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Five Winter Things to Do in The Loop

By Alex Bean on February 10, 2016


We put together a list of five winter things to do in the Loop for you, since Chicago has a cold weather reputation. Winter weather can be a burden in disguise. Watching snow falling is always magical, of course. Gridlocked traffic and frigid temperatures are decidedly less delightful. Every activity we list here is indoors, fun, and easily accessible by transit. Taking winter tours of the city is always highly-recommended, of course!

Art Institute of Chicago Winter lions winter things to do in the loop

1. Museums

The city’s museums lead off our list of winter things to do in the Loop. My favorite is the Art Institute of Chicago. The permanent collection spans millennia and includes art from around the world. The Modern wing is also a beautiful architectural space to visit. For me, it’s always worth going just to see Edward Hopper’s “Nighthawks” again.

Or you can go to the Museum Campus, accessible via an easy bus ride from State Street. All three museums down there are worth the trip, but the Field Museum is my recommendation. The permanent displays are always worth a visit and it gets the biggest special exhibits in the city.

2. The Union Station Headhouse

Union Station headhouse
Union Station’s Headhouse is positively glowing after recent restoration work. Photo by Alex Bean.

I’m half-surprised this space still exists. Most commonly known for its Great Hall, the Union Station Headhouse feels like something you’d only find in “Lost Chicago.” The Headhouse takes up the whole block across Canal Street from Union Station’s main terminal. The Great Hall is historically a giant waiting room. You might remember it from the big shootout scene in The Untouchables. The original architectural plan called for a skyscraper to be built above the headhouse, but that never panned out. The best activity here, beyond taking photos, is to just sit, relax and people watch among the beautiful natural light. The monumental Neoclassical architecture will make you glad it’s on your list of winter things to do in The Loop. Plus, it’s free to visit!

3. 9th Floor of the Harold Washington Library

The top floor of our central public library has a few cool attractions. A permanent exhibit tells the story of the library’s namesake, who was Chicago’s first African-American mayor. Also the current temporary exhibition, “Straight into the Camera,” shows photography of the people of Chicago’s neighborhoods.

The ninth-floor’s “Winter Garden,” like the Headhouse, is a public space illuminated with natural light. The Winter Garden‘s architecture inspires a calm and reflective atmosphere. It’s also a stark contrast to the musty stacks and heavy brick architecture you see in the rest of the building. This quiet public space is a peaceful refuge downtown for me.

And lastly, on the ninth floor you will find the library’s Special Collections, where you can view anything from Civil War artifacts to theater programs from the early 1900s. 

Harold Washington Library Winter Garden winter things to do in the loop
Even the name of the Winter Garden atop Harold Washington Library indicates that it’s the right time of year to visit. Photo  Credit: Spiro Bolos – Flickr

4. The Loop Interior Architecture Walking Tour with Pedway

Not to brag, but our Loop Interior Architecture Walking Tour with Pedway belongs on any list of winter things to do in the Loop. The two-hour walking tour weaves through the insides of buildings and some of the Pedway system of underground tunnels. Because we’re mostly indoors, this tour still runs on those cold or snowy days when it feels like nothing in town is functioning. I’ve lead this winter tour when the air temperature was zero degrees and all the guests had a great time.

architecture walking tour of pedway underground chicago
Head into the Pedway during our winter tours or with our map. You won’t need a compass

5. Make Your Own Winter Tour by Wandering the Pedway

Already been on the Loop Interior Architecture Tour? Didn’t manage to get a reservation before we sold out? Have no fear, because you can still mark this off your list of winter things to do in the Loop. Our Pedway Map lets you explore Chicago’s mysterious underground on your own. Launch a shopping expedition while you meander below Block Thirty Seven and Field’s. Or challenge yourself to explore the Pedway’s mazes underneath the Lakeshore East, which is the name for the new residential area just north of Maggie Daley Park. Some sections might be closed on weekends, but this another fun, free activity in Chicago’s Loop. Get to know the Pedway well enough and you can lead your own winter tours down there!

Now get out there and enjoy yourself this winter!

-Alex Bean, Office Manager and Tour Guide


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Loop Interior Architecture Walking Tour with Pedway


Chicago Detours offers guided walking and bus tours of architecture, history and culture to public and private groups. We are a passionate team of educators, historians, artists and storytellers, and are proud to be one of very few tour companies in Chicago that is rated five stars on both Google and TripAdvisor.


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