Fall is absolutely the BEST season in Chicago. Neighborhoods are alive with fall colors and crunchy leaves as you walk from the coffee shop to run errands on a crisp fall morning. Each neighborhood has a different vibe- from romantic Ravenswood with tree lined streets that are decorated for the season, to the hip area of the Loop where you’ll be sure to see the latest and greatest in fall fashions as women duck from the train to work, you’ll have lots to see!
Yes, to be honest- fall means we are one season closer to the dreaded winter, but this season is full of cozy and colorful things to do before it gets too chilly!
Get out and enjoy the season while it’s here, here are my favorite things to do for fall in Chicago.
The Chicago Parks District knows winter is awful, so in summer and fall, they step up their game for awesome free activities that mean you don’t have to drive out of the city to enjoy warm apple cider or pick out your perfect pumpkin at a pop-up patch. You can find local pumpkin patches in your neighborhood, which is awesome- because lugging a pumpkin on the Metra from the ‘burbs is a challenge.
In fall, they offer Halloween in the Parks, a comprehensive guide to Halloween in the Windy City. Whether you want to celebrate Dia De Los Muertos by making sugar skulls and Freida Kahlo bags, or you’d simply like to take a pumpkin home on the train if you don’t have a car, you’ll find something awesome for all ages.
The skyline is truly breathtaking from Navy Pier & nightly cruises! (Source.)
I’m sorry, but our skyline is one of the best in the world, but have you really seen it? This fall, Shoreline cruises is offering their annual hard cider tasting cruises. Tickets are $39, but it’s sure to be a unique experience and you’ll be able to get some gorgeous shots that will surely make for excellent Facebook cover photos! The Odyssey also offers Monday Night Prix Fixe cruises so you can enjoy the fall skyline without catching chill (also their NYE cruise is absolutely the best!).
Okay, this isn’t a cruise, but since we’re on the topic of sipping if you missed Riot Fest (Chicago’s way cooler-than-Lolapalooza music fest), you can always try Wine Riot. Tickets are $60, but you’ll get a souvenir glass and access to an insane amount of good wines, so you can sip your way around the world without leaving Chicago. Join the fun on Oct 16-17th. If you’ve felt you’ve wanted to try wines but the scene is too snobby, this is sure to be a fun and memorable event geared for a less pretentious crowd.
Enjoying it from the water is by far one of my favorite picks. If a cruise isn’t an option for you, enjoy the fall season and enjoy a pink skyline for Breast Cancer Awareness month by picnicking out by the planetarium for some gorgeous views.
You’ll sure to have a memorable day at the Chicago Art Institute. (Source.)
Chicago Museum Week
In the winter, you can visit the Art Institute for free on select Thursdays. If you can’t handle the wait, Chicago Museum Week offers some discounts to celebrate the cultural and educational offerings of our city from October 1st-7th. If you missed it this year, bookmark it to come back and enjoy some of the best the city has to offer.
Though it isn’t as frugal as “free,” you’re missing the insane crowds of summer and the bone-chilling winds of winter, fall is a great time to visit the various museums of Chicago. You’ll get to savor the Field Museum, Shedd Aquarium, Adler Planetarium, Museum of Science & Industry and of course, my personal favorite, the Art Institute, at a discount- but if you missed Museum Week, you can also save by getting a CityPass, or using a military or student discount.. (Insider Tip: The Art Institute is next to both a Starbucks and a Caribou Coffee….and the start of Route 66 for a photo opp. Enjoy!)
The Best Running Season, EVER.
Going for a run in the fall is a leafy, crunchy wonderland. Our tree lined streets, and prairie preserves near the lakefront path make for some of the best runs of the year. You can check out some of the best places to run in Chicago, but honestly- each neighborhood has it’s own vibe. My favorite neighborhoods are on the north end, so you can enjoy the fall decorations and gorgeous fall colors, but the Loop & Wicker Park are fun urban streets to run through to scope out places to shop and eat later.
If you’re prefer more of a guided tour of Chicago, I recently ran with Chicago Running Tours and LOVED it. On our Tragic Events Tour 5k, we got to learn about Chicago’s downtown history, prison system and yes- the notorious Chicago Fire which pretty much leveled the city in 1871. It was one of the best runs I’ve been on in the four years I’ve lived here, and tours go just about year round.
If you’re hoping to get the most out of the season, you can snack smarter with one of my favorite bars- goodnessknows. It has 100 milligrams of naturally-occurring cocoa flavanols – the good stuff found inside cocoa beans, and is a great way to satisfy your sweet tooth without reaching for a candy bar.
They also partnered with a great run that helps feed Chicago area families- the Run 10 Feed 10, a 10k that I ran last weekend. After a great 10k along the lake path, it was nice to snack on one of my favorite bars for a chocolate fix with fruits and nuts.
goodnessknows is now a partner of this blog, and is one of the tastiest things in my cupboard, great for people who need a better choice for a snack that’s both sweet and loaded with protein for sustained energy. My fave is the peach & cherry, almond dark chocolate… peach + dark chocolate is so heavenly, it makes running a 10k sort of worth it- plus, knowing that 10 Chicago families got meals is a pretty nice perk too!
Would you like to win a $100 Visa Giftcard to explore your favorite fall activities?
Comment below with your favorite things about fall, and what you’d like to do on your next Chicago visit to win!
Winner will be chosen on October 3oth, so please leave your email along with your comment so I can contact you!