I tagged along with my husband on a recent business trip to Chicago. Sadly, I only had a single day in the windy city, but I did my best to make the most of my first visit. I’m a planner and like to save money so I spent some time trying to find the best deals for the activities I thought I’d enjoy the most. I’ll share with you my successes and failures in this endeavor and you can decide, which is better for one day in a big city: plans or improvisation.

How Much Sight Seeing Can You Do In One Day?

I knew right off the bat that there were a few things I wanted to accomplish on this trip like visiting the Sears Tower (it’s not called that anymore), taking a selfie at the “Bean” (that’s not really its name) and eating deep dish pizza (also not called that on the menu–geez I had a lot to learn about Chicago). Outside of that, I wasn’t entirely sure what I should include in my one-day itinerary. After a quick look on the internet I realized that the big question really was, how much sight seeing could I do in one day? I’ve learned over time that an overly ambitious schedule stresses me out because it starts to feel like work.

Purchasing A “Money Saving” Attraction Pass

If you’ve been following our blog, you know that we are always looking for ways to save money. In my research I found two programs that seemed like a great deal for visiting the typical tourist attractions: Chicago City Pass and Go City. So what is the difference between the Chicago City Pass and Go City you may ask? Well, they both advertise up to 55% off attractions and have a range of options. The main difference is flexibility. See the City Pass is $106 and allows you to visit six attractions over nine days. I like that pace, but I didn’t have that much time on this trip. The $99 Go City All-Inclusive Pass allows you to visit 25 attractions in one day, but unless you’re just walking in and out the door, I don’t see how that is even possible. However, the Go City pass does have other options (less attractions or more days) at different price points, and I was considering purchasing their $80 3-Attraction Explorer Pass. I just wanted to check one more place–my old go-to: Groupon. Guess what, it had the Go City Card 3-Attraction Explorer Pass for only $67.50! Yay! I had a little trouble activating the Groupon voucher on the Go City App, but I called the customer service number and they resolved it right away.

Fail: Hop On Hop Off Tour

Typically if there is a hop on, hop off tour in the area I’ll take it. It usually provides a great overview of the city and a means of transportation. Two for one, good deal right? Not so great a deal with the Chicago Big Bus this cold February day. I used their app to try to locate the pick-up point nearest my first stop. Couldn’t find it, so I used their app to see when a bus was coming next thinking I’d just try to keep an eye out for it. Well, that didn’t really work out well. The real-time tracking didn’t show any movement on buses for over 15 minutes. That may not seem like a long time, but I was in Chicago in FEBRUARY! It was cold! Freezing actually! So I decided to start walking the 1/2 mile to the next stop on the bus route. Guess what? Never saw a bus or bus stop anywhere near that location either. In fact, although their website said they were operating, I never saw a Chicago Big Bus all day. And I did stay and WALK around the freezing city all day. Why? Because I paid $25 to Uber there and was going to get (the rest) of my money’s worth, darn it! Plus it helped me walk off some calories in preparation for the Chicago Pie I planned to get for dinner.

A Day In Chicago For The Win!

In spite of the cold weather and missed bus opportunity (that I paid for in advance), I still had a great first visit to the Windy City of Chicago! After all, I did get to walk on a glass floor 1,353 feet in the air. I also took a selfie at Cloud Gate (aka “the bean”), spent several hours art-gazing, and ate my fill of some Chicago-style Pizza.

SkyDeck Chicago

SkyDeck is on the 103rd floor of Willis Tower (formerly known Sears Tower). The iconic office building is the second tallest in the Western Hemisphere (the tallest is One World Trade Center). You can walk around the entire 103rd floor to get a view of Chicago, Lake Michigan, and the surrounding area. They say on a clear day, you can see four states: Illinois, Indiana, Wisconsin, and Michigan. It was a spectacular view! The best part to me was the Ledge, basically a glass box that extends out 4.3 feet from the skyscraper and allows you to look straight down all 1,353 feet to the street below! Now I’ll admit, I was a little afraid and didn’t look down until I was out on it. Even then I was pretty scared, but you can’t tell here, can you?!

The Art Institute of Chicago

Chicago is known for its renowned museums and this one topped my list. Founded in 1879, the Art Institute of Chicago is one of the oldest and largest art museums in the United States. It features galleries devoted to the art of ancient Greece, Japan, Africa, and the Americas. I choose it because it is known for having the greatest Impressionist collection outside of Paris and currently has a Rodin exhibit through March. They have a couple of free tours each day as well. I enjoyed the highlights tour because there was really no way I was going to be able to see half of what they had to offer in the 4 hours I had for this particular visit.

Millennium Park

Over 25 acres, Millennium Park boasts an outdoor collection of architecture, landscape design and art. Of course, I had to take a selfie in front of Cloud Gate, the official name for the massive, stainless steel structure that’s become Chicago’s signature landmark. Click here to read some interesting facts about it and see it during construction.

I also enjoyed watching the ice skaters at the McCormick Tribune Ice Rink. Now I want to return to visit it in the spring or summer to experience the Lurie Garden, an urban oasis that they say pays homage to Chicago’s motto — “Urbs in Horto,” or City in a Garden.

Giordano’s Famous Stuffed Deep Dish Pizza

What better way to end the day than with dinner at Giordano’s? Known for its famous stuffed deep-dish pizza, they actually use Wisconsin cheese and California tomatoes. If this looks good to you, they actually have locations in 7 other states and if yours isn’t one of them, they will ship it to you!

Looking for a Place to Stay?

Check out this awesome guide of Chicago vacation rentals.

What Did I Miss?

Now I realize that there was so much more to Chicago than I was able to glimpse on this short visit. Please let me know in the comments below what I should put on my list for my next trip to Chicago.