Chicago in the Fall: What to Do, Eat, & Pack
If you’re thinking about heading to Chicago in the fall, consider this your sign to book the trip and start planning that itinerary!
I never thought I’d fall in love with Chicago.
Cities have never really been my thing. Growing up in a small town in Alabama, I sometimes find the fast-paced lifestyle of a big city overwhelming.
And as a solo traveler, I’m always a little more cautious about exploring unfamiliar downtown areas on my own.
But a work trip to Chicago this October was all it took to change my mind.
Between the beautiful architecture, incredible food, and the charm of exploring the city in the fall, I discovered that Chicago has a lot more to offer than I thought.
Whether you are planning your first visit or looking for some new ideas, I’m sharing what you need to know to plan a Chicago getaway this season that’s right for you.
If you’re looking for popular attractions, local spots off the beaten path, restaurants to try, or simply what to pack in your carry-on, I’ve got you covered.
How to Get to Chicago
For this trip, my coworkers and I took a 2.5 hour flight from IAH in Houston to O’Hare International Airport. I prefer O’Hare to Midway since it’s an international hub with multiple airline options.
However, if you’re looking to book with Southwest, Midway International Airport may be the better option since Southwest operates extensively out of Midway.
Since we were on the company card, we paid for an UberX directly to our hotel downtown.
A one-way uber drive costs upwards of $100 for us, and it took about 45 minutes to go 18 miles. I was sick when I heard the price and was glad it wasn’t on my dime.
However, prices are dependent on what uber service you choose, time of day, time of year, and overall demand.
Still, to be clear, if I was alone, I would absolutely not pay for that. I would 100% take the train to save the money.
The train’s blue line runs 24/7 and costs about $5 per way from the airport to downtown. It still takes about 45 minutes, but you save a significant amount.
It lets off at several stops within the loop and you can walk, transfer trains, or catch a ride to your final destination from there.
Beware, public transit can be less than comfortable when it comes to noise, space, and ride. At the end of the day, it’s up to you to decide what works best for your travel style.
Where to Stay in Chicago
Our conference was held in the Chicago Marriott Downtown Magnificent Mile so we were able to stay close to all the attractions on our bucket list.
A walk from the hotel to the river was about 7 minutes and Millennium Park took us about 20 minutes give or take. Other attractions like the Harry Potter Store and Starbucks Reserve are just a few blocks over as well.
One thing you should keep in mind while booking your stay for the Fall is that the Chicago Marathon takes place on a Sunday in October. This can significantly increase prices for lodging.
We had to fly in the same day as the conference started because hotels that weekend were close to $1000 total for two additional nights, especially downtown near the race. Specifically, the Marriott ranged from $400-750 per night that weekend.
This also made it pretty crowded on our first day, but after the participants started heading home, the streets and the hotel seemed to clear out some. However, it was hard to tell since we were surrounded by people there for our event.
For those planning their trips for next fall, the Chicago Marathon is scheduled for October 10, 2027.
What to Pack for Chicago in the Fall
Okay, so this is where I messed up!
I came into this trip expecting quintessential fall: changing leaves, crisp weather, and the chance to wear a freaking sweater without sweating.
Now, don’t get me wrong, the trees were changing colors. But coming from 90-degree weather, I needed a little breeze.
Did I get one? No.
Not the first night, anyway, when I wore thigh-high boots, a skirt, and a scratchy, circa-2016 Tumblr sweater.
I was sweating like I was still in the middle of the South. And don’t get me started on the shoes.
Remember how I said the river was only a 7-minute walk from the hotel? Yeah, I felt every inch of that 0.3 miles both ways.
So, check the weather before buying all the Pinterest outfits you’ve pinned. On the first day of our trip, it wasn’t just warm. It was hot.
The second day, however, rain and a cold front rolled through, cooling things off a little. I traded the sweater for a light windbreaker and the skirt for jeans.
And please, wear comfortable walking shoes. I was about two seconds away from taking my boots off in Walgreens and showing them how we get down in Alabama.
What to Eat in Chicago
You can’t go to Chicago without trying a Chicago dog, deep-dish pizza, and pasta. The holy trinity of Chicago, if you’d like.
As soon as we dropped our bags in our room, we were out on the street looking for our first delicacy to check off the list.
The Chicago Dog
We found ourselves at Portillo’s, just off Ontario Street. And if you’re ever craving a midnight snack, they’re open daily from 10 AM to 1 AM.
The place felt like a blast from the past, with neon signs, prohibition-era decor, and two levels of dining space. The menu featured Italian beef sandwiches, burgers, and, of course, the iconic Chicago-style hot dog we came for.
Dessert is also a staple at Portillo’s, where you can try their famous chocolate cake or chocolate cake shake. The shake came highly recommended to us, and it did not disappoint!
I ordered a Chicago-style hot dog, fries, and a drink for a little over $11.
I was a little nervous to try the hot dog. While I do love a hot dog real bad (I quoted the Jennifer Coolidge clip from Legally Blonde several times while we were there), I can be a little picky, and the toppings were throwing me off.
A Chicago-style hot dog comes with mustard, relish, onions, sliced tomatoes, a full kosher pickle slice, and sport peppers. Despite my reservations about the tomatoes and sport peppers, I had to try one just to say I’d had a real Chicago dog.
So I tried it, and I enjoyed it!
Chicago Deep Dish Pizza
The next item on our Chicago bucket list was deep-dish pizza, and lucky for us, Lou Malnati’s was just a 7-minute walk from our hotel.
It was also our stop before the Architecture Boat Tour since the restaurant is only a minute or two from the dock.
For a Tuesday night, the restaurant was popping, so I’d highly recommend making a reservation beforehand. We didn’t have one and were told upon arrival that the wait would be about 30 minutes.
That was fine since it was around 5:30 PM and our tour started at 7 PM. Luckily, we were seated after only 18 minutes. However, once we sat down, we were told the pizzas would take another 30 minutes.
I started watching the clock. That would put us at around 6:15, and both the tour company and tour reviews recommended arriving at the dock around 6:30 for good seats.
But we risked it anyway. You just can’t go to Chicago without trying deep-dish pizza.
We all ordered and began our race against the clock. I ordered a personal cheese deep-dish pizza and cheesy garlic bread.
The bread came first, and it was a 10/10 banger. It was also way too much for one person, so I shared it with the table.
With 6:30 approaching, we asked if we could get our pizzas to go and eat them on the boat.
One thing to keep in mind: Google summaries don’t always reflect the actual policies of tour companies.
Google had said outside food was allowed, but when I anxiously checked again at the dock with our pizzas in hand, I found out it was strictly prohibited.
So, once again, we risked it with a bulky to-go bag haphazardly covered by a jacket. Thankfully, we made it onto the boat without any issues.
Security was mainly checking purses and seemed to assume my friend was carrying a very large jacket.
I was especially glad my $30 pizza and garlic bread hadn’t gone to waste.
It also made for such a cool experience. We felt like we were living the Chicago tourist dream, eating deep-dish pizza while cruising past the skyline.
My only issue was that the pizza had gone cold by the time we could eat it, though I’m sure it would have been great at the table. My friends loved theirs, though!
After this experience, I still prefer Giordano’s deep-dish pizza, which I tried on another trip to Chicago in high school. Its style and generous amounts of mozzarella are a winner for me.
Chicago Pasta
Our final stop to complete our Chicago bucket list was Eataly on Ohio St in downtown. What we thought was a single restaurant is actually a full Italian market with two separate restaurants, cafes, and grocery selections.
We headed upstairs to the restaurant area and were seated at Vino. After looking at the menu and asking the waiter, we figured out there was another restaurant available.
Once our waiter brought us the other menu, we decided to switch to La Pizza & La Pasta, just a few feet away. Vino was pretty expensive, and the menu was a little more sophisticated than what I personally wanted.
Honestly, Eataly’s setup can be confusing for first-time visitors, especially if you’re just stopping in for a meal like we were.
Prices were still on the higher side, but we lucked out with a lunch special that all four of us ordered. For $25 per person, we got an entree and a side in the dinner portion size. I chose spinach and ricotta ravioli with fried russet potatoes, though you could also opt for a salad instead.
One thing I wish we’d ordered was the fettuccine alfredo, which is prepared table side in a wheel of Parmigiano cheese. I’ll definitely have to keep that in mind for next time!
This ended up being the best food we had in Chicago, and the dining experience was great, too. To finish things off, we headed downstairs for gelato and sampled just about every flavor before making our choices.
Things to Do in Chicago in the Fall
Chicago is full of activities, views, and experiences. We took full advantage of our two and half days in the city and packed in as much as we could.
Architecture Tours
When I found out Chicago was our conference destination, I knew we had to take an architecture tour. It was my one request for the entire trip after seeing so many recommendations online, and let me just say, it was worth it!
We booked with Wendella Tours & Cruises, which offers two tour lengths: 90 minutes and 45 minutes.
The 90-minute tour is a deeper dive into the city’s architecture, covering all three branches of the Chicago River for around $45 per person.
We chose the 7 PM, 45-minute tour because it fit our schedule better and cost only $28 per person. It was also a better fit for what we wanted out of the experience. While we enjoyed learning some of the history behind Chicago’s architecture, we were more interested in the nighttime views and photo opportunities.
My biggest recommendation is to arrive early. Boarding begins about 15 minutes before departure, but I’d suggest getting there at least 30 minutes ahead of time. The line was insanely long, and we were lucky to snag some of the last seats on the top deck.
Overall, it was an amazing experience, and I’d recommend it to anyone visiting Chicago!
Visit Millennium Park
Another iconic Chicago stop is Millennium Park, home to Cloud Gate, more commonly known as “The Bean.”
We walked about 20 minutes from our hotel on the Magnificent Mile and spent a whopping five minutes at the Bean. For us, it was more of a photo op than anything else.
However, there’s more to explore than just the famous sculpture. We didn’t have time to see everything, but Lurie Garden is a great option for those looking to escape some of the city noise and enjoy the fall foliage.
The park is also home to the Jay Pritzker Pavilion, where architecture and music meet. If you’re visiting during the summer, it’s worth checking out the free concerts held over a ten-week period. Millennium Park also hosts large events and festivals, including Lollapalooza.
Walk Along the Chicago River
Walking along the Chicago River is a budget-friendly way to take in the city. Aside from the boat tour, this was my favorite part of the trip because the views were breathtaking.
As someone who isn’t usually fond of cities, this experience completely changed my mind. I loved walking along the river, taking in the towering buildings, watching the boats cruise by, and meeting friendly people along the way.
I was genuinely surprised by how clean and comfortable the city felt to explore. I’d always heard about the dangers associated with Chicago, but I felt comfortable walking around on my own, both during the day and at night.
There are also plenty of attractions and dining options along the river to explore. If I return, one of the first things I’d love to do is rent a kayak and see the city from the water.
Enjoy a Rooftop View
If you love taking in the skyline, try seeing it from a different angle at a rooftop bar. After grabbing a bite along the river, we headed to London House, a hotel known for its rooftop bar and city views.
Seating is limited and requires a reservation, but standing room is available to take in the views. It also made a great spot for photos and content.
By this point, my feet were officially over the boots, so I was thankful to snag one of the few seats available to the public. I got to rest my feet while chatting with a local who joined me.
Browse a Few Unique City Stops
Chicago has plenty of unique attractions to explore, depending on your interests. During our trip, we visited the Harry Potter Store, Starbucks Reserve, and The Redhead Piano Bar.
Harry Potter Store
Since we’re all Potterheads, we knew we had to visit the Harry Potter Store. Here, you can get sorted into your Hogwarts house by the Sorting Hat, try Butterbeer, and shop for your favorite merch.
They also had an adorable fall collection featuring everything from apparel to knickknacks inspired by Hagrid’s Hut. If you’re visiting closer to the holidays, it’s also a fun place to browse for gifts!
Starbucks Reserve
Just a block from the Harry Potter Store, Starbucks Reserve is worth a stop, even if you’re not a coffee drinker like me.
The four-story shop has something on every level, but the highlight is the fourth-floor bar, where you can order coffee cocktails. You can also book experiences like coffee tastings and espresso martini classes.
The Redhead Piano Bar
Finally, we headed to The Redhead Piano Bar, where you can request songs from just about any era. The atmosphere felt like a mix of locals and tourists, though the crowd leaned a little more mature.
One thing to know before visiting: you’ll need to show ID to get in, even if you don’t plan on drinking.
What I Would Visit if I Had More Time
Unfortunately, we had limited time to explore outside of our conference. In my opinion, two nights just isn’t enough to experience everything Chicago has to offer.
If you have more time, I’d recommend catching a sporting event or exploring the Art Institute of Chicago.
Chicago has plenty of sports options, including the Bears (NFL), Bulls (NBA), Blackhawks (NHL), two Major League Baseball teams, and several women’s professional teams.
October can be a great time to catch a game, with some sports seasons just getting started while others are approaching the postseason.
Another option is the Art Institute of Chicago, which houses thousands of works, from iconic masterpieces to a wide range of other collections.
Is Chicago Worth Visiting in the Fall
Yes, visiting Chicago in the fall was well worth it! Even though my trip was sponsored by work for a conference, I’d happily spend my own money to go back.
I absolutely fell in love with Chicago, and I’m not going to lie, it might be my favorite major city I’ve visited. The city itself was surprisingly clean and well-maintained, which became a constant topic of conversation throughout our trip.
The weather was fantastic, but what stood out most was how comfortable I felt exploring the city on my own. There’s also so much to do, no matter what your interests are.
I’d highly recommend a fall trip to Chicago. Just do yourself a favor and leave the boots at home!
If you’re looking for more photos from the trip, check out my Photography Portfolio.