Chicago Connected | Fall 2023

Crisp, colorful leaves grace the streets of Chicagoland, the weather grows chillier, and the residents of our Windy City and suburbs gather to celebrate the season in style. Fall is here, which means we at Jameson Sotheby's International Realty have gathered a cornucopia of events, activities, and recommendations that are as picturesque as they are delightful. Celebrate autumn in Chicagoland with our full seasonal guide!

 

Chicago Events

Chilly nights and colorful Chicagoland days are upon us! Autumn is arriving to the city and suburbs, which means a whole new roster of spectacular events including film festivals, fall celebrations, and spooky Halloween staples.


Northalsted Halloween Parade

Halstead & Belmont, Chicago
October 31, 6:30pm - 10:00pm

 

Open House Chicago

Various Locations, Chicago
October 14 - 15

 

Chicago International Film Festival

Various Locations, Chicago
October 11 - 12

 

Chicago Food Truck Festival

La Bagh Woods, Chicago
October 7 - 8, 10:00am - 6:00pm

 

Grove Folk Fest

1421 Milwaukee Ave, Glenview
October 1, 11:00am - 5:00pm

 

Destinos Chicago International Latino Theater Festival

Multiple Locations, Chicago
September 28 - November 12

 

Magnificent Mile Lights Festival

401 North Michigan Ave, Chicago
November 18, 11:00am - 5:30pm

 

Fall Hiking Trails

A brisk walk on a chilly day with friends, family, or pets, is made all the more special by the incredible colors that grace Chicagoland’s hiking trails during this season. Before settling in for the winter, make a day of visiting one of these spectacular trails that offers the perfect amount of outdoor escape.


Starved Rock State Park
One Lodge Ln, Oglesby

 

Chicago Botanic Garden
1000 Lane Cook Rd, Glencoe

 

Morton Arboretum
4100 Illinois Route 53, Lisle

 

Promontory Point
5491 S. Jean-Baptiste Pointe DuSable, Chicago

 

Waterfall Glen Forest Preserve
900 S Frontage Rd, Woodridge

 

Patio Dining

Make your reservations for a truly unique dining experience this season and enjoy Chicagoland’s myriad of patio dining spots before the cold weather takes over! With a vast selection of flavors to choose from, and picturesque views of the season’s changing colors as you dine, it’s easy to try something truly delicious this fall.


Piccolo Sogno
464 N Halsted St, Chicago

 

Soul & Smoke
1601 Payne St, Evanston

 

Oaken Bistro + Bar
200 N Field Dr, Lake Forest

 

Maya Del Sol
144 S Oak Park Ave, Oak Park

 

Fuller House
35 E. First St, Hinsdale

 

Bev's
245 S. Washington Street, Naperville

 

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