Getting into Montrose for less than $450 is a great deal, less than $400 is unheard of — and maybe happens two or three times a year. Today just happens to be one of those days — made even better if you invested in an Epic Pass (got mine!) in which case you have 7 days of riding to burn at each resort this winter.
Boston to Montrose is almost always $600+ — these cheap ski trips save 45% and get you there with OneStop on American Airlines.
As mentioned above these flights have a single stop in either direction — which is amazing — since many options to Montrose are 2 plus stops each way for double the price. There is generally just no easy way to get there... but I hear it is 100% worth the trip.
I've been trying to get out to Telluride for years — my uncle lived out there for most of the 70s telemarking the backcountry. At this price it very well might be time to get in on a little of that action myself.
Cheap Montrose Flight Availability
So the date range on this one is pretty broad, starting in November and running through to February (minus the major Holidays). That being said Telluride generally opens near Thanksgiving (November 23rd last year) and Crested Butte opens generally a few days before (or after).
Most trips require a Saturday stay and there are relatively few 3-4 day options (even though I personally think you want to go for at least 5 days — due to distance / length of flight).
See below for a few quick links or hit Google Flights and plug in BOS to MTJ for full availability. When searching make sure you double check the Stops (some flights have two each direction)!