$237 Cheap Flights from Madison (MSN) to Chicago (MDW)

View $237 flight on Wed, Jun 4, 2025Opens in a new window

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

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Find available prices by choosing your travel dates.

Cheap Flights from Madison to Chicago (MSN-MDW)

Prices were available within the past 7 days and start at $237 for one-way flights and $305 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Delta
Wed, Sep 3 - Tue, Sep 9
MSN
Madison
MDW
Chicago
$305 Roundtrip, found 15 hours ago
$305
Roundtrip
found 15 hours ago
Select Delta flight, departing Wed, Sep 3 from Madison to Chicago, returning Tue, Sep 9, priced at $305 found 15 hours ago
Delta
Sat, Sep 6 - Tue, Sep 9
MSN
Madison
MDW
Chicago
$342 Roundtrip, found 15 hours ago
$342
Roundtrip
found 15 hours ago
Select Delta flight, departing Sat, Sep 6 from Madison to Chicago, returning Tue, Sep 9, priced at $342 found 15 hours ago
Delta
Wed, Sep 3 - Fri, Sep 5
MSN
Madison
MDW
Chicago
$353 Roundtrip, found 15 hours ago
$353
Roundtrip
found 15 hours ago
Select Delta flight, departing Wed, Sep 3 from Madison to Chicago, returning Fri, Sep 5, priced at $353 found 15 hours ago
Delta
Thu, Sep 4 - Tue, Sep 9
MSN
Madison
MDW
Chicago
$365 Roundtrip, found 15 hours ago
$365
Roundtrip
found 15 hours ago
Select Delta flight, departing Thu, Sep 4 from Madison to Chicago, returning Tue, Sep 9, priced at $365 found 15 hours ago
Delta
Wed, Sep 3 - Sun, Sep 7
MSN
Madison
MDW
Chicago
$367 Roundtrip, found 15 hours ago
$367
Roundtrip
found 15 hours ago
Select Delta flight, departing Wed, Sep 3 from Madison to Chicago, returning Sun, Sep 7, priced at $367 found 15 hours ago
Delta
Tue, Jun 3 - Tue, Jun 17
MSN
Madison
MDW
Chicago
$389 Roundtrip, found 5 days ago
$389
Roundtrip
found 5 days ago
Select Delta flight, departing Tue, Jun 3 from Madison to Chicago, returning Tue, Jun 17, priced at $389 found 5 days ago
Delta
Fri, Sep 5 - Tue, Sep 9
MSN
Madison
MDW
Chicago
$392 Roundtrip, found 15 hours ago
$392
Roundtrip
found 15 hours ago
Select Delta flight, departing Fri, Sep 5 from Madison to Chicago, returning Tue, Sep 9, priced at $392 found 15 hours ago
Delta
Thu, Sep 4 - Sat, Sep 6
MSN
Madison
MDW
Chicago
$402 Roundtrip, found 15 hours ago
$402
Roundtrip
found 15 hours ago
Select Delta flight, departing Thu, Sep 4 from Madison to Chicago, returning Sat, Sep 6, priced at $402 found 15 hours ago
Delta
Sat, Sep 6 - Sun, Sep 7
MSN
Madison
MDW
Chicago
$404 Roundtrip, found 15 hours ago
$404
Roundtrip
found 15 hours ago
Select Delta flight, departing Sat, Sep 6 from Madison to Chicago, returning Sun, Sep 7, priced at $404 found 15 hours ago
Delta
Wed, Jun 4 - Tue, Jun 17
MSN
Madison
MDW
Chicago
$405 Roundtrip, found 2 days ago
$405
Roundtrip
found 2 days ago
Select Delta flight, departing Wed, Jun 4 from Madison to Chicago, returning Tue, Jun 17, priced at $405 found 2 days ago
Flights from Madison (MSN) to Chicago (MDW)
Origin airport
Dane County Regional
Destination airport
Midway Intl.
Airlines serving
Delta
Roundtrip price
$305
Distance
123 mi

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 September. 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 2025. You can also book with separate airlines for your outbound and return journeys, from $237 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.

Frequently asked questions

How much does a flight from Dane County Regional Airport (MSN) to Midway Intl. Airport (MDW) cost?
Discover the latest flight deals from MSN to MDW by entering your preferred travel dates and searching on Expedia. Easily compare prices by departure date if you have flexibility with your schedule and use handy filters to explore prices for your preferred journey. As a member of One Key™, our free loyalty program, you can use Price Tracking to watch fares and receive notifications if prices go up or down.
What is the cheapest month to fly from MSN to MDW?
The cheapest flights from MSN to MDW are usually during off-peak season, when demand is lower. To save money, avoid flying during public holidays, school breaks and major local events.
What is the cheapest airline that flies from MSN to MDW?
Use the filter tool on Expedia to compare airlines and find the cheapest carrier that’ll take you from MSN to MDW. Sort your results by “Price (lowest to highest)” to snap up a great deal.
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.

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*Available to One Key members.