Search Cheap Flights to
Wellesley

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Wellesley Flights as Low as $102

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

Breeze Airways
Wed, Oct 22 - Wed, Oct 22
MCO
Orlando Intl.
PSM
Portsmouth Intl.
$102 Roundtrip, just found
$102
Roundtrip
just found
Select Breeze Airways flight, departing Wed, Oct 22 from Orlando Intl. to Portsmouth Intl., returning Wed, Oct 22, priced at $102 just found
Breeze Airways
Wed, Oct 22 - Wed, Oct 22
MCO
Orlando Intl.
PSM
Portsmouth Intl.
$107 Roundtrip, found 3 days ago
$107
Roundtrip
found 3 days ago
Select Breeze Airways flight, departing Wed, Oct 22 from Orlando Intl. to Portsmouth Intl., returning Wed, Oct 22, priced at $107 found 3 days ago
American Airlines
Tue, Oct 28 - Tue, Nov 4
DCA
Ronald Reagan Washington National
BOS
Logan Intl.
$111 Roundtrip, found 9 hours ago
$111
Roundtrip
found 9 hours ago
Select American Airlines flight, departing Tue, Oct 28 from Ronald Reagan Washington National to Logan Intl., returning Tue, Nov 4, priced at $111 found 9 hours ago
American Airlines
Mon, Sep 1 - Tue, Sep 2
DCA
Ronald Reagan Washington National
BOS
Logan Intl.
$113 Roundtrip, found 22 hours ago
$113
Roundtrip
found 22 hours ago
Select American Airlines flight, departing Mon, Sep 1 from Ronald Reagan Washington National to Logan Intl., returning Tue, Sep 2, priced at $113 found 22 hours ago
Frontier Airlines
Fri, Aug 1 - Sat, Aug 16
MCO
Orlando Intl.
BOS
Logan Intl.
$114 Roundtrip, just found
$114
Roundtrip
just found
Select Frontier Airlines flight, departing Fri, Aug 1 from Orlando Intl. to Logan Intl., returning Sat, Aug 16, priced at $114 just found
American Airlines
Tue, Oct 28 - Tue, Nov 4
DCA
Ronald Reagan Washington National
BOS
Logan Intl.
$116 Roundtrip, found 9 hours ago
$116
Roundtrip
found 9 hours ago
Select American Airlines flight, departing Tue, Oct 28 from Ronald Reagan Washington National to Logan Intl., returning Tue, Nov 4, priced at $116 found 9 hours ago
Delta
Tue, Oct 28 - Tue, Nov 4
DCA
Ronald Reagan Washington National
BOS
Logan Intl.
$117 Roundtrip, found 9 hours ago
$117
Roundtrip
found 9 hours ago
Select Delta flight, departing Tue, Oct 28 from Ronald Reagan Washington National to Logan Intl., returning Tue, Nov 4, priced at $117 found 9 hours ago
Delta
Thu, Sep 11 - Thu, Sep 11
DCA
Ronald Reagan Washington National
BOS
Logan Intl.
$119 Roundtrip, found 7 hours ago
$119
Roundtrip
found 7 hours ago
Select Delta flight, departing Thu, Sep 11 from Ronald Reagan Washington National to Logan Intl., returning Thu, Sep 11, priced at $119 found 7 hours ago
United
Wed, Aug 20 - Sat, Sep 6
ORD
O'Hare Intl.
BOS
Logan Intl.
$121 Roundtrip, found 1 day ago
$121
Roundtrip
found 1 day ago
Select United flight, departing Wed, Aug 20 from O'Hare Intl. to Logan Intl., returning Sat, Sep 6, priced at $121 found 1 day ago
Spirit Airlines
Fri, Aug 1 - Sat, Aug 16
MCO
Orlando Intl.
BOS
Logan Intl.
$122 Roundtrip, just found
$122
Roundtrip
just found
Select Spirit Airlines flight, departing Fri, Aug 1 from Orlando Intl. to Logan Intl., returning Sat, Aug 16, priced at $122 just found
Frontier Airlines
Fri, Aug 1 - Sat, Aug 16
MCO
Orlando Intl.
BOS
Logan Intl.
$123 Roundtrip, just found
$123
Roundtrip
just found
Select Frontier Airlines flight, departing Fri, Aug 1 from Orlando Intl. to Logan Intl., returning Sat, Aug 16, priced at $123 just found
American Airlines
Wed, Aug 20 - Sat, Sep 6
ORD
O'Hare Intl.
BOS
Logan Intl.
$123 Roundtrip, found 1 day ago
$123
Roundtrip
found 1 day ago
Select American Airlines flight, departing Wed, Aug 20 from O'Hare Intl. to Logan Intl., returning Sat, Sep 6, priced at $123 found 1 day ago
JetBlue Airways
Thu, Sep 4 - Mon, Sep 8
ORD
O'Hare Intl.
BOS
Logan Intl.
$127 Roundtrip, found 2 days ago
$127
Roundtrip
found 2 days ago
Select JetBlue Airways flight, departing Thu, Sep 4 from O'Hare Intl. to Logan Intl., returning Mon, Sep 8, priced at $127 found 2 days ago
American Airlines
Wed, Aug 20 - Thu, Aug 21
MCO
Orlando Intl.
ORH
Worcester Regional
$156 Roundtrip, found 1 hour ago
$156
Roundtrip
found 1 hour ago
Select American Airlines flight, departing Wed, Aug 20 from Orlando Intl. to Worcester Regional, returning Thu, Aug 21, priced at $156 found 1 hour ago
American Airlines
Wed, Aug 20 - Fri, Aug 22
ORD
O'Hare Intl.
ORH
Worcester Regional
$186 Roundtrip, found 15 hours ago
$186
Roundtrip
found 15 hours ago
Select American Airlines flight, departing Wed, Aug 20 from O'Hare Intl. to Worcester Regional, returning Fri, Aug 22, priced at $186 found 15 hours ago
Delta
Mon, Nov 24 - Tue, Dec 2
DCA
Ronald Reagan Washington National
ORH
Worcester Regional
$232 Roundtrip, found 1 day ago
$232
Roundtrip
found 1 day ago
Select Delta flight, departing Mon, Nov 24 from Ronald Reagan Washington National to Worcester Regional, returning Tue, Dec 2, priced at $232 found 1 day ago

Cheap Flights to Wellesley

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

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

Frequently Asked Questions About flights to Wellesley

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

What is the cheapest month to fly to Wellesley?

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 Wellesley are in October, but when you book your flight on Hotwire, savings are always in season.

How many airlines fly to Wellesley?

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 Wellesley.

What airport is best to fly into Wellesley?

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

How much are flights to Wellesley?

Got very cheap flights on your vacation itinerary? When you book your airline tickets to Wellesley on Hotwire, you may just get what’s on your getaway wish list. With tickets as low as $102, 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 Wellesley?

The trick to saving a stack of cash on your flight to Wellesley? 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 $102 right now, why wait?

Wellesley Flight Information
Destination airport
Portsmouth Intl.
Destination airport IATA code
PSM
Roundtrip price
$101

Last Minute Hotel Deals in Wellesley

Omni Boston Hotel at the Seaport

Omni Boston Hotel at the Seaport

4 out of 5
450 Summer Street, Boston, MA
Stay at this 4-star spa hotel in Boston. Enjoy free WiFi, a full-service spa, and 4 restaurants. Our guests praise the breakfast and the pool in our reviews. ...
9/10 Wonderful! (3,707 reviews)
"It was great"

Reviewed on Jul 23, 2025

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Omni Boston Hotel at the Seaport
citizenM Boston Back Bay

citizenM Boston Back Bay

4 out of 5
408 Newbury street, Boston, MA
Stay at this 4-star hotel in Boston. Enjoy free WiFi, breakfast (surcharge), and a 24-hour fitness center. Popular attractions Fenway Park and Copley Square ...
9.2/10 Wonderful! (1,481 reviews)
"Very nice and modern, easy to move around nicely located."

Reviewed on Jul 22, 2025

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citizenM Boston Back Bay
citizenM Boston North Station

citizenM Boston North Station

4 out of 5
80-120 Causeway Street, Boston, MA
Stay at this 4-star business-friendly hotel in Boston. Enjoy free WiFi, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the breakfast ...
9.2/10 Wonderful! (3,572 reviews)
"It was an amazing experience especially for my first time in boston, however, my fiancee was walked into by an employee while he was in a stall using the bathroom. His stall door was wide open and she just started cleaning it like he wasnt there. Other than that amazing workers, very kind and ..."

Reviewed on Jul 22, 2025

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citizenM Boston North Station
Harborside Inn Of Boston

Harborside Inn Of Boston

4 out of 5
185 State St, Boston, MA
Stay at this 4-star 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 ...
9/10 Wonderful! (5,380 reviews)
"I wish they’d offer coffee in the morning. But that wasn’t a deal breaker for us. Great staff!!"

Reviewed on Jul 23, 2025

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Harborside Inn Of Boston
Copley Square Hotel, a FOUND Hotel

Copley Square Hotel, a FOUND Hotel

4 out of 5
47 Huntington Ave, Boston, MA
Stay at this 4-star boutique hotel in Boston. Enjoy free WiFi, valet parking (surcharge), and a 24-hour front desk. Our guests praise the restaurant and the ...
8.4/10 Very Good! (3,778 reviews)
"Thank you to the staff at Copley Square- you made are stay in Boston comfortable and enjoyable."

Reviewed on Jul 22, 2025

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Copley Square Hotel, a FOUND Hotel
The Revolution Hotel

The Revolution Hotel

3.5 out of 5
40 Berkeley Street, Boston, MA
Stay at this 3.5-star hotel in Boston. Enjoy free WiFi, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the restaurant and the helpful ...
8.8/10 Excellent! (2,095 reviews)
"I appreciate the communal living concept of this hotel. The staff was friendly and helpful. The location of this hotel is walkable and convenient."

Reviewed on Jul 23, 2025

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The Revolution Hotel
The Godfrey Hotel Boston

The Godfrey Hotel Boston

4 out of 5
505 Washington Street, Boston, MA
Stay at this 4-star boutique hotel in Boston. Enjoy breakfast (surcharge), room service, and a 24-hour fitness center. Our guests praise the restaurant and the ...
9.4/10 Exceptional! (4,205 reviews)
"Gre"

Reviewed on Jul 23, 2025

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The Godfrey Hotel Boston
Hyatt Regency Boston/Cambridge

Hyatt Regency Boston/Cambridge

4 out of 5
575 Memorial Drive, Cambridge, MA
Stay at this 4-star business-friendly hotel in Cambridge. Enjoy free WiFi, a 24-hour health club, and valet parking (surcharge). Our guests praise the restaurant ...
8.8/10 Excellent! (2,019 reviews)
"Very helpful staff! Spacious rooms"

Reviewed on Jul 23, 2025

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Hyatt Regency Boston/Cambridge
See all 3,534 properties in Wellesley
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.