$260 Cheap Flights from Nassau (NAS) to Chicago (MDW)

View $260 flight on Fri, Oct 31, 2025Opens in a new window

Popular airlines from Lynden Pindling Intl. Airport (NAS) to Chicago Midway Airport (MDW)

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Cheap Flights from Nassau to Chicago (NAS-MDW)

Prices were available within the past 7 days and start at $260 for one-way flights and $422 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Southwest Airlines
Wed, Nov 12 - Sun, Nov 16
NAS
Nassau
MDW
Chicago
$422 Roundtrip, found 4 days ago
$422
Roundtrip
found 4 days ago
Select Southwest Airlines flight, departing Wed, Nov 12 from Nassau to Chicago, returning Sun, Nov 16, priced at $422 found 4 days ago
Delta
Wed, Nov 12 - Sun, Nov 16
NAS
Nassau
MDW
Chicago
$449 Roundtrip, found 4 days ago
$449
Roundtrip
found 4 days ago
Select Delta flight, departing Wed, Nov 12 from Nassau to Chicago, returning Sun, Nov 16, priced at $449 found 4 days ago
Southwest Airlines
Tue, Dec 2 - Tue, Dec 9
NAS
Nassau
MDW
Chicago
$482 Roundtrip, found 4 days ago
$482
Roundtrip
found 4 days ago
Select Southwest Airlines flight, departing Tue, Dec 2 from Nassau to Chicago, returning Tue, Dec 9, priced at $482 found 4 days ago
Southwest Airlines
Fri, Nov 14 - Sun, Nov 16
NAS
Nassau
MDW
Chicago
$483 Roundtrip, found 1 day ago
$483
Roundtrip
found 1 day ago
Select Southwest Airlines flight, departing Fri, Nov 14 from Nassau to Chicago, returning Sun, Nov 16, priced at $483 found 1 day ago
Southwest Airlines
Tue, Dec 2 - Tue, Dec 9
NAS
Nassau
MDW
Chicago
$486 Roundtrip, found 4 days ago
$486
Roundtrip
found 4 days ago
Select Southwest Airlines flight, departing Tue, Dec 2 from Nassau to Chicago, returning Tue, Dec 9, priced at $486 found 4 days ago
Delta
Wed, Nov 12 - Sun, Nov 16
NAS
Nassau
MDW
Chicago
$495 Roundtrip, found 4 days ago
$495
Roundtrip
found 4 days ago
Select Delta flight, departing Wed, Nov 12 from Nassau to Chicago, returning Sun, Nov 16, priced at $495 found 4 days ago
Southwest Airlines
Tue, Dec 2 - Tue, Dec 9
NAS
Nassau
MDW
Chicago
$500 Roundtrip, found 4 days ago
$500
Roundtrip
found 4 days ago
Select Southwest Airlines flight, departing Tue, Dec 2 from Nassau to Chicago, returning Tue, Dec 9, priced at $500 found 4 days ago
Southwest Airlines
Tue, Dec 2 - Tue, Dec 9
NAS
Nassau
MDW
Chicago
$504 Roundtrip, found 4 days ago
$504
Roundtrip
found 4 days ago
Select Southwest Airlines flight, departing Tue, Dec 2 from Nassau to Chicago, returning Tue, Dec 9, priced at $504 found 4 days ago
Delta
Wed, Jul 1 - Mon, Jul 6
NAS
Nassau
MDW
Chicago
$515 Roundtrip, found 3 days ago
$515
Roundtrip
found 3 days ago
Select Delta flight, departing Wed, Jul 1 from Nassau to Chicago, returning Mon, Jul 6, priced at $515 found 3 days ago
Southwest Airlines
Fri, Oct 17 - Fri, Oct 24
NAS
Nassau
MDW
Chicago
$522 Roundtrip, found 5 days ago
$522
Roundtrip
found 5 days ago
Select Southwest Airlines flight, departing Fri, Oct 17 from Nassau to Chicago, returning Fri, Oct 24, priced at $522 found 5 days ago

Find the cheapest month to fly from Nassau (NAS) to Chicago (MDW)

October is typically the cheapest month to fly

From $433 - $1,081 per traveler.

Graph displaying average flight prices per month

Alternative airports near Chicago

Prices were available within the past 7 days. Prices and availability are subject to change.

Select flight to O'Hare Intl. ORD. Average driving time to city center is 23 minutes. Flights from $625
ORD
O'Hare Intl.
Average driving time to city center23 min
Flights from $625
Flights from Nassau (NAS) to Chicago (MDW)
Origin airport
Lynden Pindling Intl.
Destination airport
Midway Intl.
Airlines serving
Delta, Southwest Airlines
Roundtrip price
$421
Distance
1297 mi

Nassau to Chicago Flights

The cheapest times to fly from Nassau 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 Nassau to Chicago are during the month of November. You can find some of the cheapest flights from Nassau to Chicago with Expedia's search tool and vast selection of airlines.

 

The best time to book a flight from Nassau to Chicago

Sunday is one of the best days to book for cheap flights from Nassau 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 Nassau 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 Nassau to Chicago in 2025. You can also book with separate airlines for your outbound and return journeys, from $260 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 Nassau 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 Nassau 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.

 

Frequently asked questions

How much does a flight from Lynden Pindling Intl. Airport (NAS) to Midway Intl. Airport (MDW) cost?
Secure a cheap one-way flight from $260 or cheap return flight from $422 from Lynden Pindling Intl. Airport (NAS) to Midway Intl. Airport (MDW) with Expedia. Enter your travel dates and sort by "Price (lowest to highest)" to see our cheapest flight offers on this route.
What is the cheapest month to fly from Lynden Pindling Intl. Airport (NAS) to Midway Intl. Airport (MDW)?
Planning your trip for November may help you find better deals, as it's the cheapest month for flights between NAS and MDW. You'll often find the lowest fares during off-peak months.
What is the cheapest airline that flies from Lynden Pindling Intl. Airport (NAS) to Midway Intl. Airport (MDW)?
To find the cheapest airline flying from NAS to MDW, use Expedia's filter tool. Customize your search based on what matters most to you, such as preferred carriers and number of stops. You can then sort your results by "Price (lowest to highest)" to discover the cheapest flight right away.
How many flights per day from Lynden Pindling Intl. Airport (NAS) to Midway Intl. Airport (MDW)?
There are no daily direct flights available from Lynden Pindling Intl. Airport (NAS) to Midway Intl. Airport (MDW). But you can book flights with layovers. Filter your search results on Expedia to include one or two stops, and you'll be soaring above the clouds before you know it.
What day of the week has the most flights from NAS to MDW?
Friday is generally the busiest day for flights, while Tuesday is often the quietest.* Just remember that flight schedules can vary depending on a number of factors, including the airline and season.*Busiest/quietest day to travel is based on Expedia flight demand through January to December 2024.
What is the best time to fly from Lynden Pindling Intl. Airport (NAS) to Midway Intl. Airport (MDW)?
To land at Midway Intl. Airport (MDW) on schedule, select a flight that takes off from Lynden Pindling Intl. Airport (NAS) before 3 PM. The chance 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.
What airports do you fly into for Chicago from Lynden Pindling Intl. Airport (NAS)?
O'Hare Intl. Airport (ORD) is the only airport in Chicago with direct flights from Lynden Pindling Intl. Airport (NAS). Consider the options and discover cheap fares on Expedia.
Is it cheaper to buy a plane ticket from Lynden Pindling Intl. Airport (NAS) to Midway Intl. Airport (MDW) last-minute?
Waiting until right before your break to book a flight from NAS to MDW generally means paying more. While you might find some last-minute discounts, they aren't always guaranteed. Keep your travel plans flexible to maximize your chances of snagging a bargain.
Is it cheaper to book a NAS to MDW flight and hotel package?
You'll typically save money by securing a NAS to MDW flight and hotel package compared to booking separately. In fact, travelers could save hundreds of dollars by bundling with Expedia. And it's easy to manage everything in one place. After choosing your preferred flights and accommodations, consider adding extras such as activities, car rentals and tours.
Can I cancel or change the date of my flight from Lynden Pindling Intl. Airport (NAS) to Midway Intl. Airport (MDW)?
If you booked your NAS to MDW flight in the last 24 hours, you may be able to cancel or modify it without any fees. Depending on the airline and the type of fare you have, additional charges may apply for changes beyond this timeframe. Airline policies and contact information can be found in your itinerary or confirmation email. Or, head to our Customer Service portal for more information.

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*Available to One Key members.