Best to book flight by...?

There are no longer any "rules" about when to book air tickets to get the best price. The best current advice is:

1. First, accept that the airlines have decades of experience as well as very powerful computers that they have harnessed to the task of getting the maximum possible fares. While you can try to "beat them at their own game," it's not easy.
2. Next, realize that airlines have aggressively cut capacity and planes are fuller than ever. For this reason, prices can be significantly higher than just a few years ago. So, don't go by what someone paid in 2009 as a guideline for what you'll pay to travel the same route in 2014.
3. Start looking at prices now (as you are doing). Check Kayak as well as the airline's own websites, and sign up for fare alerts (for open jaw tickets such as yours, you will usually have to sign up for two alerts - round trip ORD-LON and round trip ORD-FCO).
4. Figure out the various options and which ones you and your traveling companions will and will not accept (layover airports, transfer times, airlines, etc)
5. Have your passport and credit card information handy (so you won't lose a fare by being delayed getting these)
6. When you see the flights you want at a price you can live with, book immediately. Fares can disappear in an hour. On the other hand, if you've missed a fare, sometimes it reappears; of course, sometimes it doesn't.
7. Once you've booked, don't look back. Accept that you may have indeed gotten the best price, or that you may not have.

Oh, and check STA Travel for student fares (if these even still exist).

I haven't flown Aer Lingus. Turkish Air is very nice, with substantially better food than I've had in coach on other airlines, if you don't mind the extra flying time (Istanbul is "out of the way" for London or Rome). And LOT was fine. They fly 787's which concerned me, but my flights in September 2013 went off without a hitch, and there is an electrical outlet as well as a USB charging port at every seat, if you like to keep busy on your electronics during the flight. Warsaw airport is relatively small and easy to get around in, but do be prepared; if you are changing planes, there is a security check IMMEDIATELY after immigration. If you upgrade to Premium Economy, you get 2-3-2 seating instead of 3-3-3 seating, and it only costs about $220 more each way.

Buying airline tickets are always touch and go, I'm also a college student who happens to be studying travel and tourism and it's still just a toss up game. I'm going on a trip to Europe in April as well and bought my tickets back in September and have been keeping tabs on prices and so far have only seen them rise. Personally, I've never seen options for college discounts (really wish there was), as far as airlines, I've heard Aer Lingus is good, I'll be taking my first flight with them on this upcoming trip. For my long haul flight across the pond I'll be flying Delta to give my parents peace of mind and my ticket was just over $1000 for open jaw arriving in Dublin and leaving from Paris. I'd say keep an eye on prices for the next couple of weeks to see when prices tend to rise and fall, it's usually more expensive to buy on the weekend, also if you can be flexible on your flying days, it's cheaper to fly Mon-Wed. That's just my opinion. If you feel like you're getting a reasonable deal, don't hesitate to take it, I waited and could have saved myself a small amount of money, but seeing as to what fares have risen to I'm still happy with what I got.

Pay attention to flight times. Often, unusually low prices indicate some type of catch. In Turkish's case, its a 5 hour layover in Instanbul and a somewhat longer time in the air due to backtracking. I've heard nothing but good things about the airline itself, so see if you can add a few days' free stopover in Turkey. Flying back from London using Aer Lingus would work great because its physically the closest place in "Europe" to Chicago. Again, if you can get a few days in Dublin, so much the better.
There can be a big variation based on length of stay and departure date. For instance, a 26 day round trip to Rome on Turkish is $1153 leaving on April 29. A 25 day trip leaving April 30 is $808. Play around with ITA Matrix Calendar to see if there are any sweet spots.
http://matrix.itasoftware.com/search.htm

Meg,

welcome and congrats on your future travels.

I book my flights as soon as i can get a handle on my itinerary and that is usually 6+ months out. Im planning for my Sept 2014 trip right and hope to book it by feb 2014 at the latest.. The sooner the better. I dont want to gamble by playing the wait n see game.

if you plan on going back, you will have a better idea on costs everytime you go.

maybe someone that flys in/out of chicago alot can give you an idea on R/T cost to particular places.

happy trails.

"Turkish Air is very nice, with substantially better food than I've had in coach on other airlines"

Exactly my opinion of Turkish Air. Kind of like Emirates, Turkish Air is trying to expand more into Europe by positioning itself as an "affordable luxury" hybrid. During nearly every commercial break on Eurosport last spring, you would see an advert for Turkish Air featuring Kobe Bryant, of all people.

I would gladly fly this airline again.

Thank you all so much for your helpful replies!

We just came back to Portland via Dublin and Chicago on Aer Lingus. It was perfectly fine, and would use them again.

As was suggested above, we turned the Dublin stop into a two-day layover, and had a great time there.

The Dublin Airport has a US Customs facility. As of the time of our trip (September 30), however, only passengers on flights to JFK had the opportunity to clear US Customs before departure. Perhaps this might be extended to other US destinations by the time of your trip. It would be welcome to arrive in the US treated as a domestic flight. Check the Dublin Airport and US Customs websites.

Turkish Airlines is very nice and a winner in the annual best airlines competition. The only drawback is having to fly through Istanbul both ways, which is several hours east of both Rome and London. It adds a considerable amount of time onto the transatlantic trip. Aerlingus is more direct. Don't know LOT. Look at Icelandaire, too.

You might want to look a little closer and the airlines mentioned above. Turkish Airlines takes between 28 and 36 hours to get to Rome. United flies to Rome in 12-14 hrs. for about $223 more. London to Chicago takes Turkish Airlines between 25 and 31 hours to get to Chicago. United flies it in 9 hours.

Lot flies to Rome in 15 hours and back from London in 13 hours, but you'd only save $30 over United.

Often, the lowest price is not your best value in airfares.

I don't know your groups' itinerary, but have you considered reversing your route--into London and out of Rome? I was thinking Heathrow had very high taxes on flights leaving there for the U.S. You might save there.

2014 prices are again expected to be high due to 3 airline affiliations controlling the market to and from Europe. Prices are the cheapest Tuesday-Wednesday, and Spring airfares rise substantially on 3/28/2014.

When I'm looking to fly anywhere, I look at flights every few days @ http://matrix.itasoftware.com I'm trying to get a baseline price, and watch for any changes/trends. I recently bought a 3/25/2014 open jaw airfare on a one day sale to Budapest and home from Prague for $728. The flight has been running $1,050. Today, the airfare dropped to $835-863, so this would be a good day to buy.

I would suggest you watching your planned flight dates and airfares for a few weeks. After the Christmas Holidays and the first of the year, there's a good chance that more one day sales will be posted.

The Kayak alerts are not always reliable. I had happened to check prices one Sunday and found a great price and purchased tickets. I got an alert to that price three days later.

Now for some advice you didn't ask for:

*You may want to book lodging before you book your flights. BUT do not book anything non-refundable. Your itinerary may change, or you may find that great cheap hotel is miles away from the city center and will cost so much more to get into town. Keep record of where you book so you can cancel. (Don't wait until the last minute to cancel. That's not fair to the innkeeper.)

*Each of you should pay for your share as you go along. No one should be on the hook for someone else's trip. Things happen and plans change, especially at your age. Decide if you'd go alone if the others cancel. (You should.) Deciding that before a crisis/drama makes it easier to deal with if it happens.

Hi Meg. I live in Chicago and I watch the Chicago - Europe flights obsessively. The poster that told you the rules are changing in the airline industry is correct: the best advice I can give it to constantly track your fares and be ready to buy on the spot the second a good fare comes in.

Personally, I prefer to buy as early as possible, rather than wait for the cheapest possible option. You may save a few $$ that way, but end up losing money when you find the cheap hotels are full (and they do fill up in advance). Also, I need to time to plan my itinerary.

All the airlines you list are fine, and it's true that Turkish Airlines has the cheapest fares out of Chicago right now, but beware of the really long layovers on that airline. I would advise you to avoid flying on Alitalia. My favorite airline is Lufthansa.

I don't know if there are student airfares any more, but you can get cheaper train tickets as a student. Have a look at statravel.com . There's a branch in Evanston you could visit.

Good luck and have a fantastic trip!

STA and their student (or under-26) fares are alive and well. I booked a roundtrip flight Seattle-Amsterdam in October 2010 for about $650. I'm sure the prices are higher now, a few years later, but yes, student fares still exist.