Cheap flights To Manchester-by-the-Sea (BOS) from $44

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Cheap Flights to Manchester-by-the-Sea from $44 One Way, $87 Round Trip

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

Thu, Oct 2 - Sat, Oct 4
MCO
Orlando Intl.
BOS
Logan Intl.
$87 Roundtrip, found 3 hours ago
$87
Roundtrip
found 3 hours ago
Select Spirit Airlines flight, departing Thu, Oct 2 from Orlando Intl. to Logan Intl., returning Sat, Oct 4, priced at $87 found 3 hours ago
Thu, Oct 2 - Tue, Oct 7
MCO
Orlando Intl.
BOS
Logan Intl.
$102 Roundtrip, found 4 hours ago
$102
Roundtrip
found 4 hours ago
Select Spirit Airlines flight, departing Thu, Oct 2 from Orlando Intl. to Logan Intl., returning Tue, Oct 7, priced at $102 found 4 hours ago
Wed, Oct 29 - Sat, Nov 1
MCO
Orlando Intl.
PSM
Portsmouth Intl.
$102 Roundtrip, found 1 hour ago
$102
Roundtrip
found 1 hour ago
Select Breeze Airways flight, departing Wed, Oct 29 from Orlando Intl. to Portsmouth Intl., returning Sat, Nov 1, priced at $102 found 1 hour ago
Fri, Oct 3 - Sat, Oct 4
MCO
Orlando Intl.
BOS
Logan Intl.
$103 Roundtrip, found 2 hours ago
$103
Roundtrip
found 2 hours ago
Select JetBlue Airways flight, departing Fri, Oct 3 from Orlando Intl. to Logan Intl., returning Sat, Oct 4, priced at $103 found 2 hours ago
Sat, Oct 4 - Sat, Oct 25
MCO
Orlando Intl.
PSM
Portsmouth Intl.
$106 Roundtrip, found 4 days ago
$106
Roundtrip
found 4 days ago
Select Breeze Airways flight, departing Sat, Oct 4 from Orlando Intl. to Portsmouth Intl., returning Sat, Oct 25, priced at $106 found 4 days ago
Sat, Dec 6 - Wed, Dec 10
MCO
Orlando Intl.
PSM
Portsmouth Intl.
$107 Roundtrip, just found
$107
Roundtrip
just found
Select Breeze Airways flight, departing Sat, Dec 6 from Orlando Intl. to Portsmouth Intl., returning Wed, Dec 10, priced at $107 just found
Sat, Oct 25 - Sat, Nov 1
MCO
Orlando Intl.
PSM
Portsmouth Intl.
$107 Roundtrip, found 1 hour ago
$107
Roundtrip
found 1 hour ago
Select Breeze Airways flight, departing Sat, Oct 25 from Orlando Intl. to Portsmouth Intl., returning Sat, Nov 1, priced at $107 found 1 hour ago
Sat, Oct 4 - Sat, Oct 4
MCO
Orlando Intl.
PSM
Portsmouth Intl.
$109 Roundtrip, just found
$109
Roundtrip
just found
Select Breeze Airways flight, departing Sat, Oct 4 from Orlando Intl. to Portsmouth Intl., returning Sat, Oct 4, priced at $109 just found
Fri, Oct 31 - Mon, Nov 3
MCO
Orlando Intl.
BOS
Logan Intl.
$110 Roundtrip, just found
$110
Roundtrip
just found
Select Frontier Airlines flight, departing Fri, Oct 31 from Orlando Intl. to Logan Intl., returning Mon, Nov 3, priced at $110 just found
Sat, Nov 1 - Wed, Nov 5
MCO
Orlando Intl.
PSM
Portsmouth Intl.
$112 Roundtrip, found 23 hours ago
$112
Roundtrip
found 23 hours ago
Select Breeze Airways flight, departing Sat, Nov 1 from Orlando Intl. to Portsmouth Intl., returning Wed, Nov 5, priced at $112 found 23 hours ago

Manchester-by-the-Sea BOS Flight Information

Traveling To
Manchester-by-the-Sea
Destination Airport IATA Code
BOS
Number of Airlines Serving
10
Airlines
Spirit Airlines, Breeze Airways, Frontier Airlines, JetBlue Airways, Delta
Flight Price
$87
Earliest Departing Flight
DL 5663 9:10AM EDT
Latest Departing Flight
AF 2710 Sep 30 7:13PM EDT

Book Your Flight & Hotel Together & Save

Manchester-by-the-Sea economy flight packages

Price found within the past 48 hours. Click for updated prices.
Best Western Springfield West Inn
2.5-star property

Best Western Springfield West Inn

Nov 7 - Nov 10

3 night stay

Dallas (DFW) to Boston (BOS)

American Airlines • Coach

Boston (BOS) to Dallas (DFW)

Spirit Airlines • Coach
Price was $531, price is now $375 per person
$375
per person
found 1 day ago
Raffles Boston
5.0-star property

Raffles Boston

Oct 23 - Oct 26

3 night stay

Chicago (CHI) to Boston (BOS)

Spirit Airlines • Non-stop • Coach

Boston (BOS) to Chicago (CHI)

United • Non-stop • Coach
Save 100% on your flight
Price was $1,965, price is now $1,358 per person
$1,358
per person
found 1 day ago
The Verve Hotel Boston Natick, Tapestry Collection by Hilton
3.5-star property

The Verve Hotel Boston Natick, Tapestry Collection by Hilton

Oct 26 - Oct 31

5 night stay

Dallas (DFW) to Boston (BOS)

Southwest Airlines • Coach

Boston (BOS) to Dallas (DFW)

Spirit Airlines • Coach
Price was $769, price is now $539 per person
$539
per person
found 8 hours ago
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Manchester-by-the-Sea premium economy flight packages

Price found within the past 48 hours. Click for updated prices.
citizenM Boston North Station
4.0-star property

citizenM Boston North Station

9.2/10 Wonderful! (3,784 reviews)

Oct 24 - Oct 27

3 night stay

Chicago (ORD) to Boston (BOS)

Delta • Roundtrip • PremiumEconomy
Price was $1,118, price is now $870 per person
$870
per person
found 1 day ago
The property itself was quite good. Standouts were the lobby area and the view from the room. Not-so-nice were the cubicle bathrooms that had minimal privacy and the extra soft beds (personal preference though I understand). Overall I would recommend but be aware the beds are very soft, the bathrooms aren't too private, and you need your mobile phone or an iPad to get the most out of the room controls. The staff was wonderful and the rooms were clean and quiet.

Reviewed on Sep 11, 2025

Raffles Boston
5.0-star property

Raffles Boston

9.8/10 Exceptional! (160 reviews)

Oct 24 - Oct 27

3 night stay

Chicago (ORD) to Boston (BOS)

Delta • Roundtrip • PremiumEconomy
Save 100% on your flight
Price was $2,177, price is now $1,570 per person
$1,570
per person
found 1 day ago
Excellent services.

Reviewed on Dec 29, 2024

The Langham, Boston
5.0-star property

The Langham, Boston

9.6/10 Exceptional! (1,002 reviews)

Oct 24 - Oct 27

3 night stay

Chicago (ORD) to Boston (BOS)

Delta • Roundtrip • PremiumEconomy
Save 100% on your flight
Price was $1,775, price is now $1,386 per person
$1,386
per person
found 1 day ago
Was hoping for more.

Reviewed on Jul 31, 2025

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Fare, taxes & fees: Fares include all taxes and fees, except baggage fees. Rates shown reflect fares found by other Orbitz users over the past 7 days. Due to rapidly changing airline prices & seat availability, these fares may no longer be available.

Refunds/changes/cancellations: Itinerary changes, if permitted for the fare, will have a $30 service fee charged by Orbitz. Additional airline charges may apply.

Other conditions: Schedules, fares and rules are subject to change without notice. Seats are limited and may not be available on all flights/dates or in all markets. Lower fares may be available. Fares will not be honored retroactively or in exchange for any wholly/partially unused ticket. Tickets are non-transferable and non-refundable. Fare rules are provided for the selected itinerary before booking.