Five Reasons to Visit Chicago in Winter

There are tons of great reasons to visit Chicago in winter. No, it won’t be very warm. Yes, the odds are relatively high that you’ll get buried in a blizzard. But don’t let that deter you! You can always take a winter tour that keeps you toasty. Here’s at least five great reasons to visit Chicago in winter.

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#1. Awesome Museums

Art Institute of Chicago Winter lions reasons to visit Chicago in winter
Visiting the Art Institute of Chicago makes for a great winter activity. Photo Credit: David WilsonFlickr

The obvious place to start is obvious. But that doesn’t make it any less correct. Chicago’s collection of museums is world-class, many are clustered near transit, and they’re open year-round (duh). An easy #1 pick for the best reasons to visit Chicago in winter.

Personally, my favorite wintertime museum is the Art Institute, which is located just a few blocks from where our Loop Interior Architecture Tour ends. Voted the single best museum in the world a few years ago, it’s a great way to let a cold, grey day slip away. The collection is vast and comprehensive, with awesome rotating special exhibits. I’m perpetually happy to visit world-famous masterpieces like Nighthawks, American Gothic, and The Old Guitarist. But, truth be told, I find the collection too big for a single visit. I’ve never even tried to go to every wing in one go. My feet and eyes just run out of gas. Which means repeat visits!

Chicago history fans, or guests from our 1893 World’s Fair Tour, should also visit the Museum of Science and Industry. MSI is, of course, an awesome science museum. The indoor thunder storms, model train skyline, and authentic German U-boat are exhibits I still recall clearly years and years later. But, for those history nerds, the building itself is a piece of history. It was originally the Palace of Fine Arts for the famous World’s Columbian Exposition of 1893. In fact, it’s the only structure left from the fair, which opened 125 years ago. That alone is worth the visit, if you ask me.

#2. Weird, Crazy Weather Phenomena

five reasons to visit Chicago in winter weather ice cool
It may be freezing, but Chicago’s winter can look awfully cool. Photo by Alex Bean

Not to sound too much like a lifelong Midwesterner, but winter can be a pretty awesome season for breathtaking landscapes. Few things in life are finer than the sight of snow slowly drifting down through the city lights. Even when there’s no snow, the cold clear light of the low winter sun lends Chicago a certain Siberian beauty. Heck, you might even be lucky enough to visit Chicago in winter just in time for a blizzard. Those are a lot of fun. What? No, I don’t have Stockholm syndrome. Why do you ask?

visit Chicago in winter Museum Campus skyline

Personally, I really love the weird stuff that the winter cold does to the lakefront. Our waterfront parks are separated from Lake Michigan by a mix of beaches and concrete breakwaters. The former are pretty forlorn in the bleak midwinter, but the latter become fascinating ice sculptures. The splashes from frigid waves accumulate over the course of months until they become gargantuan, misshapen abstract expressions of winter itself. On top of just appreciating the beauty, they can be a great subject for photography.

Our current deep freeze has also reminded me of an even-weirder phenomena: the lake itself steaming. Every few years we’re subject to a “polar vortex.” That’s when a mass of bone-cold air drifts down from the Arctic Circle and then just…sits here. Chicago has been soldiering through one as 2017 gave way to 2018.

But an even worse one hit a few years ago. The city rarely climbed into the teens for about a month. In that time, the air temperature was so much colder than the water temperature that it caused Lake Michigan’s surface to writhe with steam. It made our great inland sea look like a nice, warm jacuzzi. While I wouldn’t advise swimming when the lake steams, it doesn’t mean it doesn’t happen!

#3. Fewer Crowds!

Federal Plaza Calder Flamingo Mies van der Rohe
Photo by Alex Bean

As lovely as Chicago can be in the summer, any locals can tell you how much they hate the crowds. Throngs of people crowd the sidewalks, streets, and beaches during the sunny season. I can’t tell you how many times I’ve silently cussed out slow pedestrians and crowds when on a mission to get to one of our walking tours.

Which makes winter in Chicago a surprisingly great time to go out and do things. As our Marketing Coordinator, Marie, said earlier “When I go out to brunch in February, there’s no wait. Just, boom, straight to a table.” The same is true for any other fun urban activity that’s seasonally appropriate. Go to the zoo. Stroll down the Mag Mile. See a show at Kingston Mines or The Green Mill after taking our Jazz, Blues, and Beyond Tour. Cheer on the Bulls or Blackhawks at the United Center. Chicago in the winter is your oyster, go ahead and eat it.

visit Chicago in winter Millennium Park Bean
Notice the lack of people? Photo by Andrew E. Larson via Flickr

#4. Restaurant Week

Speaking of, there’s no better time to dine out than Chicago’s annual Restaurant Week. Some of the finest restaurants in town set up special prix fixe menus at discount prices for your culinary pleasure. This tradition started back in 2007 and has been a midwinter highlight ever since.

Chicago, of course, has become a gourmand’s paradise over the past few decades. World-famous chefs like Rick Bayless and Stephanie Izard have created culinary empires in the shadow of the Loop. We even played host to the James Beard Awards for a few years. So, if Michelin star-studded restaurants like avec or Dusek’s Board & Beer are on the to-do list, then Restaurant Week is the time.

#5. Interior Architecture and History Tours

Loop Interior Architecture Walking Tour Public Tours Chicago Detours fun people
You can have a good time while staying toasty on our Loop Interior Architecture Tour.

(Learn more about why we switched to offering Virtual Events.)

Not for nothing, but taking an indoor tour is a pretty great reason to visit Chicago in winter. As I say at the start of the Loop Interior Architecture Walking Tour, “the inside of buildings is where we spend most of our time, it has a huge impact on human psychology, and it can tell us an awful lot about the city’s history.” That’s certainly true of the Loop Interior Architecture Tour, but it stands for all three of our year-round tours that stay mostly indoors.

Of course, we’re not the only game in town. Our friends at Chicago Running Tours offer (non-running) tours of those famous Chicago museums. If you’re looking to dine out while diving into Chicago’s history, Chicago Food Planet has several food tours that run through the winter.

Have Fun While Visiting Chicago in Winter!

No matter what you get up to, it’s fair to say that there are plenty of reasons to visit Chicago in winter.

– Alex Bean, Content Manager and Tour Guide


In business since 2010, Chicago Detours is a passionate team of educators, historians and storytellers. We applied a decade of experience as one of Chicago’s top-rated tour companies to become a virtual event company in 2020. We bring curious people to explore, learn and interact about Chicago’s history, architecture and culture through custom tours, content production, and virtual events.


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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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