What to Wear in Chicago: A Visitor's Guide| Travel With A Plan

This post may contain affiliate links, view our disclosure policy.

If you’re wondering what to wear to Chicago during your upcoming visit, you’re in the right place!

Depending on when you visit, your trip to Chicago may be affected by wind, rain, heat, or snow.

With four distinct seasons and a significant breeze off of Lake Michigan, it is especially important to consider what to wear in Chicago if you’re visiting there.

As one of our favorite family vacation destinations, let’s take a look at our seasonal packing tips and determine exactly how to dress for Chicago during every season!

The links on this page are Amazon affiliate links. If you click on the links and make a purchase, I receive a small commission at no extra cost to you.

Table of Contents

What to Wear in Chicago

Chicago, Illinois is home to stunning skyscrapers, world-class museums such as the art institute, famous Chicago foods, and the iconic Millennium Park.

In addition, visitors flock to Chicago for its superior shopping, public parks, and world-famous attractions at Chicago’s Navy Pier.

No matter when you visit, what you wear in Chicago will be determined by which of the four seasons the city is in, as well as the influences of its lakefront location on Lake Michigan.

Chicago temperatures are 10-15 degrees colder at the lakefront compared to further inland.

In general, the warm season in Chicago is spring, the hot season is summer, the cool season is fall, and the cold weather is in winter.

Being that Chicago is a walkable city and that you will spend a lot of time outdoors no matter when you visit, it is important that your Chicago outfits always reflect the day’s predicted weather.

If you’re wondering what to wear in Chicago today, here are our overall year-round tips:

No matter what season it is, your travel wardrobe should always include layers when packing for Chicago. Mornings and evenings are cool and there is almost always a chilly breeze off of the lake.
Always wear comfortable walking shoes when touring Chicago. Opt for good support over fashion.
Bring a trendy backpack or cross-body bag that can fit your wallet, snacks, water bottles, and your layers (when you need to take them off, i.e. inside a restaurant or attraction).
In terms of how do people dress in Chicago, Chicago tourists dress comfortably and casually. Similar to being a tourist in other big cities like New York, there is no need for your Chicago outfits to be fancy.

Oh, and psst…we LOVE Chicago so much that we’ve written several other guides that’ll help you plan your trip!

What to Wear in Chicago in Spring

Springtime in Chicago means that the weather is warming, flowers are beginning to bloom, and activity along the thawing lakefront is coming back to life.

It is important to know that when visiting Chicago during the months of March, April, or May, the weather is unpredictable and changes from day to day and even hour to hour.

Temperatures start warming to the 50s and 60s, however, you might still encounter colder temperatures and even snow.

Likewise, rain and thunderstorm can be prevalent, so it’s best to use our general travel packing tips that involve checking the forecast beginning 3 days before your trip.

In general, what to wear in Chicago in May and the other spring months involves light warmth and layers.

Your Chicago packing list should include:

Sunglasses
Comfortable, closed toe walking shoes or comfortable rain boots (For walking along Magnificent Mile or for spending time in Millennium Park)
Pants or jeans
T-shirt or 3/4 sleeve shirt
Sweatshirt
Lightweight, outerlayer jacket
Lightweight hat and mittens (if you tend to get cold easily)
Portable umbrella for pop-up showers

What to Wear in Chicago in Summer

Summers in Chicago are characterized by sunshine and warmth, as well as outdoor festivals, flower-filled sidewalks, rooftop and patio dining, and activities on and around the lake.

On a typical summer day in June and July, temperatures are typically in the mid to high 70s.

The temperature in Chicago in August, on the other hand, is a bit more humid and ranges in the mid-80s to low 90s.

For this reason, many visitors get out and enjoy Chicago activities at night as the warm temps last well into the evening hours.

As always, be sure to check the forecast for rain, however, as showers can be common in June, July, and August.

And last, although Lake Michigan does have an effect on Chicago weather in the summer, it is not as prevalent as during the spring.

In general, how to dress in Chicago in July is similar to what to wear in Chicago in August as it simply involves clothes such as shorts, t-shirts, and layers.

Your packing list for Chicago in summer should include:

Sunglasses
Comfortable walking shoes or supportive walking sandals
Shorts or skirts
T-shrits or tank tops
Sundresses for women (or other capsule wardrobe favorites!)
Lightweight sweatshirt or summer jacket
Portable umbrella for pop-up showers

Additional planning tip: If you’re visiting in summer, be sure to check out one of Chicago’s many beaches!

In addition, check out our beach packing list, as well as our updated list of the best beach bags for moms.

What to Wear in Chicago in Fall

In the fall, the Chicago weather becomes milder, and beautiful fall colors emerge while the leaves begin to gently fall from the trees.

The average temperature remains in the 70s in September, drops to the 60s in October, and winds up in the 50s during November as it slowly transitions to winter.

The city of Chicago continues to bustle in the fall, however, making the months of September, October, and November some of the most popular months to visit.

In general, what to wear in Chicago in September and what to wear in Chicago in October both involve light warmth and layers.

Our Chicago fashion packing guide for fall includes:

Sunglasses
Comfortable, closed-toe walking shoes
Shorts, pants, or comfortable joggers
Long-sleeve T-shirts
Lightweight sweater or sweatshirt
Lightweight, outer-layer jacket or fall vest

Additional planning tip: Read here for our perfect 3-Day Chicago family itinerary when we visited Chicago in September!

What to Wear in Chicago in Winter

Winter temperatures in Chicago are cold, however, much like the rest of the northern USA, they can vary tremendously.

With winter average temperatures in the mid-30s during the day, temperatures occasionally drop to or below 0 °F at night.

In addition to the cold, Chicago becomes a white, snow-covered winter wonderland during the months of December, January, and February.

Though the snowfall is quite picturesque, it will definitely affect what to wear if you happen to be visiting then.

In general, how to dress in Chicago in December and January, as well as what to wear in Chicago in February, involves heavy fabrics and layered winter gear.

Your cold-weather outfit for the Windy City should include:

Comfortable, closed-toe walking shoes or snow boots
Warm pants or jeans
Thermals for layering (if you tend to get cold easily)
Long-sleeved shirt
Sweater or sweatshirt
Cold-weather winter jacket
Winter hat (I love pom hats!)
Warm mittens or gloves
Scarf (for wind protection on your face)

Additional planning tip: Now that you know how to dress for Chicago winters, read here for our perfect 3-day itinerary (including the best things to do!) when visiting Chicago in winter!

Plus, with the inevitable prevalence of snow and cold, be sure to review our winter road trip packing list if you’re driving to Chicago in winter.

*Wondering what to wear in Chicago right now, check your favorite weather app and use our helpful guide! Likewise, if you’re curious about the current Chicago fashion trends, keep up with the Fashion section of their local newspaper, The Chicago Tribune.

If you enjoyed reading our packing lists and what to wear in Chicago, continue planning your trip to Chicago here:

*Before leaving, be sure to check our Travel Resources Page to find exclusive travel discounts and to book hotels, rental cars, and guided tours.*