Chicago is no ordinary city in the wintertime. Between it being considered “the Windy City,“ it also can reach frigid real time temperatures, as well as “feels like” temperatures. For instance, the temperature may be 32°, but on the weather app, with noted 20 to 30 mph wind gusts, it could feel like 15°. In January and February, it’s rarely above freezing. But you don't want to miss out on the sights, smells, noises and the force of that wind by taking and Uber or a cab, so take a walk in Chicago in the wintertime.
It’s worth it to walk, to be able to slow down and experience Chicago with more of your senses than just sights. Enjoy viewing the fantastic, diverse architecture up close, observe the people and their hats, coats and shoes. Feel the brisk wind, smell the garlic and ganja, and hear the sounds of drummers, loud cars, and people chattering with each other or on the phone in many different languages and accents.Here is a short instructional walking guide document for those that may be visiting Chicago, or have just recently moved here over the summer when the weather is mild and beautiful.
Shoes
First and foremost, wear comfortable shoes! You can find fashionable, good-looking shoes that are comfortable if you wish to walk more than a mile. In the wintertime, this may require a little more thought, as Birkenstock sandals won’t cut the cold. If you’re going for a recreational walk, it’s best to wear some form of athletic shoes. However, many tennis shoes are web–based or made out of fabric, and the cold air seeps right through that fabric. So, wear exercise shoes that are leather, or more tightly woven material to protect from the cold air. My favorites are Hoka, New Balance and Sketchers.
Wool socks will provide much more protection as well. Other advice would be to wear ankle or knee socks, rather than crop socks.
Boots are appropriate, depending on how long of a walk you’ll be taking, their comfort, and the heel height, but in downtown Chicago, comfortable shoes are the key. Just to make sure I’m clear, you will also not want to wear stiletto heels, or any pumps that may either be uncomfortable, or wedge into a crack on the sidewalk.
Timing
The sun sets early in Chicago, so head out earlyish (10 am) to mid-afternoon (2 pm) to not need to walk around in the dark, when it becomes colder. On December 7, 2024 the sunset time is at 4:18 p.m., rather early for me, and if and once the sun goes down, temperatures will reduce even more, so be sure you are dressed warmly enough for evening weather. After the winter solstice (December 21), the day begins to lengthen, with sunset around 5 pm by the end of January, and 5:44 pm by February 28 (or 29).
The shadows cast by the tall buildings eliminate sunshine in many spaces, also brought on by the sun in the southern sky during winter. The sun rises at about 7:30 am in December, so you have about 9 hours to tour the city during daylight hours. With stores and museums not opening until about 10 am, you can explore coffee shops, breakfast nooks, and storefronts before they open if you like to get out early. The sun is also rising earlier at the same rate, so by the end of February, you have 11 ½ hours of daylight, that is, if it’s not cloudy, rainy or snowy.
Wind and rain advice
Chili is a mild word for what it feels like to encounter a cold and windy day in Chicago. I will admit that I have not faced under 18° yet. But that 18° day was a “feels like 10 degrees day” and it was more than chill, it was ice cold! Cover all of your skin, including your head with a hat, your neck with a scarf, a windproof jacket, warm socks and non-porous shoes.
If it happens to be raining, be prepared with a sturdy umbrella that will either withstand being turned inside out by the wind and go back to regular function, or not flip. If you experience such wind, which has happened to me as I walked to a dentist appointment, turn the umbrella around to face the oncoming wind and it will flip. Hold the umbrella pointed towards the wind if possible, protecting your body and head. Wear waterproof pants and a jacket, with galoshes or rain boots, which come in very handy, especially if they are comfortable. My favorite brand, and actually the only brand I’ve tried is Chooka.
Clothing
When it’s cold outside, you will want every part of your visible body covered, with 32 degree leg warmers and shirt as your first layer (after under’s). Whatever you have over that doesn’t matter as much as the outer layers. If you have a long coat, the top part of your legs will be covered. If not, a short coat will do as long as you have leg warmers and jeans, corduroy or other winter weather fabric.
The Outer Layers
Besides comfortable shoes, to walk in Chicago in the winter, the outer layers are the most important! A down-filled jacket is my recommendation, and I’ve had a short jacket by Eddie Bauer for many years, and another full length jacket by Bernardo. Then, a hat to warm your head and keep your ears warm is imperative. If you only have a cheap woven beanie or a baseball cap, it’s better than nothing, especially if you have on a hoodie under your coat. I have a puffy, eastern European looking London Fog hat that covers the back of my head to my eyebrows and is snug and warm. You’ll find a wide variety of hats on Etsy, ebay or Amazon.
Gloves are best when made out of tightly woven yarn of wool preferably, but leather, suede, and fabricated material work when nicely lined with satin or other fabric. A scarf can be used to cover your mouth and face because it's rare that it's not windy in Chicago. Or, wear a cowl-necked shirt and pull it up over your mouth. Many coats have collars that can be brought up to cover the face as well. If it's sunny, and maybe even it it's not, sunglasses will protect your eyes from cold air while walking the streets of Chicago.
Indoor outdoor advice
Oh, it may be 20° outside, but the majority of locations you will enter after walking in Chicago in the winter will be warm, and almost to the point of being hot at times. And if you’ve walked for a quarter to half mile or more, you’re going to be warm already. My advice is to wear layers. And if your coat is warm enough, made with down and waterproof/windbreaker material, even if you are dressed lighter underneath with just the 32 Degree shirt and an overshirt, you’ll be warm enough. Take off your hat first, to cool from the top, then gloves and scarf and put them in your bag (see below), then carry your jacket or place it under your backpack or bag straps.
OTHER Year-round walking advice that applies to winter too!
Bring a bag or backpack
So many things to buy in Chicago! Whether it is a trinket from the Art Institute of Chicago or the Field Museum, a fun t-shirt, leftover pizza or deli sandwich, or pamphlets from the incredible downtown Harold Washington Library or Chicago Cultural Center, being able to place them into a bag will uncomplicate the things you pick up. It’s also good for storing gloves, hats and a water bottle or snack. I learned the hard way because I stored a pair of gloves in my unzipped coat pocket, and after the jostling of pulling off the coat and putting it back on while inside, I lost my gloves.
Chicago Cultural Center - Warm, with light thru Tiffany!Traffic signal advice
Chicago has a very organized system of welcoming and making pedestrians safe. Crosswalk signals are developed so that they display the time available to walk before the light turns red, and a person walking flashed underneath the traffic signal. The countdown can be anywhere from 30 to 15 seconds, depending on how wide the crossing is. After the light is green and the walking icon appears, you will see a countdown in the place of the icon. For longer distances (4-5 lanes), numbers will start at 30 seconds, for shorter distances, it may start at 15 seconds (2-3 lanes).
The system is very helpful to me, as when I am walking and if I see the walking icon, and I know that it is a shorter distance to cross, I can speed up my walk to cross before the countdown ends. If it is already in the countdown stage, and I have less than 10 seconds, I typically stop.
Awareness Advice
Be aware at all times, and say something if you see something (Chicago OEMC) while walking in Chicago. No, Chicago is not the most dangerous city to walk in the country, but yes, crime occurs occasionally and there is the remote possibility that you might be involved. But do you avoid driving in case you encounter a person driving under the influence of drugs or alcohol and there is the possibility that they have an accident with you? Do you not purchase food at a restaurant for fear that you may suffer from food poisoning? If so, I would still recommend that you go walk around in Chicago, for the chances of any of the above happening are so slim that it’s not worth missing out on the joy of walking the Chicago streets.
Up-close architecture details are beautiful!Aroma Awareness
In the summertime, there are many more people about, and many more food vendors luring you in with the scent of hot dogs, popcorn, tacos and pizza. In the winter you might pass by a restaurant cooking with extreme garlic or smell the exhaust of a non-inspected vehicle, but won’t have the flavorful aromas of the summer. Year-round, however, you will encounter the smell of marijuana (ganja). It is legal to sell and consume in Illinois, and I have encountered its scent while walking in every month. No worries though, you can’t get high by smelling it, and it won’t show up on your work drug test if your employer regularly screens for it.
And that sums up my tutorial for Walking In the Winter in Chicago. Please comment if you have anything to add, or even if you disagree with anything I wrote. Keep warm and comfortable!