$247 Cheap Flights from Madison (MSN) to Chicago (MDW)

View $247 flight on Tue, Apr 7, 2026Opens in a new window

Popular airlines from Dane County Regional Airport (MSN) to Chicago Midway Airport (MDW)

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Cheap Flights from Madison to Chicago (MSN-MDW)

Prices were available within the past 7 days and start at $247 for one-way flights and $419 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Delta
Sat, Apr 18 - Mon, Apr 20
MSN
Madison
MDW
Chicago
$419 Roundtrip, found 2 days ago
$419
Roundtrip
found 2 days ago
Select Delta flight, departing Sat, Apr 18 from Madison to Chicago, returning Mon, Apr 20, priced at $419 found 2 days ago
Delta
Wed, Apr 1 - Sat, Apr 11
MSN
Madison
MDW
Chicago
$432 Roundtrip, found 6 days ago
$432
Roundtrip
found 6 days ago
Select Delta flight, departing Wed, Apr 1 from Madison to Chicago, returning Sat, Apr 11, priced at $432 found 6 days ago
Delta
Wed, Apr 1 - Sat, Apr 11
MSN
Madison
MDW
Chicago
$446 Roundtrip, found 6 days ago
$446
Roundtrip
found 6 days ago
Select Delta flight, departing Wed, Apr 1 from Madison to Chicago, returning Sat, Apr 11, priced at $446 found 6 days ago
Delta
Sat, Apr 18 - Mon, Apr 20
MSN
Madison
MDW
Chicago
$461 Roundtrip, found 2 days ago
$461
Roundtrip
found 2 days ago
Select Delta flight, departing Sat, Apr 18 from Madison to Chicago, returning Mon, Apr 20, priced at $461 found 2 days ago
Delta
Sat, Apr 18 - Mon, Apr 20
MSN
Madison
MDW
Chicago
$469 Roundtrip, found 2 days ago
$469
Roundtrip
found 2 days ago
Select Delta flight, departing Sat, Apr 18 from Madison to Chicago, returning Mon, Apr 20, priced at $469 found 2 days ago
Delta
Sat, May 2 - Sun, May 10
MSN
Madison
MDW
Chicago
$480 Roundtrip, found 1 day ago
$480
Roundtrip
found 1 day ago
Select Delta flight, departing Sat, May 2 from Madison to Chicago, returning Sun, May 10, priced at $480 found 1 day ago
Delta
Wed, Apr 1 - Sat, Apr 11
MSN
Madison
MDW
Chicago
$482 Roundtrip, found 6 days ago
$482
Roundtrip
found 6 days ago
Select Delta flight, departing Wed, Apr 1 from Madison to Chicago, returning Sat, Apr 11, priced at $482 found 6 days ago
Delta
Wed, Apr 1 - Sat, Apr 11
MSN
Madison
MDW
Chicago
$486 Roundtrip, found 6 days ago
$486
Roundtrip
found 6 days ago
Select Delta flight, departing Wed, Apr 1 from Madison to Chicago, returning Sat, Apr 11, priced at $486 found 6 days ago
Delta
Thu, Apr 16 - Sat, Apr 25
MSN
Madison
MDW
Chicago
$492 Roundtrip, found 2 days ago
$492
Roundtrip
found 2 days ago
Select Delta flight, departing Thu, Apr 16 from Madison to Chicago, returning Sat, Apr 25, priced at $492 found 2 days ago
Delta
Thu, Apr 16 - Sat, Apr 25
MSN
Madison
MDW
Chicago
$494 Roundtrip, found 2 days ago
$494
Roundtrip
found 2 days ago
Select Delta flight, departing Thu, Apr 16 from Madison to Chicago, returning Sat, Apr 25, priced at $494 found 2 days ago

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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. Cheapest option available. Average driving time to city center is 23 minutes. Flights from $194
ORD
O'Hare Intl.
Cheapest
Average driving time to city center23 min
Flights from $194

Frequently asked questions

How much does a flight from Dane County Regional Airport (MSN) to Midway Intl. Airport (MDW) cost?
Snag a cheap one-way flight from $247 or cheap return flight from $419 from Dane County Regional Airport (MSN) 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 Dane County Regional Airport (MSN) to Midway Intl. Airport (MDW)?
April is the cheapest month to fly from MSN to MDW. Traveling during quieter months is often the key to finding a great deal.
What is the cheapest airline that flies from Dane County Regional Airport (MSN) to Midway Intl. Airport (MDW)?
Use the filters on Expedia to compare different airlines and find the most affordable carrier that'll take you from MSN to MDW. Then, sort your results by "Price (lowest to highest)" to snap up the best deal available.
How many flights per day from Dane County Regional Airport (MSN) to Midway Intl. Airport (MDW)?
Direct flights from Dane County Regional Airport (MSN) to Midway Intl. Airport (MDW) aren't available daily, so you'll have to take a flight with a layover. Explore your options with Expedia's filters. Enter your travel dates and click on either "1 Stop" or "2+ Stops."
What day of the week has the most flights from MSN to MDW?
Friday is generally the busiest day for flights, while Tuesday is often the quietest.* Just remember that flight schedules can change based on a number of factors, including the carrier 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 Dane County Regional Airport (MSN) to Midway Intl. Airport (MDW)?
To avoid possible delays on the Dane County Regional Airport (MSN) to Midway Intl. Airport (MDW) route, travel before 3 PM. Later departures have a 22% higher chance of being canceled.**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 Dane County Regional Airport (MSN)?
Compare your flight options from Dane County Regional Airport (MSN) to O'Hare Intl. Airport (ORD). This is the only Chicago airport you can fly into if you're taking a direct flight.
Is it cheaper to buy a plane ticket from Dane County Regional Airport (MSN) to Midway Intl. Airport (MDW) last-minute?
Booking your plane ticket from MSN to MDW shortly before your trip is typically more expensive. However, if you're flexible with your travel dates and times, you could snag a cheap last-minute fare.
Is it cheaper to book a MSN to MDW flight and hotel package?
Securing a MSN to MDW flight and hotel package is usually cheaper than booking separately. With Expedia, you can enjoy the ease of organizing your travels in one place. Select from our impressive range of stays and then add car rentals, flights and activities to your booking. Bundle it all together, and you could save hundreds of dollars.
Can I cancel or change the date of my flight from Dane County Regional Airport (MSN) to Midway Intl. Airport (MDW)?
Typically, you're able to reschedule or cancel your MSN to MDW flight. However, there may be additional charges, especially if your booking was made more than 24 hours ago. Check your itinerary for the airline's fees and policies on flight changes, or if you want more details, go to our Customer Service portal.

Travel information

Origin airport
Dane County Regional
Destination airport
Midway Intl.
Airlines serving
Delta
Roundtrip price
$418
Distance
123 mi

Book with confidence

Madison to Chicago Flights

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

 

The best time to book a flight from Madison to Chicago

Sunday is one of the best days to book for cheap flights from Madison 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 Madison 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 Madison to Chicago in 2026. You can also book with separate airlines for your outbound and return journeys, from $247 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 Madison 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 Madison 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.

 

Madison to Chicago Flights

*Flight schedules are subject to change.

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