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Cheap flights from Chicago to Boston from $108

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Chicago to Boston departing on 6/9. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
1 adult
1 adult, Economy, 0 bags

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Cheap round-trip flights

Enter your travel dates to find the best prices.
American Airlines Logo
5:00 am - 11:56 am
ORD
-
MVY
5h 56m
1 stop
American Airlines Logo
4:55 pm - 11:25 pm
MVY
-
ORD
7h 30m
1 stop
$216American Airlines
Sat, Aug 22 - Sat, Aug 29
Delta Logo
6:00 am - 11:20 am
ORD
-
MVY
4h 20m
1 stop
Delta Logo
12:15 pm - 5:48 pm
MVY
-
ORD
6h 33m
1 stop
$236Delta
Tue, Jul 7 - Tue, Jul 14
American Airlines Logo
6:00 am - 1:21 pm
ORD
-
MVY
6h 21m
1 stop
American Airlines Logo
2:50 pm - 9:37 pm
MVY
-
ORD
7h 47m
1 stop
$318American Airlines
Sun, Jun 21 - Sat, Jun 27
Delta Logo
7:10 am - 4:17 pm
ORD
-
MVY
8h 07m
2 stops
Delta Logo
3:10 pm - 9:36 pm
MVY
-
ORD
7h 26m
1 stop
$378Delta
Sat, Aug 22 - Sat, Aug 29
Delta Logo
6:00 am - 11:20 am
ORD
-
MVY
4h 20m
1 stop
Delta Logo
4:59 pm - 10:43 pm
MVY
-
ORD
6h 44m
1 stop
$382Delta
Tue, Jul 7 - Mon, Jul 13
Delta Logo
7:10 am - 4:17 pm
ORD
-
MVY
8h 07m
2 stops
Delta Logo
3:10 pm - 11:57 pm
MVY
-
ORD
9h 47m
2 stops
$383Delta
Sat, Aug 22 - Sat, Aug 29
American Airlines Logo
6:40 am - 11:52 am
ORD
-
MVY
4h 12m
1 stop
American Airlines Logo
12:22 pm - 5:26 pm
MVY
-
ORD
6h 04m
1 stop
$404American Airlines
Tue, Jul 14 - Sat, Jul 18
American Airlines Logo
6:00 am - 1:21 pm
ORD
-
MVY
6h 21m
1 stop
American Airlines Logo
1:09 pm - 3:16 pm
MVY
-
ORD
3h 07mnonstop
$413American Airlines
Sun, Jun 21 - Sat, Jun 27
American Airlines Logo
6:34 am - 2:48 pm
ORD
-
MVY
7h 14m
1 stop
American Airlines Logo
4:55 pm - 11:25 pm
MVY
-
ORD
7h 30m
1 stop
$423American Airlines
Thu, Aug 13 - Mon, Aug 17
JetBlue Logo
9:33 am - 4:00 pm
ORD
-
MVY
5h 27m
1 stop
JetBlue Logo
4:55 pm - 8:44 pm
MVY
-
ORD
4h 49m
1 stop
$447JetBlue
Wed, Aug 19 - Fri, Aug 21

Delta flights from Chicago to West Tisbury

Our best Delta deals on Chicago to West Tisbury flight tickets
Delta
Jul 7
ORD6:00 amChicago O'Hare Intl
4h 20m
1 stop
MVY11:20 amWest Tisbury Martha's Vineyard
Jul 14
MVY12:15 pmWest Tisbury Martha's Vineyard
6h 33m
1 stop
ORD5:48 pmChicago O'Hare Intl
$236
Delta
Aug 22
ORD7:10 amChicago O'Hare Intl
8h 07m
2 stops
MVY4:17 pmWest Tisbury Martha's Vineyard
Aug 29
MVY3:10 pmWest Tisbury Martha's Vineyard
7h 26m
1 stop
ORD9:36 pmChicago O'Hare Intl
$378
Delta
Jul 7
ORD6:00 amChicago O'Hare Intl
4h 20m
1 stop
MVY11:20 amWest Tisbury Martha's Vineyard
Jul 13
MVY4:59 pmWest Tisbury Martha's Vineyard
6h 44m
1 stop
ORD10:43 pmChicago O'Hare Intl
$382

American Airlines flights from Chicago to West Tisbury

Our best American Airlines deals on Chicago to West Tisbury flight tickets
American Airlines
Aug 22
ORD5:00 amChicago O'Hare Intl
5h 56m
1 stop
MVY11:56 amWest Tisbury Martha's Vineyard
Aug 29
MVY4:55 pmWest Tisbury Martha's Vineyard
7h 30m
1 stop
ORD11:25 pmChicago O'Hare Intl
$216
American Airlines
Jun 21
ORD6:00 amChicago O'Hare Intl
6h 21m
1 stop
MVY1:21 pmWest Tisbury Martha's Vineyard
Jun 27
MVY2:50 pmWest Tisbury Martha's Vineyard
7h 47m
1 stop
ORD9:37 pmChicago O'Hare Intl
$318
American Airlines
Jul 14
ORD6:40 amChicago O'Hare Intl
4h 12m
1 stop
MVY11:52 amWest Tisbury Martha's Vineyard
Jul 18
MVY12:22 pmWest Tisbury Martha's Vineyard
6h 04m
1 stop
ORD5:26 pmChicago O'Hare Intl
$404

momondo Fare Finder

 
Customize your flight search to find flights from Chicago to West Tisbury that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, momondo users made 832,500 searches. Data last updated March 10, 2026.
Use the filters below to find and compare flights from Chicago to West Tisbury that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

ChicagoWest Tisbury

ORD - MVY

ORDMVY

Chicago O'Hare Intl

Sat 8/22

5:00 am-11:56 am

1 stop5h 56m

West Tisbury Martha's Vineyard

Sat 8/29

4:55 pm-11:25 pm

1 stop7h 30m

$216

ChicagoWest Tisbury

ORD - MVY

ORDMVY

Chicago O'Hare Intl

Tue 7/7

6:00 am-11:20 am

1 stop4h 20m

West Tisbury Martha's Vineyard

Tue 7/14

12:15 pm-5:48 pm

1 stop6h 33m

$236

ChicagoWest Tisbury

ORD - MVY

ORDMVY

Chicago O'Hare Intl

Sun 6/21

6:00 am-1:21 pm

1 stop6h 21m

West Tisbury Martha's Vineyard

Sat 6/27

2:50 pm-9:37 pm

1 stop7h 47m

$318

ChicagoWest Tisbury

ORD - MVY

ORDMVY

Chicago O'Hare Intl

Sat 8/22

7:10 am-4:17 pm

2 stops8h 07m

West Tisbury Martha's Vineyard

Sat 8/29

3:10 pm-9:36 pm

1 stop7h 26m

$378

ChicagoWest Tisbury

ORD - MVY

ORDMVY

Chicago O'Hare Intl

Tue 7/7

6:00 am-11:20 am

1 stop4h 20m

West Tisbury Martha's Vineyard

Mon 7/13

4:59 pm-10:43 pm

1 stop6h 44m

$382

ChicagoWest Tisbury

ORD - MVY

ORDMVY

Chicago O'Hare Intl

Sat 8/22

7:10 am-4:17 pm

2 stops8h 07m

West Tisbury Martha's Vineyard

Sat 8/29

3:10 pm-11:57 pm

2 stops9h 47m

$383

ChicagoWest Tisbury

ORD - MVY

ORDMVY

Chicago O'Hare Intl

Tue 7/14

6:40 am-11:52 am

1 stop4h 12m

West Tisbury Martha's Vineyard

Sat 7/18

12:22 pm-5:26 pm

1 stop6h 04m

$404
Quickest round-trip

ChicagoWest Tisbury

ORD - MVY

ORDMVY

Chicago O'Hare Intl

Sun 6/21

6:00 am-1:21 pm

1 stop6h 21m

West Tisbury Martha's Vineyard

Sat 6/27

1:09 pm-3:16 pm

Nonstop3h 07m

$413

ChicagoWest Tisbury

ORD - MVY

ORDMVY

Chicago O'Hare Intl

Thu 8/13

6:34 am-2:48 pm

1 stop7h 14m

West Tisbury Martha's Vineyard

Mon 8/17

4:55 pm-11:25 pm

1 stop7h 30m

$423

ChicagoWest Tisbury

ORD - MVY

ORDMVY

Chicago O'Hare Intl

Wed 8/19

9:33 am-4:00 pm

1 stop5h 27m

West Tisbury Martha's Vineyard

Fri 8/21

4:55 pm-8:44 pm

1 stop4h 49m

$447

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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How to get the cheapest flight ticket from Chicago to West Tisbury

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

What is the cheapest Chicago to West Tisbury Martha's Vineyard flight route?

Fly from Chicago O'Hare Intl to West Tisbury Martha's Vineyard for the best Chicago - West Tisbury Martha's Vineyard flight prices

What cabin class options are available on Chicago to West Tisbury Martha's Vineyard flights?

There is only 1 cabin class available to choose from on Chicago to West Tisbury Martha's Vineyard flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

Can stopping save me money on Chicago to West Tisbury flights?

You could potentially save up to 21% on your flight if you consider stops on a Chicago to West Tisbury flight.

When to book flights from Chicago to West Tisbury

Are you open to changing your travel dates? Check out the ideal times to fly from Chicago to West Tisbury according to our flight data. Find out which month and days have the cheapest flights.
Estimated round-trip price

Cheap Chicago to West Tisbury (CHI to MVY) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Chicago to West Tisbury

Fastest flight time

2h 44m

Direct flights

Sun

Airports in West Tisbury

1 airport
The fastest flight from Chicago to West Tisbury takes 2h 44m
Direct flights go from Chicago to West Tisbury on Sunday. There are no airlines offering direct flights.
There is 1 airport in West Tisbury. From Chicago there are direct flights to West Tisbury Martha's Vineyard (MVY).
Search flight deals

  • How far is Chicago to West Tisbury Martha's Vineyard by plane?

    A flight from Chicago to West Tisbury Martha's Vineyard will travel around 874.2 mi. In terms of flight time, this usually takes a little over 2h 44m.

  • When did momondo last update prices for flights from Chicago to West Tisbury Martha's Vineyard Airport?

    Prices for flights from Chicago to West Tisbury Martha's Vineyard Airport are refreshed on a daily basis.

  • How many operators does momondo search for flights from Chicago to West Tisbury Martha's Vineyard Airport?

  • How old do you have to be to fly from Chicago to West Tisbury Martha's Vineyard Airport?

    The minimum age for a child to fly alone is five, but airlines that offer an unaccompanied minor (UNMR) service may have their own age limitations. Flight duration, scheduling, and layovers are among the considerations that may influence age limits. We recommend that you double-check with the airline you are booking with for travel from Chicago to West Tisbury Martha's Vineyard Airport.

  • What documentation or ID do you need to fly to West Tisbury Martha's Vineyard Airport?

    The required travel and health documents for your West Tisbury Martha's Vineyard Airport trip may vary depending on your itinerary and personal circumstances. As a general rule, you should carry multiple documents, including a national ID card or driver's license and a passport valid for six months after your intended arrival at West Tisbury Martha's Vineyard Airport. We recommend that you seek guidance from your airline or a reliable third party such as IATA.

  • What is the most popular plane model from Chicago to West Tisbury?

  • What is the most popular airline from Chicago to West Tisbury?

Best airlines flying from Chicago to West Tisbury

Compare and see reviews for airlines that fly from Chicago to West Tisbury with momondo
Airline
Rating
Free Cancellation
Price
American AirlinesPriceFrom $399Free CancellationRating
7.1
11,414 reviews
Search American Airlines flights

Traveling to a place near Boston?

Book flights to Boston if you plan to visit one of these locations
Oak Bluffs
Edgartown
Vineyard Haven

Why use momondo?

Why should I use momondo to find a flight deal from Chicago to West Tisbury?

momondo collates all your flight options in one place and lets you filter them to find the perfect flight from Chicago to West Tisbury. momondo saves you time and could save you money on your trip.

Can I find flights from Chicago to West Tisbury with flexible booking policies on momondo?

Yes. momondo allows you to filter the results for Chicago to West Tisbury flights to just show those with flexible booking policies.

How can momondo help me find flights from Chicago to West Tisbury?

momondo helps you find the best flight between Chicago and West Tisbury by providing filters to narrow your choice of flights to those matching your criteria. You can select flights based on numerous factors such as price, departure and landing times, airport and airline.

I’m not ready to book a flight from Chicago to West Tisbury right now. Can momondo alert me if prices change?

Of course. momondo tracks the price of Chicago to West Tisbury flights. All you need is a valid email address and we will do the rest; it is that quick and easy.

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