Cheap airfare: wait or book now? Will fares go down? (date locked, but any destination)

If a person feels that they can accurately predict airline prices and what prices will be in the future, then they are probably interested in becoming a day trader as well.

Looking at a calendar, December 1 seems to be the Sunday after Thanksgiving -- a date that is usually high-demand, high-price for U.S. flights. Maybe flying home on November 30 would be less chaotic in your arrival airport ... and possibly cheaper.
No crystal ball, so I can't advise on when bargain fares will be available.

Airfares go up and down based on complex algorithms that are impossible for consumers to outguess. Generally, the closer you get to a travel date the higher the fare. But not always. I know this doesn’t help you but if you find someone who can answer this definitively let me know as I’ll need their advice on the stock market!

Any interest, say, in trying out Mexico City or Oaxaca? I think you can get a flight more like in the $300 range to either. I've gone to Mexico just around that timeframe several times but my flights originate in the DC area.

There are always airfare sales to Europe in Fall on the budget airlines, but even on those, < $500 is really cheap so I wouldn't count on it. Turkish Airlines flies from your airport and they have competitive prices and good service, even to Europe. The downside is the added connection in Istanbul.

I don't think I would book on an impulse or "fear of losing out". You'll still be plunking down hundreds of dollars, so go where you're genuinely interested in going to. It may require some more research to draw up a list, but then again it would be really easy for me to rule many places out based on temperatures alone (that many not be true for you since you live in Chicago).

I think there are websites out there that are perfect for this kind of "open ended" search, but I can't recall whether Skyscanner is one of them.

You might call a travel agent (yes, there are still travel agents :) ) and see what special deals they are offering, since you're open on destination.

Search everyday using Google Flights.
It will let you put in more than one airport code as a destination and list the prices for each
For example From ORD To EZE, GIG,

I think you are looking at London or Dublin for $675 pp. When you say you must travel certain dates, you have given up all your negotiating power. How bad will you feel if prices only go up from here? If you come back a day early (Nov 30), you can get under $500 to London by taking a plane change in Toronto on the way home.

Because everybody knows travel agents get lower airfare prices than the average traveler...😂😂😂😉

Fares for September, October, and November have already dropped in several markets, but you are looking at Thanksgiving week when more and more people are taking short vacations. It’s highly unlikely anything will drop for that week unless you find a new airline trying to attract customers on a Chicago route. That’s IMHO.

Travel agents can find a deal! My sister got a heck of deal through an agent who was able to turn her layover into a stopover for her flight to DTW to Paris to Milano last year. They are a good source for some people, especially those who aren't savvy travelers or internet savvy.

I have been looking for me exact same dates. Have you looked at London and then to Wherever from there. I found Boston and New York to London for about $400. I have not priced Chicago but you might try

Another trick have you tried booking a vacation with Delta vacations, American Airlines vacations or Expedia? I got vacation from Atlanta to Paris for that hotel room about $900 total (only 4 nights hotel)

I guess my observation is that getting $500 tickets out of Chicago might be too optimistic if you are talking Europe. If you wait to try and lock in a deal, you likely will end up paying a $1000, $2000, or more. That leaves something like the Carribean, Mexico, or maybe Iceland. Heck, you may not even be able to fly to Nashville for $500. Do some searches on locations you are interested in, that will give you an idea of costs, maybe try to find some historical data, but generally, I would say you are setting your target too low.

If you can raise your budget both Madrid and Dublin are around $570 11/23 to 12/1

You have picked a week that tends to be expensive due to the Thanksgiving travel period. I am not so sure you will get prices under $500.00 even from a large hub like Chicago when there is at least some competition. For November. I would suggest somewhere like Spain. Madrid, Barcelona, or even Andalusia (Sevilla and Granada). You don't have many days in country - but its doable. I did Spain for Spring break (March) and while it was a whirlwind tour - we had the best time - perfect weather and safe. We used ALSA buses and trains. (2 middle aged female travelers) and stayed at 3 star hotels. The prices were around $90.00 a night and food and entry tickets all very cheap. So even if you pay more for an airline ticket, it may be OK if the destination is cheaper. I use Chicago all the time for European trips. Always buy through the airline and just keep monitoring prices every day. There is no trick or best time, it just depends on the algorithms. No need for a travel agent. They may not spend the time researching pricing, airlines, and destinations like you can.

Margaret

Norwegian Air Shuttle is not posting their November/December flights right now. But their October flights from ORD TO London Gatwick can be purchased for $390 as their lowest fare round trip.

Check flights into Canada. British Columbia is a beautiful place to visit. Waiting will not do much as u are planning for peak season holiday time. Gd luck on your search.
Also look into southwest air they have some destinations out of USA.

Lol yes BC is beautiful but it’s really not the best time to visit - rain and cool - mountains cloaked in cloud cover - and can be snow starting in mountain passes ...

How about Portugal ? Flying into Faro .

I think Carol's idea to check air/hotel-package offerings on airline websites is a good one. I know some folks have gotten very good deals that way.

I would second the suggestion of Google flights. Have you played around with that at all? You can put in your originating airport and dates, it will show you on a map different prices to different locations. Once you pick one, it will also tell you if the price is generally high, average, or low for that route, which gives you a feel for whether you should wait a bit or pull the trigger. It takes some time to figure out and get a feel for it, so I suggest setting aside some time to just mess around on it.

And yes, some of the responses you got were pretty obnoxious considering there are tools like this out there to answer these very questions, if you know about them (which is the point of this forum, right?).

Good luck, let us know what you land on.

One more thing about Google flights - it lets you put alerts on flights you might be interested in, and then you will get an e-mail as the price of the flight changes. I find that more useful when I'm looking at flights a little further out than your time frame here (for me I find it most helpful in the 6-10 month range), but you might want to try that as well.

You can fly nonstop on Aer Lingus from Chicago to Dublin for $376 (Saver fare - no checked bag or advance seat selection) or $496 (Regular Economy). This would be for a 12/2 return date - 12/1 would be more expensive by at least $100

From Dublin you could take an inexpensive budget airline almost anywhere in Europe. You could also check other connecting flight options with Aer Lingus.

We like Aer Lingus because you can go through US customs and immigration in Dublin on the way home.