Chicago’s a city with four distinct seasons, each worthy of a visit in its own right.
Often overshadowed by the promise of cool temps and sandy beaches along Lake Michigan in summer, fall is truly the greatest time to enjoy Chicago, for locals and visitors alike.
Head to the Windy City in October to experience Chicago’s best weather window: a month full of cooler temps and abundant sunshine, which leads to brilliant leaf colors popping against a backdrop of bluebird skies.
As October transitions to November expect wind, overcast skies, and even a chance for snow. The days grow shorter rapidly, and being so close to the eastern end of the time zone, the sun sets in late afternoon.
The period between Halloween and Thanksgiving is one of preparation and change in Chicagoland. Not much happens downtown, which makes it a great time to visit to avoid crowds at the regular Chicago hotspots like the Museum Campus, Navy Pier, Millennium Park, and the sky decks.
Here are eight ways to experience the unique twists Chicago has on the traditional fall holidays of harvest, Halloween, Día de los Muertos, and Thanksgiving.
1. Find your perfect pumpkin in the heart of the city.
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Throughout Chicagoland you will find pumpkin patches on farms offering apple cider, hay rides and Instagrammable photo ops. The place to go for pumpkins – over 10,000 of them – in the city is Jack’s Pumpkin Pop–Up.
Located just west of Goose Island, Jack’s has carnival games, fortune tellers, photo ops, ax throwing, craft beers, and of course pumpkins packed into two acres bursting with fall fun. It even boasts Chicago’s largest corn maze, which has a hidden bar inside.
Open daily from the end of September through Halloween, Jack’s is family-friendly during the day and cranks up the scary after 7 p.m.
2. Immerse yourself in Chicago’s haunted history.
Most cities offer a plethora of haunted houses promising to scare visitors in the fall. Chicago capitalizes on its history of vice and ghosts by taking visitors back in time to visit Prohibition-era establishments and haunted locations in real life.
Chicago has a haunted experience for every person, with self-guided tours available, as well as guided tours by boat, bus, foot, and even kayak. If you enjoy walking tours, head to Lincoln Park. The site of the infamous St. Valentine’s Day Massacre, as well as the former Chicago cemetery, Lincoln Park is widely considered the most haunted part of Chicago.
Here you can embark on a ghost pub crawl with Nightly Spirits to visit bars, alleys, and buildings, while a guide shares haunting tales of the leaders of vice that used to frequent these locations. You will leave being able to say you drank at the same place as Al Capone.
If pub crawls aren’t your thing, try Chicago’s only public ghost hunt tour with American Ghost Walks. A guide will lead you around Lincoln Park and teach you about the ghosts of the Lincoln Park Zoo, the missing graves, and more.
Experience the ghosts, gangsters, mystery and mayhem of Chicago firsthand via bus tour with Weird Chicago. The hop on and off again tour takes you beyond the hauntings of Lincoln Park into downtown.
Water Riders offers Ghosts and Gangsters kayak tours on the Chicago River through the second week of October. If you’re too late, don’t worry, Seadog operates haunted river tours weekend evenings in October through Halloween night.
3. Attend a fall festival.
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Every city has its own version, whether it’s a harvest festival, OktoberFest, fall fest, etc. There’s so many to choose from in Chicagoland. If you’re willing to head out to the far west suburbs, Scarecrow Weekend, in St. Charles, Illinois, is the best.
Set downtown St. Charles along the banks of the Fox River, Scarecrow Weekend is an award winning festival for good reason. It features all the standard fall festival staples, like seasonal snacks and beverages, festive photo ops, carnival rides, and live entertainment. Then there’s the magician, bubble artist, magic show, and pumpkin carving demonstrations.
Each year attendees vote for their favorites from 85+ hand-crafted scarecrows on display throughout the festival grounds. You can also pick up a “scarecrow in a box” set to make your own at home. On the other side of the river in Pottawatomie Park, peruse the booths with unique crafts at the Autumn on the Fox craft show.
Related read: 10 Best Weekend Road Trips From Chicago, Illinois
4. Take in all the fall colors.
While people often rave about the fall color displays in Door County and other places in Wisconsin, Chicagoland has plenty of leaf-peeping to rival these without the drive. Mid to late October are the best times to witness the trees of Chicago light up with deep crimsons, vibrants oranges, and golden yellows.
Here are six of the best places to peep leaves around Chicago this fall, from south to north.
Located in the Hyde Park neighborhood, the “Point” is a manmade feature that juts out into Lake Michigan. From here you can enjoy views of the lake and the Chicago skyline from the southside, as well as wander the tree-lined paths of Burnham Park.
Known as the site of the 1893 Chicago World’s Fair and current location of the Museum of Science and Industry, this giant greenspace features an island between two lagoons that houses a Japanese garden, as well as three harbors and a beach along Lake Michigan.
Be sure to walk among the cherry blossom trees as they light up red and orange in the fall.
Head 30 minutes straight west of downtown to the Morton Arboretum in Lisle, Illinois. Here you will find trees changing color from around the world, including a variety of maples, oaks, Ginkgos, and birch, along wood-chipped and paved trails.
The arboretum offers fall foliage walking tours, and features scarecrows created by local boy scout troops during October.
Lincoln Park’s a popular place in fall in Chicago. At night it’s a great starting place for ghost and gangster haunted tours.
During the day, immerse yourself in fall foliage as you explore the zoo, Diversey Harbor, Peggy Notebaert Nature Museum, or walk along the miles of tree-lined trails past lagoons, ponds, and statues.
Located north of Wrigleyville and west of Montrose Harbor, the Graceland Cemetery is an intricately designed garden and arboretum as well as the final resting place for many prominent figures in Chicago history.
Enjoy the contrast of elaborate tombs and gravestones against bluebird fall skies and brilliant hued maple leaves as you walk the peaceful grounds.
Chicago Botanic Gardens
Located north of the city in Glencoe, Illinois, the botanic gardens feature 27 gardens and nine islands to explore, all putting on a show during the fall.
If that doesn’t satisfy your leaf peeping needs, cross Dundee Road head south on the Black Spur of the North Branch Trail to hike the inner trail at Skokie Lagoons. Here you can enjoy dirt trails under your feet and as fall colors surround you.
5. Enjoy Night of 1,000 Jack-o’-Lanterns.
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The Chicago Botanic Garden lights up brisk fall nights for two long weekends in October with more than 1,000 hand-carved, real pumpkins on display. Night of 1,000 Jack-o’-Lanterns is an annual event perfect for everything from date night to a family adventure, and it’s wheelchair accessible.
The gardens close at 5 p.m. and reopen at 6 p.m. all aglow. Spend an evening outside admiring the pumpkins, watching live carving demos, and enjoying costumed entertainers.
Keep the following in mind when planning your trip. The Chicago Botanic Gardens are located in Glencoe, Illinois, northwest of downtown near Ravinia and not far from Lake Michigan.
It will take you an hour in rush hour traffic to drive from downtown, so plan accordingly. Non members need to purchase a parking pass online along with admission. This event sells out annually. Plan ahead so you don’t miss out!
Related read: 11 Best Cabin Rentals in Illinois For an Outdoor Getaway
6. Experience Chicago Halloweek.
One of the most unique fall celebrations in the Windy City is Chicago Halloweek. Creative organizations from across the city band together to create two large-scale events in an effort to provide safe celebrations and showcase the artistic side of Halloween.
First, the Upside Down Parade kicks off Chicago Halloweek two Saturdays prior to Halloween. Costumed families walk through 20+ performance groups in Washington Park, on the South Side, in a reverse parade during the afternoon.
The following Saturday, an amalgamation of Chicago’s artistic organizations band together to put on the Arts in the Dark Parade. This family-friendly parade makes its way down State Street from Lake to Van Buren. Expect floats, costumed performers, puppets, lanterns, and more to light up the crisp fall air.
7. Honor the past at Día de los Muertos celebrations.
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Día de los Muertos (Day of the Dead) is a two-day holiday celebrated in Mexico and elsewhere by people of Mexican heritage. Families honor the dead by welcoming back the souls of their deceased relatives through celebrations complete with music, food, flowers, and altars.
The two best neighborhoods in Chicago to celebrate Día de los Muertos are Pilsen and Little Village, both located on the southwest side of the city. Logan Square and Back of the Yards neighborhoods also put on annual celebrations worth checking out.
The National Museum of Mexican Art is located in Pilsen at Harrison Park. It features a special exhibition honoring the holiday, which runs from the end of September through mid December.
The weekend of Día de los Muertos, the museum puts on an annual ticketed event the “Love Never Dies Ball” with food and beverages catered by local restaurants as well as live music and a local DJ.
Pilsen celebrates Día de los Muertos with art activities, face painting, musical performances, and traditional food and drinks. Over 75 ofrendas (altars) created by members of the community, and area artists and organizations, are on display.
Pilsen is also a hotbed for Mexican cuisine, live music, and public art worth visiting anytime in the fall. To fully explore it, take a walking tour to see the five major murals within a four block radius of the museum.
Little Village (La Villita) celebrates both Halloween and Día de los muertos the Saturday before Halloween with art, community resources, food, and trick or treating. The first weekend of November the neighborhood puts on its Day of the Dead Altar Walk: Recorrido de Ofrendas. Storefronts along 26th street have altars set up for public viewing.
Related read: 10 Best Illinois Glamping Rentals
8. Kick off the holiday season Chicago-style.
If you want to spend Thanksgiving weekend in the windy city, be sure to head to the Loop to watch the Thanksgiving Parade. The route runs down State Street from Ida B. Wells Drive to Randolph Street. Get your fill of balloons, dancers, floats, horses, and marching bands. Be prepared to brave the elements as flurries are a real possibility this time of year. Expect it to be windy and overcast.
To experience the parade live without dealing with the weather or crowds, consider booking a room along the parade route. The Palmer House is an iconic piece of Chicago architecture and history, and the only hotel that boasts clear views of the parade. Make sure to specifically request a room with a view of the parade when booking. You want a room on the westside or northwest corner, at least ten floors up.
The city goes all out to celebrate the holiday season. Stroll down State Street after the parade to view the elaborate holiday displays in storefront windows. Spend an afternoon at the ChristkindlMarket in Daley Plaza. Take a selfie in front of the Chicago Christmas Tree before lacing up your skates at the ice rink in Millennium Park.
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