$165 Find Cheap Flights from Vail to Massachusetts

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Vail to Massachusetts departing on 6/3. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
1 adult, Economy, 0 bags

KAYAK searches hundreds of travel sites at once for deals on flights to Massachusetts

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Vail to Massachusetts, as well as popular online travel agencies
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Vail to Massachusetts, as well as popular online travel agencies
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Flight Deals

Book Cheap Vail to Massachusetts Plane Tickets

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Vail to Massachusetts that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Vail to Massachusetts

Tue, Jun 9 - Tue, Jun 16
American Airlines Logo
2:12 pm - 11:59 pm
EGE
-
BOS
7h 47m
1 stop
American Airlines Logo
7:00 am - 1:31 pm
BOS
-
EGE
8h 31m
1 stop
$329American Airlines
Tue, Jun 9 - Tue, Jun 16
American Airlines Logo
7:50 am - 9:24 pm
EGE
-
BOS
11h 34m
2 stops
American Airlines Logo
12:39 pm - 7:04 pm
BOS
-
EGE
8h 25m
1 stop
$334American Airlines
Tue, Jun 30 - Sat, Jul 11
American Airlines Logo
10:33 am - 10:28 pm
EGE
-
BOS
9h 55m
2 stops
American Airlines Logo
9:37 am - 6:51 pm
BOS
-
EGE
11h 14m
2 stops
$339American Airlines
Thu, May 28 - Mon, Jun 1
American Airlines Logo
2:12 pm - 12:04 am
EGE
-
BOS
7h 52m
1 stop
American Airlines Logo
6:00 am - 1:31 pm
BOS
-
EGE
9h 31m
1 stop
$354American Airlines
Tue, Jun 9 - Sat, Jun 13
American Airlines Logo
2:12 pm - 11:59 pm
EGE
-
BOS
7h 47m
1 stop
American Airlines Logo
10:13 am - 7:04 pm
BOS
-
EGE
10h 51m
2 stops
$359American Airlines
Tue, Jun 9 - Sat, Jun 13
American Airlines Logo
7:50 am - 10:28 pm
EGE
-
BOS
12h 38m
2 stops
American Airlines Logo
10:13 am - 7:04 pm
BOS
-
EGE
10h 51m
2 stops
$364American Airlines
Thu, Sep 17 - Mon, Sep 21
American Airlines Logo
7:50 am - 9:45 pm
EGE
-
BOS
11h 55m
2 stops
American Airlines Logo
6:45 am - 12:20 pm
BOS
-
EGE
7h 35m
1 stop
$384American Airlines
Tue, Jun 9 - Sat, Jun 13
United Airlines Logo
3:25 pm - 11:44 pm
EGE
-
BOS
6h 19m
1 stop
United Airlines Logo
7:45 am - 12:20 pm
BOS
-
EGE
6h 35m
1 stop
$394United Airlines
Wed, Jul 29 - Mon, Aug 10
American Airlines Logo
2:12 pm - 11:33 pm
EGE
-
BDL
7h 21m
1 stop
American Airlines Logo
5:02 am - 1:28 pm
BDL
-
EGE
10h 26m
2 stops
$397American Airlines
Fri, Jul 3 - Fri, Jul 10
United Airlines Logo
1:05 pm - 11:44 pm
EGE
-
BDL
8h 39m
1 stop
United Airlines Logo
12:12 pm - 6:05 pm
BDL
-
EGE
7h 53m
1 stop
$438United Airlines
Booking Insights

KAYAK's insights & trends for Vail to Massachusetts flights

Get data-powered insights and trends into flights from Vail to Massachusetts to help you find the cheapest flights, the best time to fly and much more.

How much is a round-trip flight from Vail to Massachusetts?

This analysis is based on the cheapest round-trip price found on KAYAK in the last 12 months by searching for a flight from Vail to Massachusetts departing in June.

What is the cheapest month to fly from Vail to Massachusetts?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Vail to Massachusetts, removes the top 0.1% to account for outliers, and then takes the median of all values for each month.

The cheapest month for flights from Vail to Massachusetts is September, when tickets cost $368 (return) on average. On the other hand, the most expensive months are January and October, when the average cost of round-trip tickets is $589 and $565 respectively.

Good to know

Low seasonJanuary
Cheapest flight$165
Best time to beat the crowds but there is an average 22% increase in price.
Most popular time to fly with an average 15% increase in price.
Flight from Vail to Boston

FAQs - booking Massachusetts flights

  • How does KAYAK find such low prices on flights from Vail to Massachusetts?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Vail to Massachusetts.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Vail to Massachusetts?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight from Vail to Massachusetts is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights from Vail to Massachusetts?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly from Vail to Massachusetts with an airline and back with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Vail to Massachusetts?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying from Vail to Massachusetts up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

Reviews of the top airlines flying from Vail to Massachusetts

 
See real verified KAYAK customer reviews for airlines flying from Vail to Massachusetts. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
Need help choosing which airline to fly with from Vail to Massachusetts? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
7.4
United AirlinesOverall score based on 9594 reviews
7.7Boarding
8.1Crew
7.3Comfort
6.6Food
7.1Entertainment
Airline reviews

Every staff member was professional, friendly and courteous. The pizza twist was ok. It was warm but too much dough.

10.0 ExcellentMargaret, Apr 2026
DEN - ORD
Read more United Airlines reviews

Every staff member was professional, friendly and courteous. The pizza twist was ok. It was warm but too much dough.

Wonderful in-seat entertainment with seatback screens and huge selection of quality movies. The ability to bluetooth connect headphones was amazing.

Flight left on time and we arrived 25 minutes early! There was a gate available when we arrived so early on a busy Sunday afternoon! Flight attendants came around twice with the drinks cart.

Both of my flights arrived early and check in process was smooth

I like flying first class, and United has a nice one

Sitting on the runway after we land for almost two hours! Not sure if we should blame United or Just Dumpy Vance.

United airlines has the best customer experience from booking to arrival. I always fly United airlines. The mileage program is excellent

Flight was late - I was downgraded from first class to coach

Crew seemed a bit cranky. No seatback screens. But boarding was efficient and on time and we arrived early.

See previous note about the passenger in Denver who threw my husband's bag out of the overhead bin in order to maker room for his own. And the flight attendant back up the new passenger.

Very good I can’t complain one bit. Thank you American Airlines for making my flight enjoyable and safe!

American Airlines is a miserable experience. It is predictably miserable, in the sense that every time I fly American, I brace myself for the certainty that it will be unpleasant and uncomfortable. But it is unpredictable in the sense that I never know if the flight will be on time or delayed nine hours (both happened to me this week). I never know if I will be able to sit in the seat that I selected when I purchased the ticket or if I will be told by Customer Service (!!!) that I must relocate from first class to a seat in the back of the aircraft with no explanation (both happened to me this week). Will the food be frozen and half defrosted, or scalding hot? Will the drinks be warm? Will the flight attendants be surly and mean? Will the toilets be cramped and foul? Will the seats be narrow and uncomfortable? Will there be a real electric outlet at the seat, or just an unreliable USB-2 port? Will there be enough seats in the boarding lounge or just a few? Will the boarding process be smooth and efficient, or will the gate agents mess it up and delay it needlessly for 30 or 40 minutes? Will the catering and cleaning crew be prompt or will they take an extra 30 minutes? Will the brakes on the aircraft work properly, or will the pilot delay takeoff for four hours while the ground crew attends to what can only be described as routine maintenance that should have been done the night before? I've eexperienced every one of these unpleasant things this year, 2026. The only thing I can reliably count on is that American will find a new way to make the experience of flying as miserable as they possibly can.

Flight was fine, but not having WiFi was a major negative

When I booked my flight a month ago - I selected a seat. That seat was NOT the one I ended up with when I checked into my flight the day before. This is the second time this has occurred. So, I checked my next flight on Wednesday and Thursday and no seat was assigned. Poor, very poor customer service.

The staff and service on American Airlines were truly outstanding. I had requested wheelchair assistance for my mother due to her knee issues, and the team went above and beyond every step of the way—from boarding in Boston to our arrival in Chicago. Their care, professionalism, and attentiveness made the entire experience smooth and stress-free. I’m very grateful for the support they provided.

Incredibly delayed. First delay was due to plane coming in being late. Resulted in 30 minute delay. Boarded and then had multiple mechanical issues. Was on plane for an hour until they told people they could get off if they wanted but couldn't come back. Then gate agent rushed in and said they had lost control of who went off and we would all have to deplane and then get back on. They said flight had not been cancelled. Then while sitting waiting to board again they announced it would take two hours to get new plane and to wait at new gate. New plane arrived, reboarded only to find out that pilots had timed out. Waited for new pilots. In that time one of the flight attendants timed out. Never received food or water while waiting. Was confusing mess as to what was happening. Even flight attendants and gate agents were getting frustrated. Almost 6 hours delayed. Called American to received flight credit but can't get anywhere as Kayak reservation and don't have a ticket number. Reached out to Kayak but never heard back.

American flight was diverted and delayed but app didn’t show that information so I wasn’t able to change my connection until the last min.

Wifi was spotty. Tray table was very dirty when I sat down.

Very disappointing. Flight was delayed by 1.5 hours and food options are very underwhelming even for first class seats (same food given to economy seats)

Was not able to do a online check-in because the American Airlines system doesn't store our visa or other passport information, allowing us to have a trouble-free check-in. We were forced to have to check-in at the counter which Changes are upgrade status given that we were not able to check in much earlier.

Everything you need to know for your flight from Vail to Massachusetts

Information on your arrival and departure airports