Fall Into Chicago with The 77’s Favorite Autumn Activities

There’s a slight chill in the air. The rich green leaves on trees are beginning to shift to auburn and gold, and Chicago is shining. Fall is right around the corner, and the members of The 77, our Diversity Committee, shared their favorite fall activities in their respective communities. Check out the suggestions and add them to your calendar for autumn!

Far North Side


“Norwood Park Fall Fest on September 15th and Halloween are so much fun in Norwood Park.” – Lourdes Hernandez, Coldwell Banker Realty


“There is so much to enjoy in Uptown in the fall. As the weather gets colder, I love getting pho at some of the restaurants on Argyle. It’s also fun to catch a concert in the thriving entertainment district that features the Riviera, Aragon and Green Mill.” – Antonia Mills Wesselink, Antonia L. Mills, Attorney at Law


“Andersonville is always bustling and has street festivals that include local artists and artisans, music and food. In its 57th year, Midsommarfest (in June) kicks off festival season in the city, followed by Edgewater Arts fest in the fall.” – Mabél Guzmán, Coldwell Banker Realty

Northwest Side


“I love the farmers market located at 3945 N. Springfield that takes place from June to October on the second and fourth Sundays of the month. This year, the neighborhood is also doing something new that I am looking forward to…a garden walk!” – La’Dweena Smith, Keller Williams ONEChicago

North Side


“Logan Square Preservation house walk, which is being held on September 9th this year, is a must! Have you ever wondered what some of the homes look like inside? Select Logan Square residents open their doors to the public for guided viewing. To eat, I recommend Pilot Project Brewing at 2140 N. Milwaukee Ave. Their fall brews, food and patio are just a few of the many reasons why I love it.” – Jennifer Williams, Coldwell Banker Realty



“As an architecture and design enthusiast, the Louis Sullivan and Frank Lloyd Wright designed Charnley-Persky House at 1365 N. Astor St. hosts some of my favorite exhibitions but also can be appreciated on its own. The Magnificent Mile along with the Oak Street district each offer world-class shopping and dining. Another favorite is St. James Cathedral. All are welcome to tour the cathedral, especially on a fall day when the doors are open. For dining, I recommend the patio at Luxbar, hands down! The food, drinks and relaxing outdoor space are a must try as we enter the fall.” – Jennifer Williams, Coldwell Banker Realty


“I enjoy running in the Hot Chocolate 15K in the fall! It tends to be a bit cold, but running through the Near South Side around the Museum Campus feels familiar and warm. It gets adrenaline rushing each time. I think the best way to experience Chicago is on foot; a good jog through the neighborhood is the best view!” – Tameka Washington, Habloft LLC

West Side


“I love the Garfield Park Conservatory’s Landscape Art Under Glass. During the fall season, it seems that much more magical to see the trees change color in one of the largest botanical conservatories in the U.S. My new favorite small business coffee shop to stop at after is Dope Drip Cafe for caffeine and a snack.” – Ri Prasad, Option Realty Group

South Side


“We love the Hyde Park Farmer’s Market. It’s great to support local vendors and the options are amazing.” – DeVontae Brooks, Guaranteed Rate

Southwest Side


“I love taking photos of the trees. I am a member of the local Lions Club, and we give out Christmas gifts to lower income and younger children in the area, which we start planning early. I love to give back.” – Sandra Cruz, Shield Real Estate


“I enjoy the Englewood Jazz Festival at Hamilton Park or Englewood Music Festival hosted by Alderman Coleman. Both are happening on September 16th this year.” – Sherri Jordan, Suite 527 Realty Group


“I love going on hikes with my dogs in McKinley Park and enjoying the changing leaves and picking up coffee and a tasty treat from Kristoffer’s Cakes. The tres leches is a must try. When I crave seafood, La Palapa is a great place to go.” – Elizabeth De La Paz, Coldwell Banker Realty