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Google flights is not always the cheapest to buy tickets as mentioned above, you can also try Skyscanner and Momondo, shop around because buying direct from the airline is not always the cheapest option, it does however offer you a bit more protection in the way of support as OTAs (Online Travel Agents) can be difficult to get refunds from if something goes wrong and often can charge other fees. It’s a risk we all take when we book with them, but don’t be afraid to use them:)
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Hey, congrats on gearing up for your first trip! I'll touch on your questions then toss in a few tips after.
When's the cheapest time to buy a ticket? This is a pretty impossible factor to pin down. Flight prices are always fluctuating based on actual and expected demand for seats on a given route / day/ etc. Google flights (which I'll talk about more later) has a price gauge to give you an idea where current prices for a flight fall in respect to average prices for that route. The best advice you'll get is to buy it when you feel you can afford it. With legacy carriers (American, United, Delta) if the price goes down after you book, you can call to rebook the same flight and get a credit for the difference/ decrease in price.
When should you get a passport if going in December? Traveling from Chicago to Los Angeles does not require a passport as you aren't leaving the country. You'll need a valid photo ID (driver's license, state ID).
Cheapest place to buy? Use Google flights to compare prices for your desired dates. You might find an ULCC (an ultra low cost carrier, like spirit or frontier) has the lowest price, or a legacy carrier may. If the best options are legacy carriers there are categories of fare within the economy like basic economy vs economy that you should familiarize yourself with, as they dictate the rules regarding carryon & checked bag allowances, seating assignment, and impact your chances of being put on standby (made to fly a different flight to get where your going). For a first time traveler I strongly recommend booking a regular economy fare with a legacy carrier if priced within your comfort zone.
Bags/ Suitcases. If a ULCC (spirit or frontier) seems like the cheapest option just remember they charge quite a bit for all baggage beyond your personal item (a personal item is a small bag that fits under the seat in front of you, usually a purse or small backpack). Legacy carriers are more likely to allow both a personal item and a carry on, even on their cheapest basic economy fares (carry ons are medium sized luggage that goes in overhead storage in the cabin). You should familiarize yourself with the allowances of the carrier before you book the ticket. But in my honest opinion for 4 days a backpack (personal item) is likely sufficient if you pack light, otherwise a personal item and carry on suitcase is definitely enough for 4 days. If you need a checked bag (stored in cargo hold of the plane during flight and collected from you at the bag drop) you are over packing.
General tips? Pick a regular economy fare for your first go, having a carryon allowance and pre-selected seat will make your first trip less of a hassle. Try to fly direct, from ORD to LAX. There are more than a dozen direct flights daily, so taking a layover is unnecessary (although it might save you a few bucks).
I recommend avoiding Spirit for your first, even though their red eye from ORD to LAX will likely be the cheapest option you have. The customer service in event of delays will leave you upset with flying. They are a great airline to take if you don't mind being 1-2 hours (or days) late in getting where you're going.
Pack snacks (and 2x 50ml liquors if you drink). Everything is more expensive in the airport. Don't bring a neck pillow. Be patient with employees. Have fun!
Tysm! These tips were so helpful! Ive been seeing that you can get cheaper flights on other sites instead of buying directly from an airline. Is it true that they match your price if you find a flight cheaper elsewhere?
Tbh I have no experience with price matching, but I can warn you that booking through third party companies is full of risks including more restrictive policies, less logistical cohesion (any changes or issues need to be addressed thru third party not with the airline) etc etc. Don't recommend it, even if it seems cheaper.
All great advice except for the booze - you can bring it with you, but FAA rules prohibit you from drinking anything not served by a flight attendant on board.
I consider it a cost saving measure over drinks at an airport bar, cuz I'd usually be ordering rum & coke or a beer. But yeah OP should absolutely be aware that this is true and BYOB can get you in trouble (but again, mixing a 50ml rum into a soda bought airside is easily gonna save 6-7$ a drink with virtually zero risk unless OP is belligerently drunk)
To begin, have you read the FAQ? There's a ton of flight info there.
After reading through that if you have specific questions then come on back.
Congrats on your first trip and also getting your first Passport. (Apply anytime.)
Happy travels.