Saving money on airline tickets when buying weird route because of Epilepsy

I feel I need to post a third answer even if it is a negative one just so no one else wastes time searching this.

One trick would be breaking the trip in Iceland instead of London and while there is a daytime flight from Boston to Keflavik, unexpectedly you get stumped there because you can’t get anywhere near Krakow from Keflavik with the 10pm curfew restriction. https://azair.me/!4kKx

I need to give a second answer because it is fundamentally different from my first.

You could buy the following three tickets:

1. Chicago-London/whatever-Chicago with Oneworld (AA/BA/AY). Use ITA Matrix to search for this, see below.
2. London-Krakow with Wizz/Ryanair/maybe easyJet. Use skyscanner for searching this.
3. Krakow-Chicago with LOT, possibly fudging it with a similar Krakow-Chicago/Chicago-whatever return flight. Or Krakow-Chicago/whatever-Krakow. However, unlike with #1 I can’t seem to find a good way to lower the price of this. You can try ITA Matrix here as well but it might be necessary to just pay for the LO9 flight in itself.

and just forget about the return part of #1 (and #3 if you bought one).

What’s this lunacy? Ah, the wonderful world of traditional airlines!

1. It used to be the case that return tickets are cheaper than one ways. This is not necessarily the case any more but with transatlantic flights it still often is.
2. However, flying out from the United Kingdom has very steep fees and since we do not want to fly anyways we can just pick another airport which has cheap flights to Chicago…

Flying out on July 26 costs 809 dollars:

but if we pretend to fly back on November 15 from Paris that’s only 696 USD:

There’s just no problems not showing for the Paris-Chicago flight.

ITA Matrix allows you to search multiple cities and five days in a single search example. Then just go to Kayak or the airline to book it.

Note there is a danger in #2 because if your flight from Chicago is so late it comes the next day then you can miss it and the cost of booking another flight at last minute might be relatively high: a same day LON-KRK booking currently is 127GBP (but I have seen it going slightly above 150GBP, too), next day is 76GPB, one more day is 45 GBP. But it’s not like you are risking rebooking a transatlantic flight which runs into the thousands of dollars.

Edit: I will keep this but this is not the most comfy way doing it, see my other answer.

While ITA Matrix is an excellent tool (the extension code -redeyes was made for you) it can’t help here by itself: you have restricted your request to something not bookable on a single ticket because you nailed down you wanted to fly AA90 on the way out and LO9 on the way back and that’s not the same alliance so you can’t book a single ticket.

I tried to change the route out and that doesn’t work so we need to give up on the Krakow-Chicago direct flight and fly another route.

Once we do that, life is super easy, I hope this link works for you. If not:

Origin: ORD
Destination: KRK
Routing codes: F F (both directions)
Extension codes: -redeyes

I guess you want to pick "See calendar of lowest fares". Alas, July is the most expensive season to fly, July 26 to Aug 7 finds ~2000 USD fares, typically with transiting Helsinki on the way back, the Finnair flight lands at 3:20PM. At later dates this becomes even cheaper:

Once you found a flight, on the result screen select all, copy-paste the results into https://bookwithmatrix.com/ and there you are.

Or with Chrome you can try https://chrome.google.com/webstore/detail/ita-matrix-powertools/menecfddnlmanmpadcalononkolnplpp?hl=en but this only works with https://oldmatrix.itasoftware.com/ for now. However, it allows you to book with the airline directly which is strongly recommended. Do not get too excited: many flights Matrix finds can’t be booked any longer. A little trial and error will get you there.

Try booking two separate tickets. The first ticket is Chicago > LHR > Chicago. The second ticket is LHR > Poland > LHR.

But the temporal flight order is this:

• Chicago > LHR (the first flight on the first ticket)

• LHR > Poland (the first flight on the second ticket)

• Poland > LHR (the second flight on the second ticket)

• LHR > Chicago (the second flight on the first ticket)

Purchasing two separate unrelated itineraries may generate more attractive ticket prices than the multi-flight four-leg itinerary you’ve found to be too expensive.

And do keep in mind that airline tickets are really expensive now; some of the high prices you’ve already seen may be due to the general high level of prices.