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What to Wear in Chicago: Ultimate Year-Round Guide
Updated: Oct 7
Packing can easily be a stressful part of a trip. That's why we've made your life easier and have created the ultimate packing lists for every season in Chicago!
What to wear in Chicago highly depends on the time of year you are visiting (read best time to visit Chicago). Winters are cold here and thick coats are necessary. Summers get very warm, and spring and fall vary the most.
Keep reading to find out what to wear in Chicago so you can stay cute and comfortable while exploring the Windy City. The best news is Chicago is a city made for self-expression. You can wear whatever you want in this city and not feel out of place!
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What to Wear in Chicago Year-Round
Chicago's weather varies each season. Prepare for your trip by packing the essentials for the season you're visiting in. Stay warm in fall and winter, stay dry in spring and summer, and most importantly stay comfortable year round.
Keep reading to learn what to wear in Chicago each season.
Summer
Ahhh, the busiest yet the best time of year to explore Chicago. Summers in the city are so fun because it's nearly always sunny and in the 80s.
Festivals are happening all around the city, and the vibes are so positive. Summer is the time to wear all your cute dresses and tanks in Chicago.
Short Sleeve or Tank Tops
Shorts
Skirt or Dress
Linen Pants or Jeans
Cardigan
Rain Jacket
Sneakers & Sandals
Sunglasses
READ ALSO: 15+ Best Things to Do in Chicago
Short Sleeves or Tank Tops
When packing tops for Chicago, you'll definitely want to stick to short sleeves or tank tops. These tank tops with a built-in bra are my go-to! It might not be the hottest place on Earth, but it's usually in the 80s or even 90s. If you'll be outside a lot, make sure you wear sunscreen!
Dress up the linen button-up for a day out in the city, or stay cool with the chic floral tank top. Both of these tops are great to wear in Chicago in summer and can be layered with a jacket or cardigan.
Shop Recommended: Linen Button-Up || Floral Tank Top
Shorts, Skirts, or Dresses
You'll want to wear cooler bottoms in the summer, especially if you plan on spending time outside in the beautiful sunshine. I do recommend packing one pair of pants, joggers, or something similar. This is my rule wherever I go, even in the summer.
My favorite go-to travel dresses are super comfy and stretchy. I love that they're essentially an entire outfit in one; bra included! You can dress them up or down depending on your fashion preference, and they're so comfortable.
Shop Recommended: Black Dress || Canvas Shorts
Long Pants
I recommend bringing at least one pair of long pants if you're visiting Chicago in summer. Some days are rather cool, and a pair of pants will come in handy for chilly evenings, travel days, etc.
Jeans or linen pants are best; you can dress them both up or down how you like.
Shop Recommended: Jeans || Linen Pants
Sneakers and Sandals
Most importantly, pack comfortable walking shoes! There is great public transportation in Chicago, but it is also a very walkable city. It's fun to explore some neighborhoods on foot and truly get a feel for this Midwestern city.
Shop Recommended: Allbirds Sneakers || Sandals
Lined Rain Jacket & Cardigan
I recommend always packing a lined rain jacket when visiting Chicago, even in the summer. It gets much chillier when the sun goes down, and you never know if a restaurant or museum will be cranking the AC.
June is the rainiest month in Chicago, making a rain jacket necessary in the summer. A lined rain jacket is perfect because it is waterproof but also warm enough to wear as a normal jacket.
A cardigan is perfect for those warm summer days when you just need a light jacket in the evenings.
Shop Recommended: Cardigan || Sherpa-Lined Rain Jacket
Sunglasses
It's generally very sunny in Chicago in summer so having a good pair of sunglasses or a hat will make your life easier while exploring the city. You don't want to be squinting your entire trip!
Read Also: Getting Around Chicago
Chicago Summer Outfit
What to Wear in Spring in Chicago
While spring in Chicago can be a little less predictable than summer, there's a high chance it will still be quite chilly. You might get the odd day that reaches the 60s or even 70s, but generally, temps are in the high 40s to 50s.
It can be rainier in the spring in Chicago, but it's still a great time to visit. The city is at its greenest; flowers are blooming everywhere and the trees are full and lush.
Short Sleeve & Long Sleeve Tops
Lined Waterproof Jacket
Sneakers or Ankle Boots
Warm Socks
Long Pants
Hat, Scarf, & Gloves
Read Also: How to Get Around Chicago Without a Car
Short Sleeve & Long Sleeve Tops
The best tops to pack for visiting Chicago in spring are short sleeves, a couple of long sleeves, and a sweater. It will be colder in early spring, around March and April, than in late spring, around May.
Short sleeves are great for layering. You can wear them by themselves if it's warm enough, or you can wear them under a jacket or cardigan.
Shop Recommended: Short Sleeve Top || Long Sleeve Top
Waterproof Lined Jacket
Always bring a rain jacket or small umbrella to Chicago. Don't be the person caught in the rain getting drenched, it will put a bit of a damper on your Chicago trip.
This waterproof lined jacket is perfect for spring in Chicago. It will keep you dry if there happens to be snow or rain, and it will keep you warm on those cool spring days.
Sneakers or Boots
I mentioned in the summer packing section, having comfortable walking shoes is a must while exploring Chicago any time of year. I recommend sticking with sneakers or even cute ankle rain boots for spring.
Warm Socks
Spring in Chicago can still be chilly. Sometimes you'll even catch snow here this time of year. Keep your feet nice and warm during all of your Chicago adventures with a pair of winter socks.
Long Pants
Pack long pants, joggers, leggings, or your favorite pair of jeans for spring in Chicago. If you're feeling brave, wear a skirt or dress with some cute tights and boots! I just wouldn't recommend wearing shorts as it's still pretty chilly this time of year.
Hat, Scarf, & Gloves
It's not a bad idea to throw in a scarf, a warm hat or beanie, and a pair of gloves to explore Chicago in spring! Always check the weather on the days leading up to your departure so you can get an idea of what the weather will be like.
Spring Chicago Outfits
What to Wear in Fall in Chicago
Similar to the cooler temps of springtime in Chicago, fall has great weather, less rain, and pretty foliage. It can also get pretty chilly in fall, and occasionally it snows a little in late fall in Chicago.
Sweaters & Long Sleeve Tops
Long Pants
Coat or Thick Jacket
Boots
Thick Socks
Hat, Scarf, & Gloves
Read Also: The Best Places to Stay in Chicago
Sweaters and Longsleeves
I recommend sticking to warmer tops in the fall. You definitely won't want to wear tank tops as temps average in the 50s to 60s. Layers are a good idea this time of year as it's generally much colder in the morning and evening; the sun comes up later and goes down earlier.
Shop Recommended: Sweater || Long Sleeve Top
Long Pants
Again, long pants, jeans, or leggings are the best idea of what to wear in Chicago in the fall. Especially if you want to enjoy fall foliage and other outdoor activities, long pants are the way to go.
Shop Recommended: Straight Leg Jeans || Wide Leg Jeans
Hat, Scarf, and Gloves
Don't forget these essentials for Chicago in fall. It can get quite cold while waiting for a train or walking in a particularly windy area. Plus, they're cute and can add a pop to your outfit.
Coat or Thick Jacket
You don't want to freeze while exploring Chicago in the fall, so please remember a winter coat or thick jacket. It's better to have a coat you can throw on or take off than freeze or boil in the wrong clothes.
Shop Recommended: Down Puffer Jacket || Women's Parka
Boots
Remember comfy walking shoes, even in fall! These might be your favorite tennis shoes, slip-on Vans, or even a pair of stylish boots. Whatever your go-to walking shoes are, pack those and skip the sandals in the fall.
Warm Socks
Fall in Chicago can be quite cool. Sometimes you'll even catch snow here this time of year. Keep your feet nice and warm during all of your Chicago adventures with a pair of winter socks.
Chicago Fall Outfit
Chicago Winter Outfit
It's cold and snowy in Chicago in winter, so packing the right clothes is extra necessary this time of year. It is still a wonderful time of year to visit, but you want to stay warm and comfortable.
Enjoy the holiday season in Chicago. I have a detailed winter packing list so you can prepare for your winter getaway to Chicago easily! Below are the basics, but click the button for the full packing list for Chicago in winter.
Other Packing Essentials for Chicago:
Backpack Purse
Waist Pack
Compression Packing Cubes
Kindle (for traveling)
Portable Charger
Bluetooth Headphones
Click the image you want to shop!
Summary: What to Wear in Chicago
Chicago is an incredible city. It makes for the perfect US city travel destination as there truly is something for everyone to enjoy here!
When are you planning a trip to Chicago? Are you prepared to pack now? There is something so special about every season in Chicago, so you can't go wrong with a trip here any time of year.
TIP: Add Chicago to your weather app so you get the best idea of what the weather will be like when you're there! Keep an eye on it to see if it's getting warmer or cooler.
Now you know what to wear in Chicago, you can get packing and counting down the days to your city getaway! Read more about Chicago here so you can truly have the best time in this fantastic US city.
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