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Airplane Travel Essentials: What I Always Pack in My Carry-On

I almost never check a bag, and many of you already know that about me. But when I do, I’m very particular about what stays with me on the plane. I want the things I’ll actually use during the flight within easy reach, plus anything I’d be very unhappy to lose if my checked suitcase decides to take a trip of its own.

Over the years, I’ve pared my airplane travel essentials down to the things that keep me comfortable, the things I can’t easily replace, and enough to get me through the first day if my luggage is delayed.

Here’s what I actually pack in my carry-on and personal item when I’m checking a suitcase.

jennifer connolly from a well styled life traveling with Away Weekender Bag and Roller Carry-on bag

What I Never Put in Checked Luggage

If losing something would seriously disrupt my trip, it stays with me. That includes prescription medications, identification or passport, prescription glasses, jewelry, electronics, and anything valuable or difficult to replace.

I also keep important travel information on my phone, with screenshots or downloaded copies of hotel addresses, transportation details, and reservation numbers. Wi-Fi has an uncanny knack for disappearing just when you need it.

I bring a little more medication than the exact number of days I’ll be away, too. Flights get canceled, and plans change, and I’d rather have a small cushion than spend part of a trip trying to replace a prescription.

What to Pack in Your Personal Item

If I’m traveling with both a rolling carry-on and a personal item, anything I’ll want during the flight stays under the seat in front of me. I have no desire to wrestle with the overhead bin every time I want my glasses or headphones.

WOMAN AT AIRPORT CARRYING AWAY OVERNIGHT BAG FOR AIRPLANE
AWAY OVERNIGHT BAG

My personal item is normally my Away Overnight Bag, which carries my medications, glasses, phone, headphones, book, knitting, chargers, a change of clothes, laptop, and anything valuable. It always fits under the seat in front of me and is easy to access while sitting.

For getting through the airport and during the flight, I keep my passport, travel documents, phone, and hand sanitizer in a small waist bag. My favorites are this Waverly and this Bond Fanny Pack, which can also be worn crossbody. I like having everything within reach without digging through my larger bag. When it’s time to board, I slip the waist bag into my personal item.

I also pack this way in case my rolling carry-on has to be gate-checked. The things I absolutely need are still with me.

What I Pack in My Rolling Carry-on

I rotate among my Quince, Away Flex, and Monos Pro roller carry-ons depending on the trip and how much room I need. The roller holds what I want with me when I arrive but won’t need during the flight, including most of my clothing, underwear, sleepwear, and my main toiletry bag.

QUINCE CARRY-ON ROLLER BAG BY FRONT DOOR ON WAY TO AIRPORT
QUINCE ROLLER CARRY-ON

I try to pack the things I may want first when I land near the top rather than burying them under everything else. After a long travel day, I have very little interest in unpacking an entire suitcase to find pajamas or a clean top.

I also resist filling every available inch. A little extra room makes the bag easier to close, easier to lift, and gives me somewhere to put something I pick up along the way. An expandable carry-on is useful, but I don’t want to arrive at the airport with the zipper already begging for mercy.

WOMAN AT AIRPORT WITH AWAY HANDHELD CARRY-ON, MONOS ROLLER CARRY-ON AND WEARING WAIST BAG FOR IMPORTANT DOCUMENTS
MONOS PRO ROLLER / AWAY WEEKENDER HANDHELD / WAVERLY WAIST BAG

My In-Flight Comfort Essentials

I’ve frozen on enough airplanes to know that an extra layer is non-negotiable, even when I’m flying somewhere warm. A lightweight cardigan or wrap goes in my bag and can double as a blanket when the cabin gets downright frigid.

For longer flights, I bring compression socks, noise-canceling headphones, and an eye mask. I also carry a water bottle and a few snacks. Delays and customs lines have taught me not to leave food and water entirely to chance.

Toiletries I Keep Within Reach on a Flight

Airplane air is brutal on my skin, so I keep a few basics within reach: lip balm, hand cream, eye drops, and my favorite refillable hand sanitizer. I also bring my travel-size Chantecaille Rose de Mai Face Mist for a quick refresh when my skin starts to feel dry. I find the scent soothing too, which doesn’t hurt when travel gets stressful.

For longer or overnight flights, I add a toothbrush, toothpaste, deodorant I know works, and a rich moisturizer.

I keep this pouch small because I don’t need my entire skincare routine at 35,000 feet.

For U.S. flights, I make sure my carry-on liquids follow TSA’s 3-1-1 rule: containers of 3.4 ounces or less that fit into one quart-size bag. Medically necessary liquids can be exempt from that limit.

You can find the rest of what I travel with in my Complete Packing List of Travel Toiletries.

Tech I Keep With Me

My laptop is critical to my business, so it always stays with me in my personal item rather than going into checked luggage. I also carry a portable charger for my phone because so much of travel now depends on having a working battery.

One important thing to remember: portable chargers and power banks have to stay in the cabin. If my bag is gate-checked, I take mine out and keep it with me.

I keep my charging cables together in a small pouch, and for international trips I add my travel adapter. I also put an AirTag in each piece of luggage so I can track its location.

PORTABLE MAGNETIC PHONE CHARGER FOR TRAVEL
FAVORITE MAGNETIC PORTABLE PHONE CHARGER

How I Organize My Carry-On

QUILTED  LEATHER POUCH SET FOR TRAVEL
QUILTED DUFFLE BAG / LEATHER TRAVEL SET

A large bag can hold a lot, but without some organization, everything ends up at the bottom. I use smaller pouches to keep categories together, so I’m not digging for a charger, lip balm, or medication mid-flight.

I also pack by access. Things I may need in the air stay near the top, while anything I won’t use until I land can go underneath.

The older I get, the less interested I am in hauling things through an airport that I probably won’t use. A few well-chosen airplane travel essentials make the day easier without turning my carry-on into another piece of luggage to manage.

If you have a trip coming up, you may also want to read my guides to my favorite travel bags and comfortable walking shoes for women.

What’s one thing you always keep with you when you fly?

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