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Cheap flights from Chicago to Boston from $105

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 8/18. 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

Discover deals from 900+ travel sites with momondo.

Find the cheapest flights from Chicago to Boston

Cheap round-trip flights

Enter your travel dates to find the best prices.
JetBlue Logo
9:40 am - 4:12 pm
ORD
-
MVY
5h 32m
1 stop
JetBlue Logo
5:05 pm - 9:58 pm
MVY
-
ORD
5h 53m
1 stop
$210JetBlue
Sat, Aug 29 - Tue, Sep 1
JetBlue Logo
9:40 am - 4:12 pm
ORD
-
MVY
5h 32m
1 stop
JetBlue Logo
5:05 pm - 9:58 pm
MVY
-
ORD
5h 53m
1 stop
$220JetBlue
Sat, Aug 29 - Tue, Sep 1
JetBlue Logo
9:40 am - 4:12 pm
ORD
-
MVY
5h 32m
1 stop
JetBlue Logo
5:05 pm - 9:58 pm
MVY
-
ORD
5h 53m
1 stop
$248JetBlue
Sat, Aug 29 - Tue, Sep 1
JetBlue Logo
9:40 am - 4:10 pm
ORD
-
MVY
5h 30m
1 stop
JetBlue Logo
5:05 pm - 9:58 pm
MVY
-
ORD
5h 53m
1 stop
$301JetBlue
Mon, Aug 24 - Mon, Aug 31
JetBlue Logo
9:42 am - 3:30 pm
ORD
-
MVY
4h 48m
1 stop
JetBlue Logo
5:05 pm - 9:58 pm
MVY
-
ORD
5h 53m
1 stop
$317JetBlue
Sun, Aug 30 - Sat, Sep 5
American Airlines Logo
6:00 am - 12:58 pm
ORD
-
MVY
5h 58m
1 stop
American Airlines Logo
4:43 pm - 7:06 pm
MVY
-
ORD
3h 23mnonstop
$326American Airlines
Sun, Aug 30 - Sat, Sep 5
JetBlue Logo
9:40 am - 4:10 pm
ORD
-
MVY
5h 30m
1 stop
JetBlue Logo
5:05 pm - 9:58 pm
MVY
-
ORD
5h 53m
1 stop
$346JetBlue
Sat, Aug 22 - Mon, Aug 31
Delta Logo
7:05 am - 3:08 pm
ORD
-
MVY
7h 03m
1 stop
Delta Logo
11:53 am - 6:49 pm
MVY
-
ORD
7h 56m
2 stops
$352Delta
Sat, Aug 29 - Tue, Sep 1
JetBlue Logo
9:40 am - 4:10 pm
ORD
-
MVY
5h 30m
1 stop
JetBlue Logo
5:05 pm - 9:58 pm
MVY
-
ORD
5h 53m
1 stop
$390JetBlue
Fri, Aug 21 - Mon, Aug 31
JetBlue Logo
9:40 am - 4:10 pm
ORD
-
MVY
5h 30m
1 stop
JetBlue Logo
10:58 am - 8:43 am
MVY
-
ORD
22h 45m
2 stops
$400JetBlue
Mon, Aug 24 - Mon, Aug 31

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Delta flights from Chicago to West Tisbury

Our best Delta deals on Chicago to West Tisbury flight tickets
Delta
Aug 29
ORD7:05 amChicago O'Hare Intl
7h 03m
1 stop
MVY3:08 pmWest Tisbury Martha's Vineyard
Sep 1
MVY11:53 amWest Tisbury Martha's Vineyard
7h 56m
2 stops
ORD6:49 pmChicago O'Hare Intl
$352
Delta
Aug 24
ORD5:30 amChicago O'Hare Intl
8h 38m
2 stops
MVY3:08 pmWest Tisbury Martha's Vineyard
Aug 31
MVY3:48 pmWest Tisbury Martha's Vineyard
9h 09m
2 stops
ORD11:57 pmChicago O'Hare Intl
$513
Delta
Aug 29
ORD6:59 amChicago O'Hare Intl
7h 09m
2 stops
MVY3:08 pmWest Tisbury Martha's Vineyard
Sep 1
MVY11:53 amWest Tisbury Martha's Vineyard
10h 02m
2 stops
ORD8:55 pmChicago O'Hare Intl
$578

American Airlines flights from Chicago to West Tisbury

Our best American Airlines deals on Chicago to West Tisbury flight tickets
American Airlines
Aug 30
ORD6:00 amChicago O'Hare Intl
5h 58m
1 stop
MVY12:58 pmWest Tisbury Martha's Vineyard
Sep 5
MVY4:43 pmWest Tisbury Martha's Vineyard
3h 23m
ORD7:06 pmChicago O'Hare Intl
$326
American Airlines
Aug 23
ORD8:00 amChicago O'Hare Intl
4h 41m
1 stop
MVY1:41 pmWest Tisbury Martha's Vineyard
Aug 31
MVY12:30 pmWest Tisbury Martha's Vineyard
5h 44m
1 stop
ORD5:14 pmChicago O'Hare Intl
$416
American Airlines
Aug 29
ORD12:29 pmChicago O'Hare Intl
2h 44m
MVY4:13 pmWest Tisbury Martha's Vineyard
Sep 1
MVY12:30 pmWest Tisbury Martha's Vineyard
5h 44m
1 stop
ORD5:14 pmChicago O'Hare Intl
$420

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 July 27, 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 8/29

9:40 am-4:12 pm

1 stop5h 32m

West Tisbury Martha's Vineyard

Tue 9/1

5:05 pm-9:58 pm

1 stop5h 53m

$210

ChicagoWest Tisbury

ORD - MVY

ORDMVY

Chicago O'Hare Intl

Sat 8/29

9:40 am-4:12 pm

1 stop5h 32m

West Tisbury Martha's Vineyard

Tue 9/1

5:05 pm-9:58 pm

1 stop5h 53m

$220

ChicagoWest Tisbury

ORD - MVY

ORDMVY

Chicago O'Hare Intl

Sat 8/29

9:40 am-4:12 pm

1 stop5h 32m

West Tisbury Martha's Vineyard

Tue 9/1

5:05 pm-9:58 pm

1 stop5h 53m

$248

ChicagoWest Tisbury

ORD - MVY

ORDMVY

Chicago O'Hare Intl

Mon 8/24

9:40 am-4:10 pm

1 stop5h 30m

West Tisbury Martha's Vineyard

Mon 8/31

5:05 pm-9:58 pm

1 stop5h 53m

$301

ChicagoWest Tisbury

ORD - MVY

ORDMVY

Chicago O'Hare Intl

Sun 8/30

9:42 am-3:30 pm

1 stop4h 48m

West Tisbury Martha's Vineyard

Sat 9/5

5:05 pm-9:58 pm

1 stop5h 53m

$317
Quickest round-trip

ChicagoWest Tisbury

ORD - MVY

ORDMVY

Chicago O'Hare Intl

Sun 8/30

6:00 am-12:58 pm

1 stop5h 58m

West Tisbury Martha's Vineyard

Sat 9/5

4:43 pm-7:06 pm

Nonstop3h 23m

$326

ChicagoWest Tisbury

ORD - MVY

ORDMVY

Chicago O'Hare Intl

Sat 8/22

9:40 am-4:10 pm

1 stop5h 30m

West Tisbury Martha's Vineyard

Mon 8/31

5:05 pm-9:58 pm

1 stop5h 53m

$346

ChicagoWest Tisbury

ORD - MVY

ORDMVY

Chicago O'Hare Intl

Sat 8/29

7:05 am-3:08 pm

1 stop7h 03m

West Tisbury Martha's Vineyard

Tue 9/1

11:53 am-6:49 pm

2 stops7h 56m

$352

ChicagoWest Tisbury

ORD - MVY

ORDMVY

Chicago O'Hare Intl

Fri 8/21

9:40 am-4:10 pm

1 stop5h 30m

West Tisbury Martha's Vineyard

Mon 8/31

5:05 pm-9:58 pm

1 stop5h 53m

$390

ChicagoWest Tisbury

ORD - MVY

ORDMVY

Chicago O'Hare Intl

Mon 8/24

9:40 am-4:10 pm

1 stop5h 30m

West Tisbury Martha's Vineyard

Mon 8/31

10:58 am-8:43 am

2 stops22h 45m

$400

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
1
2

See travel insights to Boston from

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 flights?

There is only 1 cabin class available to choose from on Chicago to West Tisbury 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 14% 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 50m

Direct flights

Sun

Airports in West Tisbury

1 airport
The fastest flight from Chicago to West Tisbury takes 2h 50m
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

Frequently asked questions about flying from Chicago to West Tisbury

  • 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 50m.

  • 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 $343Free CancellationRating
7.1
11,837 reviews
Search American Airlines flights

  • American Airlines Flights From Chicago to West Tisbury

    Across 1 American Airlines flight from Chicago to West Tisbury this week, the average price was $568, with the best American Airlines deals starting from $343 round-trip. 11,837 users have rated American Airlines on momondo, with an average score of 7.1/10.

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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