HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Chicago

$119+ Cheap flights from Cape Cod and the Islands to Chicago (CHI)

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 7/29. Fares are subject to change and may not be available on all flights or dates of travel.
MVY — CHI
Mar 5 — Mar 121
Thu 3/5
Thu 3/12
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Cape Cod and the Islands to Chicago with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

Cheap flight deals from Cape Cod and the Islands to Chicago

Cheapest flights from Cape Cod and the Islands to Chicago
Explore the most affordable flight options available from Cape Cod and the Islands to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on February 3, 2026.

This JetBlue deal was found by Cheapflights users on 2/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/712:07 pm
HYA
-
ORD
1 stop6h 36m
JetBlue
Sat 2/1410:00 am
ORD
-
HYA
1 stop6h 20m
JetBlue
Deal found 2/1$449
This American Airlines deal was found by Cheapflights users on 2/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/611:59 am
MVY
-
ORD
1 stop12h 26m
American Airlines
Mon 8/106:06 am
ORD
-
MVY
1 stop9h 19m
American Airlines
Deal found 2/2$503
This United Airlines deal was found by Cheapflights users on 2/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/194:32 pm
ACK
-
ORD
Nonstop3h 15m
United Airlines
Wed 9/237:15 am
ORD
-
ACK
1 stop6h 32m
United Airlines
Deal found 2/2$538
This JetBlue deal was found by Cheapflights users on 2/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 2/41:28 pm
MVY
-
ORD
1 stop5h 15m
JetBlue
Thu 2/57:40 am
ORD
-
MVY
1 stop6h 55m
JetBlue
Deal found 2/1$582
This Delta deal was found by Cheapflights users on 1/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/2912:04 pm
MVY
-
ORD
1 stop5h 30m
Delta
Mon 6/16:00 am
ORD
-
MVY
1 stop4h 24m
Delta
Deal found 1/31$588
This JetBlue deal was found by Cheapflights users on 2/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 7/131:20 pm
HYA
-
ORD
1 stop7h 06m
JetBlue
Wed 7/1510:35 am
ORD
-
HYA
1 stop4h 45m
JetBlue
Deal found 2/3$599
This JetBlue deal was found by Cheapflights users on 1/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/283:38 pm
ACK
-
ORD
1 stop4h 48m
JetBlue
Mon 8/319:30 am
ORD
-
ACK
1 stop7h 40m
JetBlue
Deal found 1/31$662
This Orbitz deal was found by Cheapflights users on 2/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 7/611:26 am
MVY
-
ORD
1 stop9h 00m
JetBlue
Thu 7/910:35 am
ORD
-
MVY
1 stop4h 26m
JetBlue
Deal found 2/2$668
This JetBlue deal was found by Cheapflights users on 2/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 2/31:28 pm
MVY
-
ORD
1 stop5h 15m
JetBlue
Sat 2/77:40 am
ORD
-
MVY
1 stop6h 55m
JetBlue
Deal found 2/3$687
This American Airlines deal was found by Cheapflights users on 2/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/21:55 pm
MVY
-
ORD
1 stop6h 28m
American Airlines
Thu 8/66:06 am
ORD
-
MVY
1 stop7h 09m
American Airlines
Deal found 2/1$718
This Delta deal was found by Cheapflights users on 2/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/221:18 pm
MVY
-
ORD
1 stop5h 17m
Delta
Tue 5/269:25 am
ORD
-
MVY
1 stop4h 57m
Delta
Deal found 2/1$868
This Delta deal was found by Cheapflights users on 2/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/2212:04 pm
MVY
-
ORD
1 stop5h 30m
Delta
Mon 5/256:41 am
ORD
-
MVY
1 stop4h 57m
Delta
Deal found 2/1$898

Find flight deals from Cape Cod and the Islands to Chicago

Keep the following information in mind while searching for Cape Cod and the Islands to Chicago flight deals. Data was last updated February 3, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$588
(Delta)

One-way from

$119
(Delta)

Popular in

April

Cheapest in

September

Average price

$227
Provider with most accurate pricing for Boston Logan Intl-Chicago (CHI) flight deals.
Search Deals
Provider most trusted by Cheapflights users for Boston Logan Intl-Chicago (CHI) flights.
Search Deals
From Cape Cod and the Islands to Chicago (CHI)
Search Deals
One-way flight from Cape Cod and the Islands to Chicago (CHI)
Search Deals
Highest demand for flights based on searches. 10% potential increase in price ($25 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($4 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in February 2026
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Cape Cod and the Islands 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, Cheapflights users made 2,558,603 searches. Data last updated February 3, 2026.
Use the filters below to find and compare flights from Cape Cod and the Islands to Chicago that are best for you.

Fly from

Cape Cod and the Islands

Fly to

Chicago

Route

Depart

Return

Price

West TisburyChicago

MVY - ORD

MVYORD

West Tisbury Martha's Vineyard

Fri 5/29

12:04 pm-4:34 pm

1 stop5h 30m

Chicago O'Hare Intl

Mon 6/1

6:00 am-11:24 am

1 stop4h 24m

$588

HyannisChicago

HYA - ORD

HYAORD

Hyannis Barnstable

Mon 7/13

1:20 pm-7:26 pm

1 stop7h 06m

Chicago O'Hare Intl

Wed 7/15

10:35 am-4:20 pm

1 stop4h 45m

$599

West TisburyChicago

MVY - ORD

MVYORD

West Tisbury Martha's Vineyard

Mon 7/6

11:26 am-7:26 pm

1 stop9h 00m

Chicago O'Hare Intl

Thu 7/9

10:35 am-4:01 pm

1 stop4h 26m

$668

West TisburyChicago

MVY - ORD

MVYORD

West Tisbury Martha's Vineyard

Sun 8/2

1:55 pm-7:23 pm

1 stop6h 28m

Chicago O'Hare Intl

Thu 8/6

6:06 am-2:15 pm

1 stop7h 09m

$718

West TisburyChicago

MVY - ORD

MVYORD

West Tisbury Martha's Vineyard

Fri 5/22

1:18 pm-5:35 pm

1 stop5h 17m

Chicago O'Hare Intl

Tue 5/26

9:25 am-3:22 pm

1 stop4h 57m

$868

West TisburyChicago

MVY - ORD

MVYORD

West Tisbury Martha's Vineyard

Fri 5/22

12:04 pm-4:34 pm

1 stop5h 30m

Chicago O'Hare Intl

Mon 5/25

6:41 am-12:38 pm

1 stop4h 57m

$898

NantucketChicago

ACK - ORD

ACKORD

Nantucket Memorial

Wed 2/18

7:00 am-9:39 am

2 stops27h 39m

Chicago O'Hare Intl

Sun 2/22

5:15 am-7:50 pm

2 stops13h 35m

$950

HyannisChicago

HYA - ORD

HYAORD

Hyannis Barnstable

Thu 6/11

10:29 am-7:26 pm

1 stop9h 57m

Chicago O'Hare Intl

Sun 6/14

8:40 am-3:00 pm

1 stop5h 20m

$953

West TisburyChicago

MVY - ORD

MVYORD

West Tisbury Martha's Vineyard

Mon 7/6

10:41 am-5:45 pm

2 stops8h 04m

Chicago O'Hare Intl

Thu 7/9

8:50 pm-10:11 am

1 stop12h 21m

$957

West TisburyChicago

MVY - ORD

MVYORD

West Tisbury Martha's Vineyard

Mon 7/6

12:15 pm-8:24 pm

2 stops9h 09m

Chicago O'Hare Intl

Thu 7/9

7:10 am-2:19 pm

2 stops6h 09m

$1,079

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/2

Showing 1-10 of 36 results
1
2
3
4

Best time to book a flight from Cape Cod and the Islands to Chicago

Have a flexible travel schedule? Discover the best time to fly to Chicago from Cape Cod and the Islands with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

Everything you need to know about your flight from Cape Cod and the Islands to Chicago
No data available for this route at this time. Please check back soon.

Related info for your journey

Find useful and relevant information for your journey from Cape Cod and the Islands to Chicago. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • How long is the flight from Cape Cod and the Islands to Chicago?

    For as low as $588, Delta can have you in Chicago from Cape Cod and the Islands in 5h 30m. The distance between Cape Cod and the Islands and Chicago is about 891 mi. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.

  • What are the most popular routes from Cape Cod and the Islands to Chicago?

    The most popular flight routes from Cape Cod and the Islands to Chicago are West Tisbury Martha's Vineyard - Chicago O'Hare Intl, Hyannis Barnstable - Chicago O'Hare Intl and Nantucket Memorial - Chicago O'Hare Intl.

  • Can I find deals for flights from Cape Cod and the Islands to Chicago that include hotel bookings?

    Yes. In addition to deals on Cape Cod and the Islands to Chicago flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Cape Cod and the Islands to Chicago?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Cape Cod and the Islands to Chicago.

  • Can I find deals for business class flights from Cape Cod and the Islands to Chicago?

    Yes. Cheapflights offers flight deals from Cape Cod and the Islands to Chicago by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

See more FAQs

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Lansing
Merrillville
Hammond
Porter
Benton Harbor

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for Cape Cod and the Islands to Chicago

See prices for flight routes from nearby airports that may be better suited for you.
Boston to O'Hare Intl flights
Hartford to O'Hare Intl flights
Boston to Midway flights
Boston to St. Louis flights
Albany to O'Hare Intl flights
Hartford to Midway flights
Albany to Midway flights
Hartford to St. Louis flights
Albany to St. Louis flights
Boston to Rockford flights
Hartford to Moline flights
Boston to Moline flights
Worcester to O'Hare Intl flights
Hartford to Rockford flights
Boston to Peoria flights
Hartford to Peoria flights
West Tisbury to O'Hare Intl flights
Boston to Bloomington flights
Boston to Champaign flights
Albany to Evansville flights
Boston to Evansville flights
Albany to Peoria flights
Albany to Moline flights
Hartford to Evansville flights
Hyannis to O'Hare Intl flights
West Tisbury to St. Louis flights
Boston to Decatur flights
Nantucket to O'Hare Intl flights
Boston to Springfield flights
Boston to Dubuque flights
Hartford to Bloomington flights
Albany to Champaign flights
New Bedford to O'Hare Intl flights
Provincetown to O'Hare Intl flights
Boston to Paducah flights
Boston to Burlington flights
Hartford to Springfield flights
Albany to Springfield flights

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.
Site
©2026 Cheapflights