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Chelsea

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Chelsea Flights as Low as $148

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

Breeze Airways
Thu, Sep 3 - Sat, Sep 5
MCO
Orlando Intl.
PSM
Portsmouth Intl.
$148 Roundtrip, found 2 hours ago
$148
Roundtrip
found 2 hours ago
Select Breeze Airways flight, departing Thu, Sep 3 from Orlando Intl. to Portsmouth Intl., returning Sat, Sep 5, priced at $148 found 2 hours ago
Frontier Airlines
Sat, Sep 26 - Fri, Oct 2
MCO
Orlando Intl.
BOS
Logan Intl.
$150 Roundtrip, found 3 hours ago
$150
Roundtrip
found 3 hours ago
Select Frontier Airlines flight, departing Sat, Sep 26 from Orlando Intl. to Logan Intl., returning Fri, Oct 2, priced at $150 found 3 hours ago
Breeze Airways
Thu, Sep 3 - Sat, Sep 5
MCO
Orlando Intl.
PSM
Portsmouth Intl.
$153 Roundtrip, found 2 hours ago
$153
Roundtrip
found 2 hours ago
Select Breeze Airways flight, departing Thu, Sep 3 from Orlando Intl. to Portsmouth Intl., returning Sat, Sep 5, priced at $153 found 2 hours ago
Frontier Airlines
Sat, Sep 26 - Sat, Oct 3
MCO
Orlando Intl.
BOS
Logan Intl.
$154 Roundtrip, found 3 hours ago
$154
Roundtrip
found 3 hours ago
Select Frontier Airlines flight, departing Sat, Sep 26 from Orlando Intl. to Logan Intl., returning Sat, Oct 3, priced at $154 found 3 hours ago
Breeze Airways
Thu, Sep 3 - Sat, Sep 5
MCO
Orlando Intl.
PSM
Portsmouth Intl.
$158 Roundtrip, found 2 hours ago
$158
Roundtrip
found 2 hours ago
Select Breeze Airways flight, departing Thu, Sep 3 from Orlando Intl. to Portsmouth Intl., returning Sat, Sep 5, priced at $158 found 2 hours ago
Breeze Airways
Thu, Sep 3 - Sat, Sep 5
MCO
Orlando Intl.
PSM
Portsmouth Intl.
$160 Roundtrip, found 13 hours ago
$160
Roundtrip
found 13 hours ago
Select Breeze Airways flight, departing Thu, Sep 3 from Orlando Intl. to Portsmouth Intl., returning Sat, Sep 5, priced at $160 found 13 hours ago
Breeze Airways
Thu, Sep 3 - Sun, Sep 6
MCO
Orlando Intl.
PSM
Portsmouth Intl.
$163 Roundtrip, found 1 day ago
$163
Roundtrip
found 1 day ago
Select Breeze Airways flight, departing Thu, Sep 3 from Orlando Intl. to Portsmouth Intl., returning Sun, Sep 6, priced at $163 found 1 day ago
Breeze Airways
Thu, Aug 27 - Sun, Aug 30
MCO
Orlando Intl.
PSM
Portsmouth Intl.
$164 Roundtrip, found 1 day ago
$164
Roundtrip
found 1 day ago
Select Breeze Airways flight, departing Thu, Aug 27 from Orlando Intl. to Portsmouth Intl., returning Sun, Aug 30, priced at $164 found 1 day ago
JetBlue Airways
Tue, Sep 29 - Sat, Oct 3
MCO
Orlando Intl.
BOS
Logan Intl.
$199 Roundtrip, found 2 hours ago
$199
Roundtrip
found 2 hours ago
Select JetBlue Airways flight, departing Tue, Sep 29 from Orlando Intl. to Logan Intl., returning Sat, Oct 3, priced at $199 found 2 hours ago
Delta
Tue, Sep 29 - Tue, Oct 6
MCO
Orlando Intl.
BOS
Logan Intl.
$199 Roundtrip, found 3 hours ago
$199
Roundtrip
found 3 hours ago
Select Delta flight, departing Tue, Sep 29 from Orlando Intl. to Logan Intl., returning Tue, Oct 6, priced at $199 found 3 hours ago
United
Tue, Sep 29 - Sat, Oct 3
MCO
Orlando Intl.
BOS
Logan Intl.
$219 Roundtrip, found 2 hours ago
$219
Roundtrip
found 2 hours ago
Select United flight, departing Tue, Sep 29 from Orlando Intl. to Logan Intl., returning Sat, Oct 3, priced at $219 found 2 hours ago
JetBlue Airways
Tue, Sep 22 - Wed, Sep 23
SAN
San Diego Intl.
BOS
Logan Intl.
$252 Roundtrip, found 5 days ago
$252
Roundtrip
found 5 days ago
Select JetBlue Airways flight, departing Tue, Sep 22 from San Diego Intl. to Logan Intl., returning Wed, Sep 23, priced at $252 found 5 days ago
American Airlines
Wed, Sep 23 - Sat, Sep 26
SAN
San Diego Intl.
BOS
Logan Intl.
$277 Roundtrip, found 5 days ago
$277
Roundtrip
found 5 days ago
Select American Airlines flight, departing Wed, Sep 23 from San Diego Intl. to Logan Intl., returning Sat, Sep 26, priced at $277 found 5 days ago
Alaska Airlines
Thu, Sep 24 - Fri, Sep 25
SAN
San Diego Intl.
BOS
Logan Intl.
$285 Roundtrip, found 5 days ago
$285
Roundtrip
found 5 days ago
Select Alaska Airlines flight, departing Thu, Sep 24 from San Diego Intl. to Logan Intl., returning Fri, Sep 25, priced at $285 found 5 days ago
Delta
Tue, Nov 3 - Tue, Nov 17
TUS
Tucson Intl.
BOS
Logan Intl.
$355 Roundtrip, found 21 hours ago
$355
Roundtrip
found 21 hours ago
Select Delta flight, departing Tue, Nov 3 from Tucson Intl. to Logan Intl., returning Tue, Nov 17, priced at $355 found 21 hours ago
American Airlines
Wed, Sep 23 - Sat, Sep 26
CLD
McClellan-Palomar
BOS
Logan Intl.
$465 Roundtrip, found 5 days ago
$465
Roundtrip
found 5 days ago
Select American Airlines flight, departing Wed, Sep 23 from McClellan-Palomar to Logan Intl., returning Sat, Sep 26, priced at $465 found 5 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 September, 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 16 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 $148, 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 $148 right now, why wait?

Chelsea Flight Information
Destination airport
Portsmouth Intl.
Destination airport IATA code
PSM
Roundtrip price
$126

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! (1,856 reviews)
"The A/C was not turned on when we arrived, so it took a little while to cool the room."

Reviewed on Jul 17, 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. ...
9.2/10 Wonderful! (4,791 reviews)
"Great staff and awesome location. We’ve dined at Coquette, and the Turkish waiter was amazing. Thank you and we’ll be back again."

Reviewed on Jul 17, 2026

Get rates
Omni Boston Hotel at the Seaport
Hyatt Regency Boston/Cambridge

Hyatt Regency Boston/Cambridge

4 out of 5
575 Memorial Drive Cambridge MA
Book a stay at this business-friendly hotel in Cambridge. Enjoy free WiFi, breakfast (surcharge), and a 24-hour health club. Our guests praise the restaurant ...
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Hyatt Regency Boston/Cambridge
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
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 ...
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Encore Boston Harbor
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! (6,829 reviews)
"Restaurant staff were very helpful. Front desk staff not very accomodating"

Reviewed on Jul 17, 2026

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Harborside Inn Of 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.
8.2/10 Very Good! (624 reviews)
"Staff was great. The lobby clean and guest room nice size. However, the bathroom was small and coffee machine did not work. The facade okay Nice location."

Reviewed on Jul 17, 2026

Get rates
The Midtown Hotel MOD Collection by Sonesta
See all 4,180 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! (1,856 reviews)
"The A/C was not turned on when we arrived, so it took a little while to cool the room."

Reviewed on Jul 17, 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! (1,000 reviews)
"Morning breakfast was busy, took a little bit to get some coffee because it was empty, but it was quickly filled once reported to staff."

Reviewed on Jul 12, 2026

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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 ...
8.8/10 Excellent! (1,001 reviews)
"Very clean and breakfast was great."

Reviewed on Jul 16, 2026

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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 ...
8.8/10 Excellent! (1,000 reviews)
"Great Customer Service"

Reviewed on Jul 13, 2026

Get rates
TownePlace Suites Boston Logan Airport/Chelsea
See all 4,180 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.