I’m not a weekend warrior, but I’ve traveled on some of the longest flights in the world, and I’ve experienced enough conveyer belt shuffles at the end of a TSA check to give anyone a heart attack.
This is my definitive guide to air travel, from booking to packing to flying: my whole process and all my recommendations for rocking your next flight. Whether it’s a one-hour puddle jump or a 16-hour international hullabaloo, you’ll be ready to travel like a pro.
Get the best deal without constant checking.
Use Kayak for the cheapest Flights
Kayak.com is my favorite site for booking flights. Here are a few things I always do to get the best flight and price.
- Check the add nearby airports box. If you live between a couple airports, this box can open up a lot more options. Once you search the results, you can uncheck airports you don’t want to include in the search results.
- Click make my dates flexible. If you’re going on a vacation and you aren’t dead set on certain dates, flying on a Wednesday or Saturday can save you a bunch. If you’re really flexible, check the flex month option to get your best deals.
- Don’t bother with the other sites. At the bottom of the Kayak site, you can see prices from other sites like Priceline. Don’t waste your time. I’ve never seen anyone cheaper than Kayak.
Set up automatic alerts
You can set up auto alerts to send you an email digest each day (or week) of your flight options. Kayak also has a price trend on the left hand side of the search results that use an algorithm to tell you if prices are likely to go up or down with a confidence rating of how sure they are of their prediction.
Layovers are good if you have a connection
Most people are layover haters. I understand, it’s no fun to sit in an airport as you prepare to reach your final destination. But running through airports at breakneck speeds is far less fun.
A layover of an hour or less is dangerous if you’re trying to make a connection at a huge airport. If your flight is delayed, you end up needing track shoes to make your next flight.
If it’s a close call and you are on the same airline all the way through, many times they’ll start paging you on the intercom and they’ll wait for you, since others on your first flight are probably snagging the same connection.
Book flights on one airline instead of segmenting
If you book an international flight and buy a ticket to LAX and then a different ticket to Japan, you end up having to pay baggage fees on the first domestic flight, while you’ll get a certain amount of free baggage once you go international. If you’re checking a bag or two, it could be hundreds of extra dollars you pay each way to get your bags to your final spot. Then, you’ll have to go pick up your bags and recheck them for your next flight, which is a huge hassle.
If you book with one airline (which includes flights with their partner airlines) on one itinerary all the way through, once your bags are checked once, you’re good to go, and whatever baggage allowance there is for the international flight applies to the domestic connections. Hooray, free bags!
Avoid awful airports
There are lots of really awful airports that you should avoid at all costs if possible, especially if you are just making a connection there.
The reason they are normally bad is because they are so massive. In the States, I always try to fly direct, even if it is a bit more expensive (I’ll gladly pay $50 more each way to go direct because of the time savings and hassle of switching planes).
My two least favorite to make a connection in the States: Detroit and Atlanta. They are both massive, and if you get stuck at one end, you’ll be that guy running for your flight. Those two are just the tip of the iceberg.
Internationally, never connect through Charles de Gaulle in Paris. Everyone I know who connects through there loses a bag on the way.
Kayak sends you email alerts if your flight is delayed or your gate is changed, which is super helpful.
This is where the flying pros are separated from the people who are cramming crap into their backpack for twenty minutes at the pot-of-gold side of security.
Have a checklist
Don’t rely on your memory to remember your passport and your dress socks. Write down everything you think you’ll need, cross off half of the stuff because you don’t really need it, and then meticulously check and double check to make sure you have everything before you leave.
Here’s a good checklist from OneBag.com to get you started.
To get extra nerdy, I’ve created a text expansion snippet of my standard packing list so I don’t have to retype everything. Saving your standard list in Evernote works too. Save your packing list to make sure you get everything packed back up on your way home.
Bring a change of clothes on the plane for long flights
If someone spills something on you, or you yak from the turbulence, you’re going to wish you had another shirt.
If you’re going somewhere for a weekend, don’t take more than a carry on. You just don’t need it. Also, if you have a cloth roller bag carry on, don’t stuff it to the brim, because it won’t fit in the overhead compartment or under your seat.
Roll your clothes (or use space saving bags)
Rolling your clothes is a technique to save space in your bag. It really works. Here’s a (slightly nausea-inducing) video of how to roll your clothes.
If you’re moving overseas, I’m a huge fan of the space saver bags. The only problem is the bags allow you to fit way more crap than your 50 pound baggage weight limit will allow, so make sure you test the weight.
Bring snacks and a water bottle
This is a big-time money saver. You can bring pretty much whatever non-liquid food you want on a plane, so load up your backpack with peanuts and sandwiches. Also, airlines rarely even give you peanuts, so you’re going to get hungry.
Also, empty out a water bottle and toss it into your backpack or purse. You can bring any empty plastic containers you want, so you don’t need to throw away your bottle before security, just empty it.
Test the weight of your bags
Bags always weigh more than you think. Fifty pounds is normally the standard weight for checked bags, and in the US there normally isn’t a weight limit for carry ons. Overseas, the weight limit for carry ons can be as low as 16 pounds, so be sure to check your airline’s rules and regulations or you’ll be forced to pay to check your light-but-overweight carry on, which is the absolute worst.
If you want a super nice travel-sized, hand luggage scale, I recommend this one that is incredibly accurate and worth the $15 if you travel (at capacity) often.
Find out the best baggage configuration
Sometimes international flights give you two checked bags for free, but charge you if one bag is overweight. Try to condense down to one bag if you only get one free bag, but split things up if you get two and one bag would be overweight. This varies from airline to airline, so plan ahead.
Check-In and Security
Don’t get caught between a pat-down and a meltdown.
Call airlines ahead for oversized baggage
We were checking a giant box with a stroller to take to a family member, and it was underweight but oversized. Normally you’d have to pay extra, but because my genius wife called ahead, the airline put a note on the bag and waived any extra fees.
Check-in a day before
You can check in online 24-hours in advance even if you’ll need to check bags. Many times this lets you pick your seat too. On long flights, it’s worth paying to ensure you have a good seat and you’re not stuck in the middle on a 15-hour ride. Remember: aisle seat if you’re a frequent peer, window if you’re a in-flight sleeper.
Wear comfy running shoes
See note about flights being delayed and nearly missing connections. You’ll never be so glad you had your Nikes on.
Get chatty with the check-in agents
We’ve had lots of common grace in traveling lately when we have had bags be just overweight. Part of it is because we treat the airline agents like human beings and just ask them how they are doing. They are quick to let little things go when you’ve built rapport.
Put all the stuff in your pockets into your bag before security
Phone, money, wallet, whatever. Everything but your boarding pass. Then you don’t look like a dufus going through security three times because you forgot about your pocket watch, belt and fat wad of cash.
Put your boarding pass in your passport
Then you only hold one item in your hands, you can hand it to the TSA agent with your boarding pass on the page of your picture and information, and you get through quicker so they aren’t flipping your passport trying to find your mug shot.
Memorize this order: Shoes, belt, jacket, laptop, backpack, carry on
My least favorite part of flying is the absolute mad dash at the end of the 20-feet too short conveyor belt.
Here’s how to zip through security nearly as effortlessly as Jesus passes through locked doors in John 20:19: shoes first, so you can get those back on quickly. Belt next to keep your pants up, then jacket or hoody next, so you can have all your clothes on before you get to reloading your backpack. Laptop next as you tuck it into your backpack or briefcase. Put your backpack on and then grab your carry on and roll away like an absolute magician to the wonder and amazement of the people stuffing packing peanuts back into their bags.
Waiting for Takeoff
Get ready for the departure.
Get everything nice and charged (laptops and phones) if you’re in the middle of a layover. If you want to be a real boss and you know you’ll have a long layover, bring a small, thin extension cord or a power strip. It’s a bit of overkill, but if you have a 6-hour layover, anything goes.
Grab some overpriced snacks if you didn’t pack them yourself because you didn’t make a checklist.
Be willing to bump
If you’re not in a hurry to get to your final spot, go to the gate agents and tell them you’d like to be the first to be notified if the flight is overbooked and you’d be willing to take a bump.
Then, once they call you up if the flight is too full, you can start negotiating right away and get some mad free vouchers.
Boarding and In-Flight
Enjoy the ride by being prepared.
Rock the gate check if you can
On smaller flights, airlines will offer (er, force you) to gate check your carry on. That means they give you a special tag to put on it, you roll your carry on down the ramp, leave it at the airplane door and pick it up in the same place once you pop off the plane. Don’t forget to pick it back up!
Make sure you don’t pack valuable or fragile items in your gate-checked bag, or you’ll be bummed when your snow globe explodes in excitement all over your clothes.
Put your carry on overhead ASAP
If you have a bag you want to put in the overhead and you couldn’t gate check, put in your carry on in the first available spot. The worst thing you can do is play the role of salmon swimming up stream because your bag is behind where you are sitting. It makes getting off the plane nearly impossible and you annoy the socks off of everyone around you. Chuck that carry on up swiftly, even if your seat is further back, because you can always walk up and access it if you need to.
Bring a physical book
I know ebooks are all the rage (and I have a few thoughts on them) but when it comes to flying, you definitely want to bring a physical book.
You have to turn off any electronic devices before takeoff because those things will totally crash your plane if not and the blood will be on your hands.
You must switch off electronics before even leaving the gate, and those flight attendants have hawk eyes for our plane-crashing devices. Between the 20-minute taxi to takeoff and the final 20 minutes on your descent, you can cram in about an extra 40 minutes of reading a physical book vs. an ebook.
Half-plug your headphones
Most airplanes have the stupid dual-prong headphone jacks, and if you plug in your normal headphones all the way, you only get sound in one ear. You can use the airline provided headphones, but they’re pretty much worthless and uncomfortable.
I found in my last flight that you can put your headphone plug in 80% of the way with the metal making contact but not fully clicked in and you get sound in both ears like magic.
Rock the neck pillow
There is no shame in a neck pillow when you are flying for the majority of a day, and they make sleeping 100x easier.
Bring a toothbrush
Because your breath will be stanky by hour seven.
Check out the movie selection beforehand
The on-screen system for checking out entertainment on flights wonderfully features 1990s quality navigation. To alleviate your frustration and touchscreen pummeling, check your airline’s website before you leave because they often list their in-flight entertainment. Go in with a game plan instead of getting stuck watching The Land Before Time 27.
As a wise man once said to me, your two best friends when traveling are flexibility and a sense of humor. Things will go wrong, planes will get rerouted, you’ll miss connections, and people will just be weird. Relax, laugh and enjoy the ride. You’re experiencing air travel for goodness sake. I’ll end with some wisdom from Louis CK.
“People say there are delays on flights. Yeah, delays. Really? New York to California in 5 hours. That used to take 30 years and a bunch of you would die on the way there and have a baby. You’d be with a whole different group of people by the time you got there. Now you watch a movie, you take a dump and you’re home.”