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$113+ Cheap flights from Cape Cod and the Islands to Illinois

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 7/8. Fares are subject to change and may not be available on all flights or dates of travel.
MVY — ORD
Feb 11 — Feb 181
Wed 2/11
Wed 2/18
1 adult, Economy
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Cheap flight deals from Cape Cod and the Islands to Illinois

Keep the following information in mind while searching for Cape Cod and the Islands to Illinois flight deals. Data was last updated January 12, 2026.

Most accurate provider

Mytrip
3 stars

Most trusted provider

Mytrip
3 stars

Round-trip from

$410
(Priceline)

One-way from

$113
(Delta)

Popular in

March

Cheapest in

September

Average price

$202
Provider with most accurate pricing for Boston Logan Intl-Chicago (CHI) flight deals.
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Provider most trusted by Cheapflights users for Boston Logan Intl-Chicago (CHI) flights.
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From Cape Cod and the Islands to Illinois
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One-way flight from Cape Cod and the Islands to Illinois
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Highest demand for flights based on searches. 7% potential increase in price ($18 potential increase over avg. RT price).
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Cheapest flight prices on average. 0% potential price decrease ($3 potential savings vs. average RT price).
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Average for round-trip flights in January 2026
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Find flight deals from Cape Cod and the Islands to Illinois

Cheapest flights from Cape Cod and the Islands to Illinois
Explore the most affordable flight options available from Cape Cod and the Islands to Illinois. Find the lowest fares from popular airlines and budget airlines, with prices last updated on January 12, 2026.

This Priceline deal was found by Cheapflights users on 1/10. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 1/2512:07 pm
HYA
-
ORD
1 stop6h 36m
Multiple Airlines
Thu 1/297:40 am
ORD
-
HYA
1 stop8h 40m
Multiple Airlines
Deal found 1/10$410
This JetBlue deal was found by Cheapflights users on 1/9. 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 3/1612:07 pm
HYA
-
ORD
1 stop6h 17m
JetBlue
Wed 3/1810:56 am
ORD
-
HYA
1 stop5h 24m
JetBlue
Deal found 1/9$425
This JetBlue deal was found by Cheapflights users on 1/9. 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.
Sun 3/1512:07 pm
HYA
-
ORD
1 stop6h 17m
JetBlue
Tue 3/1710:56 am
ORD
-
HYA
1 stop5h 24m
JetBlue
Deal found 1/9$475
This American Airlines deal was found by Cheapflights users on 1/12. 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 7/161:02 pm
HYA
-
ORD
1 stop5h 13m
American Airlines
Sat 7/1810:50 am
ORD
-
HYA
Nonstop2h 35m
American Airlines
Deal found 1/12$478
This United Airlines deal was found by Cheapflights users on 1/9. 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 9/237:10 am
ORD
-
ACK
1 stop7h 18m
United Airlines
Deal found 1/9$519
This JetBlue deal was found by Cheapflights users on 1/11. 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.
Sun 1/181:28 pm
MVY
-
ORD
1 stop5h 15m
JetBlue
Tue 1/207:40 am
ORD
-
MVY
1 stop6h 55m
JetBlue
Deal found 1/11$559
This JetBlue deal was found by Cheapflights users on 1/11. 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.
Thu 3/2612:07 pm
HYA
-
ORD
1 stop6h 17m
JetBlue
Tue 3/3110:00 am
ORD
-
HYA
1 stop6h 20m
JetBlue
Deal found 1/11$580
This JetBlue deal was found by Cheapflights users on 1/9. 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 3/161:28 pm
MVY
-
ORD
1 stop4h 56m
JetBlue
Wed 3/1810:56 am
ORD
-
MVY
1 stop6h 54m
JetBlue
Deal found 1/9$584
This American Airlines deal was found by Cheapflights users on 1/12. 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 7/1610:41 am
MVY
-
ORD
1 stop7h 34m
American Airlines
Sat 7/181:20 pm
ORD
-
MVY
1 stop4h 45m
American Airlines
Deal found 1/12$587
This JetBlue deal was found by Cheapflights users on 1/9. 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.
Sun 3/1510:10 am
MVY
-
ORD
1 stop8h 14m
JetBlue
Tue 3/1710:56 am
ORD
-
MVY
1 stop6h 54m
JetBlue
Deal found 1/9$594
This JetBlue deal was found by Cheapflights users on 1/11. 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 1/261:28 pm
MVY
-
ORD
1 stop5h 15m
JetBlue
Fri 1/307:45 am
ORD
-
MVY
1 stop6h 50m
JetBlue
Deal found 1/11$629
This American Airlines deal was found by Cheapflights users on 1/12. 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.
Wed 7/17:35 pm
MVY
-
ORD
1 stop14h 30m
American Airlines
Fri 7/36:34 am
ORD
-
MVY
1 stop4h 22m
American Airlines
Deal found 1/12$636

Cheapflights Fare Finder

 
Customize your flight search to find flights from Cape Cod and the Islands to Illinois 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 January 12, 2026.
Use the filters below to find and compare flights from Cape Cod and the Islands to Illinois that are best for you.

Fly from

Cape Cod and the Islands

Fly to

Illinois

Route

Depart

Return

Price

HyannisChicago

HYA - ORD

HYAORD

Hyannis Barnstable

Sun 1/25

12:07 pm-5:43 pm

1 stop6h 36m

Chicago O'Hare Intl

Thu 1/29

7:40 am-5:20 pm

1 stop8h 40m

$410

HyannisChicago

HYA - ORD

HYAORD

Hyannis Barnstable

Mon 3/16

12:07 pm-5:24 pm

1 stop6h 17m

Chicago O'Hare Intl

Wed 3/18

10:56 am-5:20 pm

1 stop5h 24m

$425

HyannisChicago

HYA - ORD

HYAORD

Hyannis Barnstable

Mon 3/16

12:07 pm-5:24 pm

1 stop6h 17m

Chicago O'Hare Intl

Tue 3/17

10:56 am-5:20 pm

1 stop5h 24m

$425

HyannisChicago

HYA - ORD

HYAORD

Hyannis Barnstable

Sun 3/15

12:07 pm-5:24 pm

1 stop6h 17m

Chicago O'Hare Intl

Tue 3/17

10:56 am-5:20 pm

1 stop5h 24m

$475

HyannisChicago

HYA - ORD

HYAORD

Hyannis Barnstable

Thu 3/26

12:07 pm-5:24 pm

1 stop6h 17m

Chicago O'Hare Intl

Tue 3/31

10:00 am-5:20 pm

1 stop6h 20m

$580

West TisburyChicago

MVY - ORD

MVYORD

West Tisbury Martha's Vineyard

Mon 3/16

1:28 pm-5:24 pm

1 stop4h 56m

Chicago O'Hare Intl

Wed 3/18

10:56 am-6:50 pm

1 stop6h 54m

$584

West TisburyChicago

MVY - ORD

MVYORD

West Tisbury Martha's Vineyard

Tue 1/27

1:28 pm-5:43 pm

1 stop5h 15m

Chicago O'Hare Intl

Sat 1/31

7:40 am-3:35 pm

1 stop6h 55m

$584

West TisburyChicago

MVY - ORD

MVYORD

West Tisbury Martha's Vineyard

Mon 2/9

1:28 pm-5:43 pm

1 stop5h 15m

Chicago O'Hare Intl

Wed 2/11

7:45 am-3:35 pm

1 stop6h 50m

$584

West TisburyChicago

MVY - ORD

MVYORD

West Tisbury Martha's Vineyard

Mon 3/16

10:10 am-5:24 pm

1 stop8h 14m

Chicago O'Hare Intl

Tue 3/17

10:56 am-6:50 pm

1 stop6h 54m

$584

West TisburyChicago

MVY - ORD

MVYORD

West Tisbury Martha's Vineyard

Sun 1/25

7:09 am-5:43 pm

1 stop11h 34m

Chicago O'Hare Intl

Thu 1/29

7:45 am-3:35 pm

1 stop6h 50m

$584

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/10

Showing 1-10 of 44 results
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Best time to book a flight from Cape Cod and the Islands to Illinois

Have a flexible travel schedule? Discover the best time to fly to Illinois 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 Illinois
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 Illinois. 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 Illinois?

    A quick flight from Cape Cod and the Islands to Illinois can take about 6h 17m. JetBlue provides one of the quickest options available for as low as $425. There are 905 mi between Cape Cod and the Islands and Illinois. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.

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

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

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

    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 Illinois.

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

    Yes. Cheapflights offers flight deals from Cape Cod and the Islands to Illinois 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

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