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The Honest Chicago Weather Guide

So you’ve decided to visit Chicago...

Congratulations on being a really cool and smart person. We like you, so we’re going to help you out. You see, no matter when you visit Chicago, you’re going to need to prepare for Chicago weather. Relax, it’s not as bad as people say.

Ok, fine, it’s only sometimes as bad as people say. Read this guide, take our advice, and you’ll be more than prepared for whatever our city’s unpredictable weather decides to throw your way.

Why should you listen to us?

You've probably heard people say that if you don’t like the weather in Chicago, wait 15 minutes. Well, this is absolutely true, and we can prove it! When it comes to weather, we’ve seen it all from 94 floors above the city at 360 CHICAGO Observation Deck. And now, we're here to share everything you need to know about visiting our beautiful, cold, windy, city.

First things first...

The Lake Effect

Being located close to Lake Michigan means getting used to its ever-changing weather patterns. Ask any Chicagoan: the weather by the lake is significantly different than in more inland neighborhoods in several ways:

  • It’s colder — Take a look at your weather app and subtract 5-10° if you’re close to the lake. When in doubt, bring a coat.
  • It’s windier — Chicago’s famous winds make the lakefront refreshingly pleasant during the city’s hottest months and a frigid nightmare during winter.
  • There's more precipitation — Being near the lake means more rain, snow, and everything in between.
  • There’s also more fog — Low clouds form more often by the lake. Thankfully, Chicago’s aforementioned wind means it usually moves fast.

The Real Chicago Weather Calendar

Chicago Weather by Season

Winter I

Late October – December

Definition: Milder phase of winter when the snow hasn't yet transformed into a semi-permanent gray slush.

Chance of snow: 97%

You can expect the first snow of the year to come sometime in November, although it occasionally arrives earlier. It's the one time all year where Chicagoans might be exited to see the cold white stuff. Then we realize there are six more months of it ahead and our brief moment of childlike joy is replaced with existential dread.

If, while being pelted in the face with snow and ice, you want to say it's still Fall just because it isn't December 22nd, be our guest. But you're only lying to yourself.

Chicago Winter Essentials

  • Snow boots — If you're going to be spending any significant amount of time in Chicago during winter, you need to buy waterproof snow boots immediately. They're perfect for when you step on what looks like a pile of snow but is actually a foot-deep mini lake of half-frozen slush. Thank us later.
  • Insulated coat — You don't need to go spend a month's rent on Canada Goose (although, if you can, good for you), but you're going to need a coat that can withstand the wind. This isn't a fashion blog, but we'd advise choosing function over style anyway. The North Face is located on the first floor of the Hancock and has plenty of options to choose from.
  • Gloves — Get some good ones. More importantly, don't take them off to scroll. Once your fingers freeze, they won't warm up very quickly.
  • Face mask — We were into face masks before they were a thing. Protect your neck all the way up to your ears with a thermal face covering

Winter II

January Late March


jack nicholson frozen in the movie, The Shinin

Chance of snow: 100%

This is usually when Chicago is at its coldest and snowiest. Ever heard of a Polar Vortex? Those happen during Winter II. Wear layers and try not to stay outside for too long. Come upstairs for a beer or coffee and hibernate like the rest of us.

Lake Michigan is also known to freeze over during this second, more intense phase of winter. The ice may look sturdy, but you should never try to walk on it for... reasons.

Rainy Season

Late March – Early May

Definition: Seattle, but colder.

Chance of snow: 46%

Also known as Foggy Season. Commonly referred to as “Spring” elsewhere in the country, this dreary period brings Chicago's most grey and gloomy weather. Plenty of rain, fog, and overcast skies dominate the post-winter, pre-spring climate.

If you want to see what the Chicago skyline looks like above the clouds, this is the time of year when you just might catch some low fog drifting off the lake. Seeing it from the 94th floor is a sight to behold.

Special Category: Spring Mirage

Every March, there's an unseasonably warm day that unfairly teases Chicagoans into thinking spring has arrived. It has not. A short time after this spring mirage, temperatures return to the norm and we go back to huddling under the warming lamps on the CTA like weird little bugs.

A screenshot of an actual Chicago weather forecast where the temperature swings 60 degrees

An actual Chicago weather forecast... in March


Last Two Weeks of May

Definition: An almost non-existent season where temperatures are briefly between freezing and hot.

Chance of snow: 8%

If you haven't figured it out by now, let us be very clear: The shoulder months don't really exist in Chicago. Our short spring season usually occurs for a couple weeks right before summer. We're defining spring as any time where there is a week or more of temperatures above 65 degrees.

This is the time of year when it's finally comfortable enough to wear shorts, although real Chicagoans start wearing shorts the first time it gets above freezing.

A shirtless jogger on Lake Shore Drive

How Chicago joggers dress any time it's above 50ºF


June – Mid September

Definition: The best time to visit Chicago and the season that makes living here tolerable.

Chance of snow: 2%

Chicago summer is... amazing. Our city’s weather somewhat justifiably gets a bad rep (see above), but if you get a chance to visit in the summer, don’t hesitate. Book those tickets right now!

Summer in Chicago is so pleasant it gives Chicagoans Winter Amnesia. The city’s 24 beaches are full from Memorial Day through Labor Day. Play volleyball, ride your bike, or just catch some rays next to Lake Michigan. It could be 99° and still feel pleasant thanks to the wind.

A very crowded Oak Street Beach, as seen from above

Oak Street Beach, as seen from 360 CHICAGO


Mid September – Late October

Definition: Short season where you'll need to check your weather app daily to decide if you need a coat or not.

Chance of snow: 38%

The other mini shoulder month in Chicago lasts barely long enough for you to finish your Pumpkin Spice Latte. You'll no doubt be torn between wearing short sleeves or your winter coat, probably within a three-day period. On the bright side, watching the leaves change colors from the 94th floor is beautiful. 

Special Category: Halloween

As a general rule, the weather on Halloween is miserable. There’s no particular rhyme or reason for it, but it’s either going to be cold or rainy. You’re going to need some sort of coat. Unless you are an adult in Wrigleyville. Alcohol is your coat.

What have we learned?

  • The weather by Lake Michigan is way different than anywhere else in Chicago.
  • There are 2 winters in Chicago. Prepare for both with the right cold weather gear.
  • Spring and Fall are really short. The term "light jacket" doesn't exist in Chicago.
  • Summers in Chicago are highly underrated and will make you want to move here.
  • Choose a Halloween costume that involves layers

You can see all of our city's crazy, beautiful weather from 1,030 feet above Chicago at 360 CHICAGO Observation Deck. Sometimes in the span of 15 minutes. 

Want to know what Chicago weather is like right now? Slide into our DMs. Follow us @360chicago on Instagram. 

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