Five Winter Things to Do in The Loop

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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Private Tour Coordinator and Tour Guide

There is no shortage of things to discover in Chicago—I love being an urban explorer and uncovering its hidden places. I have an MA in Public History from Loyola University Chicago, and I have worked as a museum educator and kindergarten teacher. My desire to learn new things fuels my passion for educating others, which I get to experience every day as a Chicago tour guide. I live in the northern neighborhood of Rogers Park.

“Our guide Ellen was exceptional and gifted with a great personal touch.”


Tour Guide

Whether you are a first-time visitor or a lifelong resident, the vibrant history and modern majesty of Chicago never ceases to amaze. I’m a graduate of Columbia College with an M.A. in Interdisciplinary Art. I’ve worked for many years as an educator at City Colleges of Chicago. As tour guide at Chicago Detours, I integrate my enthusiasm for culture and architecture with my passion as an educator. West Town/Noble Square area is home for me.

“Jen was a perfect storyteller and kept us spellbound for hours.”


Tour Guide

With our Chicago neighborhoods, vibrant cultural institutions and nearly two centuries of larger-than-life stories, there’s never a dull moment here! I’m a fifth generation Chicagoan and a graduate of Washington University in St. Louis. In addition to guiding tours, I’m a creative writer and amateur genealogist. I also enjoy the city’s dynamic theater scene. You can also read overlooked stories from 19th-century newspapers on my “Second Glance History” blog. I live in River North.


Tour Guide

Chicago is unique as it always evolves into the future while holding on to the past. I’m fascinated by how people latch on to old architecture but happily pave over others. My background is in theater and performance and I’ve been a tour guide here for more than 10 years. Currently I’m finishing my Master’s in Public History at Loyola University because I love to teach the history of this scrappy city. I’m in the Edgewater neighborhood.


Operations Coordinator and Tour Guide

Chicago’s history is so fascinating, you could spend a lifetime uncovering its secrets…I’m willing to give it a try! I have an M.A. in US History from the University of Nevada-Las Vegas and then pursued doctoral studies in Urban History at the University of Illinois at Chicago. I love to learn new aspects of Chicago’s rich history and then share my knowledge as a tour guide with Chicago Detours. I live in Ravenswood.

“Marie was a bubbling fountain of information and contagious enthusiasm.”


Operations Coordinator and Tour Guide

As a fourth generation Chicagoan, I have been living and loving Chicago by bike, on foot, public transit or automobile. I am a graduate of UIC where through the College of Urban Planning and Public Affairs, began my eagerness to understand the nature, history and impacts of urban planning and development. It is incredibly rewarding to give back to this wonderful city by helping out in the office of Chicago Detours. I live in the incredibly diverse neighborhood of Albany Park.
“Sonny was extremely knowledgeable about all things Chi-town.”
Wade K


Content Manager and Tour Guide

Chicago has so many neighborhoods, buildings, and by-ways that it’s hard to go long without seeing something new, or something familiar from a new angle. I studied Cinema History for my M.A. from the University of Chicago. I’ve worked as a culture writer for various publications and as an educator of the humanities at the City Colleges of Chicago. I’m thrilled to share my love of this city’s busy past and unique architectural spaces with Chicago Detours. I live in the Chicago neighborhood of Lincoln Park.

“Alex was fascinating to listen to. He clearly knows his history and it shows.”
Katie K

Amanda Scotese

Executive Director and Tour Guide

I’m an interpreter of personal stories from the past and the city’s landscape. I love to imagine what originally happened inside old unmarked buildings, and what forces have shaped their design. I studied Chicago history, architectural history, and anything Chicago-related through my M.A. in the Humanities at the University of Chicago. My love for stories was enriched by my B.A. in Literature from the University of Michigan. I’ve written travel articles for publications like Rick Steves’ Italy best-selling travel guides, the San Francisco Bay Guardian, and The Chicago Food Encyclopedia. I live in the Chicago neighborhood of West Avondale.
“You can TELL Amanda is hyper-passionate about doing the research and getting the story that nobody’s heard before.”
Shelby F

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