A “Ferris Bueller’s Day Off” in Chicago: The Willis Tower’s Skydeck, Art Institute of Chicago & a Cubs Game!

Earlier this summer, I cruised into Chicago with only about 24 hours to spend in the Windy City. Do people even call it that? Is that how people know I’m a tourist? ; )

I’d never been to Chicago before, so I really wanted to make it count. I poured over options for things to do. Thought about this or that. And in the end, I decided that it was hard to plan a better day in Chicago than Ferris Bueller did.

So that’s what I did! After rewatching the movie for some inspiration, I made a quick list of Ferris approved activities and they fit surprisingly well into one whirlwind day in Chicago.

Ferris Bueller’s Day Off in Chicago

So if you’re looking for the ultimate day off in Chicago, here’s how to do it (Ferris style):

Breakfast at Goddess and the Baker

Ferris started his day off trying to convince his parents that he was too sick to go to school, but I like to start mine off with BREAKFAST.

The Goddess and the Baker was right next to my hotel (they have several locations across Chicago) so it drew me in with its convenience, but it was GOOD.

Yes, they have the Insta aesthetic down, but they also have great coffee, a dazzling array of sweet options, and really solid hearty breakfast dishes.

Check Out the View from the Willis Tower’s Skydeck on the 103rd Floor

Formerly (and forever to be known as) the Sears Tower, when Ferris, Cam, and Sloan checked out the view from the top, it was the tallest building in the world.

It has since lost that alcolade, but it’s still impressive.

Lines can get long later in the day so it’s the perfect thing to do first thing in the morning (I believe the first time slot is 9AM).

I booked tickets online in advance and we were able to walk right up. You’ll go through security first and then there’s quite a few exhibits to walk through that kind of help keep the line regulated. Some people buzz right through and some stop to read everything and take pictures so even within your ticket time slot, it helps disperse the crowds so you’re not all waiting for an elevator at the same time.

We didn’t wait long at all for an elevator to the top. Now I’ll be honest…I don’t love heights (I would say I have a moderate fear) and the elevator ride up was a little rough for me, but it’s pretty quick.

Once you’re on the 103rd floor, you can walk around three sides of the building at your own pace. It’s floor to ceiling glass and they have panels set up on each side to show you what you’re looking at.

And for all you Ferris Bueller fans…they have the spot where Ferris and the gang stood in the movie so you can recreate your little scene.

Once you’ve seen all you want to see, you get in line for the…duh duh dum….the Ledge!

This is the main attraction at the Willis Tower and why everybody comes, but it’s not for the faint of heart.

One one side of the building they’ve built these glass boxes so you can step OUT OF THE BUILDING.

You wait in line and when a box opens up they usher your party into it, take your picture, and then start a timer. You only get about a minute in the box and they keep it moving.

I was too chicken to actually step out onto the box, but it was still pretty cool getting to peer over the edge and look down and just see the whole thing.

Adult tickets (12+) range from $30-44 per person depending on time of day (sunset times are more expensive) and crowd levels. Children tickets (3-11) range from $22-36 and 3 and under are free.

They sell an expedited entry option (more $$ of course, but I don’t think I would pay extra for it). Go earlier in the day if you want the shortest wait possible, but they really keep the line moving pretty well at all times.

Also, check the weather before you go! It was pretty dreary the day I visited, but I didn’t have any other options (only in town for one day) so I went up anyway and I would say it was still “worth it” even though I’m sure it’s much more beautiful on a clear, sunny day.

BUT if it’s so rainy/foggy that you can’t see the sky boxes when you’re down on the street looking up, then you won’t be able to see out once you’re up there and I wouldn’t go up.

Go on a Chicago Architecture River Cruise

Okay, I know Ferris and the crew didn’t do this in the movie, but this is easily the most recommended thing to do in Chicago and if you only have one day, I think it’s a must.

Plus I think it can sub for the big parade scene in the movie ; )

There are a lot of options for companies to go with, but I went with the Chicago Architecture Foundation Center since it’s an architecture cruise and it seems like they probably have the best tour guides.

Tickets are about $52/adult for daytime cruises and a little more for the sunset ones. Cruises last about 1.5 hours.

And now I know why so many people recommend this! It’s a great way to learn about the history of the city of Chicago (skyscrapers were pretty much invented here), sightsee, but also just have a really pleasant time.

This is 100% a better way to see the city than the double decker bus tours that most big cities offer.

And our tour guide was actually a docent at the Chicago Architecture Foundation so she really knew her stuff.

And she gave us some tips on other things to see and do around the city. She tipped us off to walking around the Chicago Tribune building where they’ve incorporated pieces from famous buildings and sites from around the world into the building.

Eat Deep Dish Pizza

The debate about the best deep dish pizza in Chicago is about as fierce as the debate between New York and Chicago style. For the record, I’m a New York style kind of girl, but when in Rome…

Like I said, everybody has their favorite, but I went with Lou Malnati’s (a longtime local place that’s now a Chicago area chain).

Stroll through the Art Institute of Chicago

One of the most iconic scenes in Ferris Bueller’s Day Off is when the gang heads to the Chicago Art Institute.

Most of the scenes in the movie take place in the museum’s impressionist collection, which is truly impressive.

I believe the Chicago Art Institute actually has the largest collection of impressionist paintings in the world outside of the Louvre.

The Art Institute of Chicago is a great place to get lost in for a few hours (especially if the weather is cold or rainy) and it’s truly a world class art museum but I think it’s on a more approachable scale than say, the MET in New York.

It does get crowded though, especially in some of the more popular areas of the museum so either go first thing when they open (11AM) or just be prepared to have to filter through crowds to see the most famous paintings.

Tickets to the museum are $25/adult, $19/seniors, students, and teens, and children are free.

Also, Cloud Gate (aka the Bean) is part of the museum’s outdoor sculpture park in Millenium Park (accessible without admission) and that’s a can’t miss Chicago spot. Can you just imagine a Ferris Bueller scene with the Bean?

See the Cubs Play at Wrigley Field 

What better way to cap off the perfect day in Chicago than a Cubs game? I’m not even a big Cubs fan, but it’s such an iconic Chicago thing to do. Plus Wrigley Field is the second oldest major league baseball stadium in the country (Fenway in Boston is the oldest) so if you’re a sports fan at all it’s a must.

And even if you’re not a big sports fan, there’s just nothing better than a summer night sitting in the ballpark.

Tickets to most games are surprisingly affordable (sometimes starting around $25). I had actually looked at doing a tour of Wrigley Field, but tours are about $30/person and on days when the Cubs are playing you don’t get to see a whole lot behind the scenes anyways.

If it’s your first game at Wrigley Field, stop by the First Timer’s Booth to get a certificate.

If you’re staying in downtown Chicago, it’s really easy to get to Wrigley on the L train and even coming back after dark seems pretty safe since there’s so many people coming back from the game. A one day CTA pass is $5 (3 days for $15) plus $5 to buy the Ventra Card (a durable, reusable plastic card instead of a paper ticket).

And that’s a wrap, folks! One whirlwind day in Chicago, Ferris Bueller style. I had a blast and saw enough to know that I’ll be back!

If you’re a serious Ferris Bueller’s Day Off fan and want to see a full list of sites from the movie pulled together by a true Chicagoan that actually knows what they’re talking about, check out this post. Next time I’m in town, maybe I’ll check a few more spots off the list.