Flights To Massachusetts - Cheap Flights Starting at CA $209

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Boston

Flights
Boston

How Much Does it Cost To Fly To Massachusetts?

Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.

Wed, Sep 16 - Sat, Sep 19
YYZ
Pearson Intl.
BOS
Logan Intl.
CA $344 Roundtrip, just found
CA $344
Roundtrip
just found
Select Porter Airlines flight, departing Wed, Sep 16 from Pearson Intl. to Logan Intl., returning Sat, Sep 19, priced at CA $344 just found
Sat, Sep 5 - Sat, Sep 19
YWG
Winnipeg James Armstrong Richardson Intl.
BOS
Logan Intl.
CA $374 Roundtrip, found 3 days ago
CA $374
Roundtrip
found 3 days ago
Select Porter Airlines flight, departing Sat, Sep 5 from Winnipeg James Armstrong Richardson Intl. to Logan Intl., returning Sat, Sep 19, priced at CA $374 found 3 days ago
Tue, Sep 8 - Sat, Oct 10
YWG
Winnipeg James Armstrong Richardson Intl.
BOS
Logan Intl.
CA $415 Roundtrip, found 1 day ago
CA $415
Roundtrip
found 1 day ago
Select Delta flight, departing Tue, Sep 8 from Winnipeg James Armstrong Richardson Intl. to Logan Intl., returning Sat, Oct 10, priced at CA $415 found 1 day ago
Sat, Sep 5 - Sat, Sep 19
YWG
Winnipeg James Armstrong Richardson Intl.
BOS
Logan Intl.
CA $424 Roundtrip, found 3 days ago
CA $424
Roundtrip
found 3 days ago
Select Porter Airlines flight, departing Sat, Sep 5 from Winnipeg James Armstrong Richardson Intl. to Logan Intl., returning Sat, Sep 19, priced at CA $424 found 3 days ago
Sat, Sep 5 - Fri, Sep 11
YWG
Winnipeg James Armstrong Richardson Intl.
BOS
Logan Intl.
CA $435 Roundtrip, found 1 day ago
CA $435
Roundtrip
found 1 day ago
Select Porter Airlines flight, departing Sat, Sep 5 from Winnipeg James Armstrong Richardson Intl. to Logan Intl., returning Fri, Sep 11, priced at CA $435 found 1 day ago
Wed, Oct 14 - Sun, Oct 18
YWG
Winnipeg James Armstrong Richardson Intl.
BOS
Logan Intl.
CA $445 Roundtrip, found 1 day ago
CA $445
Roundtrip
found 1 day ago
Select Porter Airlines flight, departing Wed, Oct 14 from Winnipeg James Armstrong Richardson Intl. to Logan Intl., returning Sun, Oct 18, priced at CA $445 found 1 day ago
Fri, Oct 2 - Mon, Oct 5
YWG
Winnipeg James Armstrong Richardson Intl.
BOS
Logan Intl.
CA $445 Roundtrip, found 11 hours ago
CA $445
Roundtrip
found 11 hours ago
Select Porter Airlines flight, departing Fri, Oct 2 from Winnipeg James Armstrong Richardson Intl. to Logan Intl., returning Mon, Oct 5, priced at CA $445 found 11 hours ago
Tue, Sep 8 - Sat, Oct 10
YWG
Winnipeg James Armstrong Richardson Intl.
BOS
Logan Intl.
CA $457 Roundtrip, found 1 day ago
CA $457
Roundtrip
found 1 day ago
Select Delta flight, departing Tue, Sep 8 from Winnipeg James Armstrong Richardson Intl. to Logan Intl., returning Sat, Oct 10, priced at CA $457 found 1 day ago
Tue, Sep 8 - Sat, Oct 10
YWG
Winnipeg James Armstrong Richardson Intl.
BOS
Logan Intl.
CA $478 Roundtrip, found 1 day ago
CA $478
Roundtrip
found 1 day ago
Select Delta flight, departing Tue, Sep 8 from Winnipeg James Armstrong Richardson Intl. to Logan Intl., returning Sat, Oct 10, priced at CA $478 found 1 day ago
Tue, Nov 3 - Sat, Nov 7
YYZ
Pearson Intl.
PVD
T.F. Green
CA $486 Roundtrip, found 2 days ago
CA $486
Roundtrip
found 2 days ago
Select Delta flight, departing Tue, Nov 3 from Pearson Intl. to T.F. Green, returning Sat, Nov 7, priced at CA $486 found 2 days ago
OriginDestinationTravel datesFlights from*
LAXWindsor LocksSeptember 19 to September 26CA $300
LAXBostonSeptember 11 to September 15CA $400
PDXBostonSeptember 1 to September 5CA $420
PDXWarwickSeptember 10 to September 22CA $447
LAXWarwickSeptember 25 to September 30CA $497
PDXWindsor LocksNovember 4 to November 8CA $528
LAXMassachusettsSeptember 4 to September 11CA $717
HKGBostonSeptember 11 to September 15CA $1,304
PEKBostonNovember 5 to November 11CA $1,476
PVGBostonSeptember 14 to September 28CA $1,502
CANBostonNovember 1 to November 5CA $1,551
SZXBostonAugust 31 to September 4CA $2,534
*Prices include taxes and fees
OriginDestinationTravel datesFlights from*
PDXBostonAugust 21 to August 28CA $554
LAXBostonAugust 23 to September 3CA $641
*Prices include taxes and fees
Price found within the past 48 hours. Click for updated prices.
Boston Harbor Hotel
5.0-star property

Boston Harbor Hotel

Oct 30 - Nov 1

2 night stay

Montreal (YMQ) to Boston (BOS)

Porter Airlines • Non-stop roundtrip • Coach
Price was CA $1,806, price is now CA $1,112 per person
CA $1,112
per person
found 23 hours ago
Hotel AKA Back Bay
4.5-star property

Hotel AKA Back Bay

Aug 20 - Aug 25

5 night stay

Buffalo (BUF) to Boston (BOS)

JetBlue Airways • Roundtrip • Coach
Price was CA $2,154, price is now CA $1,521 per person
CA $1,521
per person
found 1 day ago
Raffles Boston
5.0-star property

Raffles Boston

Aug 20 - Aug 23

3 night stay

Buffalo (BUF) to Boston (BOS)

JetBlue Airways • Roundtrip • Coach
Price was CA $2,643, price is now CA $1,916 per person
CA $1,916
per person
found 1 day ago
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Travelers ❤️ These Massachusetts 🏨

Seaport Hotel Boston

Seaport Hotel Boston

4 out of 5
1 Seaport Lane Boston MA
Book a stay at this business-friendly hotel in Boston. Enjoy free WiFi, 2 restaurants, and breakfast (surcharge). Our guests praise the breakfast and the restaurant in our reviews. Popular attractions New England Aquarium and Faneuil Hall Marketplace are located nearby.
9.6/10 Exceptional! (4,794 reviews)
"Loved the location and amenities. Walls are pretty thin but the gym is huge and the staff is super friendly. Will stay here again."

Reviewed on Aug 17, 2026

Opens in a new windowSeaport Hotel Boston
Omni Boston Hotel at the Seaport

Omni Boston Hotel at the Seaport

5 out of 5
450 Summer Street Boston MA
Book a stay at this luxury hotel in Boston. Enjoy free WiFi, a full-service spa, and 4 restaurants. Our guests praise the breakfast and the pool in our reviews. Popular attractions New England Aquarium and Faneuil Hall Marketplace are located nearby.
9.2/10 Wonderful! (4,866 reviews)
"Great location and property"

Reviewed on Aug 17, 2026

Opens in a new windowOmni Boston Hotel at the Seaport
The Revolution Hotel

The Revolution Hotel

3.5 out of 5
40 Berkeley Street Boston MA
Stay at this hotel in Boston. Enjoy free WiFi, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the restaurant and the helpful staff in our reviews. Popular attractions Copley Square and Boston Common are located nearby.
9/10 Wonderful! (2,838 reviews)
"Room was small but still spacious for two people. Staff was so accommodating and helpful. Housekeeping was great with keeping shared restrooms clean throughout our stay. Walking distance from the Commoms and other attractions. Would say here again 💕"

Reviewed on Aug 17, 2026

Opens in a new windowThe Revolution Hotel
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The Dagny Boston

The Dagny Boston

4 out of 5
89 Broad Street Boston MA
Book a stay at this luxury hotel in Boston. Enjoy free WiFi, breakfast (surcharge), and room service. Our guests praise the breakfast and the restaurant in our reviews. Popular attractions Faneuil Hall Marketplace and New England Aquarium are located nearby.
9.6/10 Exceptional! (7,463 reviews)
"Wonderful service and friendly staff."

Reviewed on Aug 17, 2026

Opens in a new windowThe Dagny Boston
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Frequently asked questions

How much is the cheapest flight to Massachusetts?
To give you an idea of fares, the cheapest roundtrip flight to Massachusetts cost CA $300 during the last seven days. An easy way to score a good deal is to be flexible with your dates. This price was available on Travelocity for flights to Massachusetts departing within the next year. Prices and availability are subject to change. Additional terms apply.
Which airlines fly to Massachusetts?
With 18 airline companies flying into Massachusetts, finding your perfect fare should be hassle-free. If your vacation starts in Boston, consider the top carrier, Delta Air Lines. It operates around 3,059 services to this major city per month.
What is the cheapest month to fly to Massachusetts?
Be sure to leave September clear in your calendar, because it's the cheapest time to travel to Massachusetts. That's according to Travelocity's direct flight demand from January to December last year. With more cash in your wallet, you can go on a spending spree, go to theatre or whatever else you like!
How can I check my flight status to Massachusetts?
There are a couple of simple ways to look up the status of your flight. You'll find all the info you need in our "Trips" portal, which is located at the top of our homepage. Log in or create a new account — you can then view and amend your bookings whenever you need to. For those already on the move, the Travelocity app can also help you look up the status of your flight to Massachusetts, as well as share travel details with any members of your family flying with you.
How do I find the best deals on flights to Massachusetts?
There are several ways — book ahead of time, avoid busy periods and be flexible with your travel dates. If you don't have a specific date in mind, search for your flight to Massachusetts on Travelocity and hit "Flexible dates" above your results. This will reveal any cheaper airfares on surrounding days. CA $300 was the best deal for a return flight to Massachusetts in the last seven days. This price was available on Travelocity for flights departing within the next year. Prices and availability are subject to change. Additional terms apply.
Why should I book my flight to Massachusetts with Travelocity?
Check out cheap flights to Massachusetts with Travelocity and start planning your next adventure. With 24/7 customer support along every step of your trip and our Price Match Guarantee, we take the stress out of booking cheap family flights, hotels, activities and more. Get your hands on a fantastic deal today and brace yourself for the adventure of your dreams.
What are the most popular flight routes to Massachusetts?
To help you pick your flights to Massachusetts, here's a list of some of the busiest routes:

  • Chicago, IL (ORD-O'Hare Intl.) to Logan Intl. Airport (BOS) - 3,514 flights a month.
  • Washington, DC (DCA-Ronald Reagan Washington National) to Logan Intl. Airport (BOS) - 3,419 flights a month.
  • Atlanta, GA (ATL-Hartsfield-Jackson Atlanta Intl.) to Logan Intl. Airport (BOS) - 3,193 flights a month.

How much is a flight to Massachusetts on average?
Roundtrip flights to Massachusetts on our site cost between CA $300 and CA $2,534 in the last seven days. When you see a price that matches your budget, act quick. Cheap deals don't last long! These prices were available on Travelocity for flights departing within the next year. Prices and availability are subject to change. Additional terms apply.

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