Finding Flights to One of Many Cities
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You can do this on Kayak. Select a round-trip flight, and in the second box (destination), you can enter multiple airport codes separated by commas, up to 4. (You can also enter multiple airport codes in the origin box.)
For example, entering "DEN" and "ORD,IND,DTW,CLE" gave me this list of results for flights from Denver to any of Chicago, Indianapolis, Detroit or Cleveland, and returning to Denver. By default it includes multi-airport itineraries (e.g. DEN-ORD paired with IND-DEN) but there is a checkbox in the results page for "Depart/Return same" which will exclude those itineraries, and only show you trips where you return from the same airport where you arrived (e.g. DEN-ORD can only be paired with ORD-DEN). There are also checkboxes where you can turn some of your airports on or off.
Upvote:4
The ITA Matrix will let you search for this. (It doesn't let you book, but does tell you enough to let a travel agent recreate and book them for you, see this question for details). Simply pop in several airport codes in the from and/or to boxes separated by commas, such as shown:
Then on the search results see what was the cheapest combination. In this case, Brussels is our cheapest departure point, and combinations with different airports used are shown in red to highlight the change:
The details tab will let you get all the info you need to go off elsewhere and make the booking for the flight you prefer
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