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Hi, I'm Georgina! A coffee-loving adventure enthusiast here to share my favorite travel tips with you! My goal is to inspire others to get out and explore this wild planet by camping, hiking, or wandering around a fun new city!

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  • Georgina D'Angelo

What to Wear in Chicago: Ultimate Year-Round Guide

Updated: Mar 29

what to wear in chicago year round

Packing can easily be a stressful part of a trip. That's why we've made you're 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!

In this article...

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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.


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

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


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!

Chicago Summer Outfit

What to Wear in Spring

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

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.

Shop Recommended: Jeans || Joggers

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.

Shop Recommended: Warm Hat || Scarf || Gloves

Spring Chicago Outfits

What to Wear in Fall

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

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.

Shop Recommended: Warm Hat || Scarf || Gloves

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


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

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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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Travel Resources & a Free Planner

Join our newsletter to receive the 3 apps I use to plan a trip, my go-to travel essentials list, and a free travel planner pdf! Bi-weekly travel tips 🙂 

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Hi, I'm Georgina, adventure enthusiast and creator of Alpacka My Bags. I'm here for all of your travel and adventure planning needs! 


I've been exploring this beautiful planet since I was a child, so I decided it was time to share my travel tips with others to enjoy. After college, I knew the "traditional career path" was not for me.


I needed to travel and explore what this world has to offer. It sounds cliché but you do only live once. So I made going on adventures a priority, and soon realized that I wanted to share them with others so you can enjoy them too! 

My passion is spreading the travel bug and showing others that travel is attainable and so worth it. From itineraries to camping tips to packing lists, Alpacka My Bags has you covered!

Join me, and often my partner and my dog, as we find exciting adventures and travel recommendations for you! If you've been bit by the travel bug just as I have, I hope you find my tips useful for all of your future travels.

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