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Cheap flights from Chicago to Boston from $253

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 11/8. 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
0 bags

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Cheap round-trip flights

Enter your travel dates to find the best prices.
Cape Air Logo
8:11 pm - 12:39 pmORD-MVY
15h 28m1 stop
Cape Air Logo
8:43 am - 9:25 pmMVY-ORD
13h 42m1 stop
$560Cape Air
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Sat, Nov 15 - Mon, Nov 17
Multiple Airlines Logo
6:20 pm - 9:49 amORD-MVY
14h 29m2 stops
Multiple Airlines Logo
10:09 am - 5:10 pmMVY-ORD
8h 01m1 stop
$598Multiple Airlines
Find Deal
Sat, Nov 15 - Mon, Nov 17
Multiple Airlines Logo
6:00 am - 3:40 pmORD-MVY
32h 40m3 stops
Multiple Airlines Logo
4:10 pm - 10:50 amMVY-ORD
19h 40m2 stops
$709Multiple Airlines
Find Deal
Mon, Oct 27 - Fri, Oct 31
Multiple Airlines Logo
6:00 am - 3:40 pmORD-MVY
32h 40m3 stops
Multiple Airlines Logo
1:34 pm - 2:45 pmMVY-ORD
26h 11m3 stops
$750Multiple Airlines
Find Deal
Mon, Oct 27 - Fri, Oct 31
Multiple Airlines Logo
6:00 am - 3:50 pmORD-MVY
8h 50m2 stops
Multiple Airlines Logo
1:34 pm - 10:50 amMVY-ORD
22h 16m2 stops
$761Multiple Airlines
Find Deal
Mon, Oct 27 - Fri, Oct 31
Multiple Airlines Logo
6:40 am - 1:23 pmORD-MVY
5h 43m1 stop
Multiple Airlines Logo
9:52 am - 12:16 amMVY-ORD
15h 24m2 stops
$841Multiple Airlines
Find Deal
Mon, Oct 27 - Fri, Oct 31
JetBlue Logo
6:45 am - 1:23 pmORD-MVY
5h 38m1 stop
JetBlue Logo
1:34 pm - 5:55 pmMVY-ORD
5h 21m1 stop
$969JetBlue
Find Deal
Mon, Oct 27 - Fri, Oct 31
JetBlue Logo
6:45 am - 1:23 pmORD-MVY
5h 38m1 stop
JetBlue Logo
11:40 am - 6:46 pmMVY-ORD
8h 06m1 stop
$999JetBlue
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Fri, Dec 19 - Fri, Dec 26
JetBlue Logo
10:08 am - 3:50 pmORD-MVY
4h 42m1 stop
JetBlue Logo
1:34 pm - 5:55 pmMVY-ORD
5h 21m1 stop
$1,104JetBlue
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Fri, Oct 24 - Mon, Oct 27

JetBlue flights from Chicago to West Tisbury

Our best JetBlue deals on Chicago to West Tisbury flight tickets
JetBlue
Oct 27
ORD6:45 amChicago O'Hare Intl
5h 38m
1 stop
MVY1:23 pmWest Tisbury Martha's Vineyard
Oct 31
MVY1:34 pmWest Tisbury Martha's Vineyard
5h 21m
1 stop
ORD5:55 pmChicago O'Hare Intl
$969
Find similar
JetBlue
Dec 19
ORD6:45 amChicago O'Hare Intl
5h 38m
1 stop
MVY1:23 pmWest Tisbury Martha's Vineyard
Dec 26
MVY11:40 amWest Tisbury Martha's Vineyard
8h 06m
1 stop
ORD6:46 pmChicago O'Hare Intl
$999
Find similar
JetBlue
Oct 24
ORD10:08 amChicago O'Hare Intl
4h 42m
1 stop
MVY3:50 pmWest Tisbury Martha's Vineyard
Oct 27
MVY1:34 pmWest Tisbury Martha's Vineyard
5h 21m
1 stop
ORD5:55 pmChicago O'Hare Intl
$1,104
Find similar

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 October 14, 2025.
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

ChicagoWest Tisbury

ORD - MVY

ORDMVY

Chicago O'Hare Intl

Sat 11/15

8:11 pm-12:39 pm

1 stop15h 28m

West Tisbury Martha's Vineyard

Mon 11/17

8:43 am-9:25 pm

1 stop13h 42m

$560

ChicagoWest Tisbury

ORD - MVY

ORDMVY

Chicago O'Hare Intl

Sat 11/15

6:20 pm-9:49 am

2 stops14h 29m

West Tisbury Martha's Vineyard

Mon 11/17

10:09 am-5:10 pm

1 stop8h 01m

$598

ChicagoWest Tisbury

ORD - MVY

ORDMVY

Chicago O'Hare Intl

Mon 10/27

6:00 am-3:40 pm

3 stops32h 40m

West Tisbury Martha's Vineyard

Fri 10/31

4:10 pm-10:50 am

2 stops19h 40m

$709

ChicagoWest Tisbury

ORD - MVY

ORDMVY

Chicago O'Hare Intl

Mon 10/27

6:00 am-3:40 pm

3 stops32h 40m

West Tisbury Martha's Vineyard

Fri 10/31

1:34 pm-2:45 pm

3 stops26h 11m

$750

ChicagoWest Tisbury

ORD - MVY

ORDMVY

Chicago O'Hare Intl

Mon 10/27

6:00 am-3:50 pm

2 stops8h 50m

West Tisbury Martha's Vineyard

Fri 10/31

1:34 pm-10:50 am

2 stops22h 16m

$761

ChicagoWest Tisbury

ORD - MVY

ORDMVY

Chicago O'Hare Intl

Mon 10/27

6:40 am-1:23 pm

1 stop5h 43m

West Tisbury Martha's Vineyard

Fri 10/31

9:52 am-12:16 am

2 stops15h 24m

$841

ChicagoWest Tisbury

ORD - MVY

ORDMVY

Chicago O'Hare Intl

Mon 10/27

6:45 am-1:23 pm

1 stop5h 38m

West Tisbury Martha's Vineyard

Fri 10/31

1:34 pm-5:55 pm

1 stop5h 21m

$969

ChicagoWest Tisbury

ORD - MVY

ORDMVY

Chicago O'Hare Intl

Fri 12/19

6:45 am-1:23 pm

1 stop5h 38m

West Tisbury Martha's Vineyard

Fri 12/26

11:40 am-6:46 pm

1 stop8h 06m

$999

ChicagoWest Tisbury

ORD - MVY

ORDMVY

Chicago O'Hare Intl

Fri 10/24

10:08 am-3:50 pm

1 stop4h 42m

West Tisbury Martha's Vineyard

Mon 10/27

1:34 pm-5:55 pm

1 stop5h 21m

$1,104

ChicagoWest Tisbury

ORD - MVY

ORDMVY

Chicago O'Hare Intl

Sat 11/8

3:26 pm-3:50 pm

2 stops23h 24m

$253

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 19 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 day to depart on your flight to West Tisbury?

The cheapest day to depart from Chicago to West Tisbury is on a Tuesday when prices can be found for as low as $316. Flights from Chicago to West Tisbury on a Sunday will generally be more expensive and average around $688. Keep in mind that these prices on both days could fluctuate depending on the season and the demand.

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?

No. A direct flight is the cheapest option for a flight between Chicago to West Tisbury.

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

Direct flights

None
There are no direct flights from Chicago to West Tisbury. There are no popular flight routes from Chicago to West Tisbury.
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  • 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 4h 42m.

  • 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 $407Free CancellationRating
7.2
11,042 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.

An easier way to manage your West Tisbury trip

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