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Old 08-23-2012, 07:26 AM
 
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Fly to Denver, take a flight to Billings. That is probably the cheapest. United has four flights a day from Denver to Billings. Check out Jet Blue and Alligent Air. You may be able to make an interesting and cost effective trip using those airlines...but not the quickest route.
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Old 08-25-2012, 08:28 PM
 
Location: Wyoming
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Just doing a quick search I found a roundtrip flight from Portland, Me to Billings for $571 and another from Boston to Billings for $482.

Billings would probably be my choice, as you'd get to enter via the Beartooth Highway and/or Cody-Chief Joseph Highway. The variable in there might be the price of a rental car. I've often rented cars in Billings, but never for more than a short weekend.
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