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$96+ 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 7/22. Fares are subject to change and may not be available on all flights or dates of travel.
ACK — CHI
Jul 1 — Jul 81
Tue 7/1
Tue 7/8
1 adult, Economy
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Cheap 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 June 26, 2025.

Round-trip from

$197
(JetBlue)

One-way from

$96
(JetBlue)

Popular in

March

Cheapest in

September

Average price

$225
From Cape Cod and the Islands to Chicago (CHI)
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One-way flight from Cape Cod and the Islands to Chicago (CHI)
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Highest demand for flights based on searches. 9% potential increase in price ($23 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease ($3 potential savings vs. average RT price).
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Average for round-trip flights in June 2025
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Find 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 June 26, 2025.

This JetBlue deal was found by Cheapflights users on 6/24. 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 8/224:48 pmACK - ORD
1 stop6h 40mJetBlue
Tue 8/266:15 amORD - ACK
1 stop4h 38mJetBlue
Deal found 6/24$197
This Delta deal was found by Cheapflights users on 6/25. 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 8/224:49 pmACK - ORD
2 stops18h 31mDelta
Tue 8/269:25 amORD - ACK
1 stop5h 44mDelta
Deal found 6/25$258
This American Airlines deal was found by Cheapflights users on 6/24. 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 7/231:40 pmHYA - ORD
1 stop5h 14mAmerican Airlines
Wed 7/308:05 amORD - HYA
1 stop5h 09mAmerican Airlines
Deal found 6/24$292
This American Airlines deal was found by Cheapflights users on 6/26. 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 8/142:46 pmMVY - ORD
1 stop9h 39mAmerican Airlines
Tue 8/266:06 amORD - MVY
1 stop8h 31mAmerican Airlines
Deal found 6/26$299
This American Airlines deal was found by Cheapflights users on 6/24. 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.
Fri 7/184:27 pmACK - ORD
1 stop7h 24mAmerican Airlines
Sun 7/207:00 amORD - ACK
1 stop5h 21mAmerican Airlines
Deal found 6/24$313
This Delta deal was found by Cheapflights users on 6/25. 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 8/223:20 pmMVY - ORD
2 stops25h 53mDelta
Mon 8/259:10 amORD - MVY
2 stops27h 23mDelta
Deal found 6/25$400
This JetBlue deal was found by Cheapflights users on 6/26. 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 7/255:15 pmHYA - ORD
1 stop6h 13mJetBlue
Mon 7/288:40 amORD - HYA
1 stop7h 58mJetBlue
Deal found 6/26$417
This JetBlue Airways deal was found by Cheapflights users on 6/24. 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 Airways is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/85:15 pmHYA - ORD
1 stop6h 13mMultiple Airlines
Thu 7/104:27 pmORD - HYA
1 stop24h 11mMultiple Airlines
Deal found 6/24$432
This JetBlue deal was found by Cheapflights users on 6/26. 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 7/254:57 pmMVY - ORD
1 stop6h 31mJetBlue
Mon 7/288:40 amORD - MVY
1 stop4h 30mJetBlue
Deal found 6/26$503
This United Airlines deal was found by Cheapflights users on 6/24. 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.
Fri 7/114:46 pmACK - ORD
1 stop7h 55mUnited Airlines
Sat 7/1210:35 amORD - ACK
Nonstop2h 54mUnited Airlines
Deal found 6/24$539
This Mytrip deal was found by Cheapflights users on 6/25. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/1010:40 pmMVY - ORD
3 stops35h 15mMultiple Airlines
Mon 7/145:05 amORD - MVY
2 stops26h 00mMultiple Airlines
Deal found 6/25$715
This Mytrip deal was found by Cheapflights users on 6/24. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/115:20 pmACK - ORD
2 stops16h 35mMultiple Airlines
Sat 7/1211:21 amORD - ACK
2 stops20h 49mMultiple Airlines
Deal found 6/24$718

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 June 26, 2025.
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

NantucketChicago

ACK - ORD

ACKORD

Nantucket Memorial

Fri 8/22

4:48 pm-10:28 pm

1 stop6h 40m

Chicago O'Hare Intl

Tue 8/26

6:15 am-11:53 am

1 stop4h 38m

$197

NantucketChicago

ACK - ORD

ACKORD

Nantucket Memorial

Fri 8/22

4:49 pm-10:20 am

2 stops18h 31m

Chicago O'Hare Intl

Tue 8/26

9:25 am-4:09 pm

1 stop5h 44m

$258

HyannisChicago

HYA - ORD

HYAORD

Hyannis Barnstable

Wed 7/23

12:20 pm-4:53 pm

1 stop5h 33m

Chicago O'Hare Intl

Wed 7/30

8:05 am-2:14 pm

1 stop5h 09m

$292

West TisburyChicago

MVY - ORD

MVYORD

West Tisbury Martha's Vineyard

Thu 8/14

2:46 pm-11:25 pm

1 stop9h 39m

Chicago O'Hare Intl

Tue 8/26

8:41 pm-2:16 pm

1 stop16h 35m

$299

NantucketChicago

ACK - ORD

ACKORD

Nantucket Memorial

Fri 7/18

4:27 pm-10:51 pm

1 stop7h 24m

Chicago O'Hare Intl

Sun 7/20

7:00 am-1:21 pm

1 stop5h 21m

$313

West TisburyChicago

MVY - ORD

MVYORD

West Tisbury Martha's Vineyard

Fri 8/22

3:20 pm-4:13 pm

2 stops25h 53m

Chicago O'Hare Intl

Mon 8/25

9:10 am-1:33 pm

2 stops27h 23m

$400

HyannisChicago

HYA - ORD

HYAORD

Hyannis Barnstable

Fri 7/25

5:15 pm-10:28 pm

1 stop6h 13m

Chicago O'Hare Intl

Mon 7/28

8:40 am-5:38 pm

1 stop7h 58m

$417

HyannisChicago

HYA - ORD

HYAORD

Hyannis Barnstable

Tue 7/8

5:15 pm-10:28 pm

1 stop6h 13m

Chicago O'Hare Intl

Thu 7/10

4:27 pm-5:38 pm

1 stop24h 11m

$432

West TisburyChicago

MVY - ORD

MVYORD

West Tisbury Martha's Vineyard

Fri 7/25

4:57 pm-10:28 pm

1 stop6h 31m

Chicago O'Hare Intl

Mon 7/28

8:40 am-2:10 pm

1 stop4h 30m

$503

NantucketChicago

ACK - ORD

ACKORD

Nantucket Memorial

Fri 7/11

4:46 pm-11:41 pm

1 stop7h 55m

Chicago O'Hare Intl

Sat 7/12

10:35 am-2:29 pm

Nonstop2h 54m

$539

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/26

Showing 1-10 of 27 results
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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

What is the cheapest time of day to fly from KDT to CHI?

Find hourly flight availability from Cape Cod and the Islands to Chicago. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated June 26, 2025.

When flying from Cape Cod and the Islands to Chicago, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

Reviews of airlines servicing Chicago

Get insights into the airlines that provide service to Chicago. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Chicago. Reviews last updated June 26, 2025.
Peruse reviews from past customers who have flown with Delta, United Airlines, and JetBlue from Cape Cod and the Islands to Chicago to help guide your decision. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
Delta
8.0
Very good
7,964 reviews

Overall

8.0

Entertainment

7.9

Comfort

7.9

Boarding

8.2

Food

7.3

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
Delta
8.0
Very good
7,964 reviews
Delta
8.0
Very good
7,964 reviews

Overall

8.0

Entertainment

7.9

Comfort

7.9

Boarding

8.2

Food

7.3

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
United Airlines
7.4
Good
8,838 reviews
Delta
8.0
Very good
7,964 reviews

Overall

8.0

Entertainment

7.9

Comfort

7.9

Boarding

8.2

Food

7.3

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
JetBlue
7.3
Good
2,922 reviews
Delta
8.0
Very good
7,964 reviews

Overall

8.0

Entertainment

7.9

Comfort

7.9

Boarding

8.2

Food

7.3

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
American Airlines
7.2
Good
10,000 reviews
Delta
8.0
Very good
7,964 reviews

Overall

8.0

Entertainment

7.9

Comfort

7.9

Boarding

8.2

Food

7.3

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!

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.

  • What are the cheapest airlines to fly from Cape Cod and the Islands to Chicago one-way?

    One-way options have recently been found by users for as low as $96 on JetBlue. Other airlines that offer cheap prices include American Airlines from $120 and Delta from $160 one-way.

  • 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.

  • What is the cheapest month to book a flight from Cape Cod and the Islands to Chicago?

    Currently, August is the cheapest month in which you can book a flight from Cape Cod and the Islands to Chicago (average of $245). Flying from Cape Cod and the Islands to Chicago in March is currently the most expensive (average of $320). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

Traveling to a place near Cape Cod and the Islands?

Book flights to Cape Cod and the Islands if you plan to visit one of these locations
Merrillville
Lansing
Benton Harbor
Porter
Hammond
Valparaiso
Chesterton

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Alternative routes for Cape Cod and the Islands to Chicago

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