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Chicago in Winter: Advice from Guides

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So you've driven, flown, or taken a train to Chicago, Screen Shot 2015-01-18 at 7.16.23 AMIllinois and it is winter time.  It can't be THAT cold, right?  Well... Yes, actually.  It can.  In fact, the winter of 2014 was the coldest winter in 100 years.  But that does not mean that you can't enjoy our city, feast your eyes upon our architecture, and indulge in our cuisine!  There are ways to survive the infamous Chicago Winter.  Some of our Chicago guides give their best advice below for Chicago in Winter:

"My one big tip is always top of the head (top of head is THE most important part to cover because everything starts from there). Invest in a long warm scarf so that you have more warmth for neck and ears. IMG_9465My favorite item is HEADSOKZ (a combo hood and ear covering) that protects against below zero wind chills. And as far as temporary escapes from the cold for 30-60 minutes..... The Cultural Center, Harold Washington Library, Palmer House (always has a place to sit), and the East Pedway for all its hotel lobbies, food courts to sit, etc."  -Bruce, Chicago Tour Guide
"In the Midwest, being warm is always un-apologetically prioritized over being cute. Celebrate long underwear-- a pair of leggings will do. Embrace the balaclava. Wrapping your scarf around your head like a bonnet and wearing your hat over it is a great way to preserve heat. Most Chicagoans own a coat that goes past their knees.  Avoid walking along the lake and river, the water makes it a whole lot colder.  And of course: Multiple. Pairs. Of. Socks. As many as will fit in your shoe." - Claire, Chicago Tour Guide

"Wear a hat, gloves, and long underwear.  Don't worry about "looking cute" on your vacation. Being WARM is CUTE.  Don't let the cold win!  Be sure to still do all the fun things you want to do despite the cold.  Take advantage of our amazing INDOOR activities like the Art Institute, the Sears Tower (The Willis Tower), The Hancock Tower, the Field Museum, the Shedd Aquarium, the Museum of Science and Industry (I could go on here....) Oh!  And go on a Pedway Tour!"-Mel, Chicago Tour Guide

IMG_2310“My best advice is to plan ahead!  Get museum passes or better yet, get tickets to a show.  Chicago has AMAZING theatre.  Try the Goodman Theatre, Steppenwolf Theatre, Broadway in Chicago, Looking Glass Theatre, etc.  Or see some comedy.  Laughing keeps you warmer.  Check out Second City, I.O. the Annoyance, etc.  Try to do “outdoor stuff” between 10am-4pm while the sun is out.”  -Emir, Chicago Tour Guide

"Experiencing Chicago in the cold is more "the Chicago experience" than the summer. This is what people in the city live through 9 months out of the year and they are so proud. Chicago in winter is crisp, cold, and still beautiful.” –Lauren, Chicago Tour Guide

About The Author

Canden Arciniega

Canden is a historian and tour guide in Washington DC with 4 published books about the city. She has written for HuffPost Travel and has been featured in the Washington Post, WTOP, and numerous other DC papers. She's also been interviewed by the BBC, NPR, Travel Channel and Discovery Family Channel. Canden is the producer of our podcast, Tour Guide Tell All With a M.A. in History from University College London and a B.A. in History from Elon University, she is an authority on D.C. history, and has led tours in the city for over 10 years. She currently resides in DC, but has also lived in London and South Korea, and has travelled to 28 countries. Her two children (both under the age of 4) have their passports and own frequent flier accounts.
Updated: September 26th, 2021
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