$438 Cheap Flights from Nantucket (ACK) to Chicago (MDW)

View $438 flight on Fri, Oct 31, 2025Opens in a new window

Popular airlines from Nantucket, MA (ACK-Nantucket Memorial) to Chicago Midway Airport (MDW)

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Cheap Flights from Nantucket to Chicago (ACK-MDW)

Prices were available within the past 7 days and start at $438 for one-way flights and $935 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Cape Air
Tue, Nov 18 - Fri, Dec 5
ACK
Nantucket
MDW
Chicago
$935 Roundtrip, found 2 days ago
$935
Roundtrip
found 2 days ago
Select Cape Air flight, departing Tue, Nov 18 from Nantucket to Chicago, returning Fri, Dec 5, priced at $935 found 2 days ago
Cape Air
Tue, Nov 11 - Sun, Nov 23
ACK
Nantucket
MDW
Chicago
$965 Roundtrip, found 2 days ago
$965
Roundtrip
found 2 days ago
Select Cape Air flight, departing Tue, Nov 11 from Nantucket to Chicago, returning Sun, Nov 23, priced at $965 found 2 days ago
Cape Air
Tue, Oct 7 - Sat, Oct 18
ACK
Nantucket
MDW
Chicago
$1,005 Roundtrip, found 2 days ago
$1,005
Roundtrip
found 2 days ago
Select Cape Air flight, departing Tue, Oct 7 from Nantucket to Chicago, returning Sat, Oct 18, priced at $1,005 found 2 days ago
Cape Air
Tue, Oct 7 - Tue, Oct 21
ACK
Nantucket
MDW
Chicago
$1,035 Roundtrip, found 2 days ago
$1,035
Roundtrip
found 2 days ago
Select Cape Air flight, departing Tue, Oct 7 from Nantucket to Chicago, returning Tue, Oct 21, priced at $1,035 found 2 days ago
Cape Air
Fri, Nov 14 - Sun, Nov 16
ACK
Nantucket
MDW
Chicago
$1,240 Roundtrip, found 2 days ago
$1,240
Roundtrip
found 2 days ago
Select Cape Air flight, departing Fri, Nov 14 from Nantucket to Chicago, returning Sun, Nov 16, priced at $1,240 found 2 days ago
Cape Air
Fri, Nov 14 - Sun, Nov 16
ACK
Nantucket
MDW
Chicago
$1,251 Roundtrip, found 2 days ago
$1,251
Roundtrip
found 2 days ago
Select Cape Air flight, departing Fri, Nov 14 from Nantucket to Chicago, returning Sun, Nov 16, priced at $1,251 found 2 days ago
Cape Air
Fri, Nov 14 - Sun, Nov 16
ACK
Nantucket
MDW
Chicago
$1,325 Roundtrip, found 2 days ago
$1,325
Roundtrip
found 2 days ago
Select Cape Air flight, departing Fri, Nov 14 from Nantucket to Chicago, returning Sun, Nov 16, priced at $1,325 found 2 days ago
Cape Air
Fri, Nov 14 - Sun, Nov 16
ACK
Nantucket
MDW
Chicago
$1,350 Roundtrip, found 2 days ago
$1,350
Roundtrip
found 2 days ago
Select Cape Air flight, departing Fri, Nov 14 from Nantucket to Chicago, returning Sun, Nov 16, priced at $1,350 found 2 days ago
Cape Air
Fri, Nov 14 - Sun, Nov 16
ACK
Nantucket
MDW
Chicago
$1,355 Roundtrip, found 2 days ago
$1,355
Roundtrip
found 2 days ago
Select Cape Air flight, departing Fri, Nov 14 from Nantucket to Chicago, returning Sun, Nov 16, priced at $1,355 found 2 days ago
Cape Air
Fri, Nov 14 - Sun, Nov 16
ACK
Nantucket
MDW
Chicago
$1,415 Roundtrip, found 2 days ago
$1,415
Roundtrip
found 2 days ago
Select Cape Air flight, departing Fri, Nov 14 from Nantucket to Chicago, returning Sun, Nov 16, priced at $1,415 found 2 days ago

Frequently asked questions

How much does a flight from Nantucket Memorial Airport (ACK) to Midway Intl. Airport (MDW) cost?
Get a cheap one-way flight from $438 or cheap return flight from $935 from Nantucket Memorial Airport (ACK) to Midway Intl. Airport (MDW) with Expedia. Enter your travel dates and sort by "Price (lowest to highest)" to find our cheapest flight deals on this route.
What is the cheapest month to fly from Nantucket Memorial Airport (ACK) to Midway Intl. Airport (MDW)?
Planning your trip for November can help you save, as it's the cheapest month for flights between ACK and MDW. You'll often find the lowest prices during the off-season.
What is the cheapest airline that flies from Nantucket Memorial Airport (ACK) to Midway Intl. Airport (MDW)?
Expedia's filter tool lets you easily compare airlines, flight times and fares all in one place. Tailor the search to your trip, then sort by "Price (lowest to highest)" to find out which carrier offers the cheapest ACK to MDW flight.
How many flights per day from Nantucket Memorial Airport (ACK) to Midway Intl. Airport (MDW)?
There are no daily direct flights available from Nantucket Memorial Airport (ACK) to Midway Intl. Airport (MDW). But you can choose flights with layovers. Filter your search results on Expedia to include one or two stops, and you'll be on your way in no time at all.
What day of the week has the most flights from ACK to MDW?
Usually you'll have the most choice when it comes to flights on a Friday. Tuesdays are often the quietest.* However, this can change based on the time of year, carrier and other factors.*Busiest/quietest day to travel is based on Expedia flight demand through January to December 2024.
What is the best time to fly from Nantucket Memorial Airport (ACK) to Midway Intl. Airport (MDW)?
To arrive at Midway Intl. Airport (MDW) on time, book a flight that takes off from Nantucket Memorial Airport (ACK) before 3 PM. The likelihood of cancellations is 22% higher, on average, for departures after this time.**Most reliable time of the day and month to travel recommendation is based on January through August 2024 flight status data sourced from OAG's global flight data platform.
Is it cheaper to buy a plane ticket from Nantucket Memorial Airport (ACK) to Midway Intl. Airport (MDW) last-minute?
Waiting until just before your departure to book your flight from ACK to MDW generally means paying more. While you may find some last-minute deals, they aren't always guaranteed. Keep your travel schedule open to boost your chances of landing a bargain.
Is it cheaper to book an ACK to MDW flight and hotel package?
Compared with arranging flights and hotels separately, booking an ACK to MDW flight and hotel package with Expedia could result in significant savings. Better still, having everything in one easy place will take the hassle out of travel planning. Simply secure your flights and select from our extensive range of hotels, then tailor your trip with extras like car rentals and activities.
Can I cancel or change the date of my flight from Nantucket Memorial Airport (ACK) to Midway Intl. Airport (MDW)?
Generally, it's possible to reschedule or cancel your ACK to MDW flight. However, if it's been more than 24 hours since booking, additional fees may apply. Check your airline's policies in your itinerary to see what changes are possible and if any costs are involved. You'll also find further details on our Customer Service portal.

Travel information

Travel information

Origin airport
Nantucket Memorial
Destination airport
Midway Intl.
Roundtrip price
$934
Distance
913 mi

Book with confidence

Book with confidence

Nantucket to Chicago Flights

The cheapest times to fly from Nantucket to Chicago

On average, Thursday can be the cheapest time to fly, according to data from the Airlines Reporting Corporation (ARC), one of the world's biggest databases for global airline sales. The data reveals that you could save up to 16% by flying on a Thursday—the cheapest day to travel on average—instead of a Sunday—the most expensive. Some of the most affordable flights from Nantucket to Chicago are during the month of November. You can find some of the cheapest flights from Nantucket to Chicago with Expedia's search tool and vast selection of airlines.

 

The best time to book a flight from Nantucket to Chicago

Sunday is one of the best days to book for cheap flights from Nantucket to Chicago: Tickets reserved on a Sunday cost between 6% and 13% less than those reserved on a Friday, according to ARC data. The data also suggests booking early can also lead to cheaper airfares. You could save 24% by buying your tickets for domestic flights at least a month in advance and 10% by booking international flights 2 months in advance.

 

How to find cheap round-trip tickets from Nantucket to Chicago

Being flexible with your dates and using Expedia's Price Drop Protection and Price Tracking features are some of the best ways of finding a cheap ticket from Nantucket to Chicago in 2025. You can also book with separate airlines for your outbound and return journeys, from $438 one-way. Expedia also offers Price Drop Protection, so if the cost of your airfare goes down after booking, you'll receive a credit for the difference*. This is available for a small fee, and is free to One Key Gold and Platinum tier members.

 

Expedia's Price Tracking feature means you can stay on top of airfares without manually checking every day. It sends you automated price alerts for cheap Nantucket to Chicago flights and uses historical data to indicate when the best time to book is. Download Expedia's free app to activate this handy tool in a few easy taps.

 

You could also save big by booking one of Expedia's vacation packages. Bundling together your Nantucket to Chicago airfare with your accommodations and car rental is often cheaper than booking everything separately. There’s also One Key, Expedia's generous rewards program. Join for free and you could earn One Key cash on most bookings to save on future adventures.

 

*Terms apply.

 

Disclaimer: ARC The statistics are based on average round-trip ticket prices between January and August 2023. The percentages you see are averages.

 

Nantucket to Chicago Flights

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Explore a world of travel with Expedia

*Available to One Key members.