Have you heard about Chicago? Well, who hasn’t – from its immigration days, music heritage, and political bosses to Route 66 and Jack Kerouac’s tales, The Blues Brothers, to Michael Jordan, Ferris Bueller’s Day Off… Chicago is an integral part of American culture. And yet, I had never been to the Windy City - so named mainly for its weather, maybe also a little for its politicians…

This past week, my preconceptions of Chicago were put to the test during a brief trip. How would the real city compare to all of my expectations?

Cool Things to do in Chicago in Winter - Emily Perkinson

To answer this question, my boyfriend and I planned some activities that would provide a Chicago experience that would leave enough time to explore, make us think, and encourage us to come back—or at least to recommend the city to others. It must be stated right away, however, that three days proved to be a very short stay!

Cool Things to do in Chicago in Winter - Emily Perkinson - Pizza

Where to Stay

We stayed in an AirBnB room, as it was a convenient way to see the city more like the locals do and to meet some lovely people. When booking a place to stay however, keep in mind that although Chicago is now a much safer city than in previous years, certain precautions need to be taken. Always research your neighbourhood and ask for advice before making definite plans. This counts for accommodation and attractions alike.

How to get around

Once we arrived in Chicago, we purchased a $10 Ventra card for easy public transportation. These cards can be purchased in Walgreens shops or ordered online. The bus system in Chicago works very well, and it is definitely one of the easiest and cheapest ways to get around in the city. With the Ventra card, fares are $2.00, with a $.25 bus transfer fee.

Cool Things to do in Chicago in Winter - Emily Perkinson - Skyline from University Campus

As we arrived on a rainy, cold November Sunday, and the rest of our three days were to be similar in temperature and precipitation, here are 6 things to do if you visit Chicago on an early winter weekend:

1) The Museum Campus

Cool Things to do in Chicago in Winter - Emily Perkinson - Planetarium

The Museum Campus comprises an interesting layout of the Field Museum, Aquarium, Adler Planetarium, overlooking Lake Michigan. From the museum campus, there are excellent skyline views of Chicago. In the winter, fog from snow and rain quickly moves in from Lake Michigan, completely obscuring the skyline. Yet this happens to be perfect weather to be inside, enjoying the museums. The Chicago CityPASS is a great motivational way to see 5 different sites in Chicago, for about ½ of the full-fare prices. Yes, prices, as museums in the Museum Campus come with a fairly hefty entrance fee—around $40.00 per adult.

**Had the weather been nice, the first activity I would have gone for would have been to go on a free tour of Chicago, provided by Chicago Greeter.

2) Fermilab

Cool Things to do in Chicago in Winter - Emily Perkinson - Fermilab

Venturing about 1 hour out of the city via the Metra train, the Fermi particle physics laboratory, Fermilab is a unique way to spend the afternoon. Fermilab is open to visitors; there are science and educational displays, an art gallery ask-a-scientist events and much more – check their website for the programme! The Lederman Center, designed for younger students but fun for all kinds of visitors, is a nice place to start the tour and brush up on some physics concepts. The Fermi campus has some interesting architecture, a herd of bison, and even barn dancing events.

3) Christmas Market at Daley Plaza

Cool Things to do in Chicago in Winter - Emily Perkinson - Christmas market

On our way to the shopping district, the Magnificent Mile, we passed by Chicago’s Christkindlmarket at Daley Plaza. Complete with Glühwein, Lebkuchen, and all of crafts and candies, the market lends a festive spirit to Chicago. They were to light the Christmas tree one day after we left.

4) John Hancock Observatory

Cool Things to do in Chicago in Winter - Emily Perkinson - At night from John Hancock Observatory

At the north end of the Magnificent Mile, the John Hancock Observatory allows visitors to overlook “360 degrees” of Chicago —for $18 per adult. From the 94th floor (!) you will get a fantastic view anytime of the day. When we went at 10pm, the sparkly Chicago lights delineated the city and its outline along Lake Michigan, providing some perspective to the ground that we had covered.

5) University of Chicago

Cool Things to do in Chicago in Winter - Emily Perkinson - University of Chicago Library

University of Chicago—worth a visit, this private American university has played a role in many academic breakthroughs. Many a nobel prize winner has graduated from this university, and even Indiana Jones! The campus is lively, beautiful, and home to a Frank Lloyd Wright’s The Robie House. For a quick coffee break, there are cozy cafes and bookstores. Check out my favourites Plein Air Café and Z&H market.

Cool Things to do in Chicago in Winter - Emily Perkinson - Cafe

6) Millennium Park

Cool Things to do in Chicago in Winter - Emily Perkinson - The Bean at Millenium Park

Home to the beloved photo-op, the “Bean”, the Millennium Park is definitely worth a visit if just to marvel at the sculpture. The Bean’s true name is Cloud Gate, and it is one aspect of Chicago that I thought would be overrated—until I saw it. According to our Airbnb host who photographed the installation for the city when it was initially unveiled, the welding seams were still visible, much to the artist’s dismay. The welders later carefully smoothed over the surface, creating a perfectly smooth, non-distorted shell coating. The city and sky are reflected in a gorgeous way and the Bean’s atmosphere is fun: watching everyone photograph their best angles alongside the city skyline.

Cool Things to do in Chicago in Winter - Emily Perkinson - Chicago Bulls

Chicago is a well-known American city for good reason. It is a distinctly American city that seems to reveal some of its history on every street. I saw its charm, academic prestige, its grit and glamor, and a first look into its real character. I cannot wait to go back.


This is a guest post by Emily Perkinson. All photos by Guðmundur Kári Stefánsson.