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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 4 hours ago
$107
Roundtrip
found 4 hours ago
Select Breeze Airways flight, departing Sat, Nov 7 from Orlando Intl. to Portsmouth Intl., returning Sat, Nov 14, priced at $107 found 4 hours ago
Breeze Airways
Sat, Nov 7 - Sat, Nov 14
MCO
Orlando Intl.
PSM
Portsmouth Intl.
$108 Roundtrip, found 4 hours ago
$108
Roundtrip
found 4 hours ago
Select Breeze Airways flight, departing Sat, Nov 7 from Orlando Intl. to Portsmouth Intl., returning Sat, Nov 14, priced at $108 found 4 hours ago
Breeze Airways
Sat, Nov 7 - Sat, Nov 14
MCO
Orlando Intl.
PSM
Portsmouth Intl.
$112 Roundtrip, found 4 hours ago
$112
Roundtrip
found 4 hours ago
Select Breeze Airways flight, departing Sat, Nov 7 from Orlando Intl. to Portsmouth Intl., returning Sat, Nov 14, priced at $112 found 4 hours 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 4 hours ago
$117
Roundtrip
found 4 hours ago
Select Breeze Airways flight, departing Sat, Nov 7 from Orlando Intl. to Portsmouth Intl., returning Sat, Nov 14, priced at $117 found 4 hours ago
Breeze Airways
Sat, Nov 7 - Sat, Nov 14
MCO
Orlando Intl.
PSM
Portsmouth Intl.
$118 Roundtrip, found 4 hours ago
$118
Roundtrip
found 4 hours ago
Select Breeze Airways flight, departing Sat, Nov 7 from Orlando Intl. to Portsmouth Intl., returning Sat, Nov 14, priced at $118 found 4 hours ago
Allegiant Air
Sat, Oct 31 - Sat, Nov 14
FLL
Fort Lauderdale - Hollywood Intl.
BOS
Logan Intl.
$138 Roundtrip, found 16 hours ago
$138
Roundtrip
found 16 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 16 hours ago
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
JetBlue Airways
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 JetBlue Airways 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 1 hour ago
$177
Roundtrip
found 1 hour 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 1 hour 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, found 1 hour ago
$199
Roundtrip
found 1 hour ago
Select United flight, departing Sat, Oct 24 from Orlando Intl. to Logan Intl., returning Tue, Nov 10, priced at $199 found 1 hour ago
Bargain Flight
Fri, Dec 25 - Fri, Jan 1
PHL
Philadelphia Intl.
BOS
Logan Intl.
$277 Roundtrip, found 2 days ago
$277
Roundtrip
found 2 days ago
Select Bargain Flight flight, departing Fri, Dec 25 from Philadelphia Intl. to Logan Intl., returning Fri, Jan 1, priced at $277 found 2 days ago
Alaska Airlines
Thu, Dec 3 - Mon, Dec 7
MCO
Orlando Intl.
BOS
Logan Intl.
$533 Roundtrip, found 1 day ago
$533
Roundtrip
found 1 day ago
Select Alaska Airlines flight, departing Thu, Dec 3 from Orlando Intl. to Logan Intl., returning Mon, Dec 7, priced at $533 found 1 day ago
American Airlines
Tue, Sep 29 - Wed, Sep 30
TTN
Mercer
BOS
Logan Intl.
$783 Roundtrip, found 4 days ago
$783
Roundtrip
found 4 days ago
Select American Airlines flight, departing Tue, Sep 29 from Mercer to Logan Intl., returning Wed, Sep 30, priced at $783 found 4 days 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 ...
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 ...
8.6/10 Excellent! (1,001 reviews)
"Staff was nice and very helpful"

Reviewed on Sep 25, 2026

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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 ...
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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! (2,957 reviews)
"Clean hotel, best part was the Lynx gym. We stayed in the Wicked small room with a queen size bed. They’re not lying when they say it’s WICKED SMALL. The bathroom especially. Shower pressure is as really bad, but took advantage of the gym showers. The toilet is super low. Other than that, cannot ..."

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! (7,289 reviews)
"Beds were to soft and pillow could have been better"

Reviewed on Sep 26, 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 ...
9/10 Wonderful! (3,705 reviews)
"Excellent location for downtown sights."

Reviewed on Sep 25, 2026

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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 ...
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.