


Looking for an alternative to scant costumes and spilled beer? The Lyric Young Professionals present an operatic evening that promises wonder, dance, elegance and an open bar. Slip into a bewitching ensemble, and surrender to the rhythm of the night.

Oct 29 | Wrigleyville Halloween Crawl


If you ARE about a more casual night of creepery, join other crawlers as they invade Wrigley. Deuce’s, Moe’s Cantina, Rockit, Sluggers, John Barleycorn and other beloved bars await.

Oct 31 | Northalsted Halloween Parade


Spooks come in a spectrum of colors. Especially at the 20th birthday of the most pride-filled Halloween Parade. You can either perform or just attend. Consult the spirits if you must.


Images linked to sources

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