Search Cheap Flights to
Eastern Massachusetts

Search 400 airlines and 321,000 hotels worldwide.

Stop Planning & Start Exploring

FREE 24 hour cancellation on most flights

Eastern Massachusetts Flights as Low as $142

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

Frontier Airlines
Tue, May 12 - Tue, May 19
ORD
O'Hare Intl.
BOS
Logan Intl.
$142 Roundtrip, found 4 hours ago
$142
Roundtrip
found 4 hours ago
Select Frontier Airlines flight, departing Tue, May 12 from O'Hare Intl. to Logan Intl., returning Tue, May 19, priced at $142 found 4 hours ago
Spirit Airlines
Mon, Apr 13 - Tue, Apr 28
ORD
O'Hare Intl.
BOS
Logan Intl.
$163 Roundtrip, found 1 day ago
$163
Roundtrip
found 1 day ago
Select Spirit Airlines flight, departing Mon, Apr 13 from O'Hare Intl. to Logan Intl., returning Tue, Apr 28, priced at $163 found 1 day ago
American Airlines
Sat, May 9 - Sat, May 23
ORD
O'Hare Intl.
BOS
Logan Intl.
$167 Roundtrip, found 3 hours ago
$167
Roundtrip
found 3 hours ago
Select American Airlines flight, departing Sat, May 9 from O'Hare Intl. to Logan Intl., returning Sat, May 23, priced at $167 found 3 hours ago
Delta
Sat, May 9 - Sat, May 23
ORD
O'Hare Intl.
BOS
Logan Intl.
$167 Roundtrip, found 3 hours ago
$167
Roundtrip
found 3 hours ago
Select Delta flight, departing Sat, May 9 from O'Hare Intl. to Logan Intl., returning Sat, May 23, priced at $167 found 3 hours ago
United
Sat, May 9 - Sat, May 23
ORD
O'Hare Intl.
BOS
Logan Intl.
$167 Roundtrip, found 3 hours ago
$167
Roundtrip
found 3 hours ago
Select United flight, departing Sat, May 9 from O'Hare Intl. to Logan Intl., returning Sat, May 23, priced at $167 found 3 hours ago
American Airlines
Sat, May 9 - Sat, May 23
ORD
O'Hare Intl.
BOS
Logan Intl.
$167 Roundtrip, found 3 hours ago
$167
Roundtrip
found 3 hours ago
Select American Airlines flight, departing Sat, May 9 from O'Hare Intl. to Logan Intl., returning Sat, May 23, priced at $167 found 3 hours ago
JetBlue Airways
Tue, May 12 - Tue, May 19
ORD
O'Hare Intl.
BOS
Logan Intl.
$170 Roundtrip, found 4 hours ago
$170
Roundtrip
found 4 hours ago
Select JetBlue Airways flight, departing Tue, May 12 from O'Hare Intl. to Logan Intl., returning Tue, May 19, priced at $170 found 4 hours ago
JetBlue Airways
Tue, Apr 28 - Tue, May 5
DEN
Denver Intl.
BOS
Logan Intl.
$182 Roundtrip, found 12 hours ago
$182
Roundtrip
found 12 hours ago
Select JetBlue Airways flight, departing Tue, Apr 28 from Denver Intl. to Logan Intl., returning Tue, May 5, priced at $182 found 12 hours ago
Delta
Tue, Jul 14 - Wed, Jul 22
ORD
O'Hare Intl.
ORH
Worcester Regional
$202 Roundtrip, found 7 hours ago
$202
Roundtrip
found 7 hours ago
Select Delta flight, departing Tue, Jul 14 from O'Hare Intl. to Worcester Regional, returning Wed, Jul 22, priced at $202 found 7 hours ago
American Airlines
Tue, May 19 - Wed, May 27
ORD
O'Hare Intl.
PVD
T.F. Green
$237 Roundtrip, found 9 hours ago
$237
Roundtrip
found 9 hours ago
Select American Airlines flight, departing Tue, May 19 from O'Hare Intl. to T.F. Green, returning Wed, May 27, priced at $237 found 9 hours ago
American Airlines
Wed, Aug 19 - Tue, Sep 1
ORD
O'Hare Intl.
HYA
Barnstable Municipal
$265 Roundtrip, found 7 hours ago
$265
Roundtrip
found 7 hours ago
Select American Airlines flight, departing Wed, Aug 19 from O'Hare Intl. to Barnstable Municipal, returning Tue, Sep 1, priced at $265 found 7 hours ago
Alaska Airlines
Sat, May 2 - Tue, May 5
DEN
Denver Intl.
BOS
Logan Intl.
$317 Roundtrip, found 5 hours ago
$317
Roundtrip
found 5 hours ago
Select Alaska Airlines flight, departing Sat, May 2 from Denver Intl. to Logan Intl., returning Tue, May 5, priced at $317 found 5 hours ago
American Airlines
Wed, May 20 - Sun, May 24
DEN
Denver Intl.
PVD
T.F. Green
$353 Roundtrip, found 3 hours ago
$353
Roundtrip
found 3 hours ago
Select American Airlines flight, departing Wed, May 20 from Denver Intl. to T.F. Green, returning Sun, May 24, priced at $353 found 3 hours ago
American Airlines
Tue, Aug 11 - Tue, Aug 18
ORD
O'Hare Intl.
MVY
Martha's Vineyard
$354 Roundtrip, found 14 hours ago
$354
Roundtrip
found 14 hours ago
Select American Airlines flight, departing Tue, Aug 11 from O'Hare Intl. to Martha's Vineyard, returning Tue, Aug 18, priced at $354 found 14 hours ago
United
Thu, Jun 25 - Sun, Jun 28
DEN
Denver Intl.
MHT
Manchester-Boston Regional
$552 Roundtrip, found 4 days ago
$552
Roundtrip
found 4 days ago
Select United flight, departing Thu, Jun 25 from Denver Intl. to Manchester-Boston Regional, returning Sun, Jun 28, priced at $552 found 4 days ago
United
Mon, Jun 8 - Tue, Jun 9
DEN
Denver Intl.
HYA
Barnstable Municipal
$647 Roundtrip, found 3 hours ago
$647
Roundtrip
found 3 hours ago
Select United flight, departing Mon, Jun 8 from Denver Intl. to Barnstable Municipal, returning Tue, Jun 9, priced at $647 found 3 hours ago

Cheap Flights to Eastern Massachusetts

Fall in love at first flight with your vacation to Eastern Massachusetts by saving a ton of cash on your last-minute cheap flight. There’s no more scouring the internet for a good deal—book your flight to Eastern Massachusetts on Hotwire, and you’ll be up, up, and on a getaway in no time.

Because once the wheels are down in Eastern Massachusetts, the good times start rolling. So buckle up, you’re in for a fun ride.

Frequently Asked Questions About flights to Eastern Massachusetts

Don’t waste your time on endless searches for cheap airline tickets oneway or roundtrip. We’ll have you on your way to Eastern Massachusetts with a tiny bag of pretzels in your hand before you can say “tray tables in the upright position”—and for a ticket price that works for your vacay budget.

So all you have to worry about is where you’re headed after the BOS airport.

What is the cheapest month to fly to Eastern Massachusetts?

Airline ticket prices fluctuate all the time, depending on the day of the week or the month of the year. The cheapest round trip flights to Eastern Massachusetts are in May, but when you book your flight on Hotwire, savings are always in season.

How many airlines fly to Eastern Massachusetts?

Variety is the spice of life, even when it comes to booking your next trip. Want options for airlines? You’ll find 16 to choose from for your flight to Eastern Massachusetts.

What airport is best to fly into Eastern Massachusetts?

When you’re planning your trip to Eastern Massachusetts, convenience is the name of the game. Luckily, Eastern Massachusetts Plymouth Municipal Airport is nearby so you can deplane and get going on checking off everything on your Eastern Massachusetts must-do list.

How much are flights to Eastern Massachusetts?

Got very cheap flights on your vacation itinerary? When you book your airline tickets to Eastern Massachusetts on Hotwire, you may just get what’s on your getaway wish list. With tickets as low as $142, you’ll have leftover cash for at least a magazine and a bottle of water at the airport book store.

How to get cheap flights to Eastern Massachusetts?

The trick to saving a stack of cash on your flight to Eastern Massachusetts? Snatch up that Hotwire flight deal when you see a killer rate because it could be gone in a flash. And with flights as low as $142 right now, why wait?

Eastern Massachusetts Flight Information
Destination airport
Logan Intl.
Destination airport IATA code
BOS
Roundtrip price
$65

Last Minute Hotel Deals in Eastern Massachusetts

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. ...
9.2/10 Wonderful! (4,579 reviews)
Impressive

Reviewed on Apr 10, 2026

Get rates
Omni Boston Hotel at the Seaport
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 ...
9.6/10 Exceptional! (4,164 reviews)
Yes

Reviewed on Apr 11, 2026

Get rates
Seaport Hotel Boston
Hilton Boston Park Plaza

Hilton Boston Park Plaza

4 out of 5
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 ...
8.4/10 Very Good! (3,147 reviews)
Great location, cleanness and prompt service!!!

Reviewed on Apr 11, 2026

Get rates
Hilton Boston Park Plaza
Harborside Inn Of Boston

Harborside Inn Of Boston

4 out of 5
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. ...
9.2/10 Wonderful! (6,435 reviews)
Large clean room in great location

Reviewed on Apr 10, 2026

Get rates
Harborside Inn Of Boston
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 ...
9/10 Wonderful! (2,545 reviews)
Everything was great! All the staff was super nice and polite, we had a great time! 3rd time staying at the Revolution Hotel and everytime is a great time!

Reviewed on Apr 11, 2026

Get rates
The Revolution Hotel
Omni Parker House

Omni Parker House

4.5 out of 5
60 School St Boston MA
Book a stay at this luxury hotel in Boston. Enjoy free WiFi, breakfast (surcharge), and room service. Our guests praise the restaurant and the helpful staff ...
9/10 Wonderful! (3,388 reviews)
Friendly staff. Beautiful hotel

Reviewed on Apr 10, 2026

Get rates
Omni Parker House
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 ...
9.4/10 Exceptional! (7,215 reviews)
We really enjoyed our spacious suite. It was very comfortable, and we especially appreciated the safety rails in the bathtub and bathroom.

Reviewed on Apr 11, 2026

Get rates
The Dagny Boston
The Godfrey Hotel Boston

The Godfrey Hotel Boston

4 out of 5
505 Washington Street Boston MA
Book a stay at this boutique hotel in Boston. Enjoy breakfast (surcharge), room service, and a 24-hour fitness center. Our guests praise the restaurant and the ...
9.4/10 Exceptional! (4,999 reviews)
Really enjoyed our stay here, clean and comfortable. Great location. Helpful front desk staff. Thank you!

Reviewed on Apr 10, 2026

Get rates
The Godfrey Hotel Boston
See all 16,262 properties in Eastern Massachusetts
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.

Top Hotels With Free Airport Shuttle

Embassy Suites Boston Logan Airport

Embassy Suites Boston Logan Airport

3.5 out of 5
207 Porter St Boston MA
Book a stay at this business-friendly hotel in Boston. Enjoy free breakfast, a free airport shuttle, and a fitness center. Our guests praise the breakfast and ...
8.8/10 Excellent! (2,399 reviews)
Clean well laid out room

Reviewed on Apr 11, 2026

Get rates
Embassy Suites Boston Logan Airport
Holiday Inn Express Boston - Saugus by IHG

Holiday Inn Express Boston - Saugus by IHG

3 out of 5
999 Broadway Saugus MA
Book a stay at this business-friendly hotel in Saugus. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff ...
8.6/10 Excellent! (1,110 reviews)
Rooms are clean , breakfast is good

Reviewed on Apr 9, 2026

Get rates
Holiday Inn Express Boston - Saugus by IHG
DoubleTree by Hilton Hotel Boston Bayside

DoubleTree by Hilton Hotel Boston Bayside

4 out of 5
240 Mount Vernon Street Boston MA
Book a stay at this business-friendly hotel in Boston. Enjoy breakfast (surcharge), a free airport shuttle, and a free cruise terminal shuttle. Our guests praise ...
8.4/10 Very Good! (1,452 reviews)
Clean room, Good options on restaurant menu.

Reviewed on Apr 10, 2026

Get rates
DoubleTree by Hilton Hotel Boston Bayside
La Quinta Inn & Suites by Wyndham Boston Somerville

La Quinta Inn & Suites by Wyndham Boston Somerville

3 out of 5
23 Cummings St Somerville MA
Book a stay at this business-friendly hotel in Somerville. Enjoy free breakfast, free WiFi, and a free airport shuttle. Our guests praise the helpful staff and ...
7.6/10 Good! (3,278 reviews)
Most unprofessional front desk I’ve ever encountered. They don’t deserve the privilege to call themselves a “La Quinta”. Even by la Quinta standards, this place is unacceptable at best.

Reviewed on Apr 10, 2026

Get rates
La Quinta Inn & Suites by Wyndham Boston Somerville
Four Points by Sheraton Boston Logan Airport Revere

Four Points by Sheraton Boston Logan Airport Revere

3 out of 5
407 Squire Rd Revere MA
Book a stay at this business-friendly hotel in Revere. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff in our reviews. ...
8/10 Very Good! (1,004 reviews)
Beds were incredibly comfortable, especially after a long day of walking. Airport shuttle was super helpful. Everything was clean. Staff was friendly and courteous.

Reviewed on Apr 8, 2026

Get rates
Four Points by Sheraton Boston Logan Airport Revere
Courtyard by Marriott Boston Logan Airport

Courtyard by Marriott Boston Logan Airport

3 out of 5
225 William F. McClellan Highway Boston MA
Book a stay at this business-friendly hotel in Boston. Enjoy free WiFi, breakfast (surcharge), and a free airport shuttle. Our guests praise the helpful staff ...
8.6/10 Excellent! (1,413 reviews)
Staff was great

Reviewed on Apr 5, 2026

Get rates
Courtyard by Marriott Boston Logan Airport
See all 16,262 properties in Eastern Massachusetts
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.