One of the coolest features about Kiwi is that unlike it will look at ALL the cheapest possibilities, even if it means putting you on 2 totally separate flights. Other flight search engines will try to book the entire route on either the same airline or airlines with codeshares. It might not always be the fastest or more convenient, but great for anyone on a budget.
Most cash bookings can be upgraded with Avios either at the time of booking or later on, depending on availability. Only the lowest economy (World Traveller) fares (Q, O and G) cannot be upgraded with Avios at any time. There must be reward flight availability in the next cabin for you to be able to upgrade to it using Avios. You won’t be able to upgrade with Avios at the airport or on board.
Ask your travel agent. My own travel agent has a relationship with certain airlines that let her book her customers into preferred seats that are not released to everyone (usually toward the front of the plane, in exit rows and the like). She can also see upgrade availability fairly quickly, and many agents can add comments to your reservation that increase your chances of being chosen for an upgrade. Ask about these the next time you talk to your travel agent.
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Today, with profits essentially non-existent, airlines are oftentimes not releasing Premium seating for flight upgrades until an hour (or even minutes) before the flight's departure, hoping to sell those seats at full cash value. Only at this point do the airlines release the empty (non-purchased) Premium seats to their frequent flyers who use miles to get the award or the flight upgrade. So it becomes a race among frequent travelers to position themselves to obtain one of the coveted few Premium seats. And everyone you speak with seems to have their own method and strategy for getting into position to take advantage of these hard to come by flight upgrades.
The second upgrade tip is to check the upgrade availability frequently. Although upgrade seats may not be available at the time you purchased the coach ticket the inventory for upgrades is constantly changing, right up until the time of departure. You can check with your airline every day or several times a week or you can use an alert service from some online services such as ExpertFlyer.com. ExpertFlyer.com now offers Flight Alerts, a service that allows you to program your actual flight or series of preferred flights for an upgrade or award. Flight Alerts will automatically search for open availability and notify you immediately once it locates a seat. The notification can be sent to three (3) different addresses including personal or work email, cell phone or PDA so no matter where you are or what you're doing, you will be notified the moment Flight Alerts finds the Premium seat you're looking for. Flight Alerts, or a similar notification program, can also assist you in finding seats using only awards miles.
Hopper’s signature rabbit may seem a bit childish at first, but this bunny knows its stuff. The flexibility feature is especially useful: put in your home city and desired destination and Hopper will map out the entire year for you with color-coded prices. The dates are shown as month-long calendars, with colored boxes telling you when prices fall into certain categories, like less than $300 or +$500. The app-only service also predicts whether or not the price for your chosen dates may drop or not (they monitor up to 15 billion flight prices per day) and allows you to “Watch the Trip” —  a feature where Hopper will send you alerts if the price changes. If you know you need a vacation, but are flexible on your destination or dates, you can also set alerts for the app to tell you when there are destinations deals. This app is free to download. 
Most cash bookings can be upgraded with Avios either at the time of booking or later on, depending on availability. Only the lowest economy (World Traveller) fares (Q, O and G) cannot be upgraded with Avios at any time. There must be reward flight availability in the next cabin for you to be able to upgrade to it using Avios. You won’t be able to upgrade with Avios at the airport or on board.
Farecast.com: This site is best known for predicting where an airfare on a particular route is going to go (up, down, or stay the same) over a period of time. But recently it, too, got into the fare listing game. From the home page, go to the "Airline Ticket Deals" section and you'll see a select, but not very extensive, list of fares from the airport of your choice. Unlike Farecompare, Farecast uses airfare data from Cambridge, MA-based ITA Software, which in our experience is more accurate than ATPCO's data. Farecast's fares show all taxes up front, but Southwest, Allegiant, Skybus and a few other airlines' fares are not shown.
Hopper’s signature rabbit may seem a bit childish at first, but this bunny knows its stuff. The flexibility feature is especially useful: put in your home city and desired destination and Hopper will map out the entire year for you with color-coded prices. The dates are shown as month-long calendars, with colored boxes telling you when prices fall into certain categories, like less than $300 or +$500. The app-only service also predicts whether or not the price for your chosen dates may drop or not (they monitor up to 15 billion flight prices per day) and allows you to “Watch the Trip” —  a feature where Hopper will send you alerts if the price changes. If you know you need a vacation, but are flexible on your destination or dates, you can also set alerts for the app to tell you when there are destinations deals. This app is free to download. 
Having a hip chipmunk find the best airfare may initially seem weird, but the Hipmunk app makes things super clear, with user-friendly charts that map your journey by price, time of day, airline, length of layover and even whether or not your aircraft has Wi-Fi. The app will also track flight prices and provide notifications when the best time to buy is. The “discover” feature offers deals on destinations like Canada or Mexico, and also offers inspiration like “beaches” or “outdoor.” Once you’ve booked a flight you can also reserve a hotel, too. This app is free to download.
All of the sites allow you to search by preferred times but none to my knowledge allow you to set up alerts for specific arrival/departure times. Interesting idea to have sites sort flights by legroom cost, hadn’t thought of that and certainly have not seen it. Southwest used to have an alert tool called Ding, but no longer. You can include Southwest on Google flights but in its search results it only shows scheduling, you’re redirected to the Southwest website for pricing. Sorry I can’t help you more with your wish list but I sure do thank you for your comments and questions.
The second upgrade tip is to check the upgrade availability frequently. Although upgrade seats may not be available at the time you purchased the coach ticket the inventory for upgrades is constantly changing, right up until the time of departure. You can check with your airline every day or several times a week or you can use an alert service from some online services such as ExpertFlyer.com. ExpertFlyer.com now offers Flight Alerts, a service that allows you to program your actual flight or series of preferred flights for an upgrade or award. Flight Alerts will automatically search for open availability and notify you immediately once it locates a seat. The notification can be sent to three (3) different addresses including personal or work email, cell phone or PDA so no matter where you are or what you're doing, you will be notified the moment Flight Alerts finds the Premium seat you're looking for. Flight Alerts, or a similar notification program, can also assist you in finding seats using only awards miles.

And it is not just a combination of luck and automation that will shut you out of upgrades — at some airlines, it may be a matter of policy. “Most airlines state, in no uncertain terms, that their policies prohibit arbitrary upgrading, both at check-in and onboard,” says Randy Petersen of InsideFlyer. “It’s a firm rule, with no room for negotiation or interpretation.” Petersen agrees about the root cause: “This becomes understandable when you consider that upgrading is now often done electronically, rather than by queuing up at the check-in counter.”
If your specific fare class qualifies you for an upgrade if a seat becomes available, you may receive offers by email or text to purchase (most often in cash but sometimes for miles) the option to upgrade as flight time approaches and seat availability becomes more clear. These tend to disappear quickly, so if you miss the message, the seat won’t last long.

A flight alert tracks the price of a specific route or flight. When the price changes, you’ll be notified via email or push notification if the price went up or down (and by how much). Flight alerts are completely free and can be stopped at any moment. It is also possible to have multiple price alerts set up at once which is a great option if you are comparing vacation destinations. It really is a must-have tool, especially for budget travelers, because flight alerts are hands-down one of the best ways to find cheap flights, fast.
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A price alert tracks the price of a specific route or flight. When the price changes, you’ll be notified via email or push notification if the price went up or down (and by how much). Price alerts are completely free, can be stopped at any moment and you can have multiple set up at once. They are hands-down one of the best ways to find cheap flights, fast.
Airfarewatchdog – You can set up regular price alerts for favorite routes, but the real appeal for cheapskates with wanderlust is this site’s Top 50 Fares of the Day page. This tracks bargain airfares from Frontier, JetBlue, and other carriers prone to slash prices, as well as larger airlines. (Sample deal from earlier Wednesday: $40 for a roundtrip flight from Pittsburgh to Las Vegas).
Here’s where the power of ExpertFlyer comes into play. Let’s say that I wasn’t interested in crossing the Atlantic in economy. Instead of coming back to the site multiple times in the weeks and days leading up to my desired flight, I can actually set up a flight alert by clicking on the exclamation point icon (red arrow in the above screenshot). That would open up a window like this:
Internet Airfares: Long before there was a Farecast or a Farecompare, there was Internet Airfares, an easy to use if limited site that shows the best fare reductions from various cities. It's not pretty, and only about 50 departure airports in the US and Canada are covered, but it has its charms. Again, no Southwest Airlines and this site doesn't send out email alerts.

Most cash bookings can be upgraded with Avios either at the time of booking or later on, depending on availability. Only the lowest economy (World Traveller) fares (Q, O and G) cannot be upgraded with Avios at any time. There must be reward flight availability in the next cabin for you to be able to upgrade to it using Avios. You won’t be able to upgrade with Avios at the airport or on board.
If you’re looking for a specific flight on a specific date, Flight Fishing may not be for you. If you’re a bit more adventurous, you may score an exciting airfare. Registering on Flight Fishing allows you to set up a deal alert that could be as specific as one airport to another, from a specific airport to a region, or as general as from your preferred airport to anywhere.
The other nice thing about the results page is that it’ll show you connecting options (as long as you don’t limit it to nonstop flights at the outset), though bear in mind that every leg of a one- or multi-stop itinerary must have award availability in the desired class of service in order to book the entire trip with miles. Remember too that most award seat availability shown on ExpertFlyer will be at the saver level for all programs. This is nice in that it should be bookable using any partner program’s currency, but it won’t show you the expanded award inventory that’s sometimes available through certain programs. 

When requesting an eUpgrade to Business Class, you will always be offered the option to sit in the best available seat. For instance, if you originally requested an eUpgrade to Business Class, but there are no Business Class seats available at flight departure, and seats in Premium Economy are available, you will be offered a seat in Premium Economy. The eUpgrade requirements will naturally be adjusted accordingly.
Whenever airlines overbook flights and need folks to give up a seat, that is when you have the most leverage for getting concessions and upgrades from the airline. Most of us have been in airports listening to increasingly urgent announcements looking for volunteers to give up their seat; in that situation, you can go up to the gate, set your conditions and then let the airline decide if it can meet those conditions.
You will be notified every time the price changes so you can best keep track. As there is no standard for how often airfare changes, there is no maximum or minimum number of times that you will be notified. Our goal is to keep you up to date and help ensure that you get the best deal available and the best way to do this is to notify you every time there is a price increase or decrease.
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