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$200+ 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.
ACK — CHI
feb. 4 — feb. 111
mar. 2/4
mar. 2/11
1 adult, Economy
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Cheap flight deals from Cape Cod and the Islands to Chicago

Discover tips and strategies to find the most affordable flight options for your journey from Cape Cod and the Islands (zzKDT) to Chicago (CHI). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated enero 30, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$689
(JetBlue Airways)

One-way from

$200
(JetBlue)

Popular in

April

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 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. 14% potential increase in price ($41 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($5 potential savings vs. average RT price).
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Average for round-trip flights in January 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 enero 30, 2025.

This JetBlue deal was found by Cheapflights users on 1/28. 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.
mié. 1/2911:00 amHYA - ORD
1 stop7h 59mJetBlue
jue. 1/307:00 amORD - HYA
1 stop6h 40mJetBlue
Deal found 1/28$624
This JetBlue Airways deal was found by Cheapflights users on 1/29. 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.
jue. 2/1311:00 amHYA - ORD
1 stop26h 00mMultiple Airlines
lun. 2/1712:45 pmORD - HYA
1 stop24h 55mMultiple Airlines
Deal found 1/29$689
This JetBlue deal was found by Cheapflights users on 1/30. 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.
jue. 8/144:57 pmMVY - ORD
1 stop7h 28mJetBlue
lun. 8/188:40 amORD - MVY
1 stop5h 34mJetBlue
Deal found 1/30$717
This Mytrip deal was found by Cheapflights users on 1/29. 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.
jue. 2/138:04 amEWB - ORD
3 stops16h 54mMultiple Airlines
lun. 2/177:13 pmORD - EWB
3 stops22h 04mMultiple Airlines
Deal found 1/29$1,183

Find flights from Cape Cod and the Islands to Chicago within your budget

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 enero 30, 2025.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

HyannisChicago

HYA - ORD

HYAORD

Hyannis Barnstable

jue. 2/13

11:00 am-12:00 pm

1 stop26h 00m

Chicago O'Hare Intl

lun. 2/17

12:45 pm-2:40 pm

1 stop24h 55m

$689

West TisburyChicago

MVY - ORD

MVYORD

West Tisbury Martha's Vineyard

mar. 3/11

10:20 am-4:25 pm

1 stop7h 05m

Chicago O'Hare Intl

vie. 3/14

1:15 pm-7:05 pm

1 stop4h 50m

$729

HyannisChicago

HYA - ORD

HYAORD

Hyannis Barnstable

jue. 4/10

11:00 am-6:07 pm

1 stop8h 07m

Chicago O'Hare Intl

dom. 4/13

9:43 am-4:15 pm

1 stop5h 32m

$859

New BedfordChicago

EWB - ORD

EWBORD

New Bedford Regional

jue. 2/13

8:04 am-11:58 pm

3 stops16h 54m

Chicago O'Hare Intl

lun. 2/17

7:13 pm-6:17 pm

3 stops22h 04m

$1,183

West TisburyChicago

MVY - ORD

MVYORD

West Tisbury Martha's Vineyard

mar. 7/29

12:26 pm-4:56 pm

1 stop5h 30m

$200

HyannisChicago

HYA - ORD

HYAORD

Hyannis Barnstable

mié. 2/26

11:00 am-5:00 pm

1 stop7h 00m

$202

NantucketChicago

ACK - ORD

ACKORD

Nantucket Memorial

mar. 7/29

11:35 am-7:25 pm

1 stop8h 50m

$203

HyannisChicago

HYA - ORD

HYAORD

Hyannis Barnstable

vie. 2/28

3:50 pm-6:22 pm

1 stop27h 32m

$228

NantucketChicago

ACK - ORD

ACKORD

Nantucket Memorial

lun. 7/28

4:34 pm-11:25 pm

1 stop7h 51m

$240

West TisburyChicago

MVY - ORD

MVYORD

West Tisbury Martha's Vineyard

mar. 7/29

4:45 pm-7:22 am

2 stops15h 37m

$256

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/30

Showing 1-10 of 13 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.

Travel insights for flights from Cape Cod and the Islands to Chicago

Get recent, data-driven insights about flights from Cape Cod and the Islands to Chicago including ideal travel times, pricing trends, and more.

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 enero 30, 2025.
Delta
8.0
Very good
8,450 reviews

Entertainment

7.9

Overall

8.0

Crew

8.5

Boarding

8.2

Food

7.3

Comfort

8.0

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
8,450 reviews
Delta
8.0
Very good
8,450 reviews

Entertainment

7.9

Overall

8.0

Crew

8.5

Boarding

8.2

Food

7.3

Comfort

8.0

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
7.4
Good
3,153 reviews
Delta
8.0
Very good
8,450 reviews

Entertainment

7.9

Overall

8.0

Crew

8.5

Boarding

8.2

Food

7.3

Comfort

8.0

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
8,906 reviews
Delta
8.0
Very good
8,450 reviews

Entertainment

7.9

Overall

8.0

Crew

8.5

Boarding

8.2

Food

7.3

Comfort

8.0

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 $200 on JetBlue. Other airlines that offer cheap prices include Delta from $203 and United Airlines from $330 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 New Bedford Regional - 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 $325). 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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