Best Things to Do in Fall in Chicago

It's a bounty of food and fall fun in Chicago

Each season brings its own joy to Chicago and autumn does not disappoint. While exciting hotel and restaurant openings continue to entertain locals and visitors, special seasonal celebrations add the spice to the pumpkin latte. It's no wonder that the best restaurant city on the planet is host to world-class culinary events this fall including Chicago Gourmet. Festivals fusing autumn treats, live music and activities from the weird (grape spitting at Lynfred Winery's Annual Oktoberfest & Pig Roast) to the wonderful (strolling Jack's Pumpkin Glow or Jack's Pumpkin Nights), dot the calendar from September to November. Be prepared to be awed while nosing around the city's architectural wonders during the fabulous Open House Chicago or viewing the work of American icon, Andy Warhol, at the Art Institute's newest exhibition. A visit to 13th Floor will shake the cobwebs from your mind. Get to Hyde Park to try some south side vittles and take in new art installations at The Oriental Institute Museum of the University of Chicago celebrating 100 years of pioneering research and study of the earliest civilizations in the ancient Middle East. Take that big, crisp bite out of fall in Chicago. It's delicious. 


Whether your pumpkin carving skills are still toddler-esque or you're a professional squash sculptor, Jack's Pumpkin Glow will delight families, couples and young adults. You'll be an Insta maniac snapping pics of 5,000 hand-carved pumpkins and assorted glowing foliage illuminating the Sensory Garden Playground in Lisle on select dates in October. Witness life-sized sculptures, Halloween characters, superheroes, dinosaurs, musicians and movie stars lining the trail then nosh on seasonal food and beverages watching master carvers adding 1000 fresh carvings every week throughout the season. Ask the pros how to expand your carving skills and carving tips choose a specimen to tote home from the pumpkin patch. Jack's Pumpkin Glow opens at twilight beginning on Thursday, Oct, 3, 2019, and runs on select dates through Oct. 27, 2019. Tickets are sold in 30-minute intervals insuring a leisurely stroll.

Recommended for Things to Do in Fall because: Five-thousand expertly carved pumpkins, plus autumnal food and drink get locals and visitors outdoors before it gets polar.

Jacky's expert tip: There's an Autism Glows event on Sunday, Oct. 6: a sensory-friendly night open earlier with smaller crowds (only a limited amount of tickets will be available). Tickets prices are lower this night, too.

Read more about Jack's Pumpkin Glow →

If the current political climate or the daily news doesn't scare the bejesus out of you, 13th Floor Chicago is just what monsters ordered. One of the Chicago area's largest haunted houses (close to 40,000 square feet of indoor space), 13th Floor returns for a sixth season with two new haunted attractions. Classic movie monsters (Frankenstein, the Mummy and Werewolf, et. al.) have laid dormant for decades inside an abandoned theater. In Creature Feature, they emerge from the silver screen and into the present. Witness the Other Side when bikers heading to the Quarry see their friend vanish. Vampires, maniac clowns and aliens with a saliva issue insure plenty of screams. Leave Junior back home with a babysitter unless they're over 12 and not of the faint of heart. 13th Floor Chicago is open on select dates from Friday, Sept. 13, 2019, through November 9, 2019.

Recommended for Things to Do in Fall because: Who doesn't need to scream their head off these days? 13th Floor is an elaborate voluntary scare ending with laughs and a sigh of relief.

Jacky's expert tip: There's free parking at Xsport Fitness 1101 W North Ave, Melrose Park, just a few minutes walk from 13th Floor.

Read more about 13th Floor →

You'll have the answer to, "How do you like them apples," at Lincoln Square Neighborhood's 32nd Annual Apple Fest, Oct. 5-6. Hours are 9am-6pm both days that offer fresh apples, cider, dumplings, pies and other creations, plus live music and activities for the little Honey Crisps in your life at the Leland Avenue Kids Zone, featuring child-focused activities all day. Apple Fest is a comfortable way to soak up the waning rays and taste and purchase apple confections: Apple Cinnamon Empanadas; Apple & Pork Tacos; Apple Crisp; Biscuits with Apple Butter; Apple Curry Chicken; Apple Donuts, Pancakes and Scones; and Apple Smoked Beef Brisket. Count on a Pooch Costume Contest; live New Orleans Jazz, Indie, Folk and Americana music on stage. Bakers will want to visit on Sunday for the 3rd annual Apple Pie Bake-Off when the best looking and tasting pies win prizes. Admission is a suggested $5 donation.

Recommended for Things to Do in Fall because: Apple Fest is a comfortable autumn outing to soak up the waning rays of sun amid fall colors and up your antioxidant levels with apples.

Jacky's expert tip: Take a bigger bite out of your visit and amble through the neighborhood's indie shops, restaurants and attractions such as the Old Town School of Folk Music.

Read more about Lincoln Square Ravenswood Apple Fest →


Jack's Pumpkin Nights returns for locals and visitors who just want to Uber it to some favorite fall festivities right in the heart of Chicago. In its second year, the multi-sensory, outdoor, pop-up experience stretches over two acres in the Goose Island neighborhood where revelers can wander through a harvest-time land that you might not get at exurban Illinois farms. Jack's Pumpkin Nights feature Chicago's largest corn maze with a hidden bar, pumpkin carving, laugh-out-loud carnival games, colorful light displays, and an array of nightly entertainment. There's a plethora of photo opportunities and seasonal food and brews the beer and hidden cider garden. The pop-up is propped up Oct. 3 through Nov. 3, 2019.

Recommended for Things to Do in Fall because: You may not get the farm experience as at a rural autumn fair, but it's a nearby option to get outdoors and enjoy the season.

Jacky's expert tip: The fall experience works for both kids and adults. Tickets, $15-$19, are on sale at the web site, with some family and group packages, too.

Read more about Jack's Pumpkin Nights →

Entertain your inner Arnold and party Oktoberfest-style at Lynfred Winery's Annual Oktoberfest & Pig Roast. A Teutonic fall fête is as close as Roselle and before you know it, you'll be locking arms with others swaying to the strains of "Edelweiss." It's two days of German sing-a-longs and dance performances plus Insta moments like Adult and Kid Grape Spitting, Cork Tossing and Grape Stomping Contests. Those dressed in lederhosen or like Lucy stomping grapes should enter the costume contest. Enjoy roasted pig either as a sandwich or full meal, served with warm German potato salad and all the fixings. Other options include grilled bratwurst burgers, homemade chili, freshly grilled sweet corn and a dessert booth serving taffy apples, apple strudel and German chocolate cake. Naturally, you'll want to sample Lynfred's Oktoberfest wine, which will be released at the start of the festival.

Recommended for Things to Do in Fall because: It's a chance to spend time outdoors stomping grapes, sipping wine and swaying to the strains of "Edelweiss."

Jacky's expert tip: The 40th annual celebration takes place Sept. 28-29 and admission is $10 for anyone 14 and older. Tickets for food and beverage are extra.

Read more about Lynfred Winery →

Chicago museums are world-class but crowds and high admission prices can be painful. Consider a visit to The Oriental Institute Museum of the University of Chicago especially during its centennial celebrating 100 years of pioneering research and study of the earliest civilizations in the ancient Middle East. Entry is an optional suggested donation. There's a public kickoff on Saturday, Sept. 28 with music performances from the Hyde Park Jazz Festival, kids' activities and gallery talks by OI scholars and archaeologists, but if you miss that, don't fret. Witness new visual art installations by acclaimed Iraqi-American artist Michael Rakowitz and Syrian artist and architect Mohamad Hafez plus gallery displays with never-before-seen artifacts from the incredible OI collection through June 2020.

Recommended for Things to Do in Fall because: The OI Museum exhibits the largest collection of ancient Middle East artifacts in the US and admission is by donation.

Jacky's expert tip: Check the web site for Centennial events taking place throughout autumn including film screenings, gallery talks and lectures like "Frank Lloyd Wright's Vision for Greater Baghdad."

Read more about Oriental Institute Centennial →

Chicago has venues for jazz, blues, rock, indie and every other genre but you can get all that and more in one place - City Winery. A fully functioning winery, fine dining and a wonderful intimate space for concerts, the venue has a diverse line-up for fall. In October, you can see Lee Ann Womack; Paula Cole; Robbie Fulks; Justin Townes Earle, Madeleine Peyroux and John Hiatt, among others. November brings Alice in Chains frontman, William DuVall; Edwin McCain; The Flatlanders; Booker T.Jones; Jimmy Webb; Don McClean; Cherie Currie of The Runaways; Digable Planets; comic Heather McDonald; and even a Chicago Philharmonic Fall series for classical music fans. Have a cocktail, glass of wine, a mug of brew, a flatbread and, incredibly - an actual seat at a table - for a comfortable evening of live music.

Recommended for Things to Do in Fall because: Oenophiles and fans of great acoustics merge at City Winery where you can also claim fine dining like duck tacos and baked eggplant flatbread.

Jacky's expert tip: There's a separate restaurant if you want to dine before the show but food and drinks are available within the concert venue, too.

Read more about City Winery →

There are those who say the city is oversaturated with restaurants and to that we say - "eat it all up" especially at Chicago Gourmet. The event turns 12 in 2019 and the three-day high-end food festival offers a bounty of highlights. Taking place in Millennium Park Sept. 27-29, 2019. the fest's theme is "Lights, Camera, Napkin!, connecting the culinary and entertainment worlds. The cast of celebrity chefs includes Rick Bayless, Andrew Zimmern, Stephanie Izard, Joe Flamm, Tony Mantuano, Lorena Garcia, Art Smith, Jeff Mauro, Sarah Grueneberg,, Jose Garces, Carrie Nahabedian and Kwame Onwuache, as well as a roster of master sommeliers and leading spirits and beer experts. Expect interactive cooking demos, educational seminars, beverage tastings, book signings and an insane amount of food. New in 2019: Jef Comedy Jam hosted by Jeff Mauro; The Big Chill(i): Gourmet Chili Cook-Off; and a "Hamilton" event with Rick Bayless.

Recommended for Things to Do in Fall because: Chicago Gourmet stands out as one of the nation's premier culinary experiences.

Jacky's expert tip: Main event weekend passes and tickets for Encore Events sell out so be sure to purchase yours soon.

Read more about Chicago Gourmet →

Just as autumn hues peak and the air begins to chill, the Art Institute of Chicago adds another burst of color and exhilaration: the first major retrospective of Andy Warhol's work to be organized by a US institution in 30 years. From Oct 20, 2019â€"Jan 26, 2020, Andy Warhol†"From A to B and Back Again displays more than 350 works by the beloved and inspiring American Pop artist. Come on - how many times have you heard his words, " "In the future, everyone will be world-famous for 15 minutes," (hello, Insta influencers). The exhibition includes paintings, sculpture, drawings, prints, videos, archival and printed material, installation, films and media works. It's certain that Warhol was a true visionary, challenging our trust in images and cultural icons.

Recommended for Things to Do in Fall because: It's the first major retrospective of the artist and pop phenom's work organized by a US institution in 30 years.

Jacky's expert tip: Consider some of the ancillary action like a course in "Painting, Pop and Printmaking" or a sketch class in pop subjects and techniques.

Read more about Art Institute of Chicago →

Annually, and specifically Oct. 19-20 in 2019, Chicago locals and visitors have the opportunity to witness hidden architectural treasures tucked among the city's diverse neighborhoods during the Chicago Architecture Center's Open House Chicago. The free public festival is a cornucopia of behind-the-scenes access to more than 350 sites in 37 neighborhoods including skyscrapers, mansions, hidden rooms, magnificent theaters, hotels, private clubs, industrial sites, offices and sacred spaces - places that are rarely, if ever, open to the public. Some sites offer discussions and family-friendly activities. One of the largest architecture festivals in the world, the event is free and one not to be missed. In celebration of 2019 being designated the Year of Chicago Theatre, there is a new 'trail' of 40+ venues and theater-related sites, literally from A (Athenaeum Theater in Lakeview) to Z (Zap Props in Bridgeport).

Recommended for Things to Do in Fall because: Locals love it because they can get into spaces that are rarely open to the public and tourists win the architectural sweepstakes visiting this weekend.

Jacky's expert tip: Times vary by site, Saturday to Sunday, Oct. 19-20, 2019 so make a plan to visit the spaces about which you are most curious.

Read more about Open House Chicago →


Meet Jacky Runice

Born in Bucktown when bulletproof was a home safety choice and not a coffee order, Jacky Runice has been knocking around Chicago as a professional print, online and broadcast journalist and...  More About Jacky