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.)
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!)
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!
Winner will be chosen on October 3oth, so please leave your email along with your comment so I can contact you!
After reading your post, I wish I was going to Chicago for BlogHer Food this year in November as Chicago in Fall -in these pictures -is gorgeous! One of my fav fall activities is hiking and I gotta try Goodness bars the next time I go for a long one!
I love the change in weather and the fall festivals that are going on. I would visit the Navy Pier.
jslbrown2009 at aol dot com
My favorite things about Fall are just knowing that the upcoming months include lots of family time centered around some of my favorite holidays–Thanksgiving and Christmas. I have never visited Chicago, but if I did I would have to see “The Bean” of course and visit a couple of friends I know live in the Chicago area. 🙂
My favorite things about fall are the foods and flavors. During fall in Chicago, I’d enjoy some movies during the Chicago International Film Festival, take a ride on the Seadog for their Haunted Cruise and partake in some of the other Halloween festivities taking place throughout the city.
I love Chicago and usually visit every fall (was just there in September!). I always enjoy trying new restaurants and I make sure to go to at least one museum on every trip. My fave is the Art Institute. I never get tired of going there. I also try to fit in some shopping.
I went to Chicago first time in my life in September and I absolutely loved it! We had such a great time with family and friends over there, and I miss it! You got me inspired now and I guess it is time to start planning another trip now 🙂
Chicago in the fall is the best 🙂 I love wandering ANYWHERE and taking in all of the sights and crisp air – I try to walk around extra before I know I’ll be bundled up and hiding inside haha
Love the cooler weather of the Fall season as well as the Fall colors. I’ve never been to Chicago, so I guess I’d check out their famous tourist attractions like their Sears Tower Skydeck and hang out at the Navy Pier.
I’ve only been to Chicago once, and the trip was spent visiting people more than sites. It was a great one! But the next time I go, I know the husband wants to watch an MLB game, preferably when the Pirates are in town. So we’ll have to do that on top of seeing some more of those iconic things.
I would love to go to Chicago! It’s on my short-term bucket list. Ideally, I would like to take a trip there in the next few years. I would love to check out Chicago’s foodie scene! There are so many great restaurants in the city.
I absolutely love fall! Pumpkin patches, bon fires, and hayrides. Fall speaks to my soul.
I like the colors of tree leaves in Fall and would love to see them in Chicago.
With the tourist/summer season fading away, I love to get out and explore more of my city! Museums, free events, fall festivals, and outdoor parks and gardens are just a few of my favorite fall activities 🙂
I love going pumpkin picking! And I’d love to do a chicago eats tour (deep dish!).
My favorite things about fall are pumpkin and apple cider flavored everything!!
My favorite thing about fall is the drop in humidity and being able to do things without sweating all the time! My husband and I are only a state and a half away from Chicago, but neither of us have ever been despite 2 attempts to plan trips where the timing didn’t work out 🙁 I would love to see the Navy Pier in person!
I have never been to Chicago but i would love to go and visit the things you did! my favorite thing about fall is hot chocolate and cuddling!
my favorite thing about fall is the cool crisp air and warm colors. much more my style. If i had a chance to go to Chicago I would take advantage of the food scene
My favorite thing about fall is the cooler weather. I am a cold weather gal. Hopefully on my next trip to Chicago I will be buying a house. I was born and raised there but left when I was 30. It’s time for me to come back home. I miss it a lot. Sweet Home Chicago. GO CUBS!
My favorite thing about Fall is the crisp cool air. I have never been to Chicago, I would definitely want to check out The skyline .
I love the changing leaves during this season! Given the chance, I need to visit the bean!
We love Shedd Aquarium.
I’ve only ever been to Chicago in the middle of summer or dead winter, so it would be lovely to experience it in the fall! I love the cooler weather and taking time for a slow cup of tea or coffee at least once a day.
I love the beautiful scenery in fall..the changing leaves on the trees and clear skies. Next time I visit Chicago I’d love to go on a deep dish pizza tasting test spree!
I love the cooler weather and to go hiking in the fall. I would go visit the Art Institute.
My favorite thing about fall is the changing colors. I would love to do some shopping in Chicago on my next visit!
I love apple season in the fall!
I’ve been really wanting to take a architecture boat cruise in Chicago!
I love the fall colors and fall festivals. I would love to check out a baseball game.
I love Chicago! The last time I was there I had so much fun. I love the delicious restaurants and cool atmosphere!
Coleslaura2211@yahoo(dot)com
I love the leaves! The colors! The look of them on the street and on the lawns. Everything. In Chicago I would love to admire the skyline and go site seeing.
I love the brisk, cool air and the fall colored foliage!
I am interested in the architecture in Chicago, such as visiting the Rookery Building and the Wrigley Building, among many others.
CalifKitties {at} Aol {dot} com
Pumpkin patches are my favorite! I love going there in the fall. I haven’t been to Chicago, so I’d just love to explore!
In the fall I love taking my kids to the pumpkin and apple patches. They are little so you can take them anywhere to run around and see new things and they are happy!
On my next trip to Chicago I would love to do one of the dinner cruises. I have been to Chicago many times but never on the cruise so I would love to get dressed up and have a good time with my husband
I love to look at the leaves change colors! Oh man, I’ve never been to Chicago, but I think I’d have to try some of it’s amazing restaurants.
I like the cooler weather and won’t ever be visiting chicago
I love the smell of fall and the changing leaves. If I were to visit Chicago I’d love to try the food.
I like the weather in the fall. It’s a nice and mild and fun to walk outside. In Chicago I would like to just go and generally explore the city life and all it has to offer.
I LOVE running in the fall! It’s my favorite running weather. And if I ever make it up to Chicago, I’d love to try out some of the restaurants and breweries
i love the cool weather and fall colors. i would love to try a chicago pizza!
The Science museum is always interesting. The planetarium is also good. I would be interested in visiting the Brookfield Zoo, also.
Oh my next visit…I would love to visit the Navy Pier! Oh that looks so beautiful!!! My favorite things about fall….the leaves changing colors! Oh it is so beautiful outside!
e of esMy favorite thing about Fall is the cooler weather–it makes me feel more energetic. We want to visit The House of Blues in Chicago!
Fall is my absolute favorite season because I prefer the crisp cooler weather and it’s heading towards the holiday season which I live. I also love fall fashion and wearing my cute boots without the snow!
I’ve never visited Chicago but it’s on my list of places to see in the next few years. Because it would be my first time I’d take a tour of all the major touristy spots and then a sunset cruise to see the awesome skyline.
Thanks for the giveaway!
my fav thing about fall is jumping in the leaves. seeing the weather change making apple pie.
My favorite things to do in the Fall are to drive through the Smoky Mountains and see the changing of the Colors as well as enjoy seeing the children have so much fun with all the activities of Halloween, Thanksgiving and Christmas. One day if I get to visit Chicago, I would love to visit Millennium Park.
My favorite thing about fall is taking my camera out on road trips up through NY and Maine! My next visit to Chicago will include much more pizza. It is the BEST!
I love the changing leaves. Have never been to Chicago, would love to go!
We love hiking in the fall. In Chicago we would love to go geocaching!
I love the cooler weather and the leaves changing , i would like to see the Navy Pier
I like the weather and holidays
Never encounter any of 4 seasons before! My country’s weather either dry or rainy. But If I were to be happen in fall, I’ll enjoy my hot cup of hot chocolate and the leaves🍁🍁🍃
My favorite thing about fall is that the weather starts to cool off – summers are hot where I live. My favorite thing to do in Chicago is going to the top of the Sears tower to enjoy the view.
I love all the fall colors and the brisk weather we don’t get that here in Arizona. My favorite thing to do in Chicago is eat! So many amazing restaurants still on my list to try
One of my favorite things about fall is the crisp fresh air. I love to be outside when the weather is cool. My favorite thing to do in Chicago is to stay downtown & just jump on the L to some of the cool neighborhoods & walk around & explore. Chicago’s public transportation system is awesome & a great way to sight-see.
My favorite fall things are the cooler weather, the changing leaves, and pumpkin patches! Also drinking hot coffee! I’ve never been to Chicago- but I can imagine the pizza would be my favorite thing 🙂
My favorite thing to do in fall is hit some craft shows and art walks. So fun to be outside in the awesome weather thanks for all the fun tips – I love Chicago. truckredford*at* gmail *dot* com
My favorite thing to do in fall is go to the local pumpkin patch! Also I haven’t been to Chicago since i was a little girl and I would love to go to Navy Pier with my family now!
I would have to say the weather and apple picking. I would like to say visiting the cultral museum and other art museums
Fall weather in Chicago is the best weather we get. It’s perfectly warm and slightly overcast. My ideal weather for year round!
I have not been to Chicago yet, but would love to.
My favorite things about fall, cooler weather, changing of the leaves, pumpkin picking, Harvest Festival at our church, did I mention cooler weather. Hot drinks, bonfires. I love it all. I would love to go to Navy Pier in Chicago.
I love the color of fall, the weather, the festivals everywhere and of course, the outfits! boots! I love boots! Haha! I haven’t been to Chicago but would love to go there and visit the Willis Tower Skydeck!
Dhee
dheeramos@hotmail.com
https://myreviewcorner.com
I love baking with the fall harvest and I love hiking and exploring the colours of the season. I’ve never been to Chicago, so food, wines and nightlife.
I would like to see the Bean and eat some deep dish pizza.
I’d eat out at all the fun places in Chicago. I assume they have some there. lol I love the fall colors and cooler temps.
I love Chicago, even though I haven’t been there in years – would love to go back and try the cruise since we didn’t do that last time.
Stephanie
steph 0828@hotmail dot com
My favorite thing about Fall is going to the pumpkin patches! Next time I go to Chicago I definitely want to visit the Grand Luxe again!
I love to go apple picking in the Fall and would love to visit Chicago’s Navy Pier.
I love Chicago! I haven’t been in years! I hope to visits again sometime soon. My favorite spot was the Ferris wheel–just breath taking! My favorite thing about fall is sweater whether! We haven’t quite gotten there yet in Louisiana though!
I like the fall colors and going on scenic walks
My favorite thing about by fall by far is the weather and hiking to appreciate all the changing leaves. On our next trip to Chicago I would love to walk along the pier again and take in the breeze. I would also love to go shopping downtown and visit the aquarium, so many awesome things to do there.
I have never been to Chicago but would love to go and explore the art galleries and restaurants.
i love fall foods and the crisp air!
My favorite fall activities ate going to the pumpkin farm , drinking hot apple cider & seeing the leaves change. If i went to Chicago. I would love to visit American Girl; )
Fall is my absolute favorite because of the weather and the fashion! I’ve actually been dying to visit Chicago (I’ve never been) — some of my good friends live there now! These pictures make it look so fun!
Fall fashion is incredible and my most favorite. And lets not forget the lovely weather ! Chicago Art Institute seems to grasp my interest the most after seeing the picture above and how I now wish I could visit it. 🙂
I’ve lived in a country where it’s summer all year round… but i have gone to other places during fall… great memories.
My favorite thing about fall is halloween and Apple picking and if I went to Chicago I would love to do Museum week! 🙂
I love the cool weather and halloween!
I’ve never been to Chicago but it be fun to check out there music scene.
I really want to go to Wicker Park. So many people have said it’s just beautiful there, so I need to see for myself!
i love most about fall the weather and the changing scenery. i also love to bundle up (but not too much) with scarves and sweaters. i’ve never been to chicago and would so very much love to go!!! (email lyndagp at hotmail dot com)
My favorite thing about fall is the changing weather, and I love walking around the lake feeling the air turn brisk!
Well I cannot honestly say I enjoy fall but I guess my favorite thing about fall is its not yet Winter lol.
Thanks for the chance to win.
Fall is my favorite time of year. It’s the perfect weather.
My favorite things about fall are the cooler days and the beautiful stunning leaves. On my next Chicago visit I would like to visit a dear friend and also see the town.
My favorite fall activity is hiking in the cooler weather. On my trip to Chicago, I’d visit the Navy Pier.
My favorite thing about Fall is the cooler, crisper air. If I visited Chicago- I would go straight for all of the yummy Chicago food. Pizza, hot dogs, and whatever else you have that’s unique to Chicago.
I love the weather and the colors that fall brings. I live near Chicago and one of my favorite things to do is going down to Museum Campus and explore the Shedd, Field and MSI. It takes me 2 days to get through MSI though. haha! You get a beautiful view of the skyline at night too and it’s within walking distance to some amazing restaurants
Chicago sounds amazing in the fall. Traveling there is on my bucket list. Fall is lovely here in Tucson also – hiking, bicycling, or just enjoying a great book on the patio.
Sitting by the fireplace and drinking cocoa. I want to visit my friend in chicago.
I have never been to Chicago, but my favorite fall activity is crunching leaves beneath my boots and eating candy apples 🙂
My favorite fall activity is to go to apple picking with my son and then to the pumpkin patch. We decorated our pumpkins in an Avengers theme this year! I have never been to Chicago but I will proudly say I want to desperately for your deep dish pizza!!!!!!!! lol
I love to go for walks in the fall. I would love to go to Chicago to visit the C2E2 Comic Convention.
Favorite thing about fall is being able to bake delicious smelling foods to warm up the house! Next time I’m in Chicago in the Fall, I’d hope to make it to Apple Fest up in Lincoln Square for some hot cider and apple pie!
I would get the Decorative Old world Globe and some Essential Home picture frames!