What to do in Chicago in 2 Days

Chicago is the third biggest city in the USA and the fourth biggest in North America. Lots to do and see. So what if you only have 48 hours? How can you make the most of those two days? I was recently in the windy city for four days, two days of sightseeing, and two days of work. I was lucky to have a local friend to show me around and help me get my Chicago experience in 48 hours. Now I want to share with you how you can make the most out of your time in this great city!

Why Chicago?

Ah Chicago, what a great place to visit! With a population of almost three million people, it’s the third-largest city in the United States. There is a reason that 40 million people visit Chicago every year, it’s beautiful and filled with great things to do and see.

Chicago Transportation

This post is about spending two days in Chicago but of course, you could easily spend much longer there. This article will focus on some of the major sites and attractions. There are many other experiences to try such as the Willis Tower (formerly the Sears Tower). The tower is the tallest building in the Western Hemisphere. Lincoln Park Zoo is the country’s oldest public zoo. You could write an entire book on all the things to do and see in Chicago! Whether you’re visiting for two days or two weeks, you’re sure to have a great time!

When to go to Chicago

I went to Chicago in March, so the weather was not great. I didn’t let this stop me from having a great time. Whatever time of year you go, you will find something to do. Because of this, I would say that any time is a good time to visit Chicago. When I was visiting, people kept telling me that I really must visit again in the summer. As with almost any city, you can do more when the weather is nice. You can enjoy the Pier and waterfront more during the summer while the weather is nice.

What and Where to Eat and Drink In Chicago

Enjoying Chicago is as much about what you do as what you eat.  You’ve gotta try a deep-dish pizza, a Chicago style hot dog, and Garrett’s popcorn. Mmm!

Deep Dish Pizza

I asked locals and tourists alike about where to get the best deep dish pizza in Chicago. The two names I heard the most was Giordano’s and Lou Malnati’s. If I had time I would have gone to both. I chose to try Lou’s on my trip. We ordered the calamari fritti, buffalo chicken wings, and of course their famous deep-dish pizza with sausage and extra cheese. Everything was tasty and the portions were a good size. The pizza was piled high with toppings and the staff was friendly and attentive. Two thumbs up!

Chicago Style Hot Dog

Next on the list of tasty Chicago eats is the Chicago style hot dog! I didn’t even realize before my trip that the city had its own unique style of hot dog.  This dog is a Windy City favorite.  Topped with yellow mustard, green pickle relish, tomato, a slice of dill pickle, sport pepper, and celery salt. Most important is what’s not on the hot dog … ketchup! The kiosk where I picked up my dog even had a sign that said if you want ketchup you have to dance for it!

Chicago Style Popcorn

For Chicago style popcorn you’ve got to try Garretts. There are several locations in the city, I stopped and got a bag at their Navy Pier location. There is a variety of flavors to choose from. I went for the Garrett Mix, a yummy combination of Caramel Crisp and Cheese Corn. Two great flavors in one bag!

Signature Lounge on the 96th Floor

To get an unbeatable view of Chicago’s head to the Signature Lounge. It’s on the 96th floor of the John Hancock building. On the 96th floor, you can get drinks and appetizers if you want a full meal you can go one floor below. We ordered two appetizers: the flatbread and the seafood sandwich. Neither was anything special and pricey as you would imagine. But this place is not about the food – it’s all about the incredible view! Don’t forget to go to the bathroom where you will get the best view! We probably spent just as much time in the bathroom as we did in the lounge!

What to do in Chicago

Architecture River Cruise

A great way to see the city and learn some history at the same time is by doing a boat tour. I did the architecture tour and it lasted 75 minutes. I got to see a lot of the city during this tour as well as learn about major events that have shaped the city and the different styles and types of architecture that make Chicago what it is today.

Chicago Sightseeing Tours

Magnificent Mile

A great and free thing to do – take a walk down the Magnificent Mile. It’s one of the, if not the best know, parts of downtown Chicago. The mag mile is 13 blocks that go from the Chicago River to Oak Street and is lined with shops, restaurants, and beautiful buildings.

Magnificent Mile Chicago

Navy Pier

Another great place for a walk in Chicago is Navy Pier. I went during March and the weather was not great so there were not many people around but I have heard that in the summer months it’s buzzing with people and energy.  Also, during the summer there are fireworks every Wednesday and Saturday evening. The pier was built 100 years ago in 1916 and is now one of the city’s most popular tourist sites.

Chicago Navy Pier

The Bean

One super touristy thing you have to check out and get your picture at is the Bean! It’s a pretty cool and unique piece of architecture that acts as a mirror, reflecting the city’s skyline.

You can also go under the bean. I sent a picture to my friend and she said it looks like a giant squatting! Now that’s all I can think of when I see the picture. What do you think?

Art Institute of Chicago

There are lots of museums in the city, but the only one that’s been rated by TripAdvisor as the Best Museum in the World. The Art Institute of Chicago. It’s also the perfect way to enjoy the indoors on a rainy or chilly day. You could easily spend all day here and still not see everything, so if you’re on a time crunch decide which exhibitions interest you the most so that you make the most efficient use of your time. Personally, I thought the miniature rooms were pretty cool, the number of details was unbelievable!

Final Word

So there you go my friends, Chicago in 48 hours! I loved the city! Despite its large size, it was very clean and the people were friendly and nice. I would definitely go back in the summer as many locals told me that’s the best time to visit. Many thanks to my wonderful friend, tour guide, and Chicago local for the great 48 hours!

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