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Eastern Massachusetts

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Eastern Massachusetts Flights as Low as $190

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

Frontier Airlines
Tue, Sep 1 - Tue, Sep 8
ORD
O'Hare Intl.
BOS
Logan Intl.
$190 Roundtrip, found 4 days ago
$190
Roundtrip
found 4 days ago
Select Frontier Airlines flight, departing Tue, Sep 1 from O'Hare Intl. to Logan Intl., returning Tue, Sep 8, priced at $190 found 4 days ago
Delta
Wed, Jun 3 - Wed, Jun 3
ORD
O'Hare Intl.
BOS
Logan Intl.
$192 Roundtrip, found 2 days ago
$192
Roundtrip
found 2 days ago
Select Delta flight, departing Wed, Jun 3 from O'Hare Intl. to Logan Intl., returning Wed, Jun 3, priced at $192 found 2 days ago
United
Tue, Jun 2 - Wed, Jun 10
ORD
O'Hare Intl.
BOS
Logan Intl.
$192 Roundtrip, found 21 hours ago
$192
Roundtrip
found 21 hours ago
Select United flight, departing Tue, Jun 2 from O'Hare Intl. to Logan Intl., returning Wed, Jun 10, priced at $192 found 21 hours ago
American Airlines
Tue, Jun 2 - Wed, Jun 10
ORD
O'Hare Intl.
BOS
Logan Intl.
$192 Roundtrip, found 21 hours ago
$192
Roundtrip
found 21 hours ago
Select American Airlines flight, departing Tue, Jun 2 from O'Hare Intl. to Logan Intl., returning Wed, Jun 10, priced at $192 found 21 hours ago
Frontier Airlines
Tue, Jun 9 - Tue, Jun 16
ORD
O'Hare Intl.
BOS
Logan Intl.
$195 Roundtrip, found 1 day ago
$195
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Tue, Jun 9 from O'Hare Intl. to Logan Intl., returning Tue, Jun 16, priced at $195 found 1 day ago
Delta
Tue, Aug 4 - Tue, Aug 11
ORD
O'Hare Intl.
BOS
Logan Intl.
$197 Roundtrip, found 3 hours ago
$197
Roundtrip
found 3 hours ago
Select Delta flight, departing Tue, Aug 4 from O'Hare Intl. to Logan Intl., returning Tue, Aug 11, priced at $197 found 3 hours ago
Delta
Tue, Jun 9 - Tue, Jun 16
ORD
O'Hare Intl.
BOS
Logan Intl.
$199 Roundtrip, found 1 day ago
$199
Roundtrip
found 1 day ago
Select Delta flight, departing Tue, Jun 9 from O'Hare Intl. to Logan Intl., returning Tue, Jun 16, priced at $199 found 1 day ago
Frontier Airlines
Tue, Aug 25 - Tue, Sep 8
ORD
O'Hare Intl.
BOS
Logan Intl.
$199 Roundtrip, found 1 day ago
$199
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Tue, Aug 25 from O'Hare Intl. to Logan Intl., returning Tue, Sep 8, priced at $199 found 1 day ago
JetBlue Airways
Wed, Aug 5 - Wed, Aug 5
ORD
O'Hare Intl.
BOS
Logan Intl.
$200 Roundtrip, found 1 day ago
$200
Roundtrip
found 1 day ago
Select JetBlue Airways flight, departing Wed, Aug 5 from O'Hare Intl. to Logan Intl., returning Wed, Aug 5, priced at $200 found 1 day ago
American Airlines
Tue, Jun 9 - Tue, Jun 16
ORD
O'Hare Intl.
BOS
Logan Intl.
$201 Roundtrip, found 1 day ago
$201
Roundtrip
found 1 day ago
Select American Airlines flight, departing Tue, Jun 9 from O'Hare Intl. to Logan Intl., returning Tue, Jun 16, priced at $201 found 1 day ago
Delta
Fri, Aug 7 - Tue, Aug 11
ORD
O'Hare Intl.
BOS
Logan Intl.
$201 Roundtrip, found 3 hours ago
$201
Roundtrip
found 3 hours ago
Select Delta flight, departing Fri, Aug 7 from O'Hare Intl. to Logan Intl., returning Tue, Aug 11, priced at $201 found 3 hours ago
Delta
Wed, Jul 15 - Tue, Jul 21
ORD
O'Hare Intl.
ORH
Worcester Regional
$220 Roundtrip, found 2 days ago
$220
Roundtrip
found 2 days ago
Select Delta flight, departing Wed, Jul 15 from O'Hare Intl. to Worcester Regional, returning Tue, Jul 21, priced at $220 found 2 days ago
American Airlines
Mon, Aug 24 - Sat, Sep 5
ORD
O'Hare Intl.
HYA
Barnstable Municipal
$235 Roundtrip, found 1 day ago
$235
Roundtrip
found 1 day ago
Select American Airlines flight, departing Mon, Aug 24 from O'Hare Intl. to Barnstable Municipal, returning Sat, Sep 5, priced at $235 found 1 day ago
American Airlines
Tue, Aug 11 - Wed, Aug 19
ORD
O'Hare Intl.
MVY
Martha's Vineyard
$354 Roundtrip, found 2 days ago
$354
Roundtrip
found 2 days ago
Select American Airlines flight, departing Tue, Aug 11 from O'Hare Intl. to Martha's Vineyard, returning Wed, Aug 19, priced at $354 found 2 days ago
Sun Country Airlines
Thu, Jun 11 - Mon, Jun 15
ORD
O'Hare Intl.
BOS
Logan Intl.
$459 Roundtrip, found 4 days ago
$459
Roundtrip
found 4 days ago
Select Sun Country Airlines flight, departing Thu, Jun 11 from O'Hare Intl. to Logan Intl., returning Mon, Jun 15, priced at $459 found 4 days ago
United
Mon, Jun 29 - Thu, Jul 9
ORD
O'Hare Intl.
PVC
Provincetown Municipal
$566 Roundtrip, found 1 day ago
$566
Roundtrip
found 1 day ago
Select United flight, departing Mon, Jun 29 from O'Hare Intl. to Provincetown Municipal, returning Thu, Jul 9, priced at $566 found 1 day 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 September, 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 $190, 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 $190 right now, why wait?

Eastern Massachusetts Flight Information
Destination airport
Logan Intl.
Destination airport IATA code
BOS
Roundtrip price
$267

Last Minute Hotel Deals in Eastern 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 ...
9.6/10 Exceptional! (4,366 reviews)
"Excellent from beginning to end! Staff was very helpful! Rooms were excellent and checking in and out was a breeze. Will definitely stay there again and again!!j"

Reviewed on May 19, 2026

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Seaport Hotel 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! (2,624 reviews)
"Very cool hotel but beware of staying in the mezzanine floor - it is loud at night and you can’t get any sleep."

Reviewed on May 19, 2026

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The Revolution Hotel
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! (4,655 reviews)
"Breakfast was nice its alacarte , pool very poor and no service on the pool , spa slots are very limited and they are off every Tuesday and Wednesday"

Reviewed on May 19, 2026

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Omni Boston Hotel at the Seaport
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! (5,062 reviews)
"The staff were all super friendly and helpful.We did valet our car for 3 nights which was expensive ($60/night) but parking in Boston stinks anywhere and the valet was convenient so we didn't have to drive around looking for a garage.There is also a $40/night "hotel" fee which I know the city puts ..."

Reviewed on May 19, 2026

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The Godfrey Hotel Boston
Club Quarters Hotel Faneuil Hall, Boston

Club Quarters Hotel Faneuil Hall, Boston

4 out of 5
161 Devonshire St Boston MA
Book a stay at this business-friendly hotel in Boston. Enjoy free WiFi, breakfast (surcharge), and room service. Our guests praise the restaurant and the helpful ...
9/10 Wonderful! (3,099 reviews)
"Location was good and the parking next door was convenient. The staff was pleasant and the rooms were clean"

Reviewed on May 18, 2026

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Club Quarters Hotel Faneuil Hall, Boston
The Midtown Hotel MOD Collection by Sonesta

The Midtown Hotel MOD Collection by Sonesta

2 out of 5
220 Huntington Avenue Boston MA
Stay at this hotel in Boston. Enjoy free breakfast, free WiFi, and a fitness center. Popular attractions Copley Square and Fenway Park are located nearby.
8.2/10 Very Good! (349 reviews)
"It would have been nice to have a snack waiting for me"

Reviewed on May 19, 2026

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The Midtown Hotel MOD Collection by Sonesta
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! (6,585 reviews)
"Very historic and the staff are great. Bring your own coffee or get it from the restaurant. Jolia had excellent coffee and breakfast."

Reviewed on May 19, 2026

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Harborside Inn Of Boston
Encore Boston Harbor

Encore Boston Harbor

5 out of 5
1 Broadway Everett MA
Book a stay at this luxury hotel in Everett. Enjoy free WiFi, free parking, and a full-service spa. Our guests praise the helpful staff and the clean rooms in ...
9.6/10 Exceptional! (3,770 reviews)
"Beautiful resort ❤️"

Reviewed on May 19, 2026

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Encore Boston Harbor
See all 16,457 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! (2,458 reviews)
"It was a great place to stay for easy access to the airoort"

Reviewed on May 19, 2026

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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! (1,141 reviews)
"Spacious rooms. No vending machines. Individuals hang outside in parking lot. Not sure if guests or not but sitting in cars which was weird"

Reviewed on May 18, 2026

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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! (1,477 reviews)
"The complimentary shuttle was very convenient and punctual. The close location to the T. Was so handy. The staff at the desk were helpful and friendly"

Reviewed on May 19, 2026

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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! (3,340 reviews)
"Friendly efficient staff."

Reviewed on May 19, 2026

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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! (1,000 reviews)
"Hotel was nice and clean! They have a little store with food and snacks downstairs. They also have a bar that stays open until 2am. Bartender David was so awesome!! He made our night! AJ at the front desk was just as amazing!! I would definitely stay here again!"

Reviewed on May 14, 2026

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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! (1,414 reviews)
"Good: Hot shower, free shuttle to and from Logan airport, bed, temperature controls in room Bad: NO WiFi, only Bonvoy wifi, which I was unable to subscribe to. The terminals in the lobby to print boarding passes DID NOT WORK I was unable to early check in."

Reviewed on May 18, 2026

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Courtyard by Marriott Boston Logan Airport
See all 16,457 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.