A Day Trip to Chicago

Chicago Riverfront

Our trip to Chicago last summer might go down as the most random trip we’ve ever taken (which is saying something, since last week we impulse-bought plane tickets to Paris like they were a package of Mentos in a grocery store checkout line. #yolo). 

As we were looking at our upcoming travel plans, I realized I was going to end the year about $100 shy of reaching elite flyer status on Delta Airlines. So I spent a tea-fueled evening scouring online to find a “mileage run” that would put me just over the required spending threshold.

The best option I found was a quick hop to Chicago, which is about a two-hour flight from Atlanta.

Of course, Sam wasn’t about to let me go without him, and we couldn’t stand to fly to a new city just to turn around and go home—especially a cool city like Chicago that we’d never explored.

So we ended up booking a flight to Chicago first thing in the morning and then a return flight for that evening, which gave us roughly seven hours to explore the Windy City. 

Though our time in Chicago was super short, we were able to hit a lot of the highlights and, more importantly, eat multiple slices of deep-dish pizza. It was certainly a fun way to earn elite status!

Why Take a Day Trip…by Air!

chicago Riverwalk

In the age of slow travel (with many travel pros arguing that to really experience a place you should spend a minimum of four years there, learn the language, marry a local, and have a street named after you), flying somewhere for less than 24 hours seems like a total waste.

But we found that a quick day trip by air can be an awesome travel experience for several reasons:

  1. No Luggage. One of the things we loved about our trip to Chicago was that we didn’t have any luggage besides lightweight day bags, something that made navigating the airport and public transit a breeze! 
  2. Don’t have to pay for accommodations. Another thing we loved about taking a day trip was that we didn’t have to worry about finding a hotel or Airbnb, something that can be super pricy in major cities like Chicago. (Our trip to Boston earlier in the summer would have completely broken us if a friend hadn’t let us use his hotel points!) Instead, we were able to get off the plane and hit the ground running.
  3. Don’t have to use vacation days. Since we only get a few weeks of vacation per year, we always look for ways to maximize our travel. Day trips are a great way to squeeze in some extra adventure. And flying day trips are great because they allow us to travel much farther afield than we could in a car.

While taking a day trip obviously means having less time in a destination than we might otherwise have, they are still a great way to get a taste of a new place. 

On our day trip to Chicago, we were able to see and do a ton of stuff…despite the fact that I was three months pregnant and suffering from severe morning sickness!

How to See Chicago in One Day

If you’re lucky enough to visit the Windy City, but you’re short on time (like we were!), wear comfy shoes and grab some coffee, because here is everything you can squeeze into one day in Chicago.

Take a selfie in Millennium Park 

The Bean

The most iconic spot in Chicago is the Cloud Gate (aka, the Bean) in Millennium Park. Be sure to pay it a visit and take a selfie. Because if you haven’t taken a selfie with the Bean, have you even been to Chicago? Just be prepared to encounter hordes of people if you visit in the middle of the day like we did.

Lurie Garden

Once you’ve snapped a few pictures with the Bean, take some time to explore the surrounding grounds. The Lurie Garden is beautiful, and you may even be able to catch a performance at the Jay Pritzker Pavilion (there were some dancers performing when we visited).

Stroll along the banks of Lake Michigan

Lake Michigan

Though I’ve always preferred the beach to lakes, strolling along the banks of Lake Michigan in Chicago is a pretty amazing experience. The lake is so vast that from up close it actually looks like the ocean, complete with waves!

The paved paths along the water are a nice place to go for a stroll. If you’re feeling a bit more adventurous, you can rent bikes and go for a lakeside cycle. Sam really wanted to rent bikes, but I was twelve weeks pregnant and irrationally terrified of falling and hurting the baby…maybe next time.

Indulge in deep-dish pizza


If Chicago is synonymous with one thing besides inclement weather and airport delays, it’s deep-dish pizza. Which is just as impossibly, disgustingly, outrageously decadent as it sounds. And it’s amazing.

Despite the fact that I had spent the two preceding months eating nothing but saltines, I figured a chance to indulge in some deep-dish pizza right at the source was too good to pass up.

While there are lots of places to sample deep-dish pizza in Chicago—and the locals could spend days on end debating which one is the best—we decided to hit up Giordono’s.

And let me tell you, it was life changing. It was also so rich and cheesy that I ate two slices and thought I’d keel over and die on the spot from pulmonary heart failure. But, hey, there are certainly worse ways to go.

Just remember that the cooking time for deep-dish pizza is fairly long—roughly 30-40 minutes—so keep that in mind if you’re short on time! 

Stroll the Riverwalk

Chicago Riverwalk

After you’ve stuffed yourself so full of pizza that your sides hurt, you can hardly breathe, and you’ve started making yourself empty promises to become a raw vegan cross-fitter as soon as you return home, burn off some calories with a stroll along Chicago’s riverwalk. 

Our walk along the river was my favorite part of our trip to Chicago. I Ioved the juxtaposition of the river against Chicago’s highest skyscrapers. After walking for quite a while, we enjoyed sitting on the bank and watching the boats go by. There are also plenty of riverside restaurants if you need a snack (though after eating deep dish, you probably won’t be hungry for three weeks).

If you have the time, take an architecture river cruise. We skipped it on our visit because I felt seasick just looking at the water (yay pregnancy!), but it’s definitely at the top of our bucket list for our next trip to Chicago. 

Peruse the Chicago Public Library

Chicago Public Library

As I’ve mentioned before on this blog, I’m a total book nerd. (I’ve even written several posts on books to inspire travel.) In every city we visit, I try to check out at least one or two book stores and libraries. (I’ve been meaning to write a post on my favorite book stores around the world for several years now!) We didn’t have a chance to visit any bookstores on this trip, but we popped into the Chicago Public Library. Though it wasn’t as impressive as the Boston Public Library we visited earlier in the summer, it was still neat to visit.

Conquer your fear of heights on the Skydeck


Another popular attraction in Chicago is the Skydeck in Willis Tower. For brave souls who aren’t afraid of heights, seeing the city from a bird’s eye view at the top of the tower is an exhilarating experience.

We had planned to head straight to the Skydeck from the airport. But when we landed in Chicago, the weather was cloudy and uncooperative, so we decided it wasn’t worth the cost. We were super disappointed, and we will definitely try again next time we’re in Chicago.

How to get around in Chicago

The L

Using the L, the elevated rapid transit system, is the best way to get around the city cheaply. We landed at the Chicago Midway airport and were able to take it directly to the city center, and from there we were able to visit most attractions by foot.

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One Day in Chicago

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