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.
I’m a Chicago Native and must admit I’m impressed – touring the Windy City in February! Way to go!
If you ever get back to Chicago, try to see the Museum of Science and Industry, the Field Museum, and/or the Shedd Acquarium. If you visit during the warmer months, then be sure to stop by Navy Pier and couple that with the architectural boat tour on the Chicago River (right next to Navy Pier).
If you are a pizza fan, try Bonci Pizzeria in Chicago. The owner has a well established pizza place in Rome, and in 2017 he expanded to Chicago. We’ve (hubby and I) been to the Rome location and were thrilled when the Chicago location opened. You won’t be disappointed.
Thanks so much for the tips! I really hope to get back there when its warmer weather. I’d absolutely love the boat tour. I was disappointed that I didn’t at least get to see the Navy Pier, which I would have if the bus tour had worked out. I’m making a note of the museums and Bonci Pizzeria right now.
You covered a lot in one day! The only thing we did different on our day was visit Navy Pier (very touristy, though)–and had to get the famous Chicago popcorn mix–cheese and caramel. While we hit Giordanos when visiting outside of Chicago recently, the day we were in the city a couple years ago we ate at Gino’s–it was also very good and was quite interesting because almost every surface was covered with signatures of visitors (tables, chairs, walls). I loved visiting Chicago and hope to go again in a few months. Looks like you had a marvelous day!