Exploring Chicago Neighborhoods,  museums,  music,  random adventures

goodbye summer, hello fall, Chicago 2022

As a lifelong Chicagoan, it is always sad to bid summer farewell, but growing up in the Midwest, I look forward to the change of seasons. Well, maybe not the end of winter so much, but I’m working on a plan to become a snowbird. Goodbye summer, hello fall, Chicago 2022.

Soon it’ll be time to swap out my shorts & flip-flips for sweaters & boots. It’s already getting dark before 7 pm. Whatever happened to getting rid of daylight savings time? Even though temps are predicted to be pretty nice for the next week, I’m actually SUPing today, the trees have started changing colors, so cooler temps are inevitable. One thing I look forward to is Mother Nature’s ever-changing canvas. Never gets old.

While outdoor activities like concerts & festivals wind down, there is still plenty to do. Here is my list of Fall things to do in Chicago 2022.

Here’s my list of things to do | Fall in Chicago 2022

good bye summer hello fall Chicago 2022 - Chicagohenge -


In the days right before, during & and after the autumn equinox, which will take place on Thursday, 22 September 2022, this year, the sun will align perfectly with Chicago’s east-west-facing streets for both sunrise and sunset. It’s a pretty spectacular sight.

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randolph street market – 9/24 & 25

The Randolph Street Market is more of an all-year-round kind of thing to do since it takes place both inside & outside.

It’s an urban flea market with an ultra-curated, high-quality selection of antiques, vintage and modern goods, ranging from fashion to art, jewelry, decor, retro home furnishings, and global goods. Enjoy shopping along with music, drinks & food!

I haven’t been in a while and the next one is coming up soon so I’m listing it here. And I think I need some more cashmere! Read about it here.

good bye summer hello fall Chicago 2022 - hyde park jazz fest -

hyde park jazz fest – 9/24 & 25

The Hyde Park Jazz Festival is a collaborative platform dedicated to supporting the presentation and ongoing development of jazz, particularly on the South Side of Chicago. We do this by creating opportunities for a diverse community of listeners to engage with the music and its creators and by working with artists, organizational partners, and networks to celebrate the rich tradition of jazz and to support the development of new work and ideas.

The Hyde Park Jazz Festival on Chicago’s Culture Coast is co-produced with the Hyde Park Jazz Society. The 16th annual Hyde Park Jazz Festival is made possible through the support of lead and founding sponsor, the University of Chicago’s Office of Civic Engagement. Other sponsors include the David & Reva Logan Center for the Arts, the University of Chicago Medical Center, and many other corporations, organizations, individual donors, and volunteers

good bye summer hello fall Chicago 2022 - apple fest -

apple fest – 10/1 & 2

The 35th Annual Apple Fest takes place in Lincoln Square/Ravenswood to celebrate the season of everything apple. From delicious cider for kids & the adult version with food, music, and lots of activities for the kiddos. An all-around good time for everyone, even the doggos. The best apple pie IMHO is from the Chopping Block, and the best cider is locally made Right Bee. I actually prefer cherry or blueberry pie, but this apple pie is to die for. One of my favorite Fall fests, where I get to see some of my favorite people.

hideout trivia – 10/5

This fall will see the return of Hideout Trivia, the Hideout’s Chicago-centric trivia series sponsored by the Chicago History Museum and the Newberry Library.

On the first Wednesday of the month from September through November, you can grab up to five other friends and compete in three rounds of trivia that will include live interviews, readings, re-enactments, and musical performances. Each round reflects a particular theme. Prizes will be given to the teams that finish first, second and third. Click here for upcoming events at the Hideout.

good bye summer hello fall Chicago 2022 - historic pullman district -

historic pullman house tour – 10/8 & 9

Visit the Historic Pullman District and see the interior of 7 private homes as part of Chicago’s longest-running house tours.

Since 1973, Historic Pullman Foundation and Pullman Civic Organization have co-sponsored the annual Pullman House Tour, making this one of Chicago’s oldest continuing tours of homes. Select homes are chosen each year to present a cross-section of the different types of housing built in the 1880s as part of the original Town of Pullman. Pullman is a City of Chicago, State of Illinois, and U.S. Department of the Interior designated landmark district.

On February 19, 2015, Pullman was designated as a National Monument, a unit of the National Park System, and is Chicago’s only National Park facility. Owners of Pullman’s landmark houses maintain the historic details on the exterior. The private side of Pullman residences, which will be opened to the public for this tour, reflect the style and taste of our modern residents, including beautifully restored interiors as well as tasteful modern renovations.

Join our House Tour weekend October 8-9 and enjoy the Pullman National Monument — see beautiful homes, selected public buildings, exhibits, and a video on the history of this unique landmark district, and enjoy music, food, and antique cars (Sunday only), and so much more.

good bye summer hello fall Chicago 2022 - chicago marathon -

chicago marathon – 10/9

I ran the Chicago Marathon (my first & last) back in 1999. It was one of the hardest things I have ever done! This route is one of the best because it’s so flat, so a lot of people like this marathon as practice to qualify for New York & Boston. We also have lots of cheering on along the majority of the route. From music & cheerleaders in Boystown to Mariachi bands in Pilsen, lots of encouragement for all types of runners, big, small, fast, slow, young & old. If you are thinking of running, you should go check it out. It may just be the motivation you need to sign up for one. Know someone running? You can take the cta (‘L’ train) to see them at multiple points along the route. Click here for details.

good bye summer hello fall Chicago 2022 - open house chicago -

ohc – 10/15 & 16

Open House Chicago (OHC) is an annual event where you can check out some of the coolest locations in Chicago and get behind-the-scenes access that is not normally open to the public. I’ve gone multiple years and have some advice. There are over 300 sites which can be overwhelming, so pick a few each day so you can really take time to explore the neighborhood. Click here to see photos from a previous OHC.

good bye summer hello fall Chicago 2022 - graceland cemetery -

graceland cemetery tour

The Graceland Cemetery Tour is an all-year-round thing to do, but I just love coming here when the trees are changing color. There are multiple famous architects (Louis Sullivan, Mies van der Rohe & Daniel Burnham, to name a few) and well-known Chicagoans (Ernie Banks, Potter Palmer & Marshall Field) buried here. Besides being beautiful, this cemetery is a walking Chicago history tour.

good bye summer hello fall Chicago 2022 - halloween house decorations in my hood -
Halloween house decorations in my hood

halloween parades

LUMA8 and the City of Chicago are delighted to produce the Upside Down Halloween Parade as the Grand Opening of Chicago Halloweek 2022! The event takes place from 12-3pm  in Washington Park on October 22nd! The Upside Down Halloween Parade is sponsored by Blommer Chocolate Company. Click HERE for more information!

The 2022 Arts in the Dark Halloween Parade is produced by LUMA8 and the City of Chicago and will serve as the Grand Finale of Chicago Halloweek 2022! The parade is sponsored by Barry Callebaut and takes place on Saturday, October 29th from 6-8pm on State Street moving south from Lake to Van Buren.  Major support is provided by Chicago Loop Alliance.  Click HERE for more information.

Both of these events were designed to celebrate Halloween as the “artist’s holiday,” and featured cultural organizations and artists from all over the city.

We hope you can join us again next year to celebrate Chicago’s enchanting and diverse cultural community – so mark your calendars for our 2022 events!

good bye summer hello fall Chicago 2022 - dia de muertos exhibit at the national mexican museum of art -

dia de muertos

The National Museum of Mexican Art presents Día de Muertos, Memories & Offerings. The exhibition opens with a reception on September 23, 2022, at 6 pm and continues through Sunday, December 11th.

Our 36th Day of the Dead exhibition remembers the numerous individuals from Mexico and the U.S. who have died from COVID and other tragedies in the last year. Join us to experience this age-old tradition of honoring the lives of lost loved ones. Folk art, fine art, and photography make up the exhibition, bringing to life one of Mexico’s most cherished celebrations. Artists from both sides of the U.S./Mexico border express a beautiful sense of continuity and culture during this season of remembering. 

Curated by Dolores Mercado & Cesáreo Moreno.

Goodbye summer, hello fall, Chicago 2022. I hope you enjoyed my list of Fall things to do in Chicago 2022. Time to find your cozy sweaters & make your list!

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