Cheap Flights To Winchester 2025

Winchester Flights as Low as $108

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.

Frontier Airlines
Sat, Sep 20 - Sat, Oct 4
TPA
Tampa Intl.
BOS
Logan Intl.
$108 Roundtrip, found 5 days ago
$108
Roundtrip
found 5 days ago
Select Frontier Airlines flight, departing Sat, Sep 20 from Tampa Intl. to Logan Intl., returning Sat, Oct 4, priced at $108 found 5 days ago
Frontier Airlines
Sat, Sep 20 - Tue, Oct 7
TPA
Tampa Intl.
BOS
Logan Intl.
$115 Roundtrip, found 1 day ago
$115
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Sat, Sep 20 from Tampa Intl. to Logan Intl., returning Tue, Oct 7, priced at $115 found 1 day ago
Delta
Tue, Sep 23 - Sat, Oct 11
TPA
Tampa Intl.
BOS
Logan Intl.
$117 Roundtrip, found 4 days ago
$117
Roundtrip
found 4 days ago
Select Delta flight, departing Tue, Sep 23 from Tampa Intl. to Logan Intl., returning Sat, Oct 11, priced at $117 found 4 days ago
Frontier Airlines
Thu, Sep 25 - Sat, Oct 4
TPA
Tampa Intl.
BOS
Logan Intl.
$118 Roundtrip, found 5 days ago
$118
Roundtrip
found 5 days ago
Select Frontier Airlines flight, departing Thu, Sep 25 from Tampa Intl. to Logan Intl., returning Sat, Oct 4, priced at $118 found 5 days ago
Frontier Airlines
Fri, Sep 26 - Sat, Oct 4
TPA
Tampa Intl.
BOS
Logan Intl.
$121 Roundtrip, found 5 days ago
$121
Roundtrip
found 5 days ago
Select Frontier Airlines flight, departing Fri, Sep 26 from Tampa Intl. to Logan Intl., returning Sat, Oct 4, priced at $121 found 5 days ago
JetBlue Airways
Tue, Sep 23 - Wed, Oct 8
TPA
Tampa Intl.
BOS
Logan Intl.
$122 Roundtrip, found 4 days ago
$122
Roundtrip
found 4 days ago
Select JetBlue Airways flight, departing Tue, Sep 23 from Tampa Intl. to Logan Intl., returning Wed, Oct 8, priced at $122 found 4 days ago
Frontier Airlines
Sun, Sep 21 - Sat, Oct 4
TPA
Tampa Intl.
BOS
Logan Intl.
$135 Roundtrip, found 13 hours ago
$135
Roundtrip
found 13 hours ago
Select Frontier Airlines flight, departing Sun, Sep 21 from Tampa Intl. to Logan Intl., returning Sat, Oct 4, priced at $135 found 13 hours ago
Delta
Tue, Sep 23 - Wed, Oct 8
TPA
Tampa Intl.
BOS
Logan Intl.
$137 Roundtrip, found 4 days ago
$137
Roundtrip
found 4 days ago
Select Delta flight, departing Tue, Sep 23 from Tampa Intl. to Logan Intl., returning Wed, Oct 8, priced at $137 found 4 days ago
Frontier Airlines
Sat, Sep 27 - Sat, Oct 4
TPA
Tampa Intl.
BOS
Logan Intl.
$140 Roundtrip, found 13 hours ago
$140
Roundtrip
found 13 hours ago
Select Frontier Airlines flight, departing Sat, Sep 27 from Tampa Intl. to Logan Intl., returning Sat, Oct 4, priced at $140 found 13 hours ago
JetBlue Airways
Tue, Sep 23 - Sat, Oct 4
TPA
Tampa Intl.
BOS
Logan Intl.
$142 Roundtrip, found 15 hours ago
$142
Roundtrip
found 15 hours ago
Select JetBlue Airways flight, departing Tue, Sep 23 from Tampa Intl. to Logan Intl., returning Sat, Oct 4, priced at $142 found 15 hours ago
American Airlines
Tue, Sep 23 - Wed, Oct 8
TPA
Tampa Intl.
BOS
Logan Intl.
$159 Roundtrip, found 4 days ago
$159
Roundtrip
found 4 days ago
Select American Airlines flight, departing Tue, Sep 23 from Tampa Intl. to Logan Intl., returning Wed, Oct 8, priced at $159 found 4 days ago
Spirit Airlines
Sat, Sep 27 - Wed, Oct 8
TPA
Tampa Intl.
BOS
Logan Intl.
$160 Roundtrip, found 13 hours ago
$160
Roundtrip
found 13 hours ago
Select Spirit Airlines flight, departing Sat, Sep 27 from Tampa Intl. to Logan Intl., returning Wed, Oct 8, priced at $160 found 13 hours ago
United
Tue, Sep 23 - Wed, Oct 8
TPA
Tampa Intl.
BOS
Logan Intl.
$187 Roundtrip, found 4 days ago
$187
Roundtrip
found 4 days ago
Select United flight, departing Tue, Sep 23 from Tampa Intl. to Logan Intl., returning Wed, Oct 8, priced at $187 found 4 days ago
JetBlue Airways
Mon, Oct 6 - Tue, Oct 7
LAX
Los Angeles Intl.
BOS
Logan Intl.
$192 Roundtrip, found 6 days ago
$192
Roundtrip
found 6 days ago
Select JetBlue Airways flight, departing Mon, Oct 6 from Los Angeles Intl. to Logan Intl., returning Tue, Oct 7, priced at $192 found 6 days ago
Alaska Airlines
Mon, Oct 27 - Thu, Oct 30
LAX
Los Angeles Intl.
BOS
Logan Intl.
$363 Roundtrip, found 17 hours ago
$363
Roundtrip
found 17 hours ago
Select Alaska Airlines flight, departing Mon, Oct 27 from Los Angeles Intl. to Logan Intl., returning Thu, Oct 30, priced at $363 found 17 hours ago
Sun Country Airlines
Sun, Nov 16 - Sun, Nov 23
LAX
Los Angeles Intl.
BOS
Logan Intl.
$478 Roundtrip, found 6 hours ago
$478
Roundtrip
found 6 hours ago
Select Sun Country Airlines flight, departing Sun, Nov 16 from Los Angeles Intl. to Logan Intl., returning Sun, Nov 23, priced at $478 found 6 hours ago

Winchester Flights

No matter how much you fight the travel bug, sometimes there's only one solution—to hop on the next plane to Winchester. AARP Travel Center Powered by Expedia® is here to help you cure that bug with great deals on flights and activities. With the best rates from Expedia combined with members-only discounts, AARP Travel offers members the best price in travel, guaranteed.

As an AARP member, you'll get exclusive rates on:

  • Hotels
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  • Flights
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Once you have got your trip scheduled, we'll show you a full list of deals for your route. Do not forget to look at flights to alternative airports nearby, which can help you find a lower fare.

Transportation at the Airport

Once you have reserved plane tickets to Winchester, you may want to book a rental car so you can get around on your own. You can schedule a Winchester rental car under our cars tab and hop in the driver's seat right when you step outside. If you do not need a rental car, there are other ground transportation options such as shuttle, limousine, taxi, and rideshare application services.

Winchester Activities

If you aren't sure where to start, we can help you with that too. Not to worry—there's so many things to do in this city. Winchester has so much to do, and we can help you get started.

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

Where to Stay in Winchester

Winchester has hotel options in the area, make sure you check out our hotel listings tab for some great recommendations from past visitors. No matter where you stay, just remember that you'll get the best for your trip when you book your stay with us.

Booking Your Visit to Winchester

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