Cheap Flights To Medway 2025

Photo by Beth Comstock

Medway Flights as Low as $112

These prices were available within the past 7 days. Prices quoted are per person, round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Breeze Airways
Sat, Jul 19 - Sat, Aug 23
MCO
Orlando Intl.
PSM
Portsmouth Intl.
$112 Roundtrip, found 5 days ago
$112
Roundtrip
found 5 days ago
Select Breeze Airways flight, departing Sat, Jul 19 from Orlando Intl. to Portsmouth Intl., returning Sat, Aug 23, priced at $112 found 5 days ago
Breeze Airways
Sat, Jul 19 - Sat, Aug 23
MCO
Orlando Intl.
PSM
Portsmouth Intl.
$117 Roundtrip, found 5 days ago
$117
Roundtrip
found 5 days ago
Select Breeze Airways flight, departing Sat, Jul 19 from Orlando Intl. to Portsmouth Intl., returning Sat, Aug 23, priced at $117 found 5 days ago
Spirit Airlines
Wed, Sep 3 - Wed, Sep 3
MCO
Orlando Intl.
BOS
Logan Intl.
$119 Roundtrip, found 21 hours ago
$119
Roundtrip
found 21 hours ago
Select Spirit Airlines flight, departing Wed, Sep 3 from Orlando Intl. to Logan Intl., returning Wed, Sep 3, priced at $119 found 21 hours ago
Breeze Airways
Sat, Jul 19 - Sat, Aug 23
MCO
Orlando Intl.
PSM
Portsmouth Intl.
$122 Roundtrip, found 5 days ago
$122
Roundtrip
found 5 days ago
Select Breeze Airways flight, departing Sat, Jul 19 from Orlando Intl. to Portsmouth Intl., returning Sat, Aug 23, priced at $122 found 5 days ago
Spirit Airlines
Sun, Sep 7 - Sun, Sep 7
MCO
Orlando Intl.
BOS
Logan Intl.
$137 Roundtrip, found 21 hours ago
$137
Roundtrip
found 21 hours ago
Select Spirit Airlines flight, departing Sun, Sep 7 from Orlando Intl. to Logan Intl., returning Sun, Sep 7, priced at $137 found 21 hours ago
Frontier Airlines
Fri, Sep 19 - Sun, Sep 21
MCO
Orlando Intl.
BOS
Logan Intl.
$140 Roundtrip, found 2 days ago
$140
Roundtrip
found 2 days ago
Select Frontier Airlines flight, departing Fri, Sep 19 from Orlando Intl. to Logan Intl., returning Sun, Sep 21, priced at $140 found 2 days ago
Spirit Airlines
Tue, Sep 2 - Tue, Sep 2
MCO
Orlando Intl.
BOS
Logan Intl.
$145 Roundtrip, found 21 hours ago
$145
Roundtrip
found 21 hours ago
Select Spirit Airlines flight, departing Tue, Sep 2 from Orlando Intl. to Logan Intl., returning Tue, Sep 2, priced at $145 found 21 hours ago
Frontier Airlines
Mon, Sep 22 - Thu, Sep 25
MCO
Orlando Intl.
BOS
Logan Intl.
$148 Roundtrip, found 2 days ago
$148
Roundtrip
found 2 days ago
Select Frontier Airlines flight, departing Mon, Sep 22 from Orlando Intl. to Logan Intl., returning Thu, Sep 25, priced at $148 found 2 days ago
Spirit Airlines
Sat, Jul 5 - Sat, Jul 5
MCO
Orlando Intl.
BOS
Logan Intl.
$149 Roundtrip, found 13 hours ago
$149
Roundtrip
found 13 hours ago
Select Spirit Airlines flight, departing Sat, Jul 5 from Orlando Intl. to Logan Intl., returning Sat, Jul 5, priced at $149 found 13 hours ago
Spirit Airlines
Tue, Jul 1 - Mon, Jul 7
MCO
Orlando Intl.
BOS
Logan Intl.
$150 Roundtrip, found 13 hours ago
$150
Roundtrip
found 13 hours ago
Select Spirit Airlines flight, departing Tue, Jul 1 from Orlando Intl. to Logan Intl., returning Mon, Jul 7, priced at $150 found 13 hours ago
Spirit Airlines
Fri, Jul 4 - Mon, Jul 7
MCO
Orlando Intl.
BOS
Logan Intl.
$160 Roundtrip, found 13 hours ago
$160
Roundtrip
found 13 hours ago
Select Spirit Airlines flight, departing Fri, Jul 4 from Orlando Intl. to Logan Intl., returning Mon, Jul 7, priced at $160 found 13 hours ago
Spirit Airlines
Sat, Sep 6 - Mon, Sep 8
MCO
Orlando Intl.
BOS
Logan Intl.
$164 Roundtrip, just found
$164
Roundtrip
just found
Select Spirit Airlines flight, departing Sat, Sep 6 from Orlando Intl. to Logan Intl., returning Mon, Sep 8, priced at $164 just found
JetBlue Airways
Wed, Jun 25 - Tue, Jul 8
MCO
Orlando Intl.
ORH
Worcester Regional
$183 Roundtrip, found 2 days ago
$183
Roundtrip
found 2 days ago
Select JetBlue Airways flight, departing Wed, Jun 25 from Orlando Intl. to Worcester Regional, returning Tue, Jul 8, priced at $183 found 2 days ago
United
Sat, Sep 6 - Mon, Sep 8
MCO
Orlando Intl.
BOS
Logan Intl.
$197 Roundtrip, just found
$197
Roundtrip
just found
Select United flight, departing Sat, Sep 6 from Orlando Intl. to Logan Intl., returning Mon, Sep 8, priced at $197 just found
Delta
Sat, Sep 6 - Mon, Sep 8
MCO
Orlando Intl.
BOS
Logan Intl.
$208 Roundtrip, just found
$208
Roundtrip
just found
Select Delta flight, departing Sat, Sep 6 from Orlando Intl. to Logan Intl., returning Mon, Sep 8, priced at $208 just found
American Airlines
Sat, Sep 6 - Mon, Sep 8
MCO
Orlando Intl.
BOS
Logan Intl.
$228 Roundtrip, just found
$228
Roundtrip
just found
Select American Airlines flight, departing Sat, Sep 6 from Orlando Intl. to Logan Intl., returning Mon, Sep 8, priced at $228 just found

Flight Travel Guide to Medway

Book your next flight to (airport) if Medway is calling your name. And with the AARP Travel Center Powered by Expedia®, can become a reality sooner than you think. AARP Travel combines their members-only discount with the best rates from Expedia, offering members the best price in travel, guaranteed.

As an AARP member, you'll have the opportunity to take advantage of exclusive rates on:

  • Hotels
  • Car rentals
  • Flights
  • Waived booking fees on flights

If you've got a more lenient schedule, we'll have more deals to show you. In other words, you will have a better chance of finding that affordable flight you've been looking for.

Transportation at the Airport

Once you have reserved plane tickets to Medway with AARP Travel, you might want to book a rental car so you can get around on your own. You can request Medway car rentals under our cars tab and hop into the car as soon as you step outside. For more information, check out the Medway Car Rentals Guide.

Medway Activities

Not sure where to start? Not to worry—there's plenty to do in this city. No matter what you decide to do with your time, you're sure to have fun in this city.

If you're looking for some fun activities to do in Medway, make sure you look at our "Things to Do in Medway" page for excursions and activities for the whole crew.

Where to Stay in Medway

Medway has lodging to choose from, so you will have little difficulty finding a place to stay close to all the things you want to see. If you need to stay close to an attraction or the airport in Medway, check out our hotel listings page. Remember that you'll get the best for your getaway when you book with AARP.

Booking Your Trip

Once you have planned your travel dates, allow us here at AARP Travel to connect you with affordable tickets to Medway. There is no better time than now to start booking your next trip. Book one of our flights today.