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Middleborough

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Middleborough Flights as Low as $162

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

JetBlue Airways
Wed, Aug 5 - Wed, Aug 5
ORD
O'Hare Intl.
BOS
Logan Intl.
$162 Roundtrip, found 20 hours ago
$162
Roundtrip
found 20 hours ago
Select JetBlue Airways flight, departing Wed, Aug 5 from O'Hare Intl. to Logan Intl., returning Wed, Aug 5, priced at $162 found 20 hours ago
JetBlue Airways
Tue, Aug 4 - Wed, Aug 12
ORD
O'Hare Intl.
BOS
Logan Intl.
$167 Roundtrip, found 20 hours ago
$167
Roundtrip
found 20 hours ago
Select JetBlue Airways flight, departing Tue, Aug 4 from O'Hare Intl. to Logan Intl., returning Wed, Aug 12, priced at $167 found 20 hours ago
United
Tue, Jun 30 - Tue, Jul 7
ORD
O'Hare Intl.
BOS
Logan Intl.
$167 Roundtrip, found 4 days ago
$167
Roundtrip
found 4 days ago
Select United flight, departing Tue, Jun 30 from O'Hare Intl. to Logan Intl., returning Tue, Jul 7, priced at $167 found 4 days ago
JetBlue Airways
Sat, May 23 - Wed, Jun 10
ORD
O'Hare Intl.
BOS
Logan Intl.
$171 Roundtrip, found 4 days ago
$171
Roundtrip
found 4 days ago
Select JetBlue Airways flight, departing Sat, May 23 from O'Hare Intl. to Logan Intl., returning Wed, Jun 10, priced at $171 found 4 days ago
JetBlue Airways
Thu, Aug 6 - Wed, Aug 12
ORD
O'Hare Intl.
BOS
Logan Intl.
$172 Roundtrip, found 20 hours ago
$172
Roundtrip
found 20 hours ago
Select JetBlue Airways flight, departing Thu, Aug 6 from O'Hare Intl. to Logan Intl., returning Wed, Aug 12, priced at $172 found 20 hours ago
American Airlines
Wed, Aug 5 - Thu, Aug 6
ORD
O'Hare Intl.
BOS
Logan Intl.
$172 Roundtrip, found 20 hours ago
$172
Roundtrip
found 20 hours ago
Select American Airlines flight, departing Wed, Aug 5 from O'Hare Intl. to Logan Intl., returning Thu, Aug 6, priced at $172 found 20 hours ago
JetBlue Airways
Fri, Jun 5 - Wed, Jun 10
ORD
O'Hare Intl.
BOS
Logan Intl.
$176 Roundtrip, found 2 days ago
$176
Roundtrip
found 2 days ago
Select JetBlue Airways flight, departing Fri, Jun 5 from O'Hare Intl. to Logan Intl., returning Wed, Jun 10, priced at $176 found 2 days ago
United
Tue, Jun 30 - Tue, Jul 7
ORD
O'Hare Intl.
BOS
Logan Intl.
$177 Roundtrip, found 4 days ago
$177
Roundtrip
found 4 days ago
Select United flight, departing Tue, Jun 30 from O'Hare Intl. to Logan Intl., returning Tue, Jul 7, priced at $177 found 4 days ago
JetBlue Airways
Fri, Jun 5 - Mon, Jun 15
ORD
O'Hare Intl.
BOS
Logan Intl.
$181 Roundtrip, found 2 days ago
$181
Roundtrip
found 2 days ago
Select JetBlue Airways flight, departing Fri, Jun 5 from O'Hare Intl. to Logan Intl., returning Mon, Jun 15, priced at $181 found 2 days ago
Frontier Airlines
Tue, May 12 - Tue, May 19
ORD
O'Hare Intl.
BOS
Logan Intl.
$184 Roundtrip, found 3 days ago
$184
Roundtrip
found 3 days ago
Select Frontier Airlines flight, departing Tue, May 12 from O'Hare Intl. to Logan Intl., returning Tue, May 19, priced at $184 found 3 days ago
Frontier Airlines
Tue, May 12 - Sat, May 16
ORD
O'Hare Intl.
BOS
Logan Intl.
$185 Roundtrip, found 2 days ago
$185
Roundtrip
found 2 days ago
Select Frontier Airlines flight, departing Tue, May 12 from O'Hare Intl. to Logan Intl., returning Sat, May 16, priced at $185 found 2 days ago
Delta
Thu, Jun 11 - Thu, Jun 11
ORD
O'Hare Intl.
BOS
Logan Intl.
$210 Roundtrip, found 2 days ago
$210
Roundtrip
found 2 days ago
Select Delta flight, departing Thu, Jun 11 from O'Hare Intl. to Logan Intl., returning Thu, Jun 11, priced at $210 found 2 days ago
American Airlines
Tue, Aug 18 - Sat, Sep 5
ORD
O'Hare Intl.
HYA
Barnstable Municipal
$235 Roundtrip, found 2 days ago
$235
Roundtrip
found 2 days ago
Select American Airlines flight, departing Tue, Aug 18 from O'Hare Intl. to Barnstable Municipal, returning Sat, Sep 5, priced at $235 found 2 days ago
American Airlines
Tue, May 19 - Wed, May 27
ORD
O'Hare Intl.
PVD
T.F. Green
$237 Roundtrip, found 3 days ago
$237
Roundtrip
found 3 days ago
Select American Airlines flight, departing Tue, May 19 from O'Hare Intl. to T.F. Green, returning Wed, May 27, priced at $237 found 3 days ago
Spirit Airlines
Tue, May 12 - Tue, May 19
ORD
O'Hare Intl.
BOS
Logan Intl.
$354 Roundtrip, found 3 days ago
$354
Roundtrip
found 3 days ago
Select Spirit Airlines flight, departing Tue, May 12 from O'Hare Intl. to Logan Intl., returning Tue, May 19, priced at $354 found 3 days ago
American Airlines
Tue, Aug 11 - Tue, Aug 18
ORD
O'Hare Intl.
MVY
Martha's Vineyard
$354 Roundtrip, found 17 hours ago
$354
Roundtrip
found 17 hours ago
Select American Airlines flight, departing Tue, Aug 11 from O'Hare Intl. to Martha's Vineyard, returning Tue, Aug 18, priced at $354 found 17 hours ago

Cheap Flights to Middleborough

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

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

Frequently Asked Questions About flights to Middleborough

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

What is the cheapest month to fly to Middleborough?

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 Middleborough are in August, but when you book your flight on Hotwire, savings are always in season.

How many airlines fly to Middleborough?

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 Middleborough.

What airport is best to fly into Middleborough?

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

How much are flights to Middleborough?

Got very cheap flights on your vacation itinerary? When you book your airline tickets to Middleborough on Hotwire, you may just get what’s on your getaway wish list. With tickets as low as $162, 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 Middleborough?

The trick to saving a stack of cash on your flight to Middleborough? 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 $162 right now, why wait?

Middleborough Flight Information
Destination airport
Logan Intl.
Destination airport IATA code
BOS
Roundtrip price
$161

Last Minute Hotel Deals in Middleborough

Red Roof Inn & Suites Middleborough

Red Roof Inn & Suites Middleborough

2 out of 5
30 East Clark Street Middleborough MA
Book a stay at this business-friendly hotel in Middleborough. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the ...
7.2/10 Good! (1,000 reviews)
Not clean. No coffee cups at all. No breakfast at all

Reviewed on Apr 24, 2026

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Red Roof Inn & Suites Middleborough
Fairfield by Marriott Inn & Suites Raynham Middleborough/Plymouth

Fairfield by Marriott Inn & Suites Raynham Middleborough/Plymouth

3 out of 5
4 Chalet Rd Middleborough MA
Book a stay at this business-friendly hotel in Middleborough. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. ...
8.4/10 Very Good! (549 reviews)
Bathroom shower door got stuck with me my wife inside shower fortunately i was available and got her out. Lighting over sink very poor for shaving needs

Reviewed on Apr 11, 2026

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Fairfield by Marriott Inn & Suites Raynham Middleborough/Plymouth
Garner Hotel Brockton - Boston by IHG

Garner Hotel Brockton - Boston by IHG

2.5 out of 5
405 Westgate Dr. Brockton MA
Book a stay at this business-friendly hotel in Brockton. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. ...
8.2/10 Very Good! (1,001 reviews)
Mid at best hotel.

Reviewed on Apr 27, 2026

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Garner Hotel Brockton - Boston by IHG
Sea Crest Beach Resort

Sea Crest Beach Resort

3.5 out of 5
350 Quaker Rd North Falmouth MA
Book a stay at this beach hotel in North Falmouth. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff and the clean rooms ...
8/10 Very Good! (269 reviews)
The beach view is beautiful and bar and restaurant is incredible.

Reviewed on Apr 26, 2026

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Sea Crest Beach Resort
AutoCamp Cape Cod

AutoCamp Cape Cod

4 out of 5
836 Palmer Avenue Falmouth MA
Stay at this holiday park in Falmouth. Enjoy free WiFi, free parking, and free bicycles on site. Our guests praise the helpful staff in our reviews. Popular ...
9.4/10 Exceptional! (315 reviews)
Very good, very comfortable, very nice service.I love it!! I recommended one hundred %

Reviewed on Apr 21, 2026

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AutoCamp Cape Cod
Sonesta Select Boston Foxborough Mansfield

Sonesta Select Boston Foxborough Mansfield

3 out of 5
35 Foxborough Boulevard Foxborough MA
Book a stay at this business-friendly hotel in Foxborough. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and ...
8.4/10 Very Good! (1,001 reviews)
Having the balcony is the best part. Beautiful little courtyard. And the patio on the first floor is perfect for dogs

Reviewed on Apr 26, 2026

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Sonesta Select Boston Foxborough Mansfield
Red Roof Inn PLUS+ Boston - Mansfield/ Foxboro

Red Roof Inn PLUS+ Boston - Mansfield/ Foxboro

2.5 out of 5
60 Forbes Blvd Mansfield MA
Book a stay at this business-friendly hotel in Mansfield. Enjoy free WiFi, free parking, and a 24-hour front desk. Our guests praise the helpful staff and the ...
7.8/10 Good! (1,000 reviews)
Everything was good

Reviewed on Apr 23, 2026

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Red Roof Inn PLUS+ Boston - Mansfield/ Foxboro
Motel 6 Brockton, MA

Motel 6 Brockton, MA

2 out of 5
391 Westgate Dr Brockton MA
Stay at this motel in Brockton. Enjoy free WiFi, free parking, and a 24-hour front desk. Our guests praise the helpful staff and the clean rooms in our reviews. ...
6.8/10 (1,338 reviews)
Drugs & prostitution

Reviewed on Apr 21, 2026

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Motel 6 Brockton, MA
See all 1,847 properties in Middleborough
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.