Classic Frank Lloyd architecture against explosions of vibrant foliage, grinning Jack o’ Lanterns, the crisp setting, and the scent of apples and pumpkins in the air. There is absolutely nothing that can beat Chicago in fall! What made visiting the Windy City in autumn all the better for us was that we had countless ways to experience the season. Right from wandering around museums to indulging in simpler pleasures like visiting local pumpkin patches, the ‘Paris of the Prairie,’ as it’s also called, was a delight during our pre-winter visit. Whether it was taking thrilling and chilling tours, attending top-notch festivals, sipping apple cider, digging into pumpkin pies, or just strolling through its many parks, the Windy City’s autumnal possibilities are endless. Here’s a useful and comprehensive guide to visiting, exploring, and enjoying Chicago in autumn.
Table of contents
Weather
Chi-town, as Chicago is also known, is reputed for its bone-chilling cold weather, and rightfully so. However, autumn still has relatively mild temperatures, which range from the high 40s to the 50s degrees Fahrenheit. Hence, the city was still buzzing when the leaves turned to amber and gold and when the temperatures began to cool when we arrived. Usually, October is the driest month with average temperatures ranging from around 70 degrees Fahrenheit, gradually dropping into the mid-40 degrees Fahrenheit around November. So, don’t forget to pack your lightweight base layer, fall sweaters, and even fall jackets and Walmart fall boots.
What was great during our visit was that even towards the end of October, the sun was still out, which meant that we made full use of the city’s gorgeous outdoor patios.
Boat Cruise
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Even though it’s autumn, it’s still not too late to get out on the water in the Windy City. When we visited in October, many of the city’s boat tours were still setting sail. The one we indulged in was the amazing 1.5-hour Guided Architecture Cruise on the Chicago River. Running between 11:00 am and 5:00 pm even in late November (weather permitting), this cruise is one of the best ways to experience the city’s iconic architecture from the water. What’s more, we even had an excellent docent, who narrated fascinating stories of the buildings making up Chicago’s iconic skyline.
Even if you don’t want to see the city’s architecture, many other cruises run through autumn, including the Wendella Tours and Cruises, dining cruises, and even the Shoreline Sightseeing architecture tours. The best bit? Many offer climate-controlled and indoor options, so you can stay very comfortable, no matter the weather.
Haunted Spots and Ghost Tours
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It’s interesting to note that Chicago has tons of haunting history, whether it’s the sinking of the SS Eastland or the Great Chicago Fire. These events have led to the city now becoming famous for more than a few alleged supernatural sightings and a whole lot of urban legends. What’s interesting is that historic structures aren’t the sole places to have reported hauntings — the city has haunted hotels, cemeteries, music venues — well, the list is endless. The best time to experience it? Autumn, of course.
For instance, the bullet holes at Holy Name Cathedral, where the 1926 fatal hit of Al Capone’s rival Hymie Weiss took place, reportedly have supernatural qualities. Even the famed Lincoln Park is said to be haunted and is said to house thousands of unmarked graves. There were many other haunted places we saw, including the Red Lion Pub and Graceland Cemetery, which is supposedly the final resting place for many famous Chicagoans. There’s also the city’s largest cemetery, the 350-acre-huge Rosehill, and we had fun exploring its storied grounds.
Crime Tours
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Just like it has a long haunted history, Chicago also has a rather (in)famous crime history as well. There are many crime tours in the city, and fall is the perfect setting for the same. We wanted to explore the history of the seedy underbelly of the city, which is why we undertook various tours. One of these tours was a bus tour that began at Pearson St, delving into the tales of famous gangsters like John Dillinger and Al Capone. There were even night crime tours that took place under the cover of darkness, adding a layer of suspense to the atmosphere of true crime and thrill-seeking.
A great way to combine seeing haunted sights and former crime spots is the Gangsters and Ghosts Guided Walking Tour, a history-based guided walking tour. This tells tales of the city’s ghostly and crime past surrounding the Loop district. During fall, this tour is especially captivating, thanks to the crisp air making for a mysterious setting.
Did you know that the first person to be named “The Most Wanted Person in America” was shot down in a side alley in the city? We’re talking about John Dillinger, who died in a hail of FBI bullets beside Lincoln Park’s Biograph Theater.
Museums
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Do you love visiting museums? You’re going to have a grand time in the Windy City during autumn then. There are two museums right around Millenium Park, the famous Art Institute and the Museum of Contemporary Photography with its free collection of artwork. If you’re okay with grisly stuff, then visiting the Medieval Torture Museum is the perfect thing to do during autumn. Featuring an eerie atmosphere thanks to the realistic displays and dim lights, the museum boasts a vast collection of macabre historical torture devices.
Another museum we loved visiting was the National Museum of Mexican Art, which hosts the popular Day of the Dead celebrations that spill out into Harrison Park too. The festivities include sugar skull painting, decorated locals-made altars, and more cultural activities. Moreover, it also hosts the annual Día de Muertos exhibit, which runs from September to December, and the fundraising Día de los Muertos: Love Never Dies Ball, which takes place in the first week of November.
Last but not least, there’s also the stunning Museum Campus, which has three Beaux-Arts-inspired structures on Lake Michigan’s shores. Set amidst lush gardens and parks sit the Shedd Aquarium, Field Museum, and Adler Planetarium, the last of which is the Western Hemisphere’s oldest planetarium.
Gardens and Parks
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Despite being an urban jungle, Chicago boasts tons of green spaces, which boast colorful autumn foliage when the season comes around. One of the places we loved was the 385-acre-huge Chicago Botanic Gardens, which featured an “Autumn-Hued Wonderland” with a striking seasonal display. Besides hosting a Fall Festival & Bulb Sale in the first week of October, the gardens also have nature-themed activities, gardening workshops, and fall-themed displays. However, their most famous event is the “Night of 1,000 Jack-O-Lanterns,” where we saw more than 1,000 hand-carved pumpkins!
When the question of what to do in Chicago in October arises, strolling in Lincoln Park to catch the captivating display of autumn hues is always part of the answer. You could even join a guided tour of the Lincoln Park Conservatory or the Garfield Park Conservatory, one of the country’s largest, to see the foliage changes and seasonal blooms. We even walked the 2.7-mi-long elevated Bloomingdale Trail that offered up-close treetop views of the changing fall hues. If you have the time, don’t miss visiting the 40-acre Promontory Point, the Lincoln Park Zoo, the Garden of the Phoenix, and the Burnham Nature Sanctuary.
Food Fixes
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The cooler weather made us hungry all the time, so it was only natural for us to enjoy all of Chicago’s favorite foods during autumn. The Chicago Secret Food Tour took us on a delicious tour of the city’s best eating and drinking spots. Helmed by a fun, knowledgeable guide, we stopped at six different locations in the Loop district to take a bite of classic Windy City foods. Think Chicago-style hot dogs (no ketchup!), Italian beef sandwiches, deep-dish pizza, and even gourmet popcorn? Did you know that the brownie was invented in this city? Yes!
That wasn’t all, though. We had equally amazing fun on the Barrel Bus Craft Brewery Tour, as we’re huge craft beer fans! This fun and exciting tour had us boarding a barrel-shaped bus that took us to some of the city’s hippest breweries and cool taprooms. The experience was extremely immersive and we sampled as much as 45-5o oz of different craft beers on this VIP behind-the-scenes tour that also took us to Chicago’s best nano-brewery!
If you’re a gourmand, we recommend not missing one of Chicago’s signature culinary events, Chicago Gourmet, which includes an elevated tasting experience, a celebratory brunch, and even a burger competition!
Fall Festivals and Events
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The cherry on top of our autumnal Windy City vacation was the many Chicago fall events we attended, and they were all so unique and amazing that we’d recommend not missing a single one of them! At the top of the list is Halloween; Chicago’s buzzing nightlife scene is sure to get you into some or the other party, whether you’re looking for something casual or want to party until 4 a.m.!
Family-friendly events are aplenty; we especially loved Oaktoberfest in Oak Park, which combined live music, great food, and a host of fun activities for the kids, including an arts and crafts station and a petting zoo. The children also loved Highwood’s Great Highwood Pumpkin Festival, which had a parade, a pumpkin-carving contest, and thousands of jack-o’-lanterns. Moreover, Jack’s Pumpkin Pop-Up even had carnival games, axe-throwing, and a wonderful corn maze. One of the biggest fall events was the one at Lincoln Park Zoo, which had a pumpkin patch, stilt walkers, live pumpkin carvers, and whatnot. Plus, it runs from late September to late October.
We can’t talk about fall without talking about apples; think Lincoln Square Ravenswood Apple Fest. It celebrates the fall harvest with autumnal treats like apple cider, apple pie, etc., with shopping and live music thrown into the mix. If you love your brews, don’t miss the Cider and Ale Festival, the Lincoln Park Wine Festival, and the Chicago Beer Festival. The best of them all was the Island Party Hut Chicago Riverwalk Fall Fest, where we sipped fall cocktails, jumped on hayrides, roamed a pumpkin patch, and listened to live music with the Chicago River in the background.
Apple and Pumpkin Picking
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Autumn in Chicago is all about pumpkins and apples and the best places to get them. The season brings an abundance of pumpkins and apples, with the former coming in all sorts of sizes and shapes. Despite them being often carved and lit up for Halloween, even choosing pumpkins at the start of October is a tradition. Many pumpkin patches in and around the city mark the beginning of autumn with photo ops, rides, craft beer, baked goodies, and, of course, fresh produce.
So, we headed out to one of the best farms in the region, Richardson Adventure Farm, which had not only a huge pumpkin patch but also miles of maze trails. What’s more, we could carve, eat, smash, and even throw giant pumpkins off a 50-ft observation tower! The best bit? They had a host of Halloween activities such as a huge slide, a petting zoo, zorbing, zip-lining, and more.
Another aspect of autumn in Chicago that we loved was autumn fruit harvesting and picking at apple orchards. Chicago’s suburbs and countryside are full of bountiful orchards where one can pick pounds of apples for snacking, baking, and more. One such farm is Prairie Sky Orchard, which specializes in 14 varieties of Asian pears and apples. Besides the famed Honeycrisp variety, there were also Red Delicious, Fuji, and more. There’s even a Koffee Kiosk that sells apple cider donuts and hot chocolate. Beginning September 6th, the farm is open from Thursdays to Sundays between 10 am and 5 pm.
Halloween Events
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Ghoulish creatures, cackling witches, and ghosts come out to play as Chicago kicks off what is an inimitable Halloween. It’s not just about Halloween parties in the city; it’s also time for haunted house experiences, rooftop horror movies, and fake-blood-soaked events of all kinds. Of course, we also saw family-friendly events, spooky tours of haunted places, and glowing pumpkin displays.
One of our favorite events to attend was the Northalsted Halloween Parade, an OTT nighttime spectacle. The iconic parade took place in historic Boystown, a.k.a. the city’s gayborhood, and featured live music, eye-popping displays, and elaborate costumes. It kicked off as early as 6:30 p.m., allowing us to enjoy thoroughly with the kids. For more kid-friendly events, you can also try the Spooky Zoo at Lincoln Park Zoo and Brookfield Zoo’s “Boo! at the Zoo,” another excellent family-friendly celebration.
For the adults, we recommend the Sweet Dreams: The Halloween Experience, an indoor/outdoor Halloween pop-up at Rizzo’s Bar and Inn. It’s dedicated to 25 classic horror movies, including Friday the 13th, Candy Man, and Nightmare on Elm Street, lasting through Halloween.
Fall Hues
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Sitting at the top of the list is the astounding autumn aesthetics sweeping through Chicago, offering postcard views everywhere. As the Windy City transforms from green to crimson, there are multiple enchanting places to revel in the autumnal foliage.
One of our favorite things to do was indulge in a scenic drive along Lake Shore Drive for fabulous fall views of Lake Michigan framed by vibrant trees. Next, we visited Grant and Millennium Parks, completing the trifecta for enjoying both the city’s iconic skyline and its vibrant foliage. The highlight, though, was visiting The Morton Arboretum, a.k.a. the “Champions of the Trees.” This 1,700-acre tree research center and nature conservatory certainly lives up to its name and houses more than 222,000 living plants.
“Seeing an urban space swathed in fall foliage is something else, and it looks all the more beautiful when it comes to Chicago!”
WOW Travel
While the views from the ground are breathtaking enough, the views from the sky are entirely something else. We’re talking about Skydeck Chicago, one of the best places for sky-high views in the city. It boasts an observation from where we spied excellent views of Chicago’s autumnal colors, thus leaving us with a unique perspective on the Windy City’s fall transformation.
Where to Stay in Chicago?
- The Publishing House B&B: One of the most historic hotels in Chicago, the Publishing House B&B is the millennial version of a traditional B&B. Sitting in a century-old historic building with only 11 rooms, the rehabbed space boasts claw foot tubs, vintage rugs, and leafy tropical plants. We especially loved the rooms with exposed brick walls, wood floors, plush beds, flea market finds and trinkets, light-flooded windows, fluffy bathrobes, and modern bathrooms with walk-in showers. What’s more, we were treated to the most delicious breakfasts every morning in the kitchen and would end the day at the press room, a lively basement wine bar. Did we mention the living area, which also has a piano? Yep.
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- Staypineapple, An Iconic Hotel, The Loop: This Chicago boutique hotel is luxurious to the boot. Sitting in a National Historic Landmark Building, the hotel boasted plush rooms with luxurious beds, Bluetooth docking stations, mini-fridges, and Keurig coffeemakers. The suites even had complimentary in-room spa treatments and separate living rooms. Furthermore, the rest of the hotel is no less impressive, with an award-winning restaurant, complimentary treats, coffee and tea in the lobby all day, and even a gym.
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Places To Eat
- Paciugo: Who can say no to gelato, whether it’s in the fall or not? Well, the seemingly endless list of choices for gelato here has a ton of new flavors in autumn. Think seasonal flavors like amaretto pumpkin pie, pumpkin cheesecake, and many more.
- Piccolo Sogno: The autumn menu at this restaurant is all about dishes designed especially for the fall season. Think salads like the prosciutto antipasti with fall melon or the Insalata di Barbabietole with greens, fennel, and local beets. We went crazy for the will go crazy for Gnocchi D’ Autunno and Cappellacci di Zucca, which was pasta stuffed with pumpkin.
