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Cape Cod and the Islands

$340+ Cheap flights from Midway (MDW) to Cape Cod and the Islands

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 8/14. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — ACK
Jun 5 — Jun 121
Fri 6/5
Fri 6/12
1 adult, Economy
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Cheap flight deals from Midway to Cape Cod and the Islands

Cheapest flights from Midway to Cape Cod and the Islands
Explore the most affordable flight options available from Midway to Cape Cod and the Islands. Find the lowest fares from popular airlines and budget airlines, with prices last updated on May 6, 2026.

This Delta deal was found by Cheapflights users on 5/5. 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.
Tue 5/266:23 am
MDW
-
ACK
2 stops7h 57m
Delta
Tue 6/212:07 pm
ACK
-
MDW
2 stops7h 26m
Delta
Deal found 5/5$474
This Delta deal was found by Cheapflights users on 5/2. 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.
Tue 6/306:00 am
MDW
-
ACK
2 stops8h 48m
Delta
Tue 7/712:13 pm
ACK
-
MDW
2 stops7h 12m
Delta
Deal found 5/2$586
This Delta deal was found by Cheapflights users on 5/4. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/266:23 am
MDW
-
ACK
2 stops7h 57m
Delta
Thu 5/2812:07 pm
ACK
-
MDW
2 stops7h 26m
Delta
Deal found 5/4$603
This Delta deal was found by Cheapflights users on 5/5. 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 7/316:00 am
MDW
-
ACK
2 stops7h 41m
Delta
Wed 8/53:24 pm
ACK
-
MDW
2 stops8h 12m
Delta
Deal found 5/5$729
This Delta deal was found by Cheapflights users on 5/5. 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 5/276:23 am
MDW
-
ACK
2 stops7h 57m
Delta
Tue 6/212:07 pm
ACK
-
MDW
2 stops10h 02m
Delta
Deal found 5/5$764
This Delta deal was found by Cheapflights users on 5/5. 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.
Thu 7/306:00 am
MDW
-
ACK
2 stops7h 41m
Delta
Tue 8/412:25 pm
ACK
-
MDW
2 stops11h 11m
Delta
Deal found 5/5$769
This Delta deal was found by Cheapflights users on 5/5. 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.
Tue 5/266:23 am
MDW
-
ACK
2 stops7h 57m
Delta
Mon 6/112:07 pm
ACK
-
MDW
2 stops10h 02m
Delta
Deal found 5/5$849
This Delta deal was found by Cheapflights users on 5/2. 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.
Wed 5/276:23 am
MDW
-
ACK
2 stops7h 57m
Delta
Sat 5/3012:43 pm
ACK
-
MDW
2 stops6h 50m
Delta
Deal found 5/2$1,049
This Delta deal was found by Cheapflights users on 5/5. 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.
Thu 5/216:23 am
MDW
-
ACK
2 stops7h 57m
Delta
Sun 5/2412:07 pm
ACK
-
MDW
2 stops10h 02m
Delta
Deal found 5/5$1,059
This Delta deal was found by Cheapflights users on 5/5. 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 8/146:05 am
MDW
-
ACK
2 stops7h 36m
Delta
Sun 8/163:24 pm
ACK
-
MDW
2 stops8h 12m
Delta
Deal found 5/5$1,109
This Delta deal was found by Cheapflights users on 5/3. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/106:00 am
MDW
-
ACK
2 stops8h 48m
Delta
Sun 6/1412:06 pm
ACK
-
MDW
2 stops11h 11m
Delta
Deal found 5/3$1,169

Find flight deals from Midway to Cape Cod and the Islands

Keep the following information in mind while searching for Midway to Cape Cod and the Islands flight deals. Data was last updated May 6, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$459
(Delta)

One-way from

$274
(Delta)

Popular in

April

Cheapest in

January

Average price

$227
Provider with most accurate pricing for Chicago (CHI)-Boston Logan Intl flight deals.
Search Deals
Provider most trusted by Cheapflights users for Chicago (CHI)-Boston Logan Intl flights.
Search Deals
From Chicago Midway to Cape Cod and the Islands
Search Deals
One-way flight from Chicago Midway to Cape Cod and the Islands
Search Deals
Highest demand for flights based on searches. 6% potential increase in price ($16 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($5 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in May 2026
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Midway to Cape Cod and the Islands 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 May 6, 2026.
Use the filters below to find and compare flights from Chicago Midway Airport to Cape Cod and the Islands that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip
Quickest round-trip

ChicagoNantucket

MDW - ACK

MDWACK

Chicago Midway

Tue 5/26

6:23 am-3:20 pm

2 stops7h 57m

Nantucket Memorial

Tue 6/2

12:07 pm-6:33 pm

2 stops7h 26m

$474

ChicagoNantucket

MDW - ACK

MDWACK

Chicago Midway

Fri 7/31

6:00 am-2:41 pm

2 stops7h 41m

Nantucket Memorial

Wed 8/5

3:24 pm-10:36 pm

2 stops8h 12m

$729

ChicagoNantucket

MDW - ACK

MDWACK

Chicago Midway

Wed 5/27

6:23 am-3:20 pm

2 stops7h 57m

Nantucket Memorial

Tue 6/2

12:07 pm-9:09 pm

2 stops10h 02m

$764

ChicagoNantucket

MDW - ACK

MDWACK

Chicago Midway

Fri 8/14

6:05 am-2:41 pm

2 stops7h 36m

Nantucket Memorial

Sun 8/16

3:24 pm-10:36 pm

2 stops8h 12m

$1,109

ChicagoNantucket

MDW - ACK

MDWACK

Chicago Midway

Wed 6/10

6:00 am-3:48 pm

2 stops8h 48m

Nantucket Memorial

Sun 6/14

12:06 pm-10:17 pm

2 stops11h 11m

$1,169

ChicagoNantucket

MDW - ACK

MDWACK

Chicago Midway

Sat 6/13

6:00 am-3:48 pm

2 stops8h 48m

Nantucket Memorial

Sat 6/20

12:06 pm-10:17 pm

2 stops11h 11m

$1,229

ChicagoNantucket

MDW - ACK

MDWACK

Chicago Midway

Fri 9/4

9:30 am-6:05 pm

2 stops7h 35m

Nantucket Memorial

Mon 9/7

10:00 am-9:46 pm

2 stops12h 46m

$1,399
Cheapest one-way
Quickest one-way

ChicagoNantucket

MDW - ACK

MDWACK

Chicago Midway

Fri 8/14

9:30 am-6:05 pm

2 stops7h 35m

$340

ChicagoNantucket

MDW - ACK

MDWACK

Chicago Midway

Mon 6/8

12:04 pm-10:30 am

2 stops21h 26m

$406

ChicagoNantucket

MDW - ACK

MDWACK

Chicago Midway

Sun 8/2

6:00 am-2:41 pm

2 stops7h 41m

$414

Flights are sorted by cheapest round-trip flights first.

Deals found on 5/1

Showing 1-10 of 16 resultsSorted by cheapest first
1
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Best time to book a flight from Midway to Cape Cod and the Islands

Have a flexible travel schedule? Discover the best time to fly to Cape Cod and the Islands from Midway 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 Chicago Midway Airport to Cape Cod and the Islands
No data available for this route at this time. Please check back soon.

Related info for your journey

Find useful and relevant information for your journey from Midway to Cape Cod and the Islands. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • How long is the flight from Chicago Midway Airport to Cape Cod and the Islands?

    Departing from Chicago Midway Airport to Cape Cod and the Islands will take you 7h 57m. The distance from Chicago Midway Airport to Cape Cod and the Islands is about 913 mi.

  • Can I find deals for flights from Midway to Cape Cod and the Islands that include hotel bookings?

    Yes. In addition to deals on Midway to Cape Cod and the Islands flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Midway to Cape Cod and the Islands?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Midway to Cape Cod and the Islands.

  • Can I find deals for business class flights from Midway to Cape Cod and the Islands?

    Yes. Cheapflights offers flight deals from Midway to Cape Cod and the Islands by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

See more FAQs

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