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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 hour ago
$107
Roundtrip
found 1 hour ago
Select Breeze Airways flight, departing Sat, Nov 7 from Orlando Intl. to Portsmouth Intl., returning Sat, Nov 14, priced at $107 found 1 hour ago
Breeze Airways
Sat, Nov 7 - Sat, Nov 14
MCO
Orlando Intl.
PSM
Portsmouth Intl.
$108 Roundtrip, found 1 hour ago
$108
Roundtrip
found 1 hour ago
Select Breeze Airways flight, departing Sat, Nov 7 from Orlando Intl. to Portsmouth Intl., returning Sat, Nov 14, priced at $108 found 1 hour ago
Breeze Airways
Sat, Nov 7 - Sat, Nov 14
MCO
Orlando Intl.
PSM
Portsmouth Intl.
$112 Roundtrip, found 1 hour ago
$112
Roundtrip
found 1 hour ago
Select Breeze Airways flight, departing Sat, Nov 7 from Orlando Intl. to Portsmouth Intl., returning Sat, Nov 14, priced at $112 found 1 hour ago
Breeze Airways
Sat, Nov 7 - Sat, Nov 14
MCO
Orlando Intl.
PSM
Portsmouth Intl.
$113 Roundtrip, found 1 day ago
$113
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 $113 found 1 day ago
Breeze Airways
Sat, Nov 7 - Sat, Nov 14
MCO
Orlando Intl.
PSM
Portsmouth Intl.
$117 Roundtrip, found 1 hour ago
$117
Roundtrip
found 1 hour ago
Select Breeze Airways flight, departing Sat, Nov 7 from Orlando Intl. to Portsmouth Intl., returning Sat, Nov 14, priced at $117 found 1 hour ago
Breeze Airways
Sat, Nov 7 - Sat, Nov 14
MCO
Orlando Intl.
PSM
Portsmouth Intl.
$118 Roundtrip, found 1 hour ago
$118
Roundtrip
found 1 hour ago
Select Breeze Airways flight, departing Sat, Nov 7 from Orlando Intl. to Portsmouth Intl., returning Sat, Nov 14, priced at $118 found 1 hour ago
Breeze Airways
Sat, Nov 7 - Sat, Nov 14
MCO
Orlando Intl.
PSM
Portsmouth Intl.
$122 Roundtrip, found 1 day ago
$122
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 $122 found 1 day ago
Allegiant Air
Sat, Oct 31 - Sat, Nov 14
FLL
Fort Lauderdale - Hollywood Intl.
BOS
Logan Intl.
$138 Roundtrip, found 7 hours ago
$138
Roundtrip
found 7 hours ago
Select Allegiant Air flight, departing Sat, Oct 31 from Fort Lauderdale - Hollywood Intl. to Logan Intl., returning Sat, Nov 14, priced at $138 found 7 hours ago
JetBlue Airways
Sat, Oct 24 - Tue, Nov 10
MCO
Orlando Intl.
BOS
Logan Intl.
$159 Roundtrip, just found
$159
Roundtrip
just found
Select JetBlue Airways flight, departing Sat, Oct 24 from Orlando Intl. to Logan Intl., returning Tue, Nov 10, priced at $159 just found
Delta
Tue, Oct 20 - Tue, Oct 27
MCO
Orlando Intl.
BOS
Logan Intl.
$159 Roundtrip, found 2 hours ago
$159
Roundtrip
found 2 hours ago
Select Delta flight, departing Tue, Oct 20 from Orlando Intl. to Logan Intl., returning Tue, Oct 27, priced at $159 found 2 hours ago
American Airlines
Tue, Oct 20 - Tue, Oct 27
MCO
Orlando Intl.
BOS
Logan Intl.
$159 Roundtrip, found 2 hours ago
$159
Roundtrip
found 2 hours ago
Select American Airlines flight, departing Tue, Oct 20 from Orlando Intl. to Logan Intl., returning Tue, Oct 27, priced at $159 found 2 hours ago
Southwest Airlines
Wed, Nov 4 - Tue, Nov 10
FLL
Fort Lauderdale - Hollywood Intl.
BOS
Logan Intl.
$177 Roundtrip, found 12 hours ago
$177
Roundtrip
found 12 hours ago
Select Southwest Airlines flight, departing Wed, Nov 4 from Fort Lauderdale - Hollywood Intl. to Logan Intl., returning Tue, Nov 10, priced at $177 found 12 hours ago
Frontier Airlines
Sat, Oct 17 - Sat, Oct 24
MCO
Orlando Intl.
BOS
Logan Intl.
$192 Roundtrip, found 1 day ago
$192
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Sat, Oct 17 from Orlando Intl. to Logan Intl., returning Sat, Oct 24, priced at $192 found 1 day ago
United
Sat, Oct 24 - Tue, Nov 10
MCO
Orlando Intl.
BOS
Logan Intl.
$199 Roundtrip, just found
$199
Roundtrip
just found
Select United flight, departing Sat, Oct 24 from Orlando Intl. to Logan Intl., returning Tue, Nov 10, priced at $199 just found
Bargain Flight
Wed, Oct 21 - Tue, Nov 10
ATL
Hartsfield-Jackson Atlanta Intl.
BOS
Logan Intl.
$232 Roundtrip, found 1 day ago
$232
Roundtrip
found 1 day ago
Select Bargain Flight flight, departing Wed, Oct 21 from Hartsfield-Jackson Atlanta Intl. to Logan Intl., returning Tue, Nov 10, priced at $232 found 1 day ago
Alaska Airlines
Thu, Dec 3 - Mon, Dec 7
MCO
Orlando Intl.
BOS
Logan Intl.
$533 Roundtrip, found 17 hours ago
$533
Roundtrip
found 17 hours ago
Select Alaska Airlines flight, departing Thu, Dec 3 from Orlando Intl. to Logan Intl., returning Mon, Dec 7, priced at $533 found 17 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 ...
8.6/10 Excellent! (2,111 reviews)
"This was a nice one night stay after a long cruise and an early flight. Got there early, they secured my luggage which allowed me to walk the Freedom Trail. The staff was friendly and helpful and the shuttle got me to Logan right on time."

Reviewed on Sep 25, 2026

Get rates
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
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! (5,034 reviews)
"The hotel was clean and the fresh flowers in the lobby were beautiful. The bartender in the bar made a delicious espresso martini. Our room was clean, but the bathroom fan did not work and the tub had a huge piece scraped off. Also, the light in the coffee station was burned out. Overall, we enjoyed ..."

Reviewed on Sep 25, 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 ...
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The Revolution Hotel
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! (2,956 reviews)
"This hotel is all about location—very convenient to all Boston activities. The rooms were small and tired."

Reviewed on Sep 25, 2026

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Hilton Boston Park Plaza
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! (7,286 reviews)
"My stay was lovely, helpful staff and great location."

Reviewed on Sep 25, 2026

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The Dagny Boston
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 ...
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Omni Parker House
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 ...
8.6/10 Excellent! (2,111 reviews)
"This was a nice one night stay after a long cruise and an early flight. Got there early, they secured my luggage which allowed me to walk the Freedom Trail. The staff was friendly and helpful and the shuttle got me to Logan right on time."

Reviewed on Sep 25, 2026

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! (1,011 reviews)
"This was the perfect place to stay after a late night flight to Logan Airport. The shuttle driver was very friendly and the hotel was clean and the room was very comfortable. Our room had a kitchenette, which we didn't use, but it would be very useful for families or for a long-term stay."

Reviewed on Sep 25, 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.