$194 Find Cheap Flights from Aspen to Massachusetts - Compare and Save

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Aspen to Massachusetts departing on 9/23. 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

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Cheap Flights from Aspen to Massachusetts

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
Boston
Boston1 stop$387
Albany
Albany1 stop$477
Boston
Boston1 stop$387
Albany
Albany1 stop$477

Book Cheap Aspen 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 Aspen 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 Aspen to Massachusetts

Thu, Sep 24 - Mon, Sep 28
American Airlines Logo
7:00 am - 5:35 pm
ASE
-
BOS
8h 35m
1 stop
American Airlines Logo
4:29 pm - 9:29 pm
BOS
-
ASE
7h 00m
1 stop
$387American Airlines
Fri, Dec 11 - Mon, Dec 14
American Airlines Logo
7:33 am - 7:30 pm
ASE
-
BOS
9h 57m
1 stop
American Airlines Logo
11:30 am - 7:38 pm
BOS
-
ASE
10h 08m
1 stop
$387American Airlines
Wed, Nov 4 - Sun, Nov 8
Delta Logo
7:30 am - 5:11 pm
ASE
-
BOS
7h 41m
1 stop
Delta Logo
5:30 am - 11:24 am
BOS
-
ASE
7h 54m
1 stop
$387Delta
Wed, Nov 4 - Sun, Nov 8
Delta Logo
7:30 am - 5:11 pm
ASE
-
BOS
7h 41m
1 stop
Delta Logo
5:30 am - 11:24 am
BOS
-
ASE
7h 54m
1 stop
$387Delta
Thu, Sep 10 - Sun, Sep 13
American Airlines Logo
12:53 pm - 12:30 am
ASE
-
BOS
9h 37m
1 stop
American Airlines Logo
6:00 am - 12:21 pm
BOS
-
ASE
8h 21m
1 stop
$387American Airlines
Fri, Sep 18 - Mon, Sep 21
American Airlines Logo
7:00 am - 5:35 pm
ASE
-
BOS
8h 35m
1 stop
American Airlines Logo
4:29 pm - 9:29 pm
BOS
-
ASE
7h 00m
1 stop
$387American Airlines
Sat, Oct 10 - Sat, Oct 17
United Airlines Logo
1:15 pm - 11:59 pm
ASE
-
BOS
8h 44m
2 stops
United Airlines Logo
5:01 pm - 9:58 pm
BOS
-
ASE
6h 57m
1 stop
$392United Airlines
Wed, Nov 4 - Sun, Nov 8
Delta Logo
7:30 am - 7:29 pm
ASE
-
BOS
9h 59m
2 stops
Delta Logo
5:30 am - 11:24 am
BOS
-
ASE
7h 54m
1 stop
$392Delta
Fri, Sep 18 - Mon, Sep 21
United Airlines Logo
1:15 pm - 9:59 pm
ASE
-
BOS
6h 44m
1 stop
United Airlines Logo
7:46 am - 2:23 pm
BOS
-
ASE
8h 37m
2 stops
$467United Airlines
Thu, Oct 1 - Tue, Oct 6
United Airlines Logo
1:15 pm - 11:59 pm
ASE
-
BDL
8h 44m
2 stops
United Airlines Logo
3:35 pm - 8:31 pm
BDL
-
ASE
6h 56m
1 stop
$482United Airlines
Booking Insights

KAYAK's insights & trends for Aspen to Massachusetts flights

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

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

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Aspen 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 Aspen to Massachusetts is April, when tickets cost $0 (return) on average. On the other hand, the most expensive months are November and December, when the average cost of round-trip tickets is $1,029 and $747 respectively.

Good to know

Cheapest flight

$194
Most popular time to fly and prices are also 20% lower on average.
Flight from Aspen to Boston

FAQs - booking Massachusetts flights

  • How does KAYAK find such low prices on flights from Aspen 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 Aspen to Massachusetts.

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

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight from Aspen 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 Aspen 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 Aspen 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 Aspen 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 Aspen 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 Aspen to Massachusetts

 
See real verified KAYAK customer reviews for airlines flying from Aspen 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 Aspen 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 10046 reviews
7.3Comfort
7.7Boarding
7.1Entertainment
6.6Food
8.1Crew
Airline reviews

My service dog and I were asked to deplane just before they closed the door - clearly very last minute they couldn’t find the documentation that I have filled out many many times before that is for flying service animals. I purposely purchase 3seats (a whole row) since he is large and not all passengers want to sit next to a dog on a cross country flight. The plane departed with my husband on it!!! They made me fill out a hard copy of the same form and had to reschedule me on a later flight where they could find 3 seats together!! I’ve done this so many times before - clearly the error was on their part in a technology glitch - but really people - do better!! Very traumatic - and my husband had to wait for us when he landed ….so bad. Poor pup was confused and tired.

2.0 MediocreCatie, May 2026
SFO - BOS
Read more United Airlines reviews

My service dog and I were asked to deplane just before they closed the door - clearly very last minute they couldn’t find the documentation that I have filled out many many times before that is for flying service animals. I purposely purchase 3seats (a whole row) since he is large and not all passengers want to sit next to a dog on a cross country flight. The plane departed with my husband on it!!! They made me fill out a hard copy of the same form and had to reschedule me on a later flight where they could find 3 seats together!! I’ve done this so many times before - clearly the error was on their part in a technology glitch - but really people - do better!! Very traumatic - and my husband had to wait for us when he landed ….so bad. Poor pup was confused and tired.

Super friendly with lots of drink options an entertainment. Friendly crew.

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

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

I never flew. Flight was canceled. DIA worst airport in the country. Avoid at all costs.

Impressed with the service despite turbulence because of the weather. Both flights arrived before their scheduled times.

Good even though flight was delayed, the crew was prompt and efficient.

flights were on time, boarding was easy. maybe better snack selection, like mini kind bars?.

You could have been ON TIME! And I was miffed because I spent an extra $82 to get my seat and the steward put a woman from the back in my aisle for nothing because her movies wouldn’t work. I’ll try that next time and save $82!

Again a nearly five hour flight and pretzels is all the food you get and all you can drink water. No electric plugs in economy. Staff was totally not caring. Delta next time

I thought American Airlines did well considering the adverse weather situation over July 21 and 22. I especially appreciated the consideration given to me when I got stuck in Miami on my way to Boston from Charleston, West Virginia. Thank you for providing a voucher for an overnight stay. Though it was only a few hours of sleep, it was very helpful. I was able to reschedule my medical appointment and got back to the Boston area on the 1st flight out of Miami as a standby passenger. It was very helpful that I was given number one priority on the standby list.

I had my flight of Cedar Rapids. THen Chicago to Boston. Flight out of Cedar rapids was delayed by 12 hrs. Had to drive to Chicago to catch my flight

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.

Same plane as RDU to LGA — internet not working. Pilot issue of some sort at end of prior flight - I was on same plane for my connection. Late/delayed —

I was in last row so that is never great bc the person in front of me leaned his seat all the way back into me.

Half of the TSA checkpoints at PHL are closed. Also, there is no standby for first class passengers. You can only standby for coach. Very dated policy and inconsistent with peers.

We had a male flight attendant who was super attentive and wonderful! Very professional. I have both gluten and dairy intolerance, and was only able to get a gluten free part, and not the dairy free part of the meal. Easy to order ahead of time and I appreciate being able to do that.

No enough space plus only allowing one laggage instead of two like other airlines.

Qatar airways ,boarding arrangements at Hamid international airport could been better

It was great. It was just a commuter so I splurged on first class and it was wonderful. Wish all seats were this spacious. Enjoyed it and will do it again.

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

Information on your arrival and departure airports