Stay Warm on Indoor Chicago Tours During Winter

Indoor Chicago tours during winter are the best way to experience the city when the weather is at its worst. A boat tour or an outdoor walking tour can be a great way to view the city, but not so fun in Chiberia. So, while Old Man Winter persists in pestering us, we came up with three scenarios that explain how our indoor Chicago tours during winter can meet your needs.

#1. Sneaking Away from a Conference

Marquette Building Loop Interior Architecture Walking Tour
Tour guides show you gorgeous interior spaces, avoiding the worst of Chicago weather. Photo by Pawel Skrabacz.

Many wintertime visitors to Chicago are in town for conferences. When you’re in town for business, you may want to sneak away for a little bit of fun, especially in a town as fabulous as Chicago. Trouble is that many of the summertime pleasures, like going to the beach or taking in a concert at Millennium Park, are circumscribed by climate. That’s where indoor Chicago tours come in handy!

Our Loop Interior Architecture Walking Tour is just the thing when you need a break from McCormick Place. This downtown walking tour stays mostly indoors; guests spend about 80% of their time inside buildings or the Pedway tunnels. The route zigs and zags between historic and contemporary architecture, while Chicago Detours’ expert tour guide shares stories that bring Chicago’s past to life. It’s a great complement to the general overviews you get on boat and bus tours. The experience slows down and digs into the amazing architecture of Chicago. The Loop Interior Architecture is available seven days a week all year, even in freezing temps or snowy weather, and private groups can book it too.

#2. A Social Outing with Friends

historic chicago walking bar tour lawrys chicago tours winter
Good times are had by all on an indoor Chicago tour during winter. Photo by Pawel Skrabacz.

Social life doesn’t stop in January! The deep midwinter is, in fact, a great time to organize an outing with your friends and family. The stress crunch of the holidays are past and spring break is a long ways off yet. You don’t have to spend the winter cooped up hibernating. Reach out to arrange an indoor Chicago tour this winter. We can even put together a private group tour for your squad!

The ideal outing in this scenario is our Historic Chicago Walking Bar Tour. This mostly-indoor outing loops through the Mag Mile area, viewing famous architecture, a forgotten speakeasy, and a glamorous Jazz Age club. Of course, guests also visit three watering holes for a drink and a snack at each stop. The tour guide has all sorts of fun stories, including the famous Curse of the Billy Goat and the scandalous reputation of jazz in its early days. The mix of stories, sights, socialization and drinks make this a fantastic treat. A five-star review on Yelp sums up why this is the perfect wintertime outing for friends: “Man what a great way to get in some steps on my Fitbit, catch up with friends, learn a little history and eat/drink.

#3. Best Alternative to the River Architecture Tour

chicago tours winter
Hopping aboard a bus is a great way to tour Chicago in the winter. Photo by Marie Rowley.

The architecture boat tours here in Chicago are world famous for very good reason and a great way to get an overview of Chicago’s architecture. Sailing through the city and gawking up at its spectacular skyline is a peerless experience. So what’s one to do during these winter months when the Chicago boat tours are not running? Chicago Detours’ Chicago Highlights: Detour 101 Bus Tour for private groups is just the thing!

We designed this driving tour to be as flexible and fun as possible. It suits group sizes from two to two hundred and includes spots to disembark for photos and on-foot exploration. The tour route zips around downtown and the Near North Side, taking in magnificent sights like the skyline from Museum Campus and the canyon of historic skyscrapers on Dearborn Street. Since it’s an experience from Chicago Detours, there’s also fun and off-the-beaten-path elements. Tour guests will experience the hidden lower levels of downtown streets and see the last tomb in Lincoln Park, once the city’s cemetery.

Reach Out to Learn About More Indoor Chicago Tours in Winter

The three Chicago tours in winter that I’ve highlighted here are just the tip of the iceberg, so to speak. Also, no icebergs in Lake Michigan, just in case you’re worried about that. The city still beckons and delights at this time of year. We know just how to bring out its history, culture, and beauty without freezing. Check out the public tour schedule or give our private tours team a call!

– Alex Bean, Content 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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