What To Wear In Chicago: Visitor’s Guide For Every Season

What’s not to love about Chicago? The windy city is a great place to visit any time of year.

You can catch a Cubs game or stroll through Millenium Park in the fall. You can visit the art institutes to cool off in the air conditioning in the summer. Or, you can walk down the Magnificent Mile or along the Navy Pier in the spring. You can also escape the cold and warm up with an authentic deep dish pizza in the winter.

With so much to do, all year round, it’s no wonder that people travel from all over the world to experience Chicago for themselves. Chicago weather is pretty mild overall, but checking the forecast before you go is one of the best packing tips I can offer.

Some other words of advice: if you’re packing light, choose pieces that you can mix and match. The temperature in Chicago can vary from one day to the next and even hour by hour, so layers are essential.

What To Wear In Chicago: Visitor’s Guide For Every Season

With all that said, here’s your ultimate guide to what to wear in Chicago:

What To Wear In Chicago In The Winter

Chicago winters are cold and breezy and run from December to February. The city sees an average of 37 inches of snow each winter and the average temperature is in the mid 30’s. Temperatures quickly drop at night, sometimes even dropping below 0 degrees Fahrenheit.

The Chicago winter dress code includes plenty of cold weather outfit essentials. When you pack for your trip to Chicago in the winter, make sure you include:

Snow boots
Thick, warm pants
Jeans
Thermal layers
Long sleeve shirts
Thick sweaters or sweatshirts
Good quality winter jacket
Winter hat
Gloves/mittens
Scarf

Stripe Turtleneck Sweater, Jeans, Leather Puffer Jacket, and Snow Boots

Winter Vacation Outfit Ideas - Cozy & Casual.

Stripe Turtleneck Sweater (sold out but similar HERE) / High Waisted Jeans (sold out but similar HERE) / Jacket (sold out but similar HERE) / Pom Pom Beanie (sold out but similar HERE) / Earrings / Sunglasses / Winter Boots

Shop Chicago Winter Packing List:

What To Wear In Chicago In The Fall

Fall in Chicago runs from September to November. The mild temperatures and colorful foliage make fall the favorite season for many locals. You’re least likely to get caught in the middle of bad weather during the fall.

Temperatures tend to stay in the 70’s in September before dropping to the 60’s in October and then 50’s by November.

When packing for Chicago in the fall, make sure to include the following:

Sunglasses
Comfortable walking shoes
Shorts and pants
Lightweight sweater
Lightweight jacket
Short-sleeve and long-sleeve tops

Black and White Striped Sweater, Barbour Jacket, and Jeans

Simple Striped Sweater | Versatile Fall Outfits

Black and White Striped Sweater (sold out but similar HERE) / Barbour Jacket / High-Waisted Jeans (sold out but similar HERE) / Beige Leather and Suede Woven Bag (sold out but similar HERE) / Gold Bangle Bracelet / Pearl Stud Earrings / Veja Leather Sneakers

Camel Cashmere Crewneck Sweater with Demi-Boot Jeans

Camel Cashmere Crewneck Sweater / Demi-Boot Jeans / Black Cocoon Quilted Coat / Leather Tote Bag / Gold Hoop Earrings / Gold Adjustable Bracelet / Black Leather Loafers

Navy and White Stripe Long-Sleeve Tee with Navy Fleece Jacket

Striped T-Shirt Fall Outfits From Basics

Navy and White Stripe Long-Sleeve Tee / Navy Fleece Jacket / Jeans / Pearl Earrings / Black Leather Crossbody Flap Bag / Veja Leather Sneakers

Houndstooth Skirt with Ivory Ruffle Crewneck Sweater and a Tan Wool Coat

Ivory Ruffle Crewneck Sweater / Mini Houndstooth Skirt / Tan Wool Coat / Black Suede Boots / Gold Link Bracelet / Pearl Stud Earrings

Shop Chicago Fall Packing List:

What To Wear In Chicago In The Spring

Spring, which runs from March to May, is cool and wet in Chicago. Because Lake Michigan stays cold through most the spring, Chicago is kept cool by the air that blows off the lake. The further you travel from the shoreline, the warmer it gets, but not by much. Those contrasting temperatures are responsible for all the rain that hits Chicago in the spring.

Speaking of temperatures, you can expect lows around 30 degrees and highs around 70, but for most of spring, temperatures tend to stay in the 50’s and 60’s.

With all that in mind, here’s what you should include in your packing list if you’re visiting Chicago in the spring:

Rain boots
Comfortable, closed-toe walking shoes
Lightweight jacket
Pants or jeans
Sweatshirt
Light sweater
Portable umbrella

Black Midi Dress with Striped Button Up Sweater

Black Midi Dress (sold out but similar HERE) / Striped Button Up Sweater / Gold Square Stud Earrings / Black Leather Bag / White Canvas Sneakers

White Denim Pants with a Navy Roll Cuff Shirt

How to Style White Jeans for spring and summer

Navy Roll Cuff Shirt (sold out but similar HERE) / White Demi-Boot Jeans / Rattan Croissant Satchel Bag (sold out but similar HERE) / Gold Hoop Earrings / Raffia Belt / Raffia Mules

Floral Maxi Skirt with White T-shirt and Beige Cardigan Sweater

White T-Shirt / Floral Tiered Maxi Skirt (sold out but similar HERE)/ Beige Cardigan Sweater / Leather Mini Crossbody Bag / Mini Gold Hoop Earrings / Bar Necklace / Lace-Up Leather Sandals (sold out but similar HERE)

Skinny Jeans with a White Button Down Shirt and Green Lightweight Jacket

Versatile Spring Outfits - Spring Jacket

Relaxed White Poplin Shirt / High-Rise Skinny Jeans / Pistachio Green Jacket (sold out but similar HERE) / Woven Leather Small Crossbody Tote / Tortoise Sunglasses / Mini Gold Hoop Earrings / Veja Sneakers

Shop Chicago Spring Packing List:

What To Wear In Chicago In The Summer

Summer in Chicago is hot and humid and runs from June to August. You can expect to enjoy a lot of warm sunshine with a regular, cool breeze. With all the sunshine comes humidity, thanks to water evaporating from the surface of Lake Michigan.

On a June or July day in Chicago, temperatures are usually in the 70’s. However, once you get into the month of August, you’ll typically experience more humidity and temperatures in the mid to high 80’s.

Your Chicago summer packing lists should include:

Sunglasses
Comfortable walking shoes or sandals
Shorts, skirts, or skorts
Lightweight shirts or tank tops
Sundresses
Lightweight jacket

What is your favorite time of year to visit Chicago?

Chicago travel plans this year? Let me know below! Then, for even more preppy fashion inspiration, check out my LTK page!

What To Wear In Chicago: Visitor’s Guide For Every Season