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Cheap flights from West Tisbury to Chicago from $151

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from West Tisbury to Chicago departing on 9/5. 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

Find the cheapest flights from West Tisbury to Chicago

Cheap round-trip flights

Enter your travel dates to find the best prices.
JetBlue Logo
4:00 pm - 9:58 pmMVY  West Tisbury Martha's Vineyard-ORD Chicago O'Hare Intl
6h 58m1 stop New York John F Kennedy Intl
JetBlue Logo
7:00 am - 3:04 pmORD  Chicago O'Hare Intl-MVY West Tisbury Martha's Vineyard
7h 04m1 stop New York John F Kennedy Intl
$302JetBlue
Sat, Oct 3 - Sun, Oct 4
JetBlue Logo
4:00 pm - 9:58 pmMVY  West Tisbury Martha's Vineyard-ORD Chicago O'Hare Intl
6h 58m1 stop New York John F Kennedy Intl
JetBlue Logo
7:00 am - 3:04 pmORD  Chicago O'Hare Intl-MVY West Tisbury Martha's Vineyard
7h 04m1 stop New York John F Kennedy Intl
$343JetBlue
Fri, Sep 25 - Sun, Sep 27
JetBlue Logo
3:54 pm - 9:58 pmMVY  West Tisbury Martha's Vineyard-ORD Chicago O'Hare Intl
7h 04m1 stop New York John F Kennedy Intl
JetBlue Logo
7:00 am - 3:04 pmORD  Chicago O'Hare Intl-MVY West Tisbury Martha's Vineyard
7h 04m1 stop New York John F Kennedy Intl
$448JetBlue
Thu, Sep 17 - Mon, Sep 21
JetBlue Logo
5:05 pm - 9:58 pmMVY  West Tisbury Martha's Vineyard-ORD Chicago O'Hare Intl
5h 53m1 stop New York John F Kennedy Intl
JetBlue Logo
9:41 am - 4:12 pmORD  Chicago O'Hare Intl-MVY West Tisbury Martha's Vineyard
5h 31m1 stop New York John F Kennedy Intl
$508JetBlue
Tue, Sep 1 - Sat, Sep 5
JetBlue Logo
3:54 pm - 9:58 pmMVY  West Tisbury Martha's Vineyard-ORD Chicago O'Hare Intl
7h 04m1 stop New York John F Kennedy Intl
JetBlue Logo
7:00 am - 3:04 pmORD  Chicago O'Hare Intl-MVY West Tisbury Martha's Vineyard
7h 04m1 stop New York John F Kennedy Intl
$549JetBlue
Thu, Sep 24 - Sun, Sep 27
JetBlue Logo
5:05 pm - 9:58 pmMVY  West Tisbury Martha's Vineyard-ORD Chicago O'Hare Intl
5h 53m1 stop New York John F Kennedy Intl
JetBlue Logo
6:00 am - 4:10 pmORD  Chicago O'Hare Intl-MVY West Tisbury Martha's Vineyard
9h 10m1 stop New York John F Kennedy Intl
$581JetBlue
Wed, Sep 2 - Thu, Sep 3
JetBlue Logo
5:05 pm - 9:58 pmMVY  West Tisbury Martha's Vineyard-ORD Chicago O'Hare Intl
5h 53m1 stop New York John F Kennedy Intl
JetBlue Logo
9:41 am - 4:12 pmORD  Chicago O'Hare Intl-MVY West Tisbury Martha's Vineyard
5h 31m1 stop New York John F Kennedy Intl
$588JetBlue
Tue, Sep 1 - Sat, Sep 5
JetBlue Logo
4:00 pm - 8:48 amMVY  West Tisbury Martha's Vineyard-ORD Chicago O'Hare Intl
17h 48m2 stops New York John F Kennedy Intl Boston Logan Intl
JetBlue Logo
7:00 am - 3:04 pmORD  Chicago O'Hare Intl-MVY West Tisbury Martha's Vineyard
7h 04m1 stop New York John F Kennedy Intl
$658JetBlue
Wed, Sep 16 - Sun, Sep 20
Delta Logo
11:53 am - 4:37 pmMVY  West Tisbury Martha's Vineyard-ORD Chicago O'Hare Intl
5h 44m1 stop New York LaGuardia
Delta Logo
6:00 am - 12:38 pmORD  Chicago O'Hare Intl-MVY West Tisbury Martha's Vineyard
5h 38m1 stop New York John F Kennedy Intl
$688Delta
Thu, Sep 3 - Mon, Sep 7
Multiple Airlines Logo
4:02 pm - 8:48 amMVY  West Tisbury Martha's Vineyard-ORD Chicago O'Hare Intl
17h 46m1 stop Boston Logan Intl
Multiple Airlines Logo
7:00 am - 3:04 pmORD  Chicago O'Hare Intl-MVY West Tisbury Martha's Vineyard
7h 04m1 stop New York John F Kennedy Intl
$715Multiple Airlines
Wed, Sep 16 - Sun, Sep 20

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JetBlue flights from West Tisbury to Chicago

Our best JetBlue deals on West Tisbury to Chicago flight tickets
JetBlue
Oct 3
MVY4:00 pmWest Tisbury Martha's Vineyard
6h 58m
1 stop
ORD9:58 pmChicago O'Hare Intl
Oct 4
ORD7:00 amChicago O'Hare Intl
7h 04m
1 stop
MVY3:04 pmWest Tisbury Martha's Vineyard
$302
JetBlue
Sep 25
MVY4:00 pmWest Tisbury Martha's Vineyard
6h 58m
1 stop
ORD9:58 pmChicago O'Hare Intl
Sep 27
ORD7:00 amChicago O'Hare Intl
7h 04m
1 stop
MVY3:04 pmWest Tisbury Martha's Vineyard
$343
JetBlue
Sep 17
MVY3:54 pmWest Tisbury Martha's Vineyard
7h 04m
1 stop
ORD9:58 pmChicago O'Hare Intl
Sep 21
ORD7:00 amChicago O'Hare Intl
7h 04m
1 stop
MVY3:04 pmWest Tisbury Martha's Vineyard
$448

Delta flights from West Tisbury to Chicago

Our best Delta deals on West Tisbury to Chicago flight tickets
Delta
Sep 3
MVY11:53 amWest Tisbury Martha's Vineyard
5h 44m
1 stop
ORD4:37 pmChicago O'Hare Intl
Sep 7
ORD6:00 amChicago O'Hare Intl
5h 38m
1 stop
MVY12:38 pmWest Tisbury Martha's Vineyard
$688
Delta
Aug 19
MVY1:18 pmWest Tisbury Martha's Vineyard
11h 39m
2 stops
ORD11:57 pmChicago O'Hare Intl
Aug 22
ORD7:05 amChicago O'Hare Intl
7h 03m
1 stop
MVY3:08 pmWest Tisbury Martha's Vineyard
$689
Delta
Aug 19
MVY1:18 pmWest Tisbury Martha's Vineyard
11h 39m
2 stops
ORD11:57 pmChicago O'Hare Intl
Aug 22
ORD6:00 amChicago O'Hare Intl
8h 08m
2 stops
MVY3:08 pmWest Tisbury Martha's Vineyard
$867

momondo Fare Finder

 
Customize your flight search to find flights from West Tisbury to Chicago 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 August 11, 2026.
Use the filters below to find and compare flights from West Tisbury to Chicago that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

West TisburyChicago

MVY West Tisbury Martha's Vineyard - ORD Chicago O'Hare Intl

MVYORD

West Tisbury Martha's Vineyard

Sat 10/3

4:00 pm-9:58 pm

1 stop6h 58m

Chicago O'Hare Intl

Sun 10/4

7:00 am-3:04 pm

1 stop7h 04m

$302

West TisburyChicago

MVY West Tisbury Martha's Vineyard - ORD Chicago O'Hare Intl

MVYORD

West Tisbury Martha's Vineyard

Fri 9/25

4:00 pm-9:58 pm

1 stop6h 58m

Chicago O'Hare Intl

Sun 9/27

7:00 am-3:04 pm

1 stop7h 04m

$343

West TisburyChicago

MVY West Tisbury Martha's Vineyard - ORD Chicago O'Hare Intl

MVYORD

West Tisbury Martha's Vineyard

Thu 9/17

3:54 pm-9:58 pm

1 stop7h 04m

Chicago O'Hare Intl

Mon 9/21

7:00 am-3:04 pm

1 stop7h 04m

$448

West TisburyChicago

MVY West Tisbury Martha's Vineyard - ORD Chicago O'Hare Intl

MVYORD

West Tisbury Martha's Vineyard

Tue 9/1

5:05 pm-9:58 pm

1 stop5h 53m

Chicago O'Hare Intl

Sat 9/5

9:41 am-4:12 pm

1 stop5h 31m

$508

West TisburyChicago

MVY West Tisbury Martha's Vineyard - ORD Chicago O'Hare Intl

MVYORD

West Tisbury Martha's Vineyard

Thu 9/24

3:54 pm-9:58 pm

1 stop7h 04m

Chicago O'Hare Intl

Sun 9/27

7:00 am-3:04 pm

1 stop7h 04m

$549

West TisburyChicago

MVY West Tisbury Martha's Vineyard - ORD Chicago O'Hare Intl

MVYORD

West Tisbury Martha's Vineyard

Wed 9/2

5:05 pm-9:58 pm

1 stop5h 53m

Chicago O'Hare Intl

Thu 9/3

6:00 am-4:10 pm

1 stop9h 10m

$581

West TisburyChicago

MVY West Tisbury Martha's Vineyard - ORD Chicago O'Hare Intl

MVYORD

West Tisbury Martha's Vineyard

Tue 9/1

5:05 pm-9:58 pm

1 stop5h 53m

Chicago O'Hare Intl

Sat 9/5

9:41 am-4:12 pm

1 stop5h 31m

$588

West TisburyChicago

MVY West Tisbury Martha's Vineyard - ORD Chicago O'Hare Intl

MVYORD

West Tisbury Martha's Vineyard

Wed 9/16

4:00 pm-8:48 am

2 stops17h 48m

Chicago O'Hare Intl

Sun 9/20

7:00 am-3:04 pm

1 stop7h 04m

$658
Quickest round-trip

West TisburyChicago

MVY West Tisbury Martha's Vineyard - ORD Chicago O'Hare Intl

MVYORD

West Tisbury Martha's Vineyard

Thu 9/3

11:53 am-4:37 pm

1 stop5h 44m

Chicago O'Hare Intl

Mon 9/7

6:00 am-12:38 pm

1 stop5h 38m

$688

West TisburyChicago

MVY West Tisbury Martha's Vineyard - ORD Chicago O'Hare Intl

MVYORD

West Tisbury Martha's Vineyard

Wed 9/16

4:02 pm-8:48 am

1 stop17h 46m

Chicago O'Hare Intl

Sun 9/20

7:00 am-3:04 pm

1 stop7h 04m

$715

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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See travel insights to Chicago from

How to get the cheapest flight ticket from West Tisbury to Chicago

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 Chicago?

The cheapest day to depart on your flight to Chicago is on a Friday when prices can be found for as low as $316. This is often the case because there is less demand to fly during this day of the week. When flying out on a Sunday, the most expensive travel day of the week, you can expect to see flight prices from West Tisbury to Chicago for around $412.

What is the cheapest time of day to depart on your flight to Chicago?

Our most recent data shows that the best time of day to fly to Chicago is in the evening. Flights from West Tisbury to Chicago during this time can be as low as $275. In contrast, the most expensive time of day to depart to Chicago is at noon when prices are around $370.

When to book flights from West Tisbury to Chicago

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

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

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

Fastest flight time

5h 44m

Direct flights

Sun

Airports in Chicago

3 airports
The fastest flight from West Tisbury to Chicago takes 5h 44m
Direct flights go from West Tisbury to Chicago on Sunday. There are no airlines offering direct flights.
There are 3 airports in Chicago. From West Tisbury there are direct flights to Chicago O'Hare Intl (ORD).
Search flight deals

Frequently asked questions about flying from West Tisbury to Chicago

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

    A flight from West Tisbury Martha's Vineyard to Chicago will travel around 874.2 mi. In terms of flight time, this usually takes a little over 5h 44m.

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

    Prices for flights from West Tisbury Martha's Vineyard Airport to Chicago were last updated today.

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

    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 West Tisbury Martha's Vineyard Airport to Chicago.

  • What documentation or ID do you need to fly to Chicago?

    The required travel and health documents for your Chicago 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 Chicago. We recommend that you seek guidance from your airline or a reliable third party such as IATA.

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Merrillville
New Buffalo
Hammond
Portage
Benton Harbor
Lansing
Saint Joseph
Valparaiso
Schererville
Munster
Chesterton
Monticello
Crown Point
Porter
Griffith
Saint John

Why use momondo?

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

To find the flight that best suits your needs, momondo gathers a range of flights from a large pool of different airlines and agents; you can then use our insights and filters to find and book the right flight to Chicago from West Tisbury.

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

Flights from West Tisbury to Chicago with flexible booking policies can be found by using the search form above and then selecting our dedicated flexible booking filter, which will highlight only the flights where this policy is applied.

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

Once you have performed a search in the form on the page, momondo provides useful filters and insights. We can show you the cheapest days and times to fly as well as help filter your options to help you make an informed choice when booking flights to Chicago from West Tisbury.

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

Price alerts on flights to Chicago from West Tisbury are quick and easy to set up on momondo. Simply perform a search and select the price alert feature. It is as simple as that.

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Find better results for your trip to the United States

Fly into one of these airports located in Chicago

Airports listed have a maximum distance of 78.5 mi from Chicago
Chicago Midway Airport
Chicago O'Hare Intl Airport
Chicago Greater Rockford Airport