Disclosure: I was selected by Hampton by Hilton as a Seekender to partake in a Chicago Staycation weekend. The opinions expressed are my own.
Chicago is the one city that manages to fuse the history of San Francisco, the skyline of New York City, and the quaintness of the Midwest all in one pot. While I adore The Big Apple, Chicago offers so much and then some, with more space and scenic opportunities.
During my recent Chicago Staycation, I was able to get out and see more of Chicago. I spend so much time there for work, but I don’t get to go out and do some of the fun stuff that is available. During this trek, I was able to fit so much stuff in, including visiting the Sears Tower (Willis Tower) Skydeck, brunching at The Signature Room on 95th, John Hancock Observatory, and so much more.
In this post, I am continuing my coverage of my Chicago Staycation. I’m sharing Five Must Do Things to Do in Chicago, perfect for those who call Chicago home, or those visiting for the first time.
Skyline Architectural Boat Tour
Chicago has such a rich history, with so many stories behind the buildings and skyscrapers downtown. Thanks to Choose Chicago and Shoreline Sightseeing, we were able to participate in a Architectural Boat Tour that was very informative and entertaining.
We learned about the stories behind iconic structures like the Merchandise Mart, Marina City, Carbide and Carbon (now the Hard Rock Hotel), and much, much, more.
You can’t beat this skyline! During our recent #Seekender Staycation, we got to partake in a complimentary Architectural Boat Tour of Chicago and we enjoyed it thoroughly. If you are ever in the Windy City, this is a must! Thank you @shorelinesightseeing & @choosechicago for the tour! #mychicagopix #travel #travelblogger #traveltuesday #wanderlust #Chicago #chi #lifestyle #lifestyleblogger #hosted
Skydeck at Willis Tower
Chicagoans do not use the term Willis Tower—its Sears Tower for natives. But for the sake of this article, I am calling it by its “new” official name. You haven’t really done Chicago unless you’ve visited the Skydeck at Willis Tower and took a look at the amazing views of the city from one of the tallest buildings in the world. Steeped in history and tradition, Willis (er Sears) Tower is a Chicago institution. The clear glass of the Skydeck makes you feel like you are sitting on top of the city.
Chicago Water Tower
Most of Chicago’s original downtown was destroyed during the Great Chicago Fire of 1871. Only a few of the buildings that stood then remain to this day, and the original Chicago Water Tower is one of them. It is the second oldest water tower in the U.S., and is now used as an art gallery.
You can go inside on most days and take a look around.
Michigan Avenue (Mag Mile)
Some of the best shopping in the world awaits you on Michigan Avenue. The larger shopping district section of this area is referred to as the Magnificent Mile, a stretch of premium shops including Burberry, Ralph Lauren, Tiffany & Co., and more.
I don’t care how many times I’ve visited Chicago, I can never get enough of the Mag Mile. It’s great for eating, shopping, taking in entertainment, or just plain people watching.
Signature Room on the 95th Floor, John Hancock
For years, I’ve wanted to dine at the Signature Room, but never could get reservations. My friends at Choose Chicago were able to hook us up with brunch there, and I must say, it was amazing! The buffet is filled with favorites like fresh fruit, omelette station, ice cream bar, meats, cheeses, seafood, and more, and you can also order off of a menu of brunch favorites like Eggs Benedict.
While dining, you can take in some of the best views of the city, while being waited on by servers who are the best in the business. I cannot say enough about my experience at the Signature Room! It is something I will never forget.
When visiting Chicago, make sure to get a City Pass. This booklet can give you entry in dozens of Chicago attractions, and can also give you quick access to everything without the long wait. To learn more about City Pass and Choose Chicago, click HERE.
All the things we did while in Chicago were within walking distance of one another, so we kept the car at our hotel—Hampton by Hilton West Loop . You can also utilize a taxi or on-demand service like Uber or Lyft to get around.
Don’t get so busy that you forget to appreciate the wonderfulness in your own backyard. A Seekender Staycation is an awesome way to get to re(know) the city in which you live in while making new memories that can last a lifetime.