Thirty Hours in Chicago

Ever since I attended my Aunt and Uncle’s wedding in Chicago when I was six years old, I have been mesmerized by the fast paced, glamourous city.  While I have made multiple quick trips into the city while visiting friends and family, it had been a very long time since I last saw Chicago through the eyes of a tourist.  So when Chris convinced me to go to Whiskeyfest, I decided we needed to take a day or two to explore the city like a first time tourist.

I loved dressing up for a night on the town! I'm the little one in front of the lady in the blue dress. (My Mom)
Friday, 11:30 A.M.- We Check In
We arrived at the Hyatt Regency in Downtown Chicago.  I was extremely excited that we were staying in the middle of the action and didn’t have to walk far to get back to our room after the drinking the hooch.  We tossed our bags in our room and headed out for a tour of Chicago.

Friday 1:00 P.M.- We Take a Tour
We boarded our gangster tour bus.  It had been a while since we went on a proper tour of the city, so we took a Untouchables Tour of the city.  We learned all about the seedy side of Chicago from our tour guide, Johnny Three Knives, and saw the site of the St. Valentine’s Day Massacre.

It was nice to see the city in a comfy tour bus.

Friday 3:05 P.M.- We Eat Some Deep Dish
After a hour and forty-five minute tour, we decided it was time to catch a meal at the “birthplace of deep dish pizza”, Pizzeria Due. 

I confess, I have had Chicago style deep dish pizza before and did not like it at all.  There is something about having all of the toppings and sauce over the cheese that gives me the heebie jeebies.  

I find having the cheese below the toppings and sauce to be very confusing.

Since it was a Friday in Lent, Chris and I shared a small four cheese pesto pie.  

This was the best deep dish I ever tried.
It was INCREDIBLE!  The crust was not nearly as thick as anticipated, and the flavors were perfect.

Friday 4:15 P.M. - We Waddle Back to the Hotel to Take a Disco Nap
We needed it after we consumed the cheesy goodness.

Friday 5:00 P.M.- My Nap is Cut Short Because Someone Wants to Line Up for the VIP Hour at Whiskeyfest

I am not a whiskey drinker.  However, when Chris asked me to join him for Whiskeyfest because “All of the other wives and girlfriends were going” I felt obligated to go. 

Whiskeyfest was like a giant old man fraternity party.  A few hundred men, dressed in their favorite whiskey wear, had fabulous time sipping their favorite whiskeys, scotches, and bourbons.  

There were so many old men in one location. 
I did enjoy the sweaters, however.

I had the opportunity to taste extremely rare, expensive bourbons.  However, all of them tasted like burnt ground and rubbing alcohol.  

This was the only cocktail I enjoyed. 


Friday 9:05 P.M.-  Time for Bed
I had my fill of fun, so I crashed early. 

I was very over Whiskey by the end of the night.
There was much fun to be had the next day.

Saturday 9:00 A.M.-  We Find Breakfast at the Billy Goat Tavern.
The Billy Goat Tavern is the diner that inspired the famous “Cheezborger Cheezborger Pepsi” skit on SNL.  They have some of the best morning after breakfasts, so we decided to fuel up.

I was ready for some breakfast at the Billy Goat.

I passed up the cheezborger for some steak and eggs. So yummy!
Saturday 10:30 A.M. - We Visit VanGogh
After breakfast I was in the mood for a little culture, so we headed to the Chicago Art Institute to see the Van Gogh’s Bedroom exhibit.   I was really excited to see the original bedroom paintings after seeing a large projection of them in Shanghai.

The museum is experiencing record crowds for this exhibit, so I HIGHLY recommend purchasing tickets online.  Otherwise, you will spend a long time waiting to purchase tickets and will have another long wait to enter the exhibit.
Fortunately, I had the foresight to purchase tickets for the exhibit online, so we were able to skip the ticket and exhibit lines.  
This was the original selfie.

The exhibit had an exact replica of the room where Van Gogh created his masterpiece.  I had no idea the room was so small!
The paintings were breath taking.  It was definitely worth the wait and price of admission.

Chris had fun playing in the picture.
We really enjoyed the collections at the museum.
Saturday 1:05 P.M.- We Head to the Sears Willis Tower for a View of the City
The Willis tower was about a fifteen-minute walk from the Art Institute so we decided to take an elevator ride to the top of the building.  

The Willis Tower will always be the Sears Tower to my husband.
We were greeted with another long line.  I didn’t have the foresight to pre purchase tickets, so we hung out in line for a while.   
Many side exhibits, like this Lego replica of the tower, provided some entertainment during our wait.
We were warned that the wait would be lengthy at the beginning of the line. 

During the wait we learned all about the construction of the tower.
The Willis tower is about 300 Chrisses tall. 
Saturday 2:42 P.M.-  We Finally Take Our Elevator Ride to the Top
The view of the city was worth the 90-minute wait in line. 

This view was definitely worth the wait.

I overcame my minor fear of heights to get a picture in the plexiglass sky-walk.  
Saturday 3:30 P.M.- We Have a Final Chicago Meal at Portillo’s
My trip to Chicago would have been incomplete without an Italian Beef sandwich and a Chicago style hot dog, so we had a late lunch at Portillo’s

Portillo's has an extensive menu of classic Chicago eats.

I had eaten a Chicago style dog before this trip.  I am not a fan of having the entire contents of one's refrigerator on a hot dog.  I finally tried one for the blog.

I enjoyed the tomato, pickle, onion, pepper and mustard topping.  The flavors worked well together.

Chris got a wet Italian Beef sandwich.  While it was yummy, he prefer's Al's beef.
Saturday 5:30 P.M.- We Head Home
I was exhausted!


I fell in love with the city all over again during our thirty hours of food filled exploration. I will always have a place in my heart for my second home, Chicago.

Popular Posts

Image

My Life in Mexico

Image

¡Viva México!