$96 Find Cheap Flights from Colorado Springs 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 Colorado Springs to Massachusetts departing on 8/19. 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 Colorado Springs 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 Colorado Springs to Massachusetts, as well as popular online travel agencies
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Cheap Flights from Colorado Springs to Massachusetts

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
Boston
Boston1 stop$209
Albany
Albany1 stop$309
Boston
Boston1 stop$209
Albany
Albany1 stop$309

Book Cheap Colorado Springs 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 Colorado Springs 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 Colorado Springs to Massachusetts

Sat, Sep 5 - Sat, Sep 12
American Airlines Logo
10:12 am - 7:42 pm
COS
-
BOS
7h 30m
1 stop
American Airlines Logo
7:40 am - 2:43 pm
BOS
-
COS
9h 03m
1 stop
$209American Airlines
Fri, Aug 14 - Mon, Aug 17
Southwest Logo
4:20 pm - 12:30 am
COS
-
BOS
6h 10m
1 stop
Southwest Logo
5:40 am - 9:45 am
BOS
-
COS
6h 05m
1 stop
$237Southwest
Sat, Sep 5 - Sat, Sep 12
American Airlines Logo
8:00 am - 8:00 pm
COS
-
BOS
10h 00m
2 stops
American Airlines Logo
7:40 am - 2:43 pm
BOS
-
COS
9h 03m
1 stop
$242American Airlines
Wed, Oct 28 - Mon, Nov 2
Southwest Logo
7:00 am - 4:15 pm
COS
-
BOS
7h 15m
2 stops
Southwest Logo
10:10 am - 4:30 pm
BOS
-
COS
8h 20m
1 stop
$259Southwest
Tue, Aug 4 - Thu, Aug 6
Delta Logo
6:00 am - 4:51 pm
COS
-
BOS
8h 51m
1 stop
Delta Logo
5:30 am - 12:15 pm
BOS
-
COS
8h 45m
1 stop
$277Delta
Wed, Sep 23 - Wed, Sep 30
Southwest Logo
6:15 am - 6:35 pm
COS
-
BOS
10h 20m
2 stops
Southwest Logo
9:25 am - 4:00 pm
BOS
-
COS
8h 35m
1 stop
$280Southwest
Tue, Aug 4 - Thu, Aug 6
Delta Logo
6:00 am - 6:40 pm
COS
-
BOS
10h 40m
2 stops
Delta Logo
6:45 am - 12:15 pm
BOS
-
COS
7h 30m
1 stop
$282Delta
Wed, Sep 23 - Wed, Sep 30
Southwest Logo
6:15 am - 6:35 pm
COS
-
BOS
10h 20m
2 stops
Southwest Logo
1:20 pm - 9:45 pm
BOS
-
COS
10h 25m
2 stops
$285Southwest
Tue, Aug 18 - Tue, Aug 25
United Airlines Logo
11:55 am - 9:36 pm
COS
-
ALB
7h 41m
1 stop
United Airlines Logo
6:00 am - 10:33 am
ALB
-
COS
6h 33m
1 stop
$309United Airlines
Fri, Jul 3 - Sat, Jul 11
United Airlines Logo
1:30 pm - 11:44 pm
COS
-
BDL
8h 14m
1 stop
United Airlines Logo
6:09 am - 11:09 am
BDL
-
COS
7h 00m
1 stop
$340United Airlines
Booking Insights

KAYAK's insights & trends for Colorado Springs to Massachusetts flights

Get data-powered insights and trends into flights from Colorado Springs 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 Colorado Springs 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 Colorado Springs to Massachusetts departing in September.

What is the cheapest month to fly from Colorado Springs to Massachusetts?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Colorado Springs 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 Colorado Springs to Massachusetts is December, when tickets cost $158 (return) on average. On the other hand, the most expensive months are May and March, when the average cost of round-trip tickets is $389 and $296 respectively.

How far in advance should I book a flight from Colorado Springs to Massachusetts?

To calculate weekly average prices, KAYAK takes all prices for each week before departure over the last year for round-trip flights from Colorado Springs to Massachusetts, removes the top 0.1% to account for outliers, and then takes the average of all the values for each week.

To get a below average price on the flight from Colorado Springs to Massachusetts, you should book around 3 weeks before departure, which saves you about 34% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 23 weeks before departure.

Good to know

Low seasonJanuary
Cheapest flight$96
Best time to beat the crowds with an average 1% drop in price.
Flight from Colorado Springs to Boston

FAQs - booking Massachusetts flights

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

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

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight from Colorado Springs 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 Colorado Springs 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 Colorado Springs 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 Colorado Springs 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 Colorado Springs 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 4 airlines serving from Colorado Springs to Massachusetts

 
See real verified KAYAK customer reviews for airlines flying from Colorado Springs 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 Colorado Springs 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.
7.9
SouthwestOverall score based on 4264 reviews
8.1Boarding
8.0Comfort
7.5Entertainment
7.0Food
8.6Crew
Airline reviews

The first time I flew in the extra legroom section. It was difficult to notice a difference. I had bad luck with my neighbors. The crew was okay. Southwest has reduced the live TV options.

4.0 OkayAnonymous, May 2026
MDW - LAX
Read more Southwest reviews

The first time I flew in the extra legroom section. It was difficult to notice a difference. I had bad luck with my neighbors. The crew was okay. Southwest has reduced the live TV options.

The flight was smooth. The Southwest experience has degraded overall, but this one was okay.

No gluten free snacks. Seats felt worn or bare bones even though it was a new 737 MAX 8.

One major problem that was very unprofessional and uncalled for. Plane landed and we had to wait 20 minutes to get off the plane since they were waiting for someone to come to the gate to drive the jetway. Southwest couldn't have someone available and waiting for the plane to land? Is there only one person in Hobby airport who knows to drive the jetway? Was he at lunch? In the bar? Uncomfortable and uncalled for!

The checking experience in Orlando was terrible, almost missed the flight. Too many travelers and Southwest completely understaffed.

I'm glad it wasn't only 75% full because I could get a good seat

if I was good. Not happy that I have to pay extra money to get the seat I need for lake room, but I guess that’s a sign of the times.

Seats were very comfortable. They tilted back. Drinks and snacks were free and served 3 times. Attendants were awesome.

Plane was clean and comfortable. Flight attendants and gate staff were professional, friendly and efficient. Boarding and deplaning were orderly and efficient. All in all, the typical excellent Southwest experience.

Truly terrible. Will never willingly fly southwest again. Seats are worse than before they switched to assigned seating. One flight attendant was the opposite of helpful (rude, unhelpful, dismissive, and as my stranger seatmate said unprompted: a total prick). This caused me, 15 minutes into the flight, to book an alternate return flight home on a competing airline (first class 1.2k purchase instead of my existing planned flight) just so I would not have to ever be on that aircraft, with that terrible service person, with those horrific seats ever again.

No service flight that took 5 hrs and a stop at an unscheduled airport. Crew and pilots did their jobs

Clean planes and not take my comfort class seat away.

Weather caused a long delay, but the efficiency and updates from the pilot were helpful. We were able to make our connection fortunately.

Planes were clean, no water or snacks on either flight.

Free & relatively fast Wi-Fi. Would've liked a wider drink selection.

I continue to be satisfied with Delta’s excellent service out of LGA. The digit id works well and gets me through security in no time. Whenever possible, I choose Delta.

Was revoked with Jet Blue due to delay from Kenya Air

Enjoyed it very much. Especially liked the free WiFi that Delta offers.

Smooth flight. Left on time, and got in 15 minutes early. Onboard video was great

For some reason, TSA Atlanta didn’t have my bag on the flight on time and they don’t have to provide Delta a reason for that.

Had a one hour delay due to mechanical issue. I didn’t think I’d be able to make my connecting flight, but they waited for me and greeted me when I arrived to help things run smooth.

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.

O’hsre taxi and deboarding took 40 minutes. Needed 20 minutes extra time between connecting flights to avoid running through terminal.

Was great in general, try to respect time and excuses when slight changes have been made, appreciated!

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

Really hard landing... as in slammed into the runway then hit the brakes really hard ...

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

The flight was peaceful, just s slight turbulence, pilots and crews were all nice and made a great job! Arrived safely in the Philippines. Thank you ya’ll!

Ontario airport boarding was very easy to park and access, is clean and TSA took 10 minutes total. Check-in was a breeze and cruise was very nice.

American Airlines II: Delay Boogaloo. Multiple gate changes, delays, boarded and then MORE delays. I hate to say this won’t matter, but posting stuff about major corporations in 2026 is a post-modern “scream into the void.” Was multiple hours late coming home, so there you go.

Awful, tons of delays, I got into Chicago multiple hours late meaning I hit the very traffic I tried so desperately to avoid. Just empty apologies from American Airlines text alerts. Trash behavior from a trash airline.

The flight attendants were very friendly, efficient, and helpful. The plane was ahead of schedule, and it all went very smoothly. Thank you.

They lost my baggage and I am still struggling to the information and update

We got delayed getting out of DFW for broken overhead bins. Once the flight got underway the captain kept the seatbelt sign lit the entire flight despite little perceptible turbulence, preventing use of the rest rooms and any sort of refreshment service in the main cabin.

Flight delays for communication overall not a good experience uncomfortable on the plane. Person in front of me reclined his seat, putting them inches from my lap.

There were flight delays making our flight arrive at our destination after midnight didn’t seem to have enough crew or airplanes for the flights laid over in Dallas should’ve had plenty of time to make it to our next flight only made it because that flight was also delayed because our plane wasn’t even at the airport yet overall have not had a good experience on American

Flight left on time. Captain provided relevant announcements. We had to wait 45 minutes to desembark due to the ramp closed because of lightening.

Everything you need to know for your flight from Colorado Springs to Massachusetts

Information on your arrival and departure airports