Cheap Flights from Chicago (DPA) to Madison (MSN)

Popular airlines from Chicago, IL (DPA-Dupage) to Dane County Regional Airport (MSN)

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Frequently asked questions

How much does a flight from Dupage Airport (DPA) to Dane County Regional Airport (MSN) cost?
Lock in a cheap one-way flight or cheap return flight from Dupage Airport (DPA) to Dane County Regional Airport (MSN) 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 Dupage Airport (DPA) to Dane County Regional Airport (MSN)?
is the most affordable month to fly from DPA to MSN. Traveling outside of peak seasons is often the key to finding a great deal.
Which airlines fly direct from Dupage Airport (DPA) to Dane County Regional Airport (MSN)?
There's no direct route from Chicago, IL (DPA-Dupage) to Dane County Regional Airport (MSN). However, there are other airports that offer nonstop flights. Start your journey at O'Hare Intl. Airport (ORD) and fly straight to Madison without layovers.
What is the cheapest airline that flies from Dupage Airport (DPA) to Dane County Regional Airport (MSN)?
Use the filter tool on Expedia to compare airlines and find the cheapest carrier that'll take you from DPA to MSN. Then, sort your results by "Price (lowest to highest)" to score the best deal available.
How many flights per day from Dupage Airport (DPA) to Dane County Regional Airport (MSN)?
You'll have to catch a flight with a layover when traveling from Dupage Airport (DPA) to Dane County Regional Airport (MSN). Direct flights don't operate daily on this route. However, just filter your search to include one or more stops to find the best option for your trip.
What day of the week has the most flights from DPA to MSN?
Friday is usually the busiest day for flights, while Tuesday tends to be the quietest.* Keep in mind that flight schedules can vary depending on various 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 Dupage Airport (DPA) to Dane County Regional Airport (MSN)?
Book a flight from Dupage Airport (DPA) to Dane County Regional Airport (MSN) that leaves before 3 PM to reduce the risk of cancellations. Departures after this hour have a 22% higher chance of being canceled, on average.**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 Dupage Airport (DPA) to Dane County Regional Airport (MSN) last-minute?
Last-minute bookings from DPA to MSN are usually more expensive. To lock in the best prices, start looking for flights well in advance. That being said, if you can play around with your travel dates, you may score a cheap fare right before you leave.
Is it cheaper to book a DPA to MSN flight and hotel package?
Booking a DPA to MSN flight and hotel package is generally cheaper than booking separately. With Expedia, you can enjoy the ease of organizing your travels all in one place. Select from our wide range of hotels and then add flights, car rentals and activities to your booking. Bundle everything together, and you could save hundreds of dollars.
Can I cancel or change the date of my flight from Dupage Airport (DPA) to Dane County Regional Airport (MSN)?
Usually, it's possible to reschedule or cancel your DPA to MSN flight. However, if the booking was made more than 24 hours ago, additional fees may apply. Refer to your airline's policies in your itinerary to see what changes are possible and whether any costs are involved. You'll also find further details on our Customer Service portal.

Travel information

Origin airport
Dupage
Destination airport
Dane County Regional
Distance
101 mi

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Chicago to Madison Flights

The cheapest times to fly from Chicago to Madison

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

 

The best time to book a flight from Chicago to Madison

Sunday is one of the best days to book for cheap flights from Chicago to Madison: 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 Chicago to Madison

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 Chicago to Madison in 2026. You can also book with separate airlines for your outbound and return journeys, from 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 Chicago to Madison 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 Chicago to Madison 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.

 

Chicago to Madison Flights

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*Available to One Key members.