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$105+ 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 6/28. Fares are subject to change and may not be available on all flights or dates of travel.
ACK — CHI
Jun 17 — Jun 241
Tue 6/17
Tue 6/24
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 12, 2025.

Round-trip from

$279
(American Airlines)

One-way from

$105
(American Airlines)

Popular in

March

Cheapest in

September

Average price

$220
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 ($4 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 12, 2025.

This American Airlines deal was found by Cheapflights users on 6/12. 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.
Sat 7/1212:50 pmHYA - ORD
1 stop5h 26mAmerican Airlines
Sat 7/195:25 amORD - HYA
1 stop6h 37mAmerican Airlines
Deal found 6/12$279
This American Airlines deal was found by Cheapflights users on 6/11. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/295:19 pmACK - ORD
1 stop7h 10mAmerican Airlines
Thu 7/3111:40 amORD - ACK
1 stop4h 09mAmerican Airlines
Deal found 6/11$328
This United Airlines deal was found by Cheapflights users on 6/12. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/411:53 amACK - ORD
1 stop6h 17mUnited Airlines
Sun 7/610:35 amORD - ACK
Nonstop2h 54mUnited Airlines
Deal found 6/12$418
This Delta deal was found by Cheapflights users on 6/12. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/412:05 pmACK - ORD
2 stops12h 54mDelta
Sun 7/67:05 amORD - ACK
2 stops6h 35mDelta
Deal found 6/12$503
This JetBlue deal was found by Cheapflights users on 6/11. 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.
Tue 7/225:15 pmHYA - ORD
1 stop6h 13mJetBlue
Thu 7/248:40 amORD - HYA
1 stop7h 58mJetBlue
Deal found 6/11$510
This American Airlines deal was found by Cheapflights users on 6/12. 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.
Fri 6/2712:10 pmMVY - ORD
1 stop12h 14mAmerican Airlines
Tue 7/17:01 amORD - MVY
1 stop4h 19mAmerican Airlines
Deal found 6/12$538
This JetBlue deal was found by Cheapflights users on 6/10. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/1810:55 amPVC - ORD
1 stop5h 58mJetBlue
Tue 6/248:40 amORD - PVC
1 stop7h 59mJetBlue
Deal found 6/10$561
This Delta deal was found by Cheapflights users on 6/12. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/1811:42 amMVY - ORD
1 stop5h 56mDelta
Mon 7/217:00 amORD - MVY
1 stop5h 33mDelta
Deal found 6/12$568
This United deal was found by Cheapflights users on 6/12. 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 United is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/121:15 pmHYA - ORD
2 stops11h 22mMultiple Airlines
Sat 7/196:30 amORD - HYA
1 stop12h 57mMultiple Airlines
Deal found 6/12$593
This JetBlue Airways deal was found by Cheapflights users on 6/11. 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 Airways is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/268:56 amPVC - ORD
1 stop7h 57mMultiple Airlines
Mon 6/304:51 pmORD - PVC
1 stop14h 45mMultiple Airlines
Deal found 6/11$647
This JetBlue deal was found by Cheapflights users on 6/11. 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.
Tue 7/224:57 pmMVY - ORD
1 stop6h 31mJetBlue
Thu 7/248:40 amORD - MVY
1 stop6h 33mJetBlue
Deal found 6/11$666
This Mytrip deal was found by Cheapflights users on 6/12. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/276:10 pmMVY - ORD
2 stops24h 34mMultiple Airlines
Tue 7/15:05 amORD - MVY
3 stops31h 50mMultiple Airlines
Deal found 6/12$723

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 12, 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

HyannisChicago

HYA - ORD

HYAORD

Hyannis Barnstable

Sat 7/12

12:50 pm-5:16 pm

1 stop5h 26m

Chicago O'Hare Intl

Sat 7/19

5:25 am-1:02 pm

1 stop6h 37m

$279

NantucketChicago

ACK - ORD

ACKORD

Nantucket Memorial

Tue 7/29

5:19 pm-11:29 pm

1 stop7h 10m

Chicago O'Hare Intl

Thu 7/31

11:40 am-4:49 pm

1 stop4h 09m

$328

NantucketChicago

ACK - ORD

ACKORD

Nantucket Memorial

Fri 7/4

11:53 am-5:10 pm

1 stop6h 17m

Chicago O'Hare Intl

Sun 7/6

10:35 am-2:29 pm

Nonstop2h 54m

$418

NantucketChicago

ACK - ORD

ACKORD

Nantucket Memorial

Fri 7/4

12:05 pm-11:59 pm

2 stops12h 54m

Chicago O'Hare Intl

Sun 7/6

7:05 am-2:40 pm

2 stops6h 35m

$503

HyannisChicago

HYA - ORD

HYAORD

Hyannis Barnstable

Tue 7/22

5:15 pm-10:28 pm

1 stop6h 13m

Chicago O'Hare Intl

Thu 7/24

8:40 am-5:38 pm

1 stop7h 58m

$510

West TisburyChicago

MVY - ORD

MVYORD

West Tisbury Martha's Vineyard

Fri 6/27

12:10 pm-11:24 pm

1 stop12h 14m

Chicago O'Hare Intl

Tue 7/1

7:01 am-12:20 pm

1 stop4h 19m

$538

West TisburyChicago

MVY - ORD

MVYORD

West Tisbury Martha's Vineyard

Fri 7/18

11:42 am-4:38 pm

1 stop5h 56m

Chicago O'Hare Intl

Mon 7/21

7:00 am-1:33 pm

1 stop5h 33m

$568

HyannisChicago

HYA - ORD

HYAORD

Hyannis Barnstable

Sat 7/12

1:15 pm-11:37 pm

2 stops11h 22m

Chicago O'Hare Intl

Sat 7/19

6:30 am-8:27 pm

1 stop12h 57m

$593

ProvincetownChicago

PVC - ORD

PVCORD

Provincetown

Thu 6/26

8:56 am-3:53 pm

1 stop7h 57m

Chicago O'Hare Intl

Mon 6/30

4:51 pm-8:36 am

1 stop14h 45m

$647

West TisburyChicago

MVY - ORD

MVYORD

West Tisbury Martha's Vineyard

Tue 7/22

4:57 pm-10:28 pm

1 stop6h 31m

Chicago O'Hare Intl

Thu 7/24

8:40 am-4:13 pm

1 stop6h 33m

$666

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/11

Showing 1-10 of 25 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

Rainfall in Chicago by month

Plan your trip to Chicago by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Chicago ranges from 1.7 - 4.9 inches per month. August is typically the wettest month, when rainfall can reach 4.9 in. January is typically the driest time to visit Chicago when rainfall is around 1.7 in.

Temperature in Chicago by month

Plan your trip to Chicago by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Chicago, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 73.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 23.0 F).

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 12, 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. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Delta
8.0
Very good
7,950 reviews

Boarding

8.2

Food

7.3

Crew

8.5

Comfort

7.9

Overall

8.0

Entertainment

7.9

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
7,950 reviews
Delta
8.0
Very good
7,950 reviews

Boarding

8.2

Food

7.3

Crew

8.5

Comfort

7.9

Overall

8.0

Entertainment

7.9

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
8,790 reviews
Delta
8.0
Very good
7,950 reviews

Boarding

8.2

Food

7.3

Crew

8.5

Comfort

7.9

Overall

8.0

Entertainment

7.9

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
2,925 reviews
Delta
8.0
Very good
7,950 reviews

Boarding

8.2

Food

7.3

Crew

8.5

Comfort

7.9

Overall

8.0

Entertainment

7.9

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
7,950 reviews

Boarding

8.2

Food

7.3

Crew

8.5

Comfort

7.9

Overall

8.0

Entertainment

7.9

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 $105 on American Airlines. Other airlines that offer cheap prices include JetBlue from $113 and Delta from $209 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 Provincetown - Chicago O'Hare Intl.

  • What are the cheapest flights from Cape Cod and the Islands to Chicago?

    While on average a flight from Cape Cod and the Islands to Chicago is generally $383, our data shows the cheapest flight currently is $167. When looking at the most popular route, (West Tisbury Martha's Vineyard - Chicago O'Hare Intl), you can expect to pay $593 for that flight.

  • 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 $321). 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

See prices for flight routes from nearby airports that may be better suited for you.
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