HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Chicago

$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 5/28. Fares are subject to change and may not be available on all flights or dates of travel.
ACK — CHI
May 4 — May 111
Sun 5/4
Sun 5/11
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Cape Cod and the Islands to Chicago with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

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 29, 2025.

Most accurate provider

Mytrip
3 stars

Most trusted provider

Mytrip
3 stars

Round-trip from

$401
(United Airlines)

One-way from

$103
(Delta)

Popular in

April

Cheapest in

September

Average price

$277
Provider with most accurate pricing for Boston Logan Intl-Chicago (CHI) flight deals.
Search Deals
Provider most trusted by Cheapflights users for Boston Logan Intl-Chicago (CHI) flights.
Search Deals
From Cape Cod and the Islands to Chicago (CHI)
Search Deals
One-way flight from Cape Cod and the Islands to Chicago (CHI)
Search Deals
Highest demand for flights based on searches. 12% potential increase in price ($33 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($4 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in April 2025
Search Deals

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 29, 2025.

This United Airlines deal was found by Cheapflights users on 4/26. 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.
Sun 6/294:32 pmACK - ORD
Nonstop3h 23mUnited Airlines
Sat 7/1210:35 amORD - ACK
Nonstop2h 54mUnited Airlines
Deal found 4/26$401
This American Airlines deal was found by Cheapflights users on 4/28. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/312:10 pmMVY - ORD
1 stop8h 03mAmerican Airlines
Sun 7/66:12 amORD - MVY
1 stop10h 18mAmerican Airlines
Deal found 4/28$441
This American Airlines deal was found by Cheapflights users on 4/26. 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.
Sun 6/295:26 pmACK - ORD
1 stop6h 58mAmerican Airlines
Sat 7/128:25 pmORD - ACK
1 stop20h 56mAmerican Airlines
Deal found 4/26$451
This JetBlue Airways deal was found by Cheapflights users on 4/27. 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.
Mon 5/53:00 pmHYA - ORD
1 stop18h 00mMultiple Airlines
Mon 5/127:31 pmORD - HYA
1 stop13h 39mMultiple Airlines
Deal found 4/27$476
This JetBlue deal was found by Cheapflights users on 4/28. 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.
Thu 5/811:00 amHYA - ORD
1 stop8h 36mJetBlue
Sun 5/118:45 amORD - HYA
1 stop6h 50mJetBlue
Deal found 4/28$507
This Delta deal was found by Cheapflights users on 4/28. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/412:15 pmMVY - ORD
1 stop5h 13mDelta
Sun 6/87:00 amORD - MVY
1 stop5h 36mDelta
Deal found 4/28$522
This JetBlue deal was found by Cheapflights users on 4/28. 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.
Tue 7/2212:26 pmMVY - ORD
1 stop5h 30mJetBlue
Wed 7/238:40 amORD - MVY
1 stop4h 30mJetBlue
Deal found 4/28$562
This JetBlue deal was found by Cheapflights users on 4/27. 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 9/121:55 pmPVC - ORD
1 stop4h 40mJetBlue
Sun 9/148:40 amORD - PVC
1 stop4h 08mJetBlue
Deal found 4/27$705
This JetBlue Airways deal was found by Cheapflights users on 4/28. 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 Airways is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/132:15 pmMVY - ORD
1 stop20h 47mMultiple Airlines
Sat 5/1710:50 amORD - MVY
1 stop6h 50mMultiple Airlines
Deal found 4/28$735
This JetBlue deal was found by Cheapflights users on 4/27. 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 5/210:40 amACK - ORD
1 stop7h 55mJetBlue
Mon 5/58:50 amORD - ACK
1 stop7h 16mJetBlue
Deal found 4/27$821
This Delta deal was found by Cheapflights users on 4/26. 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.
Sun 6/293:20 pmACK - ORD
2 stops9h 39mDelta
Sat 7/125:35 amORD - ACK
2 stops8h 07mDelta
Deal found 4/26$859
This Mytrip deal was found by Cheapflights users on 4/27. 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 5/23:55 pmACK - ORD
2 stops17h 09mMultiple Airlines
Mon 5/55:07 pmORD - ACK
2 stops24h 48mMultiple Airlines
Deal found 4/27$877

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 29, 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

NantucketChicago

ACK - ORD

ACKORD

Nantucket Memorial

Sun 6/29

4:32 pm-6:55 pm

Nonstop3h 23m

Chicago O'Hare Intl

Sat 7/12

10:35 am-2:29 pm

Nonstop2h 54m

$401

West TisburyChicago

MVY - ORD

MVYORD

West Tisbury Martha's Vineyard

Thu 7/3

12:10 pm-7:13 pm

1 stop8h 03m

Chicago O'Hare Intl

Sun 7/6

6:12 am-5:30 pm

1 stop10h 18m

$441

NantucketChicago

ACK - ORD

ACKORD

Nantucket Memorial

Sun 6/29

5:26 pm-11:24 pm

1 stop6h 58m

Chicago O'Hare Intl

Sat 7/12

8:25 pm-6:21 pm

1 stop20h 56m

$451

HyannisChicago

HYA - ORD

HYAORD

Hyannis Barnstable

Tue 5/13

10:35 am-6:36 pm

1 stop9h 01m

Chicago O'Hare Intl

Sat 5/17

10:50 am-2:40 pm

1 stop26h 50m

$476

HyannisChicago

HYA - ORD

HYAORD

Hyannis Barnstable

Thu 5/8

11:00 am-6:36 pm

1 stop8h 36m

Chicago O'Hare Intl

Sun 5/11

8:45 am-4:35 pm

1 stop6h 50m

$507

West TisburyChicago

MVY - ORD

MVYORD

West Tisbury Martha's Vineyard

Wed 6/4

12:15 pm-4:28 pm

1 stop5h 13m

Chicago O'Hare Intl

Sun 6/8

7:00 am-1:36 pm

1 stop5h 36m

$522

West TisburyChicago

MVY - ORD

MVYORD

West Tisbury Martha's Vineyard

Tue 7/22

12:26 pm-4:56 pm

1 stop5h 30m

Chicago O'Hare Intl

Wed 7/23

8:40 am-2:10 pm

1 stop4h 30m

$562

ProvincetownChicago

PVC - ORD

PVCORD

Provincetown

Fri 9/12

1:55 pm-5:35 pm

1 stop4h 40m

Chicago O'Hare Intl

Sun 9/14

8:40 am-1:48 pm

1 stop4h 08m

$705

West TisburyChicago

MVY - ORD

MVYORD

West Tisbury Martha's Vineyard

Tue 5/13

2:15 pm-10:02 am

1 stop20h 47m

Chicago O'Hare Intl

Sat 5/17

10:50 am-6:40 pm

1 stop6h 50m

$735

NantucketChicago

ACK - ORD

ACKORD

Nantucket Memorial

Sun 6/29

3:20 pm-11:59 pm

2 stops9h 39m

Chicago O'Hare Intl

Sat 7/12

5:35 am-2:42 pm

2 stops8h 07m

$859

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/28

Showing 1-10 of 21 results
1
2
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.

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 29, 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
7,929 reviews

Crew

8.5

Food

7.3

Boarding

8.2

Comfort

7.9

Entertainment

7.9

Overall

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
7,929 reviews
Delta
8.0
Very good
7,929 reviews

Crew

8.5

Food

7.3

Boarding

8.2

Comfort

7.9

Entertainment

7.9

Overall

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
8,696 reviews
Delta
8.0
Very good
7,929 reviews

Crew

8.5

Food

7.3

Boarding

8.2

Comfort

7.9

Entertainment

7.9

Overall

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
7.3
Good
2,922 reviews
Delta
8.0
Very good
7,929 reviews

Crew

8.5

Food

7.3

Boarding

8.2

Comfort

7.9

Entertainment

7.9

Overall

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
American Airlines
7.2
Good
10,000 reviews
Delta
8.0
Very good
7,929 reviews

Crew

8.5

Food

7.3

Boarding

8.2

Comfort

7.9

Entertainment

7.9

Overall

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 $103 on Delta. Other airlines that offer cheap prices include JetBlue from $113 and American Airlines from $120 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 Hyannis Barnstable - Chicago O'Hare Intl, West Tisbury Martha's Vineyard - Chicago O'Hare Intl and Nantucket Memorial - 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
Hammond
Benton Harbor
Porter
Lansing
Valparaiso
Chesterton

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

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.
Boston to O'Hare Intl flights
Hartford to O'Hare Intl flights
Boston to Midway flights
Boston to St. Louis flights
Hartford to Midway flights
Albany to O'Hare Intl flights
Hartford to St. Louis flights
Albany to Midway flights
Boston to Rockford flights
Albany to St. Louis flights
Worcester to O'Hare Intl flights
Boston to Moline flights
Boston to Peoria flights
Hartford to Moline flights
Boston to Evansville flights
Boston to Springfield flights
Hyannis to O'Hare Intl flights
Nantucket to O'Hare Intl flights
West Tisbury to O'Hare Intl flights
Hartford to Evansville flights
Albany to Peoria flights
Hartford to Rockford flights
Hartford to Peoria flights
Boston to Bloomington flights
Boston to Burlington flights
Boston to Champaign flights
Boston to Decatur flights
Hartford to Bloomington flights
West Tisbury to St. Louis flights
Provincetown to O'Hare Intl flights
Hartford to Springfield flights
Boston to Paducah flights
Boston to Dubuque flights
New Bedford to O'Hare Intl flights
Albany to Moline flights
Albany to Evansville flights
Albany to Springfield flights
Albany to Champaign flights

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.