Chicago Travel Guide: How to Spend 48 Hours in Chicago

Chicago – 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, born and raised, 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!

Introduction to 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.

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 may 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 Garretts 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!

How to See Chicago in Two Days

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 city had their own unique style of hot dog.  This dog is 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!

How to See Chicago in Two Days

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 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!

How to See Chicago in Two Days

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.

Magnificent Mile

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

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’s sites.

How to See Chicago in Two Days

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.

How to See Chicago in Two Days

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?

How to See Chicago in Two Days

Art Institute of Chicago

There are lots of museums in the city, but 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 amount of details was unbelievable!

 How to See Chicago in Two Days

How to See Chicago in Two Days

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!

Get This Guide On The Go!

Planning a trip to Chicago? Download the free travel app GPSmyCity and take this article with you! Click here to download this article on your smart phone for built-in offline maps and GPS routing ability.

Happy travels and enjoy Chicago!        

Alannah McEwan


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2 thoughts on “Chicago Travel Guide: How to Spend 48 Hours in Chicago

  • November 13, 2016, 1:26 pm

    I’ve lived in Chicago for the last 5 1/2 years and I think these are all great suggestions. Although I must admit, I highly discourage visiting in January or February. March is cold but January and February can get unbearable at times. We go on vacation every February to some place warm just to get away from the Chicago winters.

  • Ray
    October 17, 2016, 11:34 pm

    Coincidentally, I was in Chicago just last month for a work trip, as well. And like yourself, I had a friend who hosted me for a couple of days before I had to meet my colleagues for our meetings. These are all great suggestions, but what I find helps if you focus on planning a theme for your trip as you’re not going to be able to see everything Chicago has to offer in a short period of time.

    You could choose a food theme, and focus on finding the hotspots of Chicago’s culinary scene, like you did with Garrett Popcorn and Lou Malnati’s. Chicago also played a prominent role during the Prohibition Era, so you could seek out all the significant places and speakeasies that famous Mobsters, like John Dillinger and Al Capone, ventured in.

    Chicago also has one of the most vibrant and fastest growing craft brewery scenes in the United States as I found out when I was down there. I didn’t have any time to go to any specific ones, but you should definitely consider going on the Goose Island Brewery tour as Goose Island is probably Chicago’s most famous brewer.

    As for myself, I opted for a sports themed weekend – Chicago Fire soccer match, Wrigley Field tour, Chicago Sports Museum, Chicago White Sox game, and Soldier Field tour. Of these, I highly recommend the Wrigley Field tour as it provides you with so much history about the Chicago Cubs and their significance on the Windy City. Now whenever I watch a Cubs game on television, I have a newfound appreciation of how difficult and unpredictable that park can be to play in.

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