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:

Chicago Winter Packing List

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

Cashmere Sweater & Skirt with Booties

Winter Vacation Outfit Ideas - Evening Dinner

Cashmere Cable-Sleeve Sweater (sold out but similar HERE) / Tiered Maxi Skirt (sold but similar HERE) / Parka Coat (sold out but similar HERE) / Crossbody Bag (sold out but similar HERE) / Mini Hoop Earrings / Waterproof Block Heel Bootie

Sweater, Fleece-lined Leggings, Puffer Coat, and Bean Boots

How to Style Bean Boots in winter

Super Soft Turtleneck Sweater (sold out but similar HERE) / Fleece Lined Leggings / Puffer Coat (sold out but similar HERE) / Scarf / Pom Pom Beanie (sold out but similar HERE) / Mittens (sold out but similar HERE) / Cashmere Socks / Shearling Lined Bean Boots

Black Midi Sweater Dress, Tan Suede Moto Jacket, and Leather Sneakers

How to Wear Dresses in Winter - Black Crew

Black Crewneck Midi Sweater Dress (sold out but similar HERE) / Suede Moto Jacket (sold out but similar HERE) / Leather Tote Bag / Bar Stud Earrings / Black Sunglasses (sold out but similar HERE) / Leather Sneakers

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:

Chicago Fall 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

Fall Workwear Outfits with loafers

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

Skirt Thanksgiving Outfit Ideas

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

Shop Chicago Fall Packing List:

Chicago Spring 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

How to Wear a Sweater Over a Dress


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

Versatile Spring Outfits - Spring Skirt

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:

Chicago Summer 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

Navy Eyelet Long Sleeve Dress

3 Versatile Summer Outfits - Elegant Evening Dress

Eyelet Long Sleeve Dress / Pearl Earrings / Cubic Zirconia Bangle / Chevron Quilted Satchel Bag (sold out but similar HERE) / Bow Block Heels

Navy and White Striped Half-Zip Sweater with White Belted Shorts

Cute & Casual Summer Sweater Outfit

Navy and White Striped Oversized Half-Zip Sweater (sold out but similar HERE) / White Belted Shorts / Gold Huggie Hoop Earrings / Ray-Ban Sunglasses / Leather Crossbody Bag (sold out but similar HERE) / Leather H-Sandals

White Shirtdress with a Straw Tote Bag

Easy Summer Vacation Outfits

White Shirtdress (one size left but similar HERE) / HERE / Gold Hoop Earrings / HERE / Woven Slide Sandals (one side left but similar HERE)

Black T-shirt Midi Dress with a Denim Jacket

T-shirt dress - Versatile Summer Outfits

Black T-Shirt Midi Dress / Denim Jacket / Pearl Huggie Hoop Earrings (sold out but similar HERE) / Leather Tote Bag / White Veja Sneakers

Shop Chicago Summer Packing List:

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!