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What You Need in your Chicago Packing List

As a packing nerd and a Chicagoan, I know how hard it can be to pack for a trip when you’re going somewhere with slightly unpredictable weather. When the temperatures between morning and afternoon can be as dramatic as a 20-degree difference, it can be hard to know how to pack effectively. 

Regardless of your packing style, thorough preparation is key to a successful trip. I’m here to empower you to make the most of your luggage when you explore Chicago! 

I want to note that the best time to travel to Chicago is also when the weather is the most unpredictable. The shoulder season in Chicago is late spring and early fall when big temperature shifts during the day are more likely. Keep that in mind while planning, and you won’t have to buy an overpriced souvenir sweatshirt when walking to breakfast (unless you want to). 

Chicago Board of Trade Building along La Salle street in Chicago Illinois. The art deco building was built in 1930 and first designated a Chicago Landmark on May 4 1977.

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Essentials for Every Traveler

When packing for Chicago, no matter the weather or season, there are some things you’ll need. These items should always be on a packing list, regardless of destination. Many of these items should never be packed in a checked bag, which could get lost, rerouted, or otherwise become unavailable to you. 

Here they are so you don’t forget while preparing for your trip: 

  • Plug adaptor (if traveling from outside of the United States)
  • Passport (or other government ID if a U.S. citizen)
  • Cash, just in case
  • More than one payment card, just in case
  • Medications/prescriptions 
Woman traveller with travel bag or luggage walking in airport terminal walkway for travel abroad.

Clothing and Footwear

The trickiest part of knowing what to pack for Chicago is your clothes. Since the weather can be unpredictable, you want to come prepared for a range of temperatures and other changes. This is especially important if you plan on visiting during a Chicago winter, which can be very cold, snowy, or just yucky and slushy. 

Just don’t worry too much about the Windy City being overly windy – that nickname has nothing to do with actual wind. Your best bet, especially for packing light, is to plan your wardrobe in layers. And don’t forget that you can bring your coat onto a plane or wear your biggest boots/shoes to avoid stuffing them into your luggage to save space. 

Being able to layer your clothes can be a lifesaver in Chicago. I’d argue that the most important Chicago essentials are a light sweater or long-sleeved t-shirt. Both are easily tucked into a backpack or day bag and accessible if you need them. They’re also terrific for Chicago riverboat tours since the additional wind can make you chilly. 

Winter essentials:

  • Sweatshirt (I recommend LSKD loungewear, which is super comfy and warm) 
  • Long underwear (if you’re outdoorsy and visiting in the wintertime, you’ll probably need this)
  • Thick socks
  • Mittens/gloves
  • Scarf
  • Winter hat
  • (optional) boot inserts to keep your feet dry
  • (optional) reusable or disposable hand warmers

Spring essentials:

  • Extra shirt, in case you get caught in the rain
  • Light cardigan or jacket
  • Poncho

Summer essentials: 

  • Fun sunnies (I love RainbowOPTX)
  • Sun hat
  • Breathable clothes, especially cotton or linen
  • Light cardigan or jacket
  • Bathing suit (our nice beaches often surprise visitors)

Fall essentials: 

  • Light cardigan or jacket
  • At least a pair of warm socks
  • Pullover sweatshirt
  • Scarf

For footwear, remember that you’ll be walking a lot. Even if you use public transportation, you may walk more than usual. Depending on how long you are in Chicago, you may want to bring two pairs of shoes so you can wear them on alternating days to allow them to air out and cushioning to reset. 

That said, be sure to pack shoes you know will keep your feet happy. 

Travel and vacation concept, happiness woman packing stuff and a lot of clothes into suitcase on bed prepare for her travel and journey trip.

Gadgets

Fellow tech junkies will know how vital it is to have your gadgets packed and ready for an adventure – near or far. Even a day downtown for me means a packed day bag just in case I need anything while I’m out and about. A little pre-planning will make all the difference when your phone dies while you’re halfway through the Field Museum.

You may see public outlets to charge your devices, though you should be careful. Juice jacking is a real issue with public outlets that only use USB to connect to your phone. Juice jacking is when a person is able to spread malware to your phone through a plug port. If you’re prompted to share data when you plug in, select charge only, or don’t use that outlet – I recommend not using that outlet. 

  • Portable battery for phone (your phone battery may drain faster than usual while you’re in the city, especially in museums where you may not get a signal)
  • Earbuds or headphones
  • Chargers for all your tech
  • 3-in-1 portable charging stand to conserve hotel nightstand space (I LOVE my iLive charging stand, which folds up and is perfect for travel)
  • LectroFan Micro2 mini sound machine/speaker (this little device is perfect for travel, it’s so small it can even fit in your pocket)
  • Camera
  • Lens wipes (for phone, camera, and/or glasses)

Gear

Regardless of what your trip to Chicago entails, you’ll want a few pieces of gear on hand. This is especially true if you plan to take any day trips from Chicago, which could include hiking for the day at Starved Rock.

Remember that some gear pieces, like backpacks, aren’t allowed everywhere. Always check a location’s policies before popping over with a large bag – some of the museums, like the Chicago History Museum, do not allow large bags. 

Some locations may have lockers to place your bags in if they’re too big. Your best bet is to call before you go to see if all the lockers are taken for the day. But I recommend packing light in a smaller bag on days when you’re visiting places that don’t allow backpacks. Save the backpack days for more packed itineraries. 

  • Backpack or day pack
  • Travel umbrella
  • Reusable water bottle or tumbler (I highly recommend anything by MyBevi for hot or cold drinks)
  • Towel (perfect for summer, I love my COR Surf towel robe, which can also double as a changing poncho)
  • Sleep mask (Manta Sleep masks are the best)

Health and Safety

All things considered, Chicago is a pretty environmentally sound place. While we have magnificent Lake Michigan and picturesque beaches, you’re not going to get the amount of UV exposure you will in tropical locales. Still, you want to be prepared with some safety items anyway. Personally, I always bring a small first aid kit with me anytime I travel. You just never know when you’ll need it. 

Toiletries

Since we all have different self-care routines, it can be tricky to recommend what toiletries to pack. Your needs will vary based on when you visit Chicago, too. So I’ll make some broad recommendations just to have on hand (particularly to address our cold weather). 

  • Deodorant (I love Crystal roll-on deodorant, which is natural and holds up against humid Chicago summers)
  • Shampoo and conditioner
  • Body wash
  • Face care products (Kuumba Made is a cruelty-free, handmade company I highly recommend for their incredible products)
Skin care. Sun protection. Woman apply sun cream. Woman With Suntan Lotion On Beach In Form Of The Sun. Portrait Of Female With Drawn Sun On A Shoulder. Suncream. Girl Holding Moisturizing Sunblock.

Adventure Activities

Unless you’re driving, I don’t recommend bringing your own watersports gear for time on Lake Michigan. If you want to do something like kayaking or paddleboarding, you can easily and affordably) rent one from one of the beachside stands. 

Packing Tips

As you can tell, some of knowing how to pack or dress in Chicago has to do with our seasons. Still, there are quite a few packing areas that aren’t weather-dependent and are more about making your trip as comfortable as possible.

I’ve rounded up the more basic (non-weather dependent) items in a checklist format below for you to use as you’re preparing for your trip. 

In the meantime, here are some packing tips to keep in mind: 

  • Remember that you can nearly always buy something if you forget it. This helps take some of the stress off of packing. If you can, try to buy it in a shop outside of your hotel to save money. 
  • Wear or carry your bulkiest items like coats or boots onto the plane to avoid packing them. 
  • Always weigh and measure your carry-on bag. This is especially important if you are using soft-sided luggage, which can overstuff and not fit into the overhead compartment. 
  • Keep all important items like medications, money, and I.D. in either your personal bag or carry-on; do not check them in with a bag. 
  • For luggage with wheels, pack your heaviest items on the bottom. This way, the extra weight will not cause the bag to tip over and make it easier to roll around.  

Chicago Packing List Updated

Author

  • Amanda Finn

    Amanda, a Chicago-based travel journalist, has explored 20 countries and 27 states since childhood. Featured in publications like Huffington Post and Ms. Magazine, they specialize in LGBTQIA+ travel, theme parks, itineraries, traveling with pets, and purposeful travel.

    View all posts https://www.tiktok.com/@finnwrites

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