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Flight Deals from West Tisbury to Chicago from $233

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Stops

  • Up to 1 stop
    $538

Airlines

  • American Airlines
    $581
  • JetBlue
    $538

Cabin Class

  • Economy
    $538

Departure Airports

  • Martha's Vineyard Airport
    $538

Arrival Airports

  • Chicago O Hare Airport
    $538

Layover Airports

  • General Edward Lawrence Logan International Airport
    $538
  • New York John F Kennedy Airport
    $584
  • New York LaGuardia Airport
    $581
  • Philadelphia International Airport
    $691
  • Reagan Washington National Airport
    $581

Best Price. GUARANTEED.

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On average save $240 per traveler
JetBlue Logo
JetBlue

07/28/25

MVY
22h 39m
BOS

07/29/25

ORD
JetBlue Logo
JetBlue

08/04/25

ORD
23h 51m
BOS

08/05/25

MVY
$538
American Airlines Logo
American Airlines

07/28/25

MVY
7h 23m
LGA

07/28/25

ORD
American Airlines Logo
American Airlines

08/04/25

ORD
18h 48m
DCA

08/05/25

MVY
$581
American Airlines Logo
American Airlines

07/28/25

MVY
7h 26m
DCA

07/28/25

ORD
American Airlines Logo
American Airlines

08/04/25

ORD
18h 48m
DCA

08/05/25

MVY
$581
JetBlue Logo
JetBlue

07/28/25

MVY
24h 55m
JFK

07/29/25

ORD
JetBlue Logo
JetBlue

08/04/25

ORD
23h 51m
BOS

08/05/25

MVY
$584
JetBlue Logo
JetBlue

07/28/25

MVY
22h 39m
BOS

07/29/25

ORD
JetBlue Logo
JetBlue

08/04/25

ORD
16h 4m
BOS

08/05/25

MVY
$588
JetBlue Logo
JetBlue

07/28/25

MVY
6h 16m
BOS

07/28/25

ORD
JetBlue Logo
JetBlue

08/04/25

ORD
23h 51m
BOS

08/05/25

MVY
$604
JetBlue Logo
JetBlue

07/28/25

MVY
12h 4m
JFK

07/28/25

ORD
JetBlue Logo
JetBlue

08/04/25

ORD
23h 51m
BOS

08/05/25

MVY
$609
JetBlue Logo
JetBlue

07/28/25

MVY
6h 30m
JFK

07/28/25

ORD
JetBlue Logo
JetBlue

08/04/25

ORD
23h 51m
BOS

08/05/25

MVY
$624
American Airlines Logo
American Airlines

07/28/25

MVY
4h 37m
LGA

07/28/25

ORD
American Airlines Logo
American Airlines

08/04/25

ORD
18h 48m
DCA

08/05/25

MVY
$631
JetBlue Logo
JetBlue

07/28/25

MVY
24h 55m
JFK

07/29/25

ORD
JetBlue Logo
JetBlue

08/04/25

ORD
16h 4m
BOS

08/05/25

MVY
$634
American Airlines Logo
American Airlines

07/28/25

MVY
7h 23m
LGA

07/28/25

ORD
American Airlines Logo
American Airlines

08/04/25

ORD
5h 47m
LGA

08/04/25

MVY
$637
American Airlines Logo
American Airlines

07/28/25

MVY
7h 26m
DCA

07/28/25

ORD
American Airlines Logo
American Airlines

08/04/25

ORD
5h 47m
LGA

08/04/25

MVY
$637
JetBlue Logo
JetBlue

07/28/25

MVY
19h 21m
JFK

07/29/25

ORD
JetBlue Logo
JetBlue

08/04/25

ORD
23h 51m
BOS

08/05/25

MVY
$644
JetBlue Logo
JetBlue

07/28/25

MVY
6h 16m
BOS

07/28/25

ORD
JetBlue Logo
JetBlue

08/04/25

ORD
16h 4m
BOS

08/05/25

MVY
$654
American Airlines Logo
American Airlines

07/28/25

MVY
18h 19m
DCA

07/29/25

ORD
American Airlines Logo
American Airlines

08/04/25

ORD
18h 48m
DCA

08/05/25

MVY
$669
American Airlines Logo
American Airlines

07/28/25

MVY
16h 24m
DCA

07/29/25

ORD
American Airlines Logo
American Airlines

08/04/25

ORD
18h 48m
DCA

08/05/25

MVY
$669
American Airlines Logo
American Airlines

07/28/25

MVY
5h 31m
LGA

07/28/25

ORD
American Airlines Logo
American Airlines

08/04/25

ORD
18h 48m
DCA

08/05/25

MVY
$671
JetBlue Logo
JetBlue

07/28/25

MVY
22h 39m
BOS

07/29/25

ORD
JetBlue Logo
JetBlue

08/04/25

ORD
4h 30m
BOS

08/04/25

MVY
$679
American Airlines Logo
American Airlines

07/28/25

MVY
4h 37m
LGA

07/28/25

ORD
American Airlines Logo
American Airlines

08/04/25

ORD
5h 47m
LGA

08/04/25

MVY
$687
American Airlines Logo
American Airlines

07/28/25

MVY
7h 26m
DCA

07/28/25

ORD
American Airlines Logo
American Airlines

08/04/25

ORD
14h 49m
PHL

08/05/25

MVY
$691
American Airlines Logo
American Airlines

07/28/25

MVY
7h 23m
LGA

07/28/25

ORD
American Airlines Logo
American Airlines

08/04/25

ORD
14h 49m
PHL

08/05/25

MVY
$691
American Airlines Logo
American Airlines

07/28/25

MVY
18h 6m
LGA

07/29/25

ORD
American Airlines Logo
American Airlines

08/04/25

ORD
14h 49m
PHL

08/05/25

MVY
$697
American Airlines Logo
American Airlines

07/28/25

MVY
7h 26m
DCA

07/28/25

ORD
American Airlines Logo
American Airlines

08/04/25

ORD
6h 47m
LGA

08/04/25

MVY
$697
American Airlines Logo
American Airlines

07/28/25

MVY
7h 26m
DCA

07/28/25

ORD
American Airlines Logo
American Airlines

08/04/25

ORD
6h 30m
PHL

08/04/25

MVY
$697
American Airlines Logo
American Airlines

07/28/25

MVY
7h 26m
DCA

07/28/25

ORD
American Airlines Logo
American Airlines

08/04/25

ORD
4h 30m
PHL

08/04/25

MVY
$697
American Airlines Logo
American Airlines

07/28/25

MVY
7h 23m
LGA

07/28/25

ORD
American Airlines Logo
American Airlines

08/04/25

ORD
6h 30m
PHL

08/04/25

MVY
$697
American Airlines Logo
American Airlines

07/28/25

MVY
7h 23m
LGA

07/28/25

ORD
American Airlines Logo
American Airlines

08/04/25

ORD
4h 30m
PHL

08/04/25

MVY
$697
JetBlue Logo
JetBlue

07/28/25

MVY
16h 8m
BOS

07/29/25

ORD
JetBlue Logo
JetBlue

08/04/25

ORD
23h 51m
BOS

08/05/25

MVY
$709
American Airlines Logo
American Airlines

07/28/25

MVY
7h 26m
DCA

07/28/25

ORD
American Airlines Logo
American Airlines

08/04/25

ORD
15h 45m
PHL

08/05/25

MVY
$711
American Airlines Logo
American Airlines

07/28/25

MVY
7h 23m
LGA

07/28/25

ORD
American Airlines Logo
American Airlines

08/04/25

ORD
15h 45m
PHL

08/05/25

MVY
$711

Top Deals on flights from West Tisbury to Chicago

West Tisbury, US (MVY) - Chicago, US (CHI)

American Airlines Logo
American Airlines

Jul 29

MVY
7h 26m
DCA

Jul 29

ORD

as low as

$233

West Tisbury, US (MVY) - Chicago, US (CHI)

American Airlines Logo
American Airlines

Jul 29

MVY
4h 37m
LGA

Jul 29

ORD

as low as

$233

West Tisbury, US (MVY) - Chicago, US (CHI)

American Airlines Logo
American Airlines

Jul 29

MVY
7h 23m
LGA

Jul 29

ORD

as low as

$233

West Tisbury, US (MVY) - Chicago, US (CHI)

JetBlue Logo
JetBlue

Jul 29

MVY
19h 21m
JFK

Jul 30

ORD

as low as

$234

West Tisbury, US (MVY) - Chicago, US (CHI)

American Airlines Logo
American Airlines

Jul 29

MVY
5h 31m
LGA

Jul 29

ORD

as low as

$258

West Tisbury, US (MVY) - Chicago, US (CHI)

American Airlines Logo
American Airlines

Jul 29

MVY
4h 41m
DCA

Jul 29

ORD

as low as

$268

West Tisbury, US (MVY) - Chicago, US (CHI)

American Airlines Logo
American Airlines

Jul 29

MVY
6h 5m
DCA

Jul 29

ORD

as low as

$268

West Tisbury, US (MVY) - Chicago, US (CHI)

JetBlue Logo
JetBlue

Jul 29

MVY
24h 55m
JFK

Jul 30

ORD

as low as

$275

West Tisbury, US (MVY) - Chicago, US (CHI)

JetBlue Logo
JetBlue

Jul 29

MVY
6h 31m
JFK

Jul 29

ORD

as low as

$296

West Tisbury, US (MVY) - Chicago, US (CHI)

American Airlines Logo
American Airlines

Jul 29

MVY
4h 53m
PHL

Jul 29

ORD

as low as

$328

West Tisbury, US (MVY) - Chicago, US (CHI)

American Airlines Logo
American Airlines

Jul 29

MVY
5h 55m
PHL

Jul 29

ORD

as low as

$328

West Tisbury, US (MVY) - Chicago, US (CHI)

JetBlue Logo
JetBlue

Jul 29

MVY
22h 39m
BOS

Jul 30

ORD

as low as

$332

Frequently Asked Questions

Are there convenient layover flights from West Tisbury to Chicago?
Yes, there are convenient 1 stop flights from Martha's Vineyard Airport to Chicago O Hare Airport. JetBlue offers a flight for $538 with a layover at General Edward Lawrence Logan International Airport and a flight time of 22 hours 39 minutes. American Airlines offers a flight for $581 with a layover at Reagan Washington National Airport and a flight time of 7 hours 26 minutes.
What are the most convenient layover airports for the flight?
For your flight from West Tisbury to Chicago, consider layovers at Logan International, LaGuardia, and Reagan Washington National airports, as they offer convenient connections with JetBlue and American Airlines.
What is the cheapest and fastest flight from West Tisbury to Chicago?
The cheapest flight is with JetBlue at $538, taking 22 hours 39 minutes. The fastest flight is with American Airlines at $631, taking 4 hours 37 minutes.
What are all possible destination arrival airports?
Possible destination arrival airports include Chicago O'Hare Airport, General Edward Lawrence Logan International Airport, New York LaGuardia Airport, and Reagan Washington National Airport.
What is the time difference between arrival and destination?
The time difference between West Tisbury and Chicago is typically one hour, with Chicago being one hour behind West Tisbury.
Is there a direct flight from West Tisbury to Chicago?
There is no direct flight from West Tisbury to Chicago. The available options are 1 stop flights with JetBlue priced at $538 and American Airlines priced at $581.