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Chelsea

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Chelsea Flights as Low as $107

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

Breeze Airways
Sat, Nov 7 - Sat, Nov 14
MCO
Orlando Intl.
PSM
Portsmouth Intl.
$107 Roundtrip, found 1 day ago
$107
Roundtrip
found 1 day ago
Select Breeze Airways flight, departing Sat, Nov 7 from Orlando Intl. to Portsmouth Intl., returning Sat, Nov 14, priced at $107 found 1 day ago
Breeze Airways
Sat, Nov 7 - Sat, Nov 14
MCO
Orlando Intl.
PSM
Portsmouth Intl.
$108 Roundtrip, found 1 day ago
$108
Roundtrip
found 1 day ago
Select Breeze Airways flight, departing Sat, Nov 7 from Orlando Intl. to Portsmouth Intl., returning Sat, Nov 14, priced at $108 found 1 day ago
Breeze Airways
Sat, Nov 7 - Sat, Nov 14
MCO
Orlando Intl.
PSM
Portsmouth Intl.
$112 Roundtrip, found 1 day ago
$112
Roundtrip
found 1 day ago
Select Breeze Airways flight, departing Sat, Nov 7 from Orlando Intl. to Portsmouth Intl., returning Sat, Nov 14, priced at $112 found 1 day ago
Breeze Airways
Sat, Nov 7 - Sat, Nov 14
MCO
Orlando Intl.
PSM
Portsmouth Intl.
$113 Roundtrip, found 2 hours ago
$113
Roundtrip
found 2 hours ago
Select Breeze Airways flight, departing Sat, Nov 7 from Orlando Intl. to Portsmouth Intl., returning Sat, Nov 14, priced at $113 found 2 hours ago
Breeze Airways
Sat, Nov 7 - Sat, Nov 14
MCO
Orlando Intl.
PSM
Portsmouth Intl.
$117 Roundtrip, found 1 day ago
$117
Roundtrip
found 1 day ago
Select Breeze Airways flight, departing Sat, Nov 7 from Orlando Intl. to Portsmouth Intl., returning Sat, Nov 14, priced at $117 found 1 day ago
Breeze Airways
Sat, Nov 7 - Sat, Nov 14
MCO
Orlando Intl.
PSM
Portsmouth Intl.
$118 Roundtrip, found 1 day ago
$118
Roundtrip
found 1 day ago
Select Breeze Airways flight, departing Sat, Nov 7 from Orlando Intl. to Portsmouth Intl., returning Sat, Nov 14, priced at $118 found 1 day ago
Breeze Airways
Sat, Nov 7 - Sat, Nov 14
MCO
Orlando Intl.
PSM
Portsmouth Intl.
$122 Roundtrip, found 2 hours ago
$122
Roundtrip
found 2 hours ago
Select Breeze Airways flight, departing Sat, Nov 7 from Orlando Intl. to Portsmouth Intl., returning Sat, Nov 14, priced at $122 found 2 hours ago
Delta
Tue, Nov 3 - Tue, Nov 17
MCO
Orlando Intl.
BOS
Logan Intl.
$159 Roundtrip, just found
$159
Roundtrip
just found
Select Delta flight, departing Tue, Nov 3 from Orlando Intl. to Logan Intl., returning Tue, Nov 17, priced at $159 just found
American Airlines
Tue, Nov 3 - Tue, Nov 17
MCO
Orlando Intl.
BOS
Logan Intl.
$159 Roundtrip, just found
$159
Roundtrip
just found
Select American Airlines flight, departing Tue, Nov 3 from Orlando Intl. to Logan Intl., returning Tue, Nov 17, priced at $159 just found
JetBlue Airways
Tue, Nov 3 - Tue, Nov 17
MCO
Orlando Intl.
BOS
Logan Intl.
$159 Roundtrip, just found
$159
Roundtrip
just found
Select JetBlue Airways flight, departing Tue, Nov 3 from Orlando Intl. to Logan Intl., returning Tue, Nov 17, priced at $159 just found
Frontier Airlines
Thu, Dec 3 - Mon, Dec 7
MCO
Orlando Intl.
BOS
Logan Intl.
$168 Roundtrip, found 2 days ago
$168
Roundtrip
found 2 days ago
Select Frontier Airlines flight, departing Thu, Dec 3 from Orlando Intl. to Logan Intl., returning Mon, Dec 7, priced at $168 found 2 days ago
Breeze Airways
Sun, Dec 20 - Thu, Dec 24
RDU
Raleigh - Durham Intl.
PSM
Portsmouth Intl.
$178 Roundtrip, found 3 days ago
$178
Roundtrip
found 3 days ago
Select Breeze Airways flight, departing Sun, Dec 20 from Raleigh - Durham Intl. to Portsmouth Intl., returning Thu, Dec 24, priced at $178 found 3 days ago
Southwest Airlines
Tue, Nov 3 - Tue, Nov 17
MCO
Orlando Intl.
BOS
Logan Intl.
$179 Roundtrip, just found
$179
Roundtrip
just found
Select Southwest Airlines flight, departing Tue, Nov 3 from Orlando Intl. to Logan Intl., returning Tue, Nov 17, priced at $179 just found
United
Tue, Nov 3 - Tue, Nov 17
MCO
Orlando Intl.
BOS
Logan Intl.
$199 Roundtrip, just found
$199
Roundtrip
just found
Select United flight, departing Tue, Nov 3 from Orlando Intl. to Logan Intl., returning Tue, Nov 17, priced at $199 just found
Bargain Flight
Mon, Nov 23 - Fri, Nov 27
RDU
Raleigh - Durham Intl.
BOS
Logan Intl.
$208 Roundtrip, found 3 days ago
$208
Roundtrip
found 3 days ago
Select Bargain Flight flight, departing Mon, Nov 23 from Raleigh - Durham Intl. to Logan Intl., returning Fri, Nov 27, priced at $208 found 3 days ago
Alaska Airlines
Sat, Oct 17 - Sat, Oct 24
MCO
Orlando Intl.
BOS
Logan Intl.
$758 Roundtrip, found 2 hours ago
$758
Roundtrip
found 2 hours ago
Select Alaska Airlines flight, departing Sat, Oct 17 from Orlando Intl. to Logan Intl., returning Sat, Oct 24, priced at $758 found 2 hours ago

Cheap Flights to Chelsea

Fall in love at first flight with your vacation to Chelsea 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 Chelsea on Hotwire, and you’ll be up, up, and on a getaway in no time.

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

Frequently Asked Questions About flights to Chelsea

Don’t waste your time on endless searches for cheap airline tickets oneway or roundtrip. We’ll have you on your way to Chelsea 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 Chelsea?

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 Chelsea are in November, but when you book your flight on Hotwire, savings are always in season.

How many airlines fly to Chelsea?

Variety is the spice of life, even when it comes to booking your next trip. Want options for airlines? You’ll find 15 to choose from for your flight to Chelsea.

What airport is best to fly into Chelsea?

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

How much are flights to Chelsea?

Got very cheap flights on your vacation itinerary? When you book your airline tickets to Chelsea on Hotwire, you may just get what’s on your getaway wish list. With tickets as low as $107, 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 Chelsea?

The trick to saving a stack of cash on your flight to Chelsea? 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 $107 right now, why wait?

Chelsea Flight Information
Destination airport
Portsmouth Intl.
Destination airport IATA code
PSM
Roundtrip price
$106

Last Minute Hotel Deals in Chelsea

Doubletree By Hilton Boston Logan Airport Chelsea

Doubletree By Hilton Boston Logan Airport Chelsea

4 out of 5
201 Everett Ave Chelsea MA
Stay at this hotel in Chelsea. Enjoy free WiFi, breakfast (surcharge), and a free airport shuttle. Our guests praise the helpful staff and the clean rooms in ...
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Doubletree By Hilton Boston Logan Airport Chelsea
Holiday Inn Boston Logan Airport - Chelsea by IHG

Holiday Inn Boston Logan Airport - Chelsea by IHG

3 out of 5
1012 BROADWAY STREET Chelsea MA
Book a stay at this business-friendly hotel in Chelsea. Enjoy free WiFi, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the helpful staff ...
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Holiday Inn Boston Logan Airport - Chelsea by IHG
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. ...
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Omni 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 ...
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The Revolution Hotel
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! (5,023 reviews)
"Arrived for a concert at Leader Bank Pavillion. Location was PERFECT! Walking distance to almost everything in the seaport district including the concert venue. Only complaint was the couch in the room was a little stained, but overall wonderful stay."

Reviewed on Sep 24, 2026

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Seaport Hotel Boston
The Midtown Hotel MOD Collection by Sonesta

The Midtown Hotel MOD Collection by Sonesta

3 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.
Get rates
The Midtown Hotel MOD Collection by Sonesta
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 ...
9.6/10 Exceptional! (7,282 reviews)
"Great stay and clean property. Location was perfect!"

Reviewed on Sep 23, 2026

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The Dagny 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 ...
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Hilton Boston Park Plaza
See all 4,029 properties in Chelsea
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

Doubletree By Hilton Boston Logan Airport Chelsea

Doubletree By Hilton Boston Logan Airport Chelsea

4 out of 5
201 Everett Ave Chelsea MA
Stay at this hotel in Chelsea. Enjoy free WiFi, breakfast (surcharge), and a free airport shuttle. Our guests praise the helpful staff and the clean rooms in ...
Get rates
Doubletree By Hilton Boston Logan Airport Chelsea
Homewood Suites by Hilton Boston Logan Airport Chelsea

Homewood Suites by Hilton Boston Logan Airport Chelsea

3 out of 5
145 Beech St Chelsea MA
Book a stay at this business-friendly hotel in Chelsea. Enjoy free breakfast, free WiFi, and a 24-hour fitness center. Our guests praise the helpful staff in ...
8.8/10 Excellent! (1,001 reviews)
"Very nice hotel"

Reviewed on Sep 23, 2026

Get rates
Homewood Suites by Hilton Boston Logan Airport Chelsea
Residence Inn Boston Logan Airport/Chelsea

Residence Inn Boston Logan Airport/Chelsea

3.5 out of 5
200 Maple St Chelsea MA
Book a stay at this business-friendly hotel in Chelsea. Enjoy free breakfast, free WiFi, and a 24-hour fitness center. Our guests praise the helpful staff in ...
Get rates
Residence Inn Boston Logan Airport/Chelsea
TownePlace Suites Boston Logan Airport/Chelsea

TownePlace Suites Boston Logan Airport/Chelsea

3 out of 5
30 Eastern Avenue Chelsea MA
Book a stay at this business-friendly hotel in Chelsea. Enjoy free breakfast, free WiFi, and a free airport shuttle. Our guests praise the helpful staff and ...
8.6/10 Excellent! (1,008 reviews)
"The property was clean and modern. The location was in a poor neighborhood that was a little difficult to find, and there was no walk ability to restaurants."

Reviewed on Sep 23, 2026

Get rates
TownePlace Suites Boston Logan Airport/Chelsea
See all 4,029 properties in Chelsea
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.