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Flight Deals from Orlando to Massachusetts from $109

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Top Deals on flights from Orlando to Boston

Orlando, US (ORL) - Boston, US (BOS)

Spirit Airlines Logo
Spirit Airlines

May 23

MCO
3h 5m
Direct

May 23

BOS
Spirit Airlines Logo
Spirit Airlines

May 26

BOS
3h 7m
Direct

May 26

MCO

as low as

$109

Orlando, US (ORL) - Boston, US (BOS)

Frontier Airlines Logo
Frontier Airlines

May 23

MCO
3h 10m
Direct

May 23

BOS
Frontier Airlines Logo
Frontier Airlines

May 26

BOS
3h 15m
Direct

May 26

MCO

as low as

$109

Orlando, US (ORL) - Boston, US (BOS)

Spirit Airlines Logo
Spirit Airlines

May 21

MCO
3h 2m
Direct

May 21

BOS
Spirit Airlines Logo
Spirit Airlines

May 24

BOS
14h 18m
FLL

May 25

MCO

as low as

$140

Orlando, US (ORL) - Boston, US (BOS)

Spirit Airlines Logo
Spirit Airlines

May 23

MCO
9h 19m
MYR

May 23

BOS
Spirit Airlines Logo
Spirit Airlines

May 26

BOS
3h 7m
Direct

May 26

MCO

as low as

$147

Orlando, US (ORL) - Boston, US (BOS)

Spirit Airlines Logo
Spirit Airlines

May 21

MCO
4h 47m
BWI

May 21

BOS
Spirit Airlines Logo
Spirit Airlines

May 24

BOS
4h 52m
BWI

May 24

MCO

as low as

$161

Orlando, US (ORL) - Boston, US (BOS)

Frontier Airlines Logo
Frontier Airlines

May 18

MCO
3h 13m
Direct

May 19

BOS
Frontier Airlines Logo
Frontier Airlines

May 25

BOS
5h 44m
RDU

May 25

MCO

as low as

$198

Orlando, US (ORL) - Boston, US (BOS)

Spirit Airlines Logo
Spirit Airlines

May 11

MCO
3h 2m
Direct

May 11

BOS
Spirit Airlines Logo
Spirit Airlines

May 14

BOS
5h 24m
ATL

May 14

MCO

as low as

$201

Orlando, US (ORL) - Boston, US (BOS)

American Airlines Logo
American Airlines

May 21

MCO
4h 53m
CLT

May 21

BOS
American Airlines Logo
American Airlines

May 24

BOS
4h 44m
CLT

May 24

MCO

as low as

$224

Orlando, US (ORL) - Boston, US (BOS)

Breeze Airways Logo
Breeze Airways

May 21

MCO
3h 3m
Direct

May 21

PSM
Breeze Airways Logo
Breeze Airways

May 24

PSM
3h 30m
Direct

May 24

MCO

as low as

$236

Orlando, US (ORL) - Boston, US (BOS)

JetBlue Logo
JetBlue

May 21

MCO
3h
Direct

May 21

BOS
JetBlue Logo
JetBlue

May 24

BOS
3h 23m
Direct

May 24

MCO

as low as

$246

Orlando, US (ORL) - Boston, US (BOS)

Delta Air Lines Logo
Delta Air Lines

May 13

MCO
3h 9m
Direct

May 13

BOS
Delta Air Lines Logo
Delta Air Lines

May 14

BOS
3h 10m
Direct

May 14

MCO

as low as

$246

Orlando, US (ORL) - Boston, US (BOS)

JetBlue Logo
JetBlue

May 15

MCO
3h 5m
Direct

May 15

BOS
JetBlue Logo
JetBlue

May 22

BOS
5h 48m
DCA

May 22

MCO

as low as

$261

Top Deals on flights from Orlando to Worcester

Orlando, US (ORL) - Worcester, US (ORH)

JetBlue Logo
JetBlue

May 30

MCO
2h 52m
Direct

May 30

ORH
JetBlue Logo
JetBlue

Jun 6

ORH
3h 10m
Direct

Jun 6

MCO

as low as

$182

Top Deals on flights from Orlando to West Tisbury

Orlando, US (ORL) - West Tisbury, US (MVY)

JetBlue Logo
JetBlue

May 30

MCO
10h 58m
BOS

May 31

MVY
Cape Air Logo
Cape Air

Jun 6

MVY
7h 4m
BOS

Jun 6

MCO

as low as

$803

Orlando, US (ORL) - West Tisbury, US (MVY)

JetBlue Logo
JetBlue

May 30

MCO
13h 43m
BOS

May 31

MVY
Cape Air Logo
Cape Air

Jun 6

MVY
7h 4m
BOS

Jun 6

MCO

as low as

$803

Orlando, US (ORL) - West Tisbury, US (MVY)

JetBlue Logo
JetBlue

May 30

MCO
10h 58m
BOS

May 31

MVY
Cape Air Logo
Cape Air

Jun 6

MVY
9h 44m
BOS

Jun 6

MCO

as low as

$803

Orlando, US (ORL) - West Tisbury, US (MVY)

JetBlue Logo
JetBlue

May 30

MCO
10h 58m
BOS

May 31

MVY
Cape Air Logo
Cape Air

Jun 6

MVY
10h 54m
BOS

Jun 6

MCO

as low as

$803

Orlando, US (ORL) - West Tisbury, US (MVY)

JetBlue Logo
JetBlue

May 30

MCO
10h 58m
BOS

May 31

MVY
Cape Air Logo
Cape Air

Jun 6

MVY
8h 28m
BOS

Jun 6

MCO

as low as

$821

Orlando, US (ORL) - West Tisbury, US (MVY)

JetBlue Logo
JetBlue

May 30

MCO
10h 58m
BOS

May 31

MVY
Cape Air Logo
Cape Air

Jun 6

MVY
7h 18m
BOS

Jun 6

MCO

as low as

$821

Orlando, US (ORL) - West Tisbury, US (MVY)

JetBlue Logo
JetBlue

May 30

MCO
4h 35m
BOS

May 30

MVY
Cape Air Logo
Cape Air

Jun 6

MVY
9h 44m
BOS

Jun 6

MCO

as low as

$833

Orlando, US (ORL) - West Tisbury, US (MVY)

JetBlue Logo
JetBlue

May 30

MCO
6h
BOS

May 30

MVY
Cape Air Logo
Cape Air

Jun 6

MVY
7h 4m
BOS

Jun 6

MCO

as low as

$833

Orlando, US (ORL) - West Tisbury, US (MVY)

JetBlue Logo
JetBlue

May 30

MCO
4h 35m
BOS

May 30

MVY
Cape Air Logo
Cape Air

Jun 6

MVY
7h 4m
BOS

Jun 6

MCO

as low as

$833

Orlando, US (ORL) - West Tisbury, US (MVY)

JetBlue Logo
JetBlue

May 30

MCO
5h 10m
BOS

May 30

MVY
Cape Air Logo
Cape Air

Jun 6

MVY
9h 44m
BOS

Jun 6

MCO

as low as

$833

Orlando, US (ORL) - West Tisbury, US (MVY)

JetBlue Logo
JetBlue

May 30

MCO
5h 10m
BOS

May 30

MVY
Cape Air Logo
Cape Air

Jun 6

MVY
12h 29m
BOS

Jun 6

MCO

as low as

$833

Orlando, US (ORL) - West Tisbury, US (MVY)

JetBlue Logo
JetBlue

May 30

MCO
5h 10m
BOS

May 30

MVY
Cape Air Logo
Cape Air

Jun 6

MVY
7h 4m
BOS

Jun 6

MCO

as low as

$833

Top Deals on flights from Orlando to Hyannis

Orlando, US (ORL) - Hyannis, US (HYA)

JetBlue Logo
JetBlue

May 30

MCO
7h 5m
BOS

May 30

HYA
JetBlue Logo
JetBlue

Jun 6

HYA
24h 51m
ACK
BOS

Jun 7

MCO

as low as

$678

Orlando, US (ORL) - Hyannis, US (HYA)

JetBlue Logo
JetBlue

May 30

MCO
7h 5m
BOS

May 30

HYA
JetBlue Logo
JetBlue

Jun 6

HYA
15h 24m
ACK
BOS

Jun 6

MCO

as low as

$678

Orlando, US (ORL) - Hyannis, US (HYA)

JetBlue Logo
JetBlue

May 30

MCO
13h 23m
BOS

May 31

HYA
JetBlue Logo
JetBlue

Jun 6

HYA
15h 24m
ACK
BOS

Jun 6

MCO

as low as

$678

Orlando, US (ORL) - Hyannis, US (HYA)

JetBlue Logo
JetBlue

May 30

MCO
13h 23m
BOS

May 31

HYA
JetBlue Logo
JetBlue

Jun 6

HYA
10h 4m
BOS

Jun 6

MCO

as low as

$684

Orlando, US (ORL) - Hyannis, US (HYA)

JetBlue Logo
JetBlue

May 30

MCO
7h 5m
BOS

May 30

HYA
JetBlue Logo
JetBlue

Jun 6

HYA
10h 4m
BOS

Jun 6

MCO

as low as

$684

Orlando, US (ORL) - Hyannis, US (HYA)

JetBlue Logo
JetBlue

May 30

MCO
13h 23m
BOS

May 31

HYA
Cape Air Logo
Cape Air

Jun 6

HYA
10h 4m
BOS

Jun 6

MCO

as low as

$689

Orlando, US (ORL) - Hyannis, US (HYA)

JetBlue Logo
JetBlue

May 30

MCO
7h 5m
BOS

May 30

HYA
Cape Air Logo
Cape Air

Jun 6

HYA
10h 4m
BOS

Jun 6

MCO

as low as

$694

Orlando, US (ORL) - Hyannis, US (HYA)

JetBlue Logo
JetBlue

May 30

MCO
8h 30m
BOS

May 30

HYA
Cape Air Logo
Cape Air

Jun 6

HYA
10h 4m
BOS

Jun 6

MCO

as low as

$694

Orlando, US (ORL) - Hyannis, US (HYA)

JetBlue Logo
JetBlue

May 30

MCO
13h 23m
BOS

May 31

HYA
JetBlue Logo
JetBlue

Jun 6

HYA
9h 28m
BOS
JFK

Jun 6

MCO

as low as

$695

Orlando, US (ORL) - Hyannis, US (HYA)

JetBlue Logo
JetBlue

May 30

MCO
7h 5m
BOS

May 30

HYA
JetBlue Logo
JetBlue

Jun 6

HYA
9h 28m
BOS
JFK

Jun 6

MCO

as low as

$695

Orlando, US (ORL) - Hyannis, US (HYA)

JetBlue Logo
JetBlue

May 30

MCO
13h 23m
BOS

May 31

HYA
JetBlue Logo
JetBlue

Jun 6

HYA
12h 58m
ACK
BOS

Jun 6

MCO

as low as

$696

Orlando, US (ORL) - Hyannis, US (HYA)

JetBlue Logo
JetBlue

May 30

MCO
7h 5m
BOS

May 30

HYA
JetBlue Logo
JetBlue

Jun 6

HYA
12h 58m
ACK
BOS

Jun 6

MCO

as low as

$696

Top Deals on flights from Orlando to Provincetown

Orlando, US (ORL) - Provincetown, US (PVC)

JetBlue Logo
JetBlue

May 29

MCO
8h 15m
BOS

May 29

PVC
JetBlue Logo
JetBlue

Jun 5

PVC
5h 13m
BOS

Jun 5

MCO

as low as

$664

Orlando, US (ORL) - Provincetown, US (PVC)

JetBlue Logo
JetBlue

May 29

MCO
5h 30m
BOS

May 29

PVC
JetBlue Logo
JetBlue

Jun 5

PVC
5h 36m
BOS

Jun 5

MCO

as low as

$664

Orlando, US (ORL) - Provincetown, US (PVC)

JetBlue Logo
JetBlue

May 29

MCO
5h 30m
BOS

May 29

PVC
JetBlue Logo
JetBlue

Jun 5

PVC
7h 39m
BOS

Jun 5

MCO

as low as

$664

Orlando, US (ORL) - Provincetown, US (PVC)

JetBlue Logo
JetBlue

May 29

MCO
6h 55m
BOS

May 29

PVC
JetBlue Logo
JetBlue

Jun 5

PVC
5h 36m
BOS

Jun 5

MCO

as low as

$664

Orlando, US (ORL) - Provincetown, US (PVC)

JetBlue Logo
JetBlue

May 29

MCO
9h 40m
BOS

May 29

PVC
Cape Air Logo
Cape Air

Jun 5

PVC
6h 1m
BOS

Jun 5

MCO

as low as

$664

Orlando, US (ORL) - Provincetown, US (PVC)

JetBlue Logo
JetBlue

May 29

MCO
5h 30m
BOS

May 29

PVC
JetBlue Logo
JetBlue

Jun 5

PVC
5h 13m
BOS

Jun 5

MCO

as low as

$664

Orlando, US (ORL) - Provincetown, US (PVC)

JetBlue Logo
JetBlue

May 29

MCO
6h 55m
BOS

May 29

PVC
JetBlue Logo
JetBlue

Jun 5

PVC
7h 39m
BOS

Jun 5

MCO

as low as

$664

Orlando, US (ORL) - Provincetown, US (PVC)

JetBlue Logo
JetBlue

May 29

MCO
5h 5m
BOS

May 29

PVC
JetBlue Logo
JetBlue

Jun 5

PVC
5h 36m
BOS

Jun 5

MCO

as low as

$664

Orlando, US (ORL) - Provincetown, US (PVC)

JetBlue Logo
JetBlue

May 29

MCO
10h 10m
BOS

May 29

PVC
Cape Air Logo
Cape Air

Jun 5

PVC
7h 26m
BOS

Jun 5

MCO

as low as

$664

Orlando, US (ORL) - Provincetown, US (PVC)

JetBlue Logo
JetBlue

May 29

MCO
8h 15m
BOS

May 29

PVC
JetBlue Logo
JetBlue

Jun 5

PVC
5h 36m
BOS

Jun 5

MCO

as low as

$664

Orlando, US (ORL) - Provincetown, US (PVC)

JetBlue Logo
JetBlue

May 29

MCO
5h 5m
BOS

May 29

PVC
JetBlue Logo
JetBlue

Jun 5

PVC
5h 13m
BOS

Jun 5

MCO

as low as

$664

Orlando, US (ORL) - Provincetown, US (PVC)

JetBlue Logo
JetBlue

May 29

MCO
6h 55m
BOS

May 29

PVC
JetBlue Logo
JetBlue

Jun 5

PVC
5h 13m
BOS

Jun 5

MCO

as low as

$664