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$103+ 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 6/3. Fares are subject to change and may not be available on all flights or dates of travel.
ACK — CHI
Apr 8 — Apr 151
Tue 4/8
Tue 4/15
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 April 3, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$522
(JetBlue)

One-way from

$103
(Delta)

Popular in

May

Cheapest in

September

Average price

$282
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 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. 11% potential increase in price ($31 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 April 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 April 3, 2025.

This JetBlue deal was found by Cheapflights users on 4/2. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/64:59 pmHYA - ORD
1 stop7h 26mJetBlue
Tue 8/128:40 amORD - HYA
1 stop6h 10mJetBlue
Deal found 4/2$522
This Delta deal was found by Cheapflights users on 4/2. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/294:45 pmMVY - ORD
1 stop5h 04mDelta
Tue 9/27:00 amORD - MVY
1 stop6h 02mDelta
Deal found 4/2$703
This Mytrip deal was found by Cheapflights users on 4/1. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/175:00 pmMVY - ORD
2 stops16h 04mMultiple Airlines
Mon 4/218:45 amORD - MVY
2 stops33h 20mMultiple Airlines
Deal found 4/1$757
This JetBlue deal was found by Cheapflights users on 4/2. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/161:05 pmMVY - ORD
1 stop7h 22mJetBlue
Wed 4/2310:42 amORD - MVY
1 stop4h 48mJetBlue
Deal found 4/2$760
This Mytrip deal was found by Cheapflights users on 4/2. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/178:04 amEWB - ORD
3 stops25h 00mMultiple Airlines
Mon 4/218:45 amORD - EWB
3 stops32h 32mMultiple Airlines
Deal found 4/2$980

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 April 3, 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

Wed 8/6

4:59 pm-11:25 pm

1 stop7h 26m

Chicago O'Hare Intl

Tue 8/12

8:40 am-3:50 pm

1 stop6h 10m

$522

West TisburyChicago

MVY - ORD

MVYORD

West Tisbury Martha's Vineyard

Fri 8/29

4:45 pm-8:49 pm

1 stop5h 04m

Chicago O'Hare Intl

Tue 9/2

7:00 am-2:02 pm

1 stop6h 02m

$703

West TisburyChicago

MVY - ORD

MVYORD

West Tisbury Martha's Vineyard

Thu 4/17

5:00 pm-8:04 am

2 stops16h 04m

Chicago O'Hare Intl

Mon 4/21

8:45 am-7:05 pm

2 stops33h 20m

$757

West TisburyChicago

MVY - ORD

MVYORD

West Tisbury Martha's Vineyard

Wed 4/16

1:05 pm-7:27 pm

1 stop7h 22m

Chicago O'Hare Intl

Wed 4/23

10:42 am-4:30 pm

1 stop4h 48m

$760

New BedfordChicago

EWB - ORD

EWBORD

New Bedford Regional

Thu 4/17

8:04 am-8:04 am

3 stops25h 00m

Chicago O'Hare Intl

Mon 4/21

8:45 am-6:17 pm

3 stops32h 32m

$980

NantucketChicago

ACK - ORD

ACKORD

Nantucket Memorial

Tue 6/3

3:45 pm-8:46 pm

1 stop6h 01m

$103

NantucketChicago

ACK - ORD

ACKORD

Nantucket Memorial

Tue 9/30

4:20 pm-8:54 pm

1 stop5h 34m

$117

NantucketChicago

ACK - ORD

ACKORD

Nantucket Memorial

Thu 7/3

5:26 pm-8:32 am

1 stop16h 06m

$154

HyannisChicago

HYA - ORD

HYAORD

Hyannis Barnstable

Thu 7/3

2:42 pm-11:24 pm

1 stop9h 42m

$160

West TisburyChicago

MVY - ORD

MVYORD

West Tisbury Martha's Vineyard

Thu 7/3

12:10 pm-7:13 pm

1 stop8h 03m

$174

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/3

Showing 1-10 of 17 results
1
2

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 April 3, 2025.
Delta
8.0
Very good
7,897 reviews

Comfort

7.9

Overall

8.0

Food

7.3

Crew

8.5

Entertainment

7.9

Boarding

8.2

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

TUS - LAX

Delta has consistently been the best U.S. airline for my travels and this flight was no exception
Delta
8.0
Very good
7,897 reviews
Delta
8.0
Very good
7,897 reviews

Comfort

7.9

Overall

8.0

Food

7.3

Crew

8.5

Entertainment

7.9

Boarding

8.2

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

TUS - LAX

Delta has consistently been the best U.S. airline for my travels and this flight was no exception
United Airlines
7.4
Good
8,619 reviews
Delta
8.0
Very good
7,897 reviews

Comfort

7.9

Overall

8.0

Food

7.3

Crew

8.5

Entertainment

7.9

Boarding

8.2

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

TUS - LAX

Delta has consistently been the best U.S. airline for my travels and this flight was no exception
JetBlue
7.3
Good
2,920 reviews
Delta
8.0
Very good
7,897 reviews

Comfort

7.9

Overall

8.0

Food

7.3

Crew

8.5

Entertainment

7.9

Boarding

8.2

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

TUS - LAX

Delta has consistently been the best U.S. airline for my travels and this flight was no exception
American Airlines
7.2
Good
10,000 reviews
Delta
8.0
Very good
7,897 reviews

Comfort

7.9

Overall

8.0

Food

7.3

Crew

8.5

Entertainment

7.9

Boarding

8.2

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

TUS - LAX

Delta has consistently been the best U.S. airline for my travels and this flight was no exception

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 $103 on Delta. Other airlines that offer cheap prices include JetBlue from $117 and American Airlines from $154 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.

  • 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
New Buffalo
Hammond
Benton Harbor
Porter
Lansing
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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