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Chicagoans know how to make life happen when it’s cold, so be sure you’re prepared both mentally and physically. The best advice, just expect it to be snowy and cold and you’ll wake up in a better mood. The snow and weather can be beautiful if you learn to expect it.

  1. Dress in layers

We don’t mean a dress shirt, a sweater, and a winter coat. That’s not enough in Chicago if you’ve got any sort of significant walk to work. There is a specific formula to get you through the subzero outdoors weather and the 65-70 degree indoor weather you’ll be shifting in and out of. Be sure to weather a breathable wick layer closest to your skin to protect yourself from sweat as your body constantly adapts to temperature changes. Over that, don a thermal shirt that transitions well from an indoor to an outdoor piece. Over that, an insulating layer (wool, fleece, etc.) to wear beneath your coat. And the most important layer, your giant marshmallow jacket. All of the Cubs fans may be gone during the winter but the puffy jackets fill up the rest of the space. Everyone new to the city tries to fight it, but trust us, buy a puffy jacket – you’re going to look like a marshmallow, but you’ll blend in well with everyone else in Chicago. Here are some seriously effective jacket brands to try. We also recommend leaving your umbrella at home. There’s always one sad tourist bracing themselves against the sideways snow and rain with a broken umbrella. If the wind isn’t too strong, give it a try but it’s more common to wear a scarf and a hood instead.

  1. Prepare for the parking space wars

There isn’t a lot of ‘owned’ parking within the city. Most folks who live in apartment complexes park along the street. Once the temps start dropping and the winter chill is in the air, parking spaces become a hot commodity. It’s hard to get your car out of a spot that’s snowy and icy, so some people snowplow their usual spot and lay salt down to dissolve the slick and sludge. Then, they’ll put chairs or traffic cones in the spot to deter others from taking it. In their eyes, they’ve put in the work to keep this spot nice and useable and that work makes it ‘their spot’. Others don’t see it that way. They see an open spot on the street and they park there because it’s open. This leads to a power struggle of epic proportions and you’re bound to see some screaming over parking during the wintertime. Here’s what we advise: wake up a bit earlier than normal and you’ll find spots closer to the office. If you’re lucky enough to get off early as well, you can beat the rush home and claim your spot. Or, avoid the hassle all together and take public transportation to and from work.

  1. Make friends with your neighbors

Winter in Chicago is the season of comradery. There’s just something about braving the sleet and hail to make it down the street to the neighborhood bar covered head to toe in Level 3 snow gear that really brings everyone together. The second you open that bar door and enter the heated space, peel away your layers of protection and sit down, you’ll make eye contact with someone else who just braved the exact same maelstrom you did. The cold really brings people together. During the colder months, it’s also more difficult to travel across the city and most people don’t want to make the effort. It’s important to make friends with the folks around your nest to make it through the winter, or try to live near friends if you’d rather stick to the people you know. It’s easy to hermit in the house when temperatures outside are below freezing. Keep in mind winter is also a good time to check out local theatre, music, and other local spots that you couldn’t normally go to in the spring and summer because they’d be overrun by tourists.

  1. Landlords are required by law to provide heat in the winter

The Chicago Heat Ordinance stipulates that from September 15 through June 1, the temperature inside your rental is required to be at least 68 degrees from 8:30 AM to 10:30 PM, and at least 66 degrees from 10:30 PM to 8:30 AM. Landlords who don’t protect tenants from cold can face hefty fines for each day they do not supply adequate heat. The reason for lack of heat does not matter -- landlords must follow the law, and apartments must be heated. If you are a renter and your landlord is not providing adequate heat or no heat at all, contact 311 to file a complaint. The Department of Buildings is pretty good about taking action against delinquent owners.

Also, remember that official information from your heat provider will come via mail and any in-person visits will be scheduled ahead of time. Be wary of Com-Ed scammers. It’s not unheard of for people to dress up like the local heating companies and knock on your door to say they need to fix something. If they try to get you to sign something that will switch your supply over to a shady third-party company, you won’t know what’s happened until you notice your heat bill rising rapidly each month.

The advice: know the law and make sure you’re careful about who comes knocking at your door. Also, invest in an electric blanket, turn it on 15 minutes before bed and climb in to the toasty sheets. There’s nothing worse than cold toes in the winter and an electric blanket might solve all your problems.

  1. Don’t be afraid to adventure outdoors

Winter in the city is endlessly romantic and there are endless activity options to explore. Go skating at Millennium amongst gorgeous sparkling lights, stroll through Lincoln Park and enjoy the light glinting off layers of freshly powdered snow. Adventure to The Bird Park, which will be mostly empty aside from the freshly fallen snow, the glittery dockyard, and the bird sanctuary.

Chicago also has a few great museums that are normally too busy during the summer months. The Field Museum has some incredible exhibits like Evolving Planet and Inside Ancient Egypt that are a must-see. Occasionally they put out special exhibitions for a limited time so you might see something that all the tourists miss out on during the warmer months.

After that, head over to High Five Ramen in downtown Chicago for the most delicious, hot bowl of ramen you’ll ever eat (seriously, we’re betting on that.)


While winter in Chicago can bring tears to your eyes (from the wind chill), it’s important to remember these tricks to stay happy and positive. Check out that popular bar that’s too bogged down with tourists during the summer or embrace the snow and ice and go ice-skating with your significant other. One thing’s certain – Chicago winters make summer that much sweeter.

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