How I Experienced the Best of Chicago in a Day

Chicago Illinois

Driving the entirety of Route 66 was the culmination of years of planning and it all started in downtown Chicago. Before tackling the Mother Road though, I arrived early in order to experience the touristy side to the city. Since it was my first time playing tourist in Chicago, I had a list of key sights I wanted to visit. Arriving into town, I first checked into the newly opened Marriott Marquis Chicago, a beautiful hotel that has some of the best design and style elements I’ve ever seen. It’s also a great home base to see the best of the Windy City. Although I didn’t have a lot of time in Chicago, I made the most of the quick day in the city including these experiences that I think are perfect for any first time visitor.

Chicago Illinois

Willis Tower (Sears Tower) & John Hancock Observatory (360 Chicago)

Before leaving home I made sure to buy the CityPASS for Chicago since it included everything I wanted to experience in the city. It’s not something I always buy, but it has helped a lot in several cities around the country and especially in Chicago. Not only did I save some money but, more importantly, I saved a lot of time. The CityPASS included Fast Pass access, allowing me to skip the very long lines to both the Willis Tower and 360 Chicago. I’m a sucker for great views and Chicago has one of the best skylines in the world. There’s nothing better than heading to the top of both of these massive towers to better appreciate the city and the shoreline of Lake Michigan.

The Cloud Gate and The Art Institute of Chicago

No first time visit to Chicago would be complete without stopping by the famous Cloud Gate, what some people call the Chicago Bean. Located in downtown Chicago, the Cloud Gate is a public art installation that has been captivating the masses since it was first erected. Made up of 168 stainless steel plates wielded together, the exterior has no visible seams which enables incredible reflections of the city skyline. It’s also a very popular spot, so if you want a great photo without many other tourists be sure to get there at dawn. Also nearby is The Art Institute of Chicago, one of the country’s premier art museums. Days could be spent exploring the collections, but if you have some time it’s well worth even a quick visit. For Route 66 buffs, the origination/ending point of the Mother Road is also close to the Cloud Gate, so be sure to look for the sign and imagine all of those intrepid souls who have traveled down the famous road.

Chicago Illinois

Architectural Cruise

There was a lot I wanted to experience during what was my first time in Chicago as a tourist, but at the top of that list was the famous architectural cruise. Long considered one of the best tours in the world, dozens of people have recommended it to me over the years and I couldn’t wait to see what all the fuss was about. A warm and sunny weekend day meant that the entire city seemed to be outside, enjoying the near perfect weather. That was certainly true on the water; I couldn’t help but notice that the cruise I was on was almost fully booked. I don’t think I ever realized that the Chicago River does indeed run through the city itself, creating not only a beautiful waterway through the heart of the city, but some natural air conditioning on those hot summer days. Chicago is a fascinating city for a number of reasons, but its relatively young age is I think amongst the most notable. Not only is it young, but it was almost completely destroyed during the Great Fire, which means the city we see today is mainly a product of the 20th century. It’s through that history that the architectural cruise sails, and the 90 minutes spent on the water learning all about the dozens of buildings along with the history of the city was one of the most fun experiences I’ve ever enjoyed. I quickly understood why the cruise is so very well regarded and it’s just one of those experiences I think everyone needs to do at least once in their lives.

Chicago’s Unusual Food Culture

Although I’m not really a fan of Chicago’s most famous food offerings, even I had to at least try some before leaving town, starting with pizza. To be clear, I am very much a fan of New York-style pizza and even Detroit-style pizza is something I love. I don’t really see Chicago deep dish as pizza, it’s more of a casserole, but of course it has legions of fans around the world. The pan in which it’s baked gives it a very high edge, which in turn allows for a huge amount of cheese and chunky tomato sauce to be added. Love it or loathe it, it’s an experience all visitors to the city should try at least once. There’s a lot more to Chicago though than it’s pizza, whether it’s traditional Polish cuisine or some of the best fine-dining restaurants in the world, there’s a little bit of everything in the Windy City.

Marriott Marquis Chicago

Although I’ve been patronizing Marriott hotels for many years, I believe that my stay in Chicago was the first time I experienced the Marriott Marquis. Marquis hotels are large, flagship properties that add many special touches to the hotel experience with extra attention paid to style and of course service. The Marriott Marquis Chicago is a new downtown hotel that impressed me right away. The enormous lobby, bustling restaurant and lounge and of course the rooms were all stylish and inviting, making this a fantastic home base for my time in the Windy City. Of special note is their restaurant, Woven + Bound that features tasty and modern cuisine in an eclectic but welcoming space.

No matter what your own perfect day in Chicago looks like, it’s a fun city to explore and I’m sure you will have just as much fun as I did.


This post was created in partnership with Marriott International, but all thoughts and opinions are entirely my own.

By: Matt Long

Matt has a true passion for travel. As someone who has a bad case of the travel bug, Matt travels the world in order to share tips on where to go, what to see and how to experience the best the world has to offer.

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