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.
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.
For more of my Seekender Staycation tips, click HERE.
The boat tour sounds fantastic however there is no way I could go into that glass room up high LOL. Thanks for the list. We may go to Chicago soon!
These are all great picks! I love Chicago. Whenever I have to go there for business, I always try to book at least an extra day to just enjoy the city.
We love to visit Chicago. There’s so much to do there. I love visiting House of Blues, myself.
Chicago looks like a blast. Definitely one of the places on my bucket list. The water tower looks great and I could easily spend the day on the Magnificent Mile.
I so want to visit Chicago! I actually already have a few local restaurants on my list and will absolutely be adding Signature Room now as well.
Chicago is one of my favorite places to go. I will have to check out the Skydeck at Willis Tower. That would be a thrill for sure.
My sister was there last year and she said the sky deck is a must try. I would love to go one day.
I haven’t been in any country! I would definitely visit USA when the time is right! 🙂 Thanks for sharing this, at least I will have an idea where to go.
I’ve only been to Chicago once. I only went through there for a short bit though. I wish I would have been able to see more when I was there.
I love Chicago and would love to take a weekend trip there with my family. It looks beautiful and full of amazing architecture.
The last time I was in Chicago I was in high school. I loved it then and I am sure that I would love it now. Chicago has always been one of my favorite cities!
I have lived and worked out there and that makes you enjoy the city less. As a tourist I may enjoy the restaurants but the traffic still brings up my blood pressure.
My husband got to go to Chicago for work. He didn’t have time to do much though. I have always wanted to see Chicago in person.
I’ve never been to Chicago before, but visiting that sky deck is something on my bucket list. I think it would be fun and definitely nice to eat in the restaurant up there.
Never been there but i guess this is such a beautiful place to visit and take in some of the best views of the city while eating.