How to Dress in Chicago (for Every Season)

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If you’re not sure of how to dress in Chicago weather, we have you covered for every month and in every season of the year.  You will want to read this because we have some of the most unpredictable temperatures in the Midwest.

Whether you are visiting for business or pleasure, packing for Chicago can be a challenge and you’ll need to be prepared for just about anything.

Surviving Chicago’s Weather: How to Dress and What to Pack

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First things first, you’ll want to check the weather forecast before you start packing and look at the 10-day forecast. I usually check and and review and compare their predictions.

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What to Pack for Chicago in Winter

couple on ice skating rink
December: Maggie Daley Ice Rink

The weather in winter season can be brutally cold mostly because the city is next to Lake Michigan.

It’s not uncommon for Chicagoans to have 2 or 3 coats of varying lengths to get through the fall and winter seasons.

I have an low-shin length coat to keep my legs warm, and a another that falls below my hips. A hooded coat lined with fleece or filled with down feathers are also good options. Brands like North Face, Columbia, and Canada Goose will keep you nice and toasty.

The temperatures range from 20°F to 40°F (-6°C to 4°C) and can drop below freezing.

At a minimum, you’ll need a warm coat, hat, gloves, and boots. The boots should be waterproof and easy to clean so that you can remove any salt residue.

  • Heavy coat and insulated clothing            
  • Hat, gloves, and scarf for cold winds         
  • Warm boots and thick socks                   
  • Thermals or layered clothes
  • Snow boots and traction for icy sidewalks

🛍️Shop Chicago Looks🛍️ coat // jacket // hat // gloves // scarf // neck warmer // boots // socks

What to wear in Chicago in December

In December, the weather in Chicago can be unpredictable. It can be mild one day and then frigid the next. So, be sure to pack layers. 

For example, bring warm base layers like thermal underwear and long sleeve shirts that you can wear under sweaters and jackets. You’ll also want to pack a warm winter coat, hat, gloves, and scarf in case the wind and cold are biting.

What to wear in Chicago in January

By January, the cold weather in Chicago is in full swing which makes the city prone to blizzards. This is the time of year to perfect your snow angel technique and turn your winter wardrobe into a stylish ensemble of Arctic-chic fashion!

Chicago has had over 10 record-breaking snow days in January that left drivers immobile due to cars buried in snow. However, don’t be surprised to hear that Chicagoans plunge into Lake Michigan this time of year.

It’s an especially slippery time of year for driving due to snow and ice.

A heavy-duty coat, insulated boots, and a warm hat are essential. Don’t forget to pack gloves and a scarf to protect your face and hands from the biting wind.

What to wear in Chicago in February

The worst of the winter weather in Chicago is usually behind us by mid- to late-February. However, temperatures can still drop below freezing.

The months of January and February can be below zero and freezing temperatures. If you need to walk outdoors, wear long underwear beneath jeans or corduroy pants, merino wool socks, and insulated boots that are water resistant.

For the upper body, wear a thermal undershirt with a long sleeve shirt. You can top it with a wool or fleece sweater for extra layering.

What to Pack for Chicago in Spring

person patting a dog
March: St. Patrick’s Day Parade

As a Chicago native, I know firsthand how unpredictable the weather can be.  Springtime in Chicago can range from chilly and rainy to sunny and warm, all in the span of a week.

The temperatures range from 50°F to 70°F (10°C to 21°C), and sometimes it snows in April.

So, what should you pack for your trip to Chicago in spring? Let me break it down for you. A light merino wool sweater is perfect for this time of year. It also great for traveling because the fabric will not wrinkle like other materials.

  • Light jacket or sweater
  • Umbrella for potential rain
  • Comfortable walking shoes
  • Layers for fluctuating temperatures
  • Sunglasses and sunscreen

🛍️Shop Chicago Looks🛍️ jacket // sweater // gloves // walking shoes // sunglasses

What to pack for Chicago in March

The grounds are still hard and frosty. If you’re visiting Chicago in March, don’t miss the NCAA Men’s Basketball Tournament, also known as March Madness, at one of Chicago’s neighborhood sports bars.

Whether you’re heading to the United Center to catch a game or just watching with friends at a local sports bar, you’ll want to dress comfortably and in layers.

Spring break is a great time of the year to visit Chicago.

I recommend packing a lightweight jacket, a cozy sweater, and comfortable shoes for walking around the city.

What to pack for Chicago in April

April in Chicago can still be a bit chilly, but you’ll start to see more sunshine and warmer days.

Towards the end of April, it’s quite rainy.

It’s the perfect time to break out your spring wardrobe and pack some lighter layers.

I suggest bringing a mix of short and long-sleeved shirts, a light jacket, and a pair of comfortable sneakers for exploring the city.

What to pack for Chicago in May

By May, spring is in full swing in Chicago. You can expect warmer temperatures and plenty of sunshine.

This is the time to pack your summer clothes, bring a light jacket or sweater for the cooler evenings.

I recommend packing a mix of shorts, dresses, and T-shirts, as well as a pair of sandals or sneakers.

What to Pack for Chicago in Summer

woman standing with cup
June: Taste of Greece Festival, Greektown

Get summer ready with this list of essentials for Chicago! We’re talking summer concerts in the park, sailing on Lake Michigan, visiting Chinatown, Oak Street beach, Navy Pier, the Aquarium, the Art Institute, jazz clubs, the Bean (Cloudgate), Cubs games, neighborhood festivals, and everything in between!

Temperatures in the Summer range from 70°F to 90°F (21°C to 32°C).

It can be hot, humid, and unpredictable. So, before you pack your bags for your summer trip to Chicago, make sure to consider the following.

  • Lightweight and breathable clothing         
  • Hat and sunglasses for sun protection        
  • Sunscreen and insect repellent               
  • Comfortable walking shoes                    
  • Swimsuit for beach or pool outings       

🛍️Shop Chicago Looks🛍️ linen shirt // linen pants // Panama hat // walking shoes // sandals

What to pack for Chicago in June

In June, the temperatures in Chicago can range from the mid-60s to mid-80s Fahrenheit.

Pack a mix of lightweight clothing and layers.

What to pack for Chicago in July

July is usually the hottest month, with temperatures reaching the high 80s or even 90s.

Pack plenty of lightweight, breathable clothing. Shorts, tank tops, and sundresses are all great options. And don’t forget to bring a hat and sunscreen to protect yourself from the sun’s rays.

Cool down with a cruise on the lakefront or some gelato on the Riverwalk.

What to pack for Chicago in August

In August, the weather in Chicago can be a bit milder, but it can still be hot and humid.

A mix of lightweight clothes and layers are the best bet.

What to Pack for Chicago in the Fall

woman near taco restaurant
October: Lincoln Park

Fall is probably my favorite season in Chicago. There are so many places to take a hike and enjoy the foliage as it turns into deep jewel tones. No matter the season, I love carrying a crossbody bag to keep my hands free.

Temperatures in Fall range from 40°F to 60°F (4°C to 16°C). Pack clothes that you can wear in layers to adjust throughout the day for temperatures changes.

  • Jacket or coat for cool temperatures      
  • Scarf and gloves for chilly evenings         
  • Sweaters and layers                          
  • Comfortable walking shoes                   
  • Umbrella for potential rain                   

🛍️Shop Chicago Looks🛍️jacket // scarf // gloves // sweater // walking shoes // crossbody bag 

What to pack for Chicago in September

September in Chicago can still feel like summer, so pack some lightweight clothing options like shorts and sundresses. However, be prepared for cooler evenings by bringing a light jacket or sweater. 

What to pack for Chicago in October

October brings cooler temperatures and the start of fall foliage in Chicago. Pack some cozy sweaters, jeans, and boots for exploring the city and taking in the beautiful autumn colors.

What to pack for Chicago in November

November in Chicago can be quite chilly, so pack your warmest clothing options like fleece jackets or heavy coats, scarves, and boots. But don’t sacrifice style for warmth – pack some cute accessories like hats and gloves to add some flair to your outfits. 

Final Thoughts on How to Dress in Chicago

I hate packing umbrellas, so I usually pack for a plastic poncho or waterproof coat when traveling during a rainy season.

Another option is to check the front desk of your hotel. Depending on the star rating, they may have amenities like the use of a complementary umbrella.

Hopefully this gives you a good idea on what to pack for Chicago weather. I know you won’t want to miss the architecture cruise. Just keep in mind that the temperatures are cooler on the lakefront.

Happy packing!

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