I’ve spent many days on one-day road trips throughout my life, but it wasn’t until I started experimenting with a little-known travel hack that the idea to replace highway slab with sky came up. First, my brother and I were going to meet up in New Orleans just for dinner because we kept missing the opportunity when I traveled to Mississippi via MSY (Louis Armstrong New Orleans Airport). \240Then I thought a date night flight or day trip would be cool. So, I shared the info with my family and friends, and we planned some trips. This was the first tourist mode day trip.  My friend (Megeen) wanted to go somewhere for her birthday.  Since I knew I would be just returning from vacation, I proposed a day trip and gave her the option of Boston, Miami, or Chicago. She chose "C" as in Chicago.  I must be fond of her because I vowed that I’d never go to Chicago after October. 

We booked flights on Spirit (Yes…they are domestic budget Bae) for $62 using the OTC (Over the Counter) hack.  One of the reasons why Chicago made the list was because of the price point and the fact that the route had an early departure and a late return which is perfect for a day trip.  Our plane departed Baltimore at 7:15 am.  By 8:45 am we were in our rental car headed into the City.

Our first stop was Chicago360.  We practically had the place to ourselves and enjoyed breathtaking views.  We decided to pay an extra $8 to do the Tilt which is an observation window that tilts out over the city. It was a scary, yet cool experience.  Unfortunately, you will not be able to capture video unless someone in your party remains on the outside of the viewer’s window.  Otherwise, you will be offered pictures at about $30 for three poses and access to download online. I mean why still pics? I’d like video of the tilt. You know...proof that I braved the Tilt.. 😏


Next, we caught the Hop-on Hop-Off bus to Giordano for its famous deep dish pizza.  I wasn’t crazy about this particular location, but the pizza was the status quo.  Skip the cocktails!

I want to mention the lovely group that we encountered on the Hop-on Hop-off bus.  We started bantering about “what you know about…foods” and I learned that they were from Mississippi.  In fact, Jackson, MS home of (Jackson State University-Thee I Love), but their family member was an high school \240classmate of mine.  Small world, I’ll tell ya!

Then we went to the Skydeck to walk on the Ledge.  The Ledge is a glass observatory box located in the Willis Tower and is approximately 1,353 feet in the air.  We liked this better than the Tilt because you can showcase your experience a bit more.  The attendants will take pictures that you can buy, but they will also take pics with your device.  Then you are allowed a bit of time to pose and take your own photos at no additional cost.

I really wanted to get a picture of Megeen and the Bean. (Pun intended)  Unfortunately, we’ll have to save it for the next time. Back to the airport we went!  We got back home about 11:00pm and Yes…we were both at work the next morning.  I love an adventure and the spontaneity of it is right up my alley. Oh yeah…and the price tag was easy on the wallet.

Headed Home!!!

Trip cost breakdown

We could’ve saved a bit more if I’d booked the rental car well in advance instead of the day before. ☺️ I won’t complain. It was a frugal day of fun. So…if you live near a cost-effective hub, look beyond the “usual suspect” places that border your town.  Why not take to the sky and maximize your day, states over, in less time?

-Kenya The Frugal

1-day Chicago Itinerary (click link below)