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I'm looking for a flight search engine that lets me search for a flight from a specific origin to a specific destination. I don't care on which weekend the flights take place, but I want to find the cheapest flight in the next 2 months that leaves one a Friday afternoon evening and returns at Sunday night or Monday morning.

I couldn't find such a flight search engine. Is there anything like that?

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Kiwi.com has this feature.

First enter your origin and destination cities.

Next, as the departure date, enter a date range over the whole period you are looking for weekend getaways. It can be over a period of several months.

Departure date rage

For the return date, enter a Time of stay as 2-3 days:

Time of stay

Then search. After the search is made, click "Filters". And click the "Days and times" filter. You can now apply filters for time of the day, and which days of the week to possibly leave and return. So click leave Friday afternoon and return on Sunday or Monday:

Days and times filter

The results will be automatically updated.

Note that since we want to include both flights that return late on Sunday and early on Monday we had to leave the return time filter at all day. This will lead to some results that are not relevant, like returning early on Sunday and late on Monday. So ignore them. Or to avoid those unwanted results, first filter for only Sunday evening, and next for only Monday morning.

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    Welcome to the site Gillespie, good answer with very good details on how to set the site for what is asked.
    – Willeke ♦
    Jul 17, 2018 at 10:57
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It seems like more and more my answers just tend to be "go to Google Flights"! In this case:

  1. Search for an itinerary on Google Flights including the origin and destination on Friday and Sunday. Apply the filters for departure time (Friday after 5pm, say; or Sunday after 4pm).
  2. Click on the first date field. Look at the numbers for all Fridays from then onwards. Those should be the prices on those Fridays, for 2 day trips, with all of your filters present!
  3. Select the cheapest and book it.

Note that you'll have to repeat this twice, once for Friday - Sunday departures, and once for Friday to Monday, but Google Flights is absurdly fast, so you should be good.

Animation of how to do this using Google Flights

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I had the same exact thought as you a few years ago and created a site to make those searches. It worked for years but then Google shut down the API I used to make my searches. My hacky fix was to add a Search Kayak button at the top of the page that opens a bunch of Kayak windows, each one a week after the previous window. Give it a try! It takes a while for all the Kayak windows to load.

Rebound Flights

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https://travelgam.com/ is a site meant for exactly this purpose. Users can define start of weekend and end of weekend in terms of both day and time. Such as Friday late evening and Monday early morning respectively.

travelgam

Outbound and Return times can be specified along with an option for "Direct flights only".

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  • While it is not against the rules to repeat an answer, if the questions are so much alike that the same answer fits both, consider whether one of the questions is a duplicate of the other and (when you have enough reputation) vote to close. And NOT post the answer on the duplicate question. If the questions are not real duplicates, please adjust your answer to fit the question it is posted to. (The system gave a warning that this is a duplicate answer, as such it must be very much alike or identical.)
    – Willeke ♦
    Jan 24, 2020 at 15:30

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