The author posing for a photo in Chicago

Chicago Packing List (29 Things People Forget to Bring)

Looking for an epic Chicago packing list? Then you’re in luck!

It’s no fun getting to your destination and realizing you’ve forgotten an item or regretted not packing something else. Or, even worse, packing way too much stuff for the wrong season.

Chicago’s unique city-on-the-lake setting gives you certain factors to consider that you don’t have to elsewhere. As a Chicago local with the inside scoop, I’m here to help make packing for Chicago a breeze. 

In this article, we’ll go over the top items to bring to Chicago, Chicago packing tips, and more. And while you’re here, be sure to bookmark my picks for the best things to do in Chicago!

Let’s dive in!

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Chicago Packing Checklist

Day Pack

Our Pick
Travelon Anti Theft Classic Backpack

If you plan on hitting the ground running with long days of activities, a day pack will make life easy.

For families or those planning lots of activities, a day pack can be incredibly helpful. They’re comfortable to wear and can carry everything from water bottles and snacks to swimsuits and flip-flops. This anti-theft day pack is fairly small, durable, and is made to give you some extra peace of mind. 

Belt Bag

Our Pick
ZORFIN Fanny Packs

If you’re looking for something small to hold just the essentials, a belt bag will be your best friend.

This belt bag is the perfect purse alternative for the city. It’s compact, comes in different colors, and you can keep your personal items secure and close to you. It’s a great way to be hands-free and still have your things accessible if you need them. Lots of Chicagoans actually use these! 

Portable Charger

Our Pick
Miady 10000mAh Dual USB Portable Charger

Stop worrying about getting stuck with a dead phone, and relax knowing you can charge it anytime. 

Let’s face it, you’ll need your phone for looking up directions, taking pictures, booking tickets, and more. Having a portable, rapid charger will save you a lot of hassle if your phone starts to die. This portable charging bank is easy to pack and can charge a phone up to 2.5 times. 


Our Pick
Sun Bum Original SPF 50 Sunscreen Lotion
Sunscreen is important all year long, but in the summer, it’s essential. This one is a personal and Travel Lemming favorite.

If you plan on spending a summer day on the lake or out in the city, then slathering on some sunscreen is a must. This sunscreen is good for you and the environment since it’s vegan, hypoallergenic, and reef-friendly (the lake might not have a reef, but it still has fish!). Protect your skin and save yourself from an uncomfortable sunburn. 

👉 Wondering when to plan your trip? This guide to the best time to visit Chicago is the perfect resource!

Hand Warmers

Our Pick
HotHands Hand Warmers

Hand warmers are small but mighty. These stay warm for hours and are perfect for putting in your pockets or gloves.

If you aren’t used to cold weather, then hand warmers could be a great addition to your packing list. These hand warmers come in two pairs and stay warm for up to 10 hours. Being from the South, these were a lifesaver during my first winter in Chicago.

Packing Cubes

Our Pick
Well Traveled Compression Packing Cubes
Save yourself the headache of trying to cram in everything on your packing list. With these compressible packing cubes, compartmentalization is a breeze.

If there’s anything I’ve learned from years of travel, it’s that packing cubes are a secret weapon. These packing cubes come in different styles and sizes and will make packing hassle-free and organized. I like to keep one packing cube for miscellaneous items, too – this makes it easy to find the little things.

👉 Pro Tip: For more storage, roll your clothes instead of folding them!

Reusable Bag

Our Pick
Foldable Reusable Grocery Bags

Save some money, help the environment, and shop smart by keeping reusable bags on hand!

Most shops in Chicago will charge a small fee for bags, so it’s an easy way to save money by bringing your own! Not to mention, it’s better for the environment. These reusable bags come in different patterns, are washable, and are of great quality. Plus, you can fold them up to throw in your purse and fit them anywhere. 

They’re perfect for a shopping spree on the Magnificent Mile!

Reusable Water Bottle

Our Pick
Healthy Human Water Bottle

Stay hydrated throughout the day, keep your water cold, and reduce plastic with a reusable water bottle!

In the summer especially, you’ll want to stay hydrated, so bring this reusable water bottle with you during the day. It has an easy-to-carry, leak-proof lid so you can have it on hand or throw it in your day pack. It’s also insulated, so your water will stay cold for a long time.


Our Pick
Rain-Mate Travel Umbrella
This umbrella is durable, windproof, and easily collapsible. It’s also Travel Lemming tested and approved!

Keeping an umbrella handy while traveling is never a bad idea. This travel umbrella is compact and easy to place in your luggage or day pack. Chicago gets its fair share of rain in the summer so it’s good to be prepared in case you experience some showers during your trip.


Our Pick
Beats Studio Buds

You’ll obviously need headphones for some entertainment, but they’re also a good idea for any audio tours that may arise.

Having headphones for listening to music and podcasts while you travel is a must, but they might also come in handy for self-guided audio walking tours and informative listening guides offered by museums. These wireless headphones are great quality, noise-canceling, and easy to throw in your bag for the day.


Our Pick
Lysian Ultra Soft Foam Earplugs

Block out the city noise and ensure you get a good night’s sleep with these earplugs.

There are plenty of great places to stay in Chicago, but I’m not going to lie, it can be noisy at night. Each hotel room is a little different based on street location, but chances are, you’ll probably hear some city noise while you’re heading off to sleep. If you aren’t used to this, bring some earplugs. Being well-rested is so important when it comes to traveling! 

Face Masks

Our Pick
GOOD MASK CO. KN95 Face Mask

These masks are comfortable, breathable, and have a sleek look. They have good filtration since they’re KN95, making them great for the city, too.

Even with mask mandates changing from time to time, you’re still going to need them for public transportation. I’ve used these KN95 masks myself, and would recommend them. They’re comfortable, adjustable, and of good quality. 

Hand Sanitizer 

Our Pick
PURELL Advanced Hand Sanitizer Variety Pack

Keep yourself and your family healthy, safe, and germ-free with these travel-size hand sanitizers.

As far as cities go, Chicago is fairly clean. But at the end of the day, it’s still a big city. Keep some hand sanitizer with you just in case. This classic hand sanitizer has a gentle formula and kills 99.99% of common germs. It also comes in a couple of different scents with holders to attach to bags and keychains.

Travel Laundry Bag

Our Pick
Kikkerland Travel-Size Laundry Bag
Organize your clean and dirty items, and make laundry easy with this foldable, travel-size laundry bag.

How cool is this travel laundry bag?! A laundry bag is an easy item to overlook on your Chicago packing list, but definitely a good one to have. Laundry might not always be accessible, so this is a good way to keep your clean and dirty items separate. If you’re concerned about space, don’t worry because this laundry bag folds up small.


Whether you’re working remotely or just using the internet like normal during your visit to Chicago, it’s a good idea to use a virtual private network (VPN). Using a VPN provides extra data security, protects web traffic, and hides your location from hackers. This ExpressVPN is Travel Lemming approved and has tons of server locations in the U.S. and around the world. 

Other Chicago Essentials to Pack

Clothing to Pack for Chicago

If there’s any advice I have for clothing to bring to Chicago, it’s this: layers are your best friend. Depending on what season you visit, your packing list will vary quite a bit. But generally, a versatile jacket and good walking shoes are a must. 

Bring clothes that you can mix, match, and layer. When it comes to the basics like shoes, jeans, and a jacket, pack light and only bring your favorites that you know you’ll wear.

So what clothing should you pack for Chicago? Here is a quick clothing checklist for Chicago: 

  • 1 pair of comfortable sneakers
  • 1 pair of winter boots
  • 1-2 pairs of jeans
  • 1 pair of nicer pants
  • 2-3 shirts
  • 1-2 dressier shirts
  • 1-2 t-shirts
  • Pajamas 
  • 1 beanie
  • 1 scarf
  • 1 pair of gloves
  • A few thermal base layers
  • 1 parka or puffer coat
  • 1 rain jacket/windbreaker
  • 1 denim or everyday jacket 
  • 1-2 sundresses
  • 1-2 swimsuits 
  • 1 pair of flip flops or water shoes
  • 1 beach coverup
  • 1 baseball cap or sunhat
  • 5-7 pairs of underwear
  • 5-7 pairs of socks

Hopefully, this list gave you a good idea of what to pack. Below, I’ll break down some specific items and details. If you’re wondering about style, know that Chicagoans can fall anywhere between dressy and stylish to casual and comfortable. 


Our Pick
ECCO Men's Soft 7 Sneaker

Good, comfortable shoes are never something you should skimp out on when it comes to travel. Keep your feet happy with some high-quality sneakers!

Whether you’re walking the Magnificent Mile, Millennium Park, or spending hours at the Art Institute, you’re going to want some comfy sneakers. This men’s pair and this women’s pair are comfortable, stylish, and versatile. Your feet will thank you!

Winter Boots 

Our Pick
Dr. Martens Unisex 2976 Smooth Leather Boot

Snowy, icy sidewalks are unavoidable in the winter. Save yourself from slipping with good boots.

In the winter, snow melts, creating icy sidewalk conditions. This is why you need waterproof boots with good grip. These unisex boots are popular among Chicagoans and I, myself, wore them all winter long. They’re comfortable, durable, and keep your feet warm with good socks.


Our Pick
Eddie Bauer Women's Lodge Down Duffle Coat

Don’t underestimate how freezing Chicago can get. Get yourself a good coat and protect yourself from the cold weather.

A good coat means everything during Chicago winters. Long, down parkas like this one for men, and this one for women, are good options. It may feel like a bulky thing to pack, but the cold weather is no joke. You’ll thank me later.


Our Pick
Carhartt Men's Knit Cuffed Beanie

Something as simple as a beanie goes a long way. It’ll shield you from the wind, keep you warm, and your hair intact. 

If your head’s warm, you’ll be warm. This beanie is a great option because it’s thick and comes in a ton of colors to suit everyone’s style. It’s a classic toboggan and easy to pair with any outfit. 

Baseball Cap 

Our Pick
Baseball Cap Amazon

You can’t go wrong with a baseball cap since it can be worn from early March through October!

A baseball cap is a great addition to your packing list. It’s a Midwestern staple that will give you a little shade and protection from the wind. Plus, it’ll be handy to have until you’re able to hit up a Cubs game and get one there! This baseball cap is made from soft cotton, is breathable, and super versatile to wear. 


Our Pick
Wander Agio Scarf

Wearing a scarf is a great way to add a little style and warmth to any winter outfit.

You’d be surprised by the difference a scarf can make. And with Chicago weather being unpredictable at times, a scarf is a great transitional item to have for the spring, fall, and winter. This scarf comes in a ton of color combinations. 


Our Pick
The North Face Etip Recycled Gloves

While you may want to skimp out on gloves, don’t. These gloves are the perfect mix of warmth, practicality, and comfort. 

Even though pockets are a thing, don’t overlook a good pair of gloves. There’s nothing worse than being so cold you lose feeling in your hands. I personally used these gloves all winter and they were warm, had great touch screen compatibility, and good grip for holding onto things.

Rain Jacket / Windbreaker 

Our Pick
The North Face Women's Resolve 2 Jacket, TNF Black, Medium

Kill two birds with one stone and have a jacket that protects you from rain and wind.

Rain and wind can be expected during all four seasons in Chicago. So, to be on the safe side, travel with a jacket that blocks out both. This men’s jacket and this women’s jacket are durable and versatile for changes in the weather.

Denim Jacket 

Our Pick
Levi's Men's Trucker Jacket

If you’re looking for a one-stop jacket for style, this is it! You can’t go wrong with a denim jacket.

Denim jackets are perfect for everyday wear in Chicago. They’re easy to layer, go with a ton of outfits, and are comfortable to wear. This men’s jacket and this women’s jacket are classic styles. Plus, they have extra pockets which are great for traveling. 

Flip Flops 

Our Pick
Reef Women's Bliss Nights Sandals

Planning on having a beach day? You’ll need some flip flops to protect your feet!

If you plan on hitting up some Lake Michigan beaches in the summertime, then you’ll need a pair of flip flops. These men’s flip flops and these women’s flip flops are thin for packing and are perfect for a day at the beach.

Beach Coverup 

Our Pick
Beach Cover Up Dress with Pockets

Travel packing hack: have a beach coverup that can also be worn in the city!

To keep life simple, bring a versatile beach coverup like this one that can be worn on and off the beach. This dress comes in a ton of different colors, has pockets, and can be dressed up or down. It’ll save room in your luggage and come in handy for multiple occasions. 

Chicago Packing Tips  


There aren’t many laundromats around the Loop or the center of Chicago, so be sure to bring enough outfits for each day of your visit. And definitely check to see if your hotel offers a laundry service!

🛑 Don’t Forget Our Guides! Ok, so you don’t have to pack them because our Chicago travel guides are online, written by locals, & 100% free. But be sure to bookmark them now so you know where to find them during your trip!


Layering in Chicago is a must, and the best way to dress for changes in the weather forecast. For example, layer a couple of shirts and wear a jacket or vest on top. Just a few warm layers can make a big difference.

Winter Accessories

I recommend bringing what I call “the holy trinity” of winter accessories: a hat, gloves, and a scarf. As long as you have at least two out of three of these accessories, you should be warm. If you aren’t used to cold weather, then go ahead and bring some hand warmers, too. If anything, it’s better to be overprepared than underprepared.

Rain and Wind

It’s called the Windy City for a reason. To be prepared for wind and rain, bring a jacket that can act as a rain jacket and windbreaker. Also, bring an umbrella, and something to tie your hair back if the wind gets crazy.

Lake Effect

Being close to Lake Michigan has its perks, especially the many beautiful beaches in Chicago that come alive during the summer. But it also comes with unpredictable weather. If you’re planning on spending time close to the lakefront, just know that it’s likely to be colder and windier.  

👉 More Packing Lists: Seattle Packing Checklist, Puerto Rico Packing Checklist, Mexico Packing Checklist

FAQs About What to Pack for Chicago

What should you not wear in Chicago?

You shouldn’t wear heels when visiting Chicago. Unless you’re attending a formal event, no one really wears heels around the city since they’re impractical for lots of walking. On a sports note, stick to Chicago team jerseys and merchandise (Chicagoans take their sports seriously!).

How should I dress for Chicago?

No style is really off-limits in Chicago. Chicagoans fall all along the style spectrum so it’s hard to stick out from just your clothing. Generally speaking, Chicagoans are more casual, but if you want to dress up, you won’t look out of place. 

What should I pack for Chicago in the summer?

Essential Chicago summer items include comfortable walking shoes such as sneakers. For clothing, think comfortable and casual. Lots of people wear hats, too. Keep in mind that Chicago doesn’t actually start to get hot until around mid-June, so still bring layers.

What should I pack for a Chicago winter weekend?

Don’t underestimate Chicago in the winter. Even if only packing for a weekend trip, pack a longer, insulated parka if you have one. Also, bring shoes (boots are recommended) that have good grip and are waterproof. There’s usually snow and ice on the ground so good shoes are important to keep you from slipping. 

🏖️ Read Next: Beach Packing Checklist


There you have it! Hopefully, this packing list was helpful and you feel better prepared for your trip to Chicago, no matter the season.

Looking for more to do in the area? Check out my picks for the top Chicago day trips!

Happy packing for Chicago!

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