Cheap Flights To Winchester 2025

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Winchester Flights as Low as $114

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.

Spirit Airlines
Thu, Jun 12 - Tue, Jun 17
DTW
Detroit Metropolitan Wayne County
BOS
Logan Intl.
$114 Roundtrip, found 4 days ago
$114
Roundtrip
found 4 days ago
Select Spirit Airlines flight, departing Thu, Jun 12 from Detroit Metropolitan Wayne County to Logan Intl., returning Tue, Jun 17, priced at $114 found 4 days ago
JetBlue Airways
Tue, Jul 29 - Tue, Aug 12
DTW
Detroit Metropolitan Wayne County
BOS
Logan Intl.
$127 Roundtrip, found 2 days ago
$127
Roundtrip
found 2 days ago
Select JetBlue Airways flight, departing Tue, Jul 29 from Detroit Metropolitan Wayne County to Logan Intl., returning Tue, Aug 12, priced at $127 found 2 days ago
Spirit Airlines
Thu, Jun 12 - Sun, Jun 15
DTW
Detroit Metropolitan Wayne County
BOS
Logan Intl.
$130 Roundtrip, found 4 days ago
$130
Roundtrip
found 4 days ago
Select Spirit Airlines flight, departing Thu, Jun 12 from Detroit Metropolitan Wayne County to Logan Intl., returning Sun, Jun 15, priced at $130 found 4 days ago
Delta
Tue, Jul 29 - Wed, Aug 13
DTW
Detroit Metropolitan Wayne County
BOS
Logan Intl.
$137 Roundtrip, found 2 days ago
$137
Roundtrip
found 2 days ago
Select Delta flight, departing Tue, Jul 29 from Detroit Metropolitan Wayne County to Logan Intl., returning Wed, Aug 13, priced at $137 found 2 days ago
United
Fri, Sep 19 - Tue, Sep 23
DTW
Detroit Metropolitan Wayne County
BOS
Logan Intl.
$144 Roundtrip, found 3 days ago
$144
Roundtrip
found 3 days ago
Select United flight, departing Fri, Sep 19 from Detroit Metropolitan Wayne County to Logan Intl., returning Tue, Sep 23, priced at $144 found 3 days ago
Spirit Airlines
Sun, Jun 8 - Sun, Jun 15
DTW
Detroit Metropolitan Wayne County
BOS
Logan Intl.
$146 Roundtrip, found 4 days ago
$146
Roundtrip
found 4 days ago
Select Spirit Airlines flight, departing Sun, Jun 8 from Detroit Metropolitan Wayne County to Logan Intl., returning Sun, Jun 15, priced at $146 found 4 days ago
Spirit Airlines
Fri, Sep 19 - Tue, Sep 23
DTW
Detroit Metropolitan Wayne County
BOS
Logan Intl.
$149 Roundtrip, found 3 days ago
$149
Roundtrip
found 3 days ago
Select Spirit Airlines flight, departing Fri, Sep 19 from Detroit Metropolitan Wayne County to Logan Intl., returning Tue, Sep 23, priced at $149 found 3 days ago
Spirit Airlines
Sat, Jun 7 - Fri, Jun 13
DTW
Detroit Metropolitan Wayne County
BOS
Logan Intl.
$152 Roundtrip, found 4 days ago
$152
Roundtrip
found 4 days ago
Select Spirit Airlines flight, departing Sat, Jun 7 from Detroit Metropolitan Wayne County to Logan Intl., returning Fri, Jun 13, priced at $152 found 4 days ago
United
Fri, Sep 19 - Tue, Sep 23
DTW
Detroit Metropolitan Wayne County
BOS
Logan Intl.
$156 Roundtrip, found 3 days ago
$156
Roundtrip
found 3 days ago
Select United flight, departing Fri, Sep 19 from Detroit Metropolitan Wayne County to Logan Intl., returning Tue, Sep 23, priced at $156 found 3 days ago
Delta
Tue, Jul 29 - Thu, Aug 7
DTW
Detroit Metropolitan Wayne County
BOS
Logan Intl.
$157 Roundtrip, found 2 days ago
$157
Roundtrip
found 2 days ago
Select Delta flight, departing Tue, Jul 29 from Detroit Metropolitan Wayne County to Logan Intl., returning Thu, Aug 7, priced at $157 found 2 days ago
Spirit Airlines
Fri, Sep 19 - Tue, Sep 23
DTW
Detroit Metropolitan Wayne County
BOS
Logan Intl.
$158 Roundtrip, found 3 days ago
$158
Roundtrip
found 3 days ago
Select Spirit Airlines flight, departing Fri, Sep 19 from Detroit Metropolitan Wayne County to Logan Intl., returning Tue, Sep 23, priced at $158 found 3 days ago
United
Fri, Sep 19 - Tue, Sep 23
DTW
Detroit Metropolitan Wayne County
BOS
Logan Intl.
$159 Roundtrip, found 3 days ago
$159
Roundtrip
found 3 days ago
Select United flight, departing Fri, Sep 19 from Detroit Metropolitan Wayne County to Logan Intl., returning Tue, Sep 23, priced at $159 found 3 days ago
American Airlines
Fri, Sep 19 - Tue, Sep 23
DTW
Detroit Metropolitan Wayne County
BOS
Logan Intl.
$160 Roundtrip, found 3 days ago
$160
Roundtrip
found 3 days ago
Select American Airlines flight, departing Fri, Sep 19 from Detroit Metropolitan Wayne County to Logan Intl., returning Tue, Sep 23, priced at $160 found 3 days ago
American Airlines
Tue, Jun 24 - Sun, Jun 29
DTW
Detroit Metropolitan Wayne County
PVD
T.F. Green
$217 Roundtrip, found 3 days ago
$217
Roundtrip
found 3 days ago
Select American Airlines flight, departing Tue, Jun 24 from Detroit Metropolitan Wayne County to T.F. Green, returning Sun, Jun 29, priced at $217 found 3 days ago
Delta
Tue, Sep 16 - Tue, Sep 23
DTW
Detroit Metropolitan Wayne County
ALB
Albany Intl.
$359 Roundtrip, found 1 day ago
$359
Roundtrip
found 1 day ago
Select Delta flight, departing Tue, Sep 16 from Detroit Metropolitan Wayne County to Albany Intl., returning Tue, Sep 23, priced at $359 found 1 day ago
American Airlines
Wed, Jun 4 - Sat, Jun 7
GRI
Central Nebraska Regional
ALB
Albany Intl.
$508 Roundtrip, found 1 day ago
$508
Roundtrip
found 1 day ago
Select American Airlines flight, departing Wed, Jun 4 from Central Nebraska Regional to Albany Intl., returning Sat, Jun 7, priced at $508 found 1 day ago

Cheap Winchester Flights

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