Chicago

$212+ 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 2/21. Fares are subject to change and may not be available on all flights or dates of travel.
ACK — CHI
Nov 26 — Dec 31
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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 November 21, 2024.

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 November 21, 2024.

This JetBlue deal was found by Cheapflights users on 11/20. 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 12/1111:00 amHYA - ORD
1 stop5h 53mJetBlue
Thu 12/128:51 amORD - HYA
1 stop4h 49mJetBlue
Deal found 11/20$523
This JetBlue deal was found by Cheapflights users on 11/21. 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 12/611:30 amMVY - ORD
1 stop5h 23mJetBlue
Tue 12/108:51 amORD - MVY
1 stop5h 49mJetBlue
Deal found 11/21$653

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 2,612,795 searches. Data last updated November 21, 2024.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

HyannisChicago

HYA - ORD

HYAORD

Hyannis Barnstable

Wed 12/11

11:00 am-3:53 pm

1 stop5h 53m

Chicago O'Hare Intl

Thu 12/12

8:51 am-2:40 pm

1 stop4h 49m

$523

West TisburyChicago

MVY - ORD

MVYORD

West Tisbury Martha's Vineyard

Fri 12/6

11:30 am-3:53 pm

1 stop5h 23m

Chicago O'Hare Intl

Tue 12/10

8:51 am-3:40 pm

1 stop5h 49m

$668

HyannisChicago

HYA - ORD

HYAORD

Hyannis Barnstable

Fri 2/21

2:48 pm-6:22 pm

1 stop4h 34m

$212

HyannisChicago

HYA - ORD

HYAORD

Hyannis Barnstable

Wed 12/18

11:00 am-3:53 pm

1 stop5h 53m

$267

West TisburyChicago

MVY - ORD

MVYORD

West Tisbury Martha's Vineyard

Fri 2/21

1:40 pm-6:22 pm

2 stops5h 42m

$267

NantucketChicago

ACK - ORD

ACKORD

Nantucket Memorial

Wed 2/19

7:00 am-12:00 pm

1 stop6h 00m

$302

West TisburyChicago

MVY - ORD

MVYORD

West Tisbury Martha's Vineyard

Sat 1/18

2:15 pm-5:59 pm

1 stop4h 44m

$302

NantucketChicago

ACK - ORD

ACKORD

Nantucket Memorial

Fri 2/21

1:51 pm-5:53 am

2 stops17h 02m

$495

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/20

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 November 21, 2024.
7.5
Good
3,389 reviews

Boarding

7.7

Entertainment

7.4

Food

6.9

Comfort

7.7

Overall

7.5

Crew

8.2

Reviews

1 / 10

we were told the night before that the flight would be delayed ~50 minutes but that we should show up on time. We did but at the new doors open time people were still deplaning from our aircraft. We finally left the gate 1:48 minutes late but the captain said an indicator showed and we weren't allowed to taxi. Maintenace came on board did some stuff, then we took off. Because of Tropical storm Debbie we went way east over the ocean. It was still rough though no fault of Jet Blue.

7.5
Good
3,389 reviews
7.5
Good
3,389 reviews

Boarding

7.7

Entertainment

7.4

Food

6.9

Comfort

7.7

Overall

7.5

Crew

8.2

Reviews

1 / 10

we were told the night before that the flight would be delayed ~50 minutes but that we should show up on time. We did but at the new doors open time people were still deplaning from our aircraft. We finally left the gate 1:48 minutes late but the captain said an indicator showed and we weren't allowed to taxi. Maintenace came on board did some stuff, then we took off. Because of Tropical storm Debbie we went way east over the ocean. It was still rough though no fault of Jet Blue.

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 most popular routes from Cape Cod and the Islands to Chicago?

  • 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, September is the cheapest month in which you can book a flight from Cape Cod and the Islands to Chicago (average of $232). Flying from Cape Cod and the Islands to Chicago in June is currently the most expensive (average of $308). 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.

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