24 Hours in Chicago

My sweetheart was working on a job in Indiana, close to the Illinois border. We decided to spend the night in Chicago and do some sightseeing before I flew home the next day. I have lived in New York and Houston, visited Las Vegas, Los Angeles, Miami and Seattle. Love them all, but there’s something about Chicago…I have experienced Chicago in the winter, spring, summer, and fall, and I fall in love with it over and over. It never disappoints and I always find something I have to come back for.

It was my sweetheart’s first visit to Chicago…how to narrow down the fun and squeeze it into 24 hours?!

When in the land of deep dish pizza, we must partake. But with so many choices, which do you choose? How about one with a colorful past? Exchequer Pub is rumored to have been the same location of a speakeasy back in the 20’s and later on, a favorite hangout of Al Capone’s. He even lived a few blocks south of it. This is definitely the place to enjoy deep dish pizza with an old Chicago vibe. Funny thing, our home team was on TV when we sat down for dinner.

Beer, Moscow Mules and the Astros!
Look at that cheesy goodness 🙂

Just a short walk from the restaurant is the “Historic Route Begins” Route 66 sign. It’s located on the corner of the tiny fenced park at Adams and Wabash.

The front of the sign had a lot of stickers on it, but the back side clearly shows
this is the spot where the “Historic Route Begins”.

Most people wanting to get a panoramic view of Chicago go to the Skydeck at the Willis Tower. The glass box hovers over 1,000 feet in the air. You need a little courage to step out onto it. However, due to our time restraint, we opted for The Signature Room at the Ninety-Fifth.

The Signature Room at the Ninety-Fifth

The Signature Room at the Ninety-Fifth is located at 875 N. Michigan Avenue. Walking there from the parking garage is a little tricky, but so worth it! You may choose to enjoy a romantic dinner overlooking Chicago, or go up another floor to the Lounge. The line is not nearly as long as the lines at the Skydeck, and the ride is FREE.

Once you arrive at the Lounge, there is a two drink minimum, but who wouldn’t want to grab a seat and admire the view while enjoying a glass of wine or two? Be sure to visit the restroom, I guarantee it has the best view of any restroom you’ve ever been in.

View from the women’s restroom at
The Signature Room at the Ninety-Fifth
View from the women’s restroom at
The Signature Room at the Ninety-Fifth

The next morning we stopped at Wildberry to warm up with a hot cup
of coffee and fuel up for the day with breakfast.

We quickly headed over to Chicago Segway Tours for our segway training. I was a little nervous because I kept picturing MY face on all the stick figure pictures demonstrating what happens if you lose your balance or fall off….it was fine though, nothing to worry about. The tour guides make sure you are completely comfortable and let you take a few practice runs before taking the group out.

Getting comfortable.
We’re pros now! LOL


Touring the city by Segway is the way to go! You cover a lot of ground in a short time and our tour guide was very knowledgeable about the local history.

Millennium Park – Chicago, Illinois
The Bean – Chicago, Illinois

Cloud Gate is the work of sculpture Sir Anish Kapoor. It’s nicknamed “The Bean” because of its bean-like shape. This work of art is made up of 168 stainless steel plates welded together, its highly polished exterior has no visible seams.

I love hunting down wall murals. Chicago has many of them! I will show you a few in a later post.

Love wall located at
1873 N Damen AveChicago, IL 60622
Artist: Matthew Hoffman
Read about the mural here.
Greetings From Chicago mural located at
2226 N Milwaukee Ave. Chicago, IL 60647
Read about the mural here.

Wrapping things up at Portillo’s with a beef and sausage sandwich and an ice cold beer…I could eat this everyday! Chicago has many delicious places to eat, but I try to visit this one as often as I can every time I visit Chicago. It was a perfect end to a fun-filled 24 hours.

Until next time, Chicago!

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