48 Hours In: Chicago

by Caitlin Boros · December 13, 2016

Chicago. It’s the American city everyone seems to be buzzing about. And after spending an all-too-short stay of 48 hours, I understand exactly why.

For years, the Windy City was somewhat overlooked, with tourists opting for the nearby metropolis of New York. However, along with a winning baseball team, the best of this city is finally starting to get the international attention it deserves. If you only have a few days to spend in beautiful Chi-Town, here’s a few things you just can’t miss.

What to Do

Chicago has an impressive list of activities for both visitors and locals alike. However, if you’re under a time crunch, consider picking up a GO Chicago Card. This flexible pass includes a build-your-own option and is a great way to save yourself time (avoid lines) and money on the city’s top attractions.

View from the Skydeck in Willis Tower. Credit: Caitlin Boros

Arguably, the best view of Chicago can be found on the 103rd floor of the Willis Tower. The Skydeck provides an incredible panoramic of the entire city and, on a clear day, visitors can see as far as four neighbouring states! As if this wasn’t enough, the building’s architects took the viewing experience one step further. After noticing prints left from guests pressing their foreheads against the glass to get a better view, the architects updated the floor to include The Ledge, four glass boxes that jut outside of the building to provide visitors an unprecedented perspective of the city.

Chicago is also known for it’s world-class museums. If you’re looking to re-enact the iconic scene from Ferris Bueller’s Day Off, head to the Art Institute of Chicago. This beautifully curated space has something to offer for every art lover, from European impressionists to American modern art. Learn all there is to know about the city at the fascinating Chicago History Museum, which contains over 600 objects documenting the city’s 200 year existence.

Cruising down the Chicago River. Credit: Caitlin Boros

Finally, there is no better way to get to know the city than a cruise down the Chicago River to explore some truly remarkable works or architecture. There are many boat tours to choose from, but all take visitors along multiple branches of the river that traverse like a canal throughout the centre of the city. Notable buildings include: Marina City (also known as the corn-cob buildings), the Civic Opera House, Aqua Tower, and 35 East Wacker – also known as the Jeweler’s Building – the top of which was once a Prohibition-era speakeasy operated by Al Capone.

What to Eat

A food-lovers dream, Chicago has everything from some of the world’s top restaurants to mouthwatering street eats. However, if there’s one dish this city is known for, it’s deep-dish pizza. This iconic pie is an entirely different beast than the Italian original. Those trying deep-dish for the first time will notice the pizza is truly more pie-like, with a deep and thick crust base. The toppings are also done a little differently. The first layer is cheese (ideally, great mozzarella from neighbouring Wisconsin), then additional toppings (the classic is simply sausage – not pepperoni!), topped off with a layer of chunky tomato sauce. While numerous local restaurants serve this hometown dish, my pick is Lou Malnati’s with their Chicago Classic.

Classic Chicago deep-dish pizza. Credit: Lou Malnatis

Rivaling the ways of nearby NYC, Chicago also has it’s own way of doing the quintessential streetfood: a hot dog. But you won’t find ketchup here. A classic Chicago dog includes an all beef sausage, yellow mustard, onions and a pickle spear. Again, this local staple can be found in restaurants and food trucks across the city, but a favourite is Portillo’s.

Chicago is truly a mecca of multicultural cuisine, with incredible food offerings representing every corner of the globe. The Humbolt Park area boasts some of the best Puerto Rican eats one can find outside of the island itself, and fantastic Mexican eats can be found in restaurants across the city. And while there is truly endless possibility when it comes to all things delicious, on a time crunch, I’d recommend heading to Cafe Ba-Ba-Reeba in the Lincoln Park neighbourhood for some delectable and authentic Spanish eats.

Where to Stay

Like most major cities, there are plenty of options for accommodations in Chicago, ranging from the luxurious to basic. That said, if time is tight but you still want to gain some of the local experience, I recommend opting for an Airbnb. With plenty of options, locations and price ranges to choose from, Chicago Airbnb’s provide some of the city’s top accommodations while putting you in the centre of city life. If you’re looking for something a little different, check out one of the city’s many boutique hotels. For contemporary comfort in the heart of the city, check out the Kinzie Hotel – and be sure to learn about the place’s namesake.

What do you love most about Chicago? Share with us in the comments below!

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Caitlin Boros

Caitlin's love for travel began at age 2 and has been a life-long affair. She's visited 13 countries, and has lived in 4. Caitlin currently resides in Paris, where she works as a Social Media Consultant at the Organisation for Economic Cooperation and Development (OECD). In her spare time, you can find Caitlin reading a good book, catching a flick at the local theatre, or eating something delicious. No matter where she is, you can bet she's thinking about her next adventure.