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$208+ 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 1/31. Fares are subject to change and may not be available on all flights or dates of travel.
ACK — CHI
Nov 9 — Nov 161
1 adult
Sat 11/9
Sat 11/16
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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 November 4, 2024.

This United deal was found by Cheapflights users on 11/3. 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.
Thu 12/53:50 pmHYA - ORD
1 stop17h 06mMultiple Airlines
Thu 12/129:20 amORD - HYA
1 stop4h 20mMultiple Airlines
Deal found 11/3$454
This JetBlue deal was found by Cheapflights users on 11/3. 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 12/411:00 amHYA - ORD
1 stop5h 53mJetBlue
Sat 12/78:51 amORD - HYA
1 stop4h 49mJetBlue
Deal found 11/3$478
This JetBlue deal was found by Cheapflights users on 11/3. 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 12/410:20 amMVY - ORD
1 stop6h 33mJetBlue
Sat 12/78:51 amORD - MVY
1 stop4h 19mJetBlue
Deal found 11/3$538
This Mytrip deal was found by Cheapflights users on 11/4. 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.
Mon 12/234:55 pmACK - ORD
2 stops28h 54mMultiple Airlines
Wed 1/11:24 pmORD - ACK
2 stops19h 11mMultiple Airlines
Deal found 11/4$649

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 2,455,398 searches. Data last updated November 4, 2024.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

HyannisChicago

HYA - ORD

HYAORD

Hyannis Barnstable

Fri 1/31

11:00 am-5:53 pm

1 stop7h 53m

$208

HyannisChicago

HYA - ORD

HYAORD

Hyannis Barnstable

Mon 2/3

3:50 pm-8:25 pm

1 stop5h 35m

$212

West TisburyChicago

MVY - ORD

MVYORD

West Tisbury Martha's Vineyard

Wed 12/4

10:20 am-2:21 pm

1 stop5h 01m

$267

West TisburyChicago

MVY - ORD

MVYORD

West Tisbury Martha's Vineyard

Wed 12/4

10:20 am-3:53 pm

1 stop6h 33m

$277

NantucketChicago

ACK - ORD

ACKORD

Nantucket Memorial

Sat 2/1

1:51 pm-5:53 pm

1 stop5h 02m

$302

NantucketChicago

ACK - ORD

ACKORD

Nantucket Memorial

Mon 2/3

1:40 pm-8:25 pm

2 stops7h 45m

$307

HyannisChicago

HYA - ORD

HYAORD

Hyannis Barnstable

Thu 12/5

3:50 pm-7:56 am

1 stop17h 06m

Chicago O'Hare Intl

Thu 12/12

9:20 am-2:40 pm

1 stop4h 20m

$454

HyannisChicago

HYA - ORD

HYAORD

Hyannis Barnstable

Wed 12/4

11:00 am-3:53 pm

1 stop5h 53m

Chicago O'Hare Intl

Sat 12/7

8:51 am-2:40 pm

1 stop4h 49m

$478

West TisburyChicago

MVY - ORD

MVYORD

West Tisbury Martha's Vineyard

Wed 12/4

10:20 am-3:53 pm

1 stop6h 33m

Chicago O'Hare Intl

Sat 12/7

8:51 am-2:10 pm

1 stop4h 19m

$538

NantucketChicago

ACK - ORD

ACKORD

Nantucket Memorial

Mon 12/23

4:55 pm-8:49 pm

2 stops28h 54m

Chicago O'Hare Intl

Wed 1/1

1:24 pm-9:35 am

2 stops19h 11m

$649

Flights are sorted by cheapest first

Deals found on 11/3

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 4, 2024.
JetBlue
7.5
Good
3,493 reviews

Entertainment

7.4

Food

7.0

Comfort

7.8

Overall

7.5

Boarding

7.7

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.

JetBlue
7.5
Good
3,493 reviews
JetBlue
7.5
Good
3,493 reviews

Entertainment

7.4

Food

7.0

Comfort

7.8

Overall

7.5

Boarding

7.7

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.

  • Can I find flights from Cape Cod and the Islands to Chicago for under $500 on Cheapflights?

    Yes, there are multiple flights from Cape Cod and the Islands to Chicago for under $500. The cheapest flight booked recently is on Multiple Airlines for just $454, but on average you can expect to pay $529.

  • 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 Hyannis Barnstable - Chicago O'Hare Intl, West Tisbury Martha's Vineyard - Chicago O'Hare Intl and Provincetown - Chicago O'Hare Intl.

  • What does ACK to ORD mean?

    ACK stands for Nantucket Memorial Airport, while ORD stands for Chicago O'Hare Intl Airport. These codes are often called IATA codes, a set of identifiers established by IATA (International Air Transport Association) that is widely used by airlines and the aviation industry. This flight route has multiple associated airports, so we think it might be helpful to learn the name and codes of them as well. They are Chicago Midway Airport (MDW), Chicago Greater Rockford Airport (RFD).

  • Can I find deals for flights from Cape Cod and the Islands to Chicago that include extra baggage allowance?

    The amount of baggage you can bring on your Cape Cod and the Islands to Chicago flight depends on the airline and the type of fare you've chosen. After entering your flight details, you'll be able to view the specific baggage policies for each deal in the search results. Keep in mind that certain deals may offer additional baggage allowance.

  • Can I find deals on flights from Cape Cod and the Islands to Chicago with specific airlines?

    Yes, Cheapflights allows you to browse and filter Cape Cod and the Islands to Chicago flight deals by airline. After entering your origin and destination, use the available filters to view flights offered by airlines.

  • 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.

  • Can I find deals for flights from Cape Cod and the Islands to Chicago that allow pets onboard?

    Many airlines flying from Cape Cod and the Islands to Chicago offer the option to travel with pets. After selecting a flight deal, you can find more information about the airline's pet policy on their official website or by contacting the airline directly. Please note that additional fees and restrictions may apply.

  • Can I find deals on last-minute flights from Cape Cod and the Islands to Chicago?

    Yes, you can often find last-minute deals on Cape Cod and the Islands to Chicago flights on Cheapflights. However, these deals can vary and may not always be available. We recommend checking back frequently or signing up for price alerts for the most up-to-date deals.

  • How recently were the Cape Cod and the Islands to Chicago flight deals updated?

    The Cape Cod and the Islands to Chicago flight deals you see on this page were last updated on 11/4.

  • 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.

See more FAQs

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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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