
Cheap Flights to Massachusetts from $44 (2026/2027)
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Boston
Flights
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.
MCO
Orlando Intl.
BDL
Bradley Intl.
$101 Roundtrip, found 1 day ago
$101
Roundtrip
found 1 day ago
MCO
Orlando Intl.
BOS
Logan Intl.
$110 Roundtrip, just found
$110
Roundtrip
just found
MCO
Orlando Intl.
PSM
Portsmouth Intl.
$122 Roundtrip, found 3 days ago
$122
Roundtrip
found 3 days ago
TPA
Tampa Intl.
PVD
T.F. Green
$132 Roundtrip, found 3 days ago
$132
Roundtrip
found 3 days ago
TPA
Tampa Intl.
PVD
T.F. Green
$143 Roundtrip, found 3 days ago
$143
Roundtrip
found 3 days ago
TPA
Tampa Intl.
BDL
Bradley Intl.
$147 Roundtrip, found 3 days ago
$147
Roundtrip
found 3 days ago
TPA
Tampa Intl.
BOS
Logan Intl.
$176 Roundtrip, found 2 hours ago
$176
Roundtrip
found 2 hours ago
TPA
Tampa Intl.
BDL
Bradley Intl.
$190 Roundtrip, found 2 days ago
$190
Roundtrip
found 2 days ago
TPA
Tampa Intl.
BDL
Bradley Intl.
$190 Roundtrip, found 3 hours ago
$190
Roundtrip
found 3 hours ago
TPA
Tampa Intl.
MHT
Manchester-Boston Regional
$191 Roundtrip, found 4 days ago
$191
Roundtrip
found 4 days ago
TPA
Tampa Intl.
ALB
Albany Intl.
$192 Roundtrip, found 5 days ago
$192
Roundtrip
found 5 days ago
| Origin | Destination | Travel Dates | Flights From* |
|---|---|---|---|
| PDX | Boston | April 9 to April 15 | $242 |
| LAX | Londonderry | June 3 to June 10 | $302 |
| PDX | Warwick | May 5 to May 8 | $314 |
| PDX | Latham | May 2 to May 6 | $413 |
| PDX | Londonderry | May 12 to May 21 | $427 |
| PDX | Nantucket | June 11 to June 15 | $632 |
| LAX | Hyannis | June 1 to June 5 | $644 |
| PDX | Massachusetts | June 30 to July 8 | $799 |
| HKG | Boston | June 4 to July 30 | $890 |
| PVG | Boston | June 2 to October 2 | $939 |
| PEK | Boston | May 19 to July 21 | $1,017 |
| CAN | Boston | April 5 to April 15 | $1,093 |
| PEK | Warwick | May 22 to May 25 | $2,208 |
| HKG | Windsor Locks | April 9 to April 14 | $2,340 |
| HKG | Latham | April 5 to April 9 | $7,440 |
| Origin | Destination | Travel Dates | Flights From* |
|---|---|---|---|
| LAX | Boston | March 29 to April 3 | $447 |
| PDX | Boston | March 29 to April 13 | $566 |
| LAX | Warwick | March 29 to September 2 | $578 |
| LAX | Latham | March 29 to April 5 | $639 |
| LAX | Windsor Locks | March 28 to April 13 | $684 |
| PDX | Warwick | March 29 to April 3 | $718 |
| PDX | Latham | March 27 to April 5 | $832 |
| PDX | Windsor Locks | March 28 to April 4 | $860 |
| HKG | Boston | March 29 to October 11 | $1,023 |
| LAX | Hyannis | March 29 to March 31 | $1,131 |
| PDX | Londonderry | March 27 to March 30 | $1,193 |
| LAX | Londonderry | March 27 to March 30 | $1,364 |
| CAN | Boston | March 27 to September 20 | $1,375 |
| PEK | Boston | March 29 to September 4 | $1,748 |
| PVG | Boston | March 29 to April 11 | $1,935 |
Best Massachusetts Flight and Hotel Packages
Price found within the past 48 hours. Click for updated prices.



3.0-star property
Sleeps 40 Heated Pool Hot Tub Fire Pit Game Room Brookside Mountain Retreat by Avantstay
Apr 6 - Apr 9
3 night stay
Fort Lauderdale (FLL) to Albany (ALB)
JetBlue Airways • Roundtrip • Coach
Save 100% on your flight
Price was $2,883, price is now $2,034 per person
$2,034
per person
found 1 day ago
Don't see what you're looking for?
See all available trips from Chicago to Massachusetts
View all tripsTravelers ❤️ These Massachusetts 🏨

Omni Boston Hotel at the Seaport
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 Boston Common are located nearby.
9.2/10 Wonderful! (4,521 reviews)
Clean room, great location and staff
Reviewed on Mar 20, 2026

Hilton Boston Park Plaza
50 Park Plaza Boston MA
Book a stay at this luxury hotel in Boston. Enjoy 2 restaurants, 2 bars/lounges, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Copley Square and Boston Common are located nearby.

Seaport Hotel Boston
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 Boston Common are located nearby.
9.6/10 Exceptional! (4,069 reviews)
Yes
Reviewed on Mar 21, 2026
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Harborside Inn Of Boston
185 State St Boston MA
Stay at this hotel in Boston. Enjoy free WiFi, a 24-hour front desk, and a business center. Our guests praise the breakfast and the restaurant in our reviews. Popular attractions New England Aquarium and TD Garden are located nearby.
9.2/10 Wonderful! (6,378 reviews)
Perfect would of liked the use of a kettle
Reviewed on Mar 21, 2026
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.
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