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How to do a multiple city trip?

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What's the best way to do a multiple city trip?

In September I need to do the following...

Seattle to Indianapolis
Indianapolis to New York City
New York City to Washington DC
Washington DC back to Seattle

I'll be in each city for about 4 or 5 days each, not that it matters.

My friend said it may be cheaper to just catch a train between NYC and Washington DC but what about Indianapolis and NYC? I don't know the East Coast very well or how far apart these places are really.

Is there a website that'll let me enter such a travel itinerary so I can buy my tickets at once?

Suggestions? Comments?

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