Fall Activities in Chicago: 2024 Festivals and Foliage Guide

Grinning Jack o’ Lanterns, explosions of fall foliage, and Frank Lloyd Wright architecture. Nothing beats Chicago in the fall. From the simple pleasures of visiting a local pumpkin patch to pondering masterpieces at the Art Institute, there are countless ways to welcome in the cooler months in the Windy City.

Follow along as we dive into the best fall activities in Chicago.

Pursue the spellbinding city skyline from a Lake Michigan cruise, or settle in for family-friendly entertainment at the Botanic Garden.

Whether you wish to celebrate autumn with a cold brew or a spine-chilling crime tour, Chi-town is chock full of Midwestern delights.

Best Time to Visit Chicago in the Fall

Ever experienced the joy of a Chicago fall? While many Chicagoans may favor the warmer summer months, there’s something undeniable about this urban oasis come September. Cooler temperatures pave the way for eager tourists to tackle a bevy of Chicago fall activities.

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Enjoy Illinois daytime temperatures in the 60s and 70s, but pack a light jacket as evening can see a nippy forecast of 40 degrees. This temperate weather is ideal for leaf gazing. Embrace your inner artist as you document the vivid Chicago fall colors of copper, yellow, orange, and red.

Looking to experience an authentic Oktoberfest? Or would you rather save your energy for apple picking? Depending on your list of things to do in Chicago in the fall, you may wish to schedule your visit for a specific time. 

Chicago Hotels

World-class restaurants, revered architecture, and a mouth-watering food scene make Chicago an enviable destination all year long. Make the most of your autumnal escape and take advantage of the plethora of things to do in the fall in Chicago, when you extend your stay and book a premier Chicago Hotel.

From boutique accommodations featuring marble tiled bathrooms to sumptuous lodgings minutes from Magnificent Mile, we have hotels for every style and taste. As always, reserve your lodgings stress-free, knowing you are always guaranteed our lowest rates online.

Things to Do in Fall Chicago

Apple and Pumpkin Picking

Got a hankering for a piping cup of apple cider or a fluffy homemade apple fritter? Those yearning for a little slice of the simple life need only head to one of the city’s apple orchards or local farms. Wander through overflowing pumpkin patches, tackle a corn maze, or pause for a fridge-worthy photo, courtesy of the fall foliage Chicago.

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Delight in the bounty of your haul when you bake up a strudel-topped apple pie or crisp. The picking season usually starts in mid-September so plan accordingly. nbsp;

Kuipers Family Farm

Kid-friendly and oh-so-fun, Kuipers Family Farm has been entertaining mini scarecrows and gourd pickers for over 20 years. Located in the picturesque town of Maple Park and just 60 miles from Chicago, Kuiper’s is home to an Apple Orchard and a Pumpkin Patch.

From the end of August through October, set your sights on Empires, Fujis, Galas, and more. The Pumpkin Patch is open for picking from mid-September through the end of October. In addition to giant gourds, your entry includes access to farm-themed attractions such as Tractor Tire Mountain, the Barnyard Ball toss, and pig races.

photo credit: Kuipers Family Farm via Facebook

Country Line Orchard

Show your special someone that they’re truly the apple of your eye when you bring home a bushel of freshly picked McIntoshes. Country Line Orchard is just 30 miles from Chi-town and delivers an overflow of festive fall charm. Little munchkins will love their themed corn maze and petting Pygmy goats.

While city dwellers will relish the scenic tractor rides and pay for what you pick prices. Visiting in October? Post apple harvest, stay tuned for some orange-hued beauties as the Pumpkin Patch opens on October 1st. Snap endless selfies in front of their famous pumpkin house, or fuel up on delectable homemade fudge and pumpkin doughnuts. 

Shoreline Sightseeing Boat Tour

Sparkling Lake Michigan, unparalleled architecture, and a healthy helping of Second City history make the Shoreline Sightseeing Boat Tour a can’t-miss activity. Immerse yourself in the beauty of skyscrapers, changing leaves, and more when you choose from various Lake and River tours.

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Uncover the roots of modern American architecture as you savor views of the Willis and Tribune Tower. All tours include expert narration, sensational views, and snacks available for purchase.

photo credit: Shoreline Sightseeing via Facebook

Fall Events Chicago Navy Pier

Classic carnival rides, delicious eats, and plenty of kid-friendly attractions make the Navy Pier an excellent choice for some open-air amusement. Climb aboard the historic carousel, soar nearly 200 feet in the sky on the Centennial Wheel, or let loose in the Children’s Museum. From authentic art spaces designed for creative play to classic Chicago hot dogs, there’s plenty to love at the ‘People’s Pier.’

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Well known for its variety of public events, programs, and artistic displays. The Pier is where visitors and locals alike collide. Stay tuned to discover their fall schedule, and pop into their Artisan Market in September for a dynamic, one-of-a-kind shopping experience. 

Morton Arboretum

Get your fill of fresh air, flowering trees, and more when you ditch the pavement for a plant oasis. Morton Arboretum has been inspiring city dwellers for nearly a century with its vast collection of trees, flowers, and gardens. Revel in natural landscapes of woodlands, prairies, lakes, and streams as you witness almost 5,000 species of plants.

Autumn at the Arboretum offers a riotous display of changing colors, ranging from the deepening Virginia creeper vines to the yellowing oak leaves. In addition, guests can enjoy festive family fall events in Chicago, including the Scarecrow Trail, a Glass Pumpkin Patch, and the Cider and Ale Festival. 

photo credit: Let me Meander via Facebook

Chicago Botanic Garden in the Fall

Nearly 400 acres on and around nine islands make up the sprawling grounds of the Chicago Botanic Garden. Green-thumbed guests can wander through 28 gardens and four natural areas, including six miles of shoreline. Envelope yourself in the European charm of the English Walled Garden, or spend time enjoying the birds and butterflies of the Barbara Brown Nature Reserve.

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For a truly Pinterest-worthy fall backdrop, stroll through the harvest-hued Dixon Prairie. Visitors popping by on select dates in October can catch a glimpse of giant gourds up to 150 pounds as they witness the Night of 1,000 Jack-o’-Lanterns.

In the evening, some of the best fall activites include professionally carved pumpkins, costumed entertainers, live demos, light snacks, and more. 

photo credit: Chicago Botanic Garden via Facebook

Fall Activities Chicago Art & Culture

Art Institute of Chicago

Besides the White Sox and Deep Dish, the Windy City is well revered for its outstanding art institutions. Gaze upon masterpieces such as Picasso’s ‘The Old Guitarist’ and works by Andy Warhol when you visit the Art Institute of Chicago. Consistently ranked one of the world’s top museums, their fine art collection is unmatched.

From Dali to Edward Hopper and Cindy Sherman, the museum is a fascinating mix of contemporary and historical works. Interested in going beyond the canvas? Book an Art Institute of Chicago Skip-the-Line Guided Tour to dive even deeper into the backstory of this expansive collection. 

Chicago Crime Tours

Like your fall activities in Chicago flavored with a touch of crime noir? Embrace the darker side of the White City with a Chicago Crime Tour. Mobsters, criminals, and gangsters of all ilks will be on full display as you explore this murky underworld.

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Climb aboard your luxury climate-controlled bus and prepare for 90 minutes of history, sightseeing, and photo opportunities. Scope out the iconic St Valentine’s Day Massacre, learn all about Al Capone, and cruise through Lincoln Park. Stuffed full of stories featuring John Dillinger and the Chicago Mob, this is the ideal tour for any true crime buff. 

man standing on steps speaking with a group of people at the CHICAGO CRIME TOURS AND EXPERIENCES-Gangsters, Mobsters and Criminals in Chicago, Illinois, USA

Night Crime Tour

Craving a smidge of spooky? Discover the secrets of Chi-town under the cover of nightfall with your 2.5-hour Night Crime Tour. Designed for guests 21 and over, this luxury bus tour cruises through the streets of Chicago to shine a light on its peppered past.

Stop by iconic crime scenes, historic bars, and landmark buildings. Snap pics of the Cook County Criminal Courthouse as you are regaled with tales of the Untouchables, Frank “The Enforcer” Nitti, and Cap George Streeter.

Fall Festivals in Chicago

Open House Chicago

Calling all architecture aficionados! Have you ever wanted to pull back the curtain on the Windy City’s most storied structures and landmarks? Every October, the Chicago Architecture Center hosts Open House Chicago. This free fall festival event is open to the public and features a month-long festival of architecture trails, talks, and programming.

Relish the unparalleled behind-the-scenes access to architecture, history, and culturally significant sites across the city. Pop by the Givins Castle, Boxville, the Chicago Observation Deck, and more. This year’s program will highlight over 20 Chi-town neighborhoods and include ten self-guided tours.

In-person site visits will be staged on October 14th and 15th, while extended programming and self-guided visits will be available all month long.

photo credit: Chicago Architecture Center via Facebook

Chicago Beer Fest

Ciders, ales, and IPAs, oh my! Usher in the autumnal season with plenty of suds when you pre-purchase your ticket to the Chicago Beer Fest.

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This annual event will take place at the legendary Field Museum in early October and features libations from over 65 breweries. Sample season flavors from Goose Island, Penrose, Brewdog, and more. Sip away on pumpkin lagers and pick up some snacks to share. Move fast, as tickets will not be available at the door!

friends holding drinks posing for photo in photobooth of Chicago Beer Fest in Chicago, Illinois, USA
photo credit: XplorChicago via Facebook

Oktoberfest Chicago

Willkommen! Raise a beer stein and prime your lederhosen for a day of German goodness at Chicago’s annual Oktoberfest. Held every September for over 100 years, this epic festival features parades, costumes, and of course, plenty of beer!

Stuff yourself silly with pretzels and sausage, and try your hand at traditional folk dancing. With plenty of carnival games for the kids and music from three German bands, this event is ideal for all ages. 

Lincoln Square Apple Fest by the Lincoln Square Ravenswood Chamber of Commerce

Juicy Mutsu, Honey Crisp, Gala, and more. Apple lovers of all shapes and sizes flock to Lincoln Square each year to savor the fall season. The Lincoln Square Ravenswood Apple Fest is a full day of carnival games, sweet eats, and live music.

The action will kick off in September and last through October. Snack on caramel-covered apples, dig into a slice of pie or sip on perfectly spiced cider. Groove along to themed music, or slide down the inflatable bounce castle. Don’t forget to bring Fido, as this is a pup-friendly affair.

crowd of people gathered in front of stage with band playing set up on middle of street at Apple Fest with stall on the side in Chicago, Illinois, USA
photo credit: The StingRays via Facebook

Infamous gangsters, unparalleled art museums, and a hearty dose of nature come together to make the Second City a timeless destination.

However, as the leaves began to change from verdant green to brilliant orange, yellow, and red, this Midwestern metropolis adopts even more charm. There is something magical about taking in the Fall foliage in Chicago. 

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Settle into the autumnal spirit as you traipse through towering Oaks and shrubs at the Arboretum or the Lincoln Park Zoo. Or marvel at Van Gogh’s brush strokes at the Art Institute.

Feel the flavors of fall welcome you as you conquer corn mazes or go to town on some hot cider donuts.

So, what are you waiting for? Celebrate this season of abundance, warmth, and family in the Second City today.

Tell us, What’s Your Favorite Thing About Fall in Chicago?

Did we miss any of the best fall activities?

Which of our best fall activities Chicago will you do first?

Leave us a comment below!

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Written by Isis Maya Nissman

A New York native, Isis-Maya spent most of her professional life working in TV production until a vacation whisked her away to Central...

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