$129 Cheap Flights from Chicago (ORD) to Madison (MSN)

View $129 flight on Sun, Aug 31, 2025Opens in a new window

Popular airlines from Chicago O'Hare Intl. Airport (ORD) to Dane County Regional Airport (MSN)

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Cheap Flights from Chicago to Madison (ORD-MSN)

Prices were available within the past 7 days and start at $129 for one-way flights and $179 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

United
Fri, Aug 15 - Mon, Aug 18
ORD
Chicago
MSN
Madison
$179 Roundtrip, just found
$179
Roundtrip
just found
Select United flight, departing Fri, Aug 15 from Chicago to Madison, returning Mon, Aug 18, priced at $179 just found
United
Fri, Aug 1 - Mon, Aug 11
ORD
Chicago
MSN
Madison
$184 Roundtrip, just found
$184
Roundtrip
just found
Select United flight, departing Fri, Aug 1 from Chicago to Madison, returning Mon, Aug 11, priced at $184 just found
United
Sat, Aug 9 - Sun, Aug 10
ORD
Chicago
MSN
Madison
$189 Roundtrip, found 1 day ago
$189
Roundtrip
found 1 day ago
Select United flight, departing Sat, Aug 9 from Chicago to Madison, returning Sun, Aug 10, priced at $189 found 1 day ago
United
Sat, Aug 30 - Mon, Sep 1
ORD
Chicago
MSN
Madison
$190 Roundtrip, found 1 day ago
$190
Roundtrip
found 1 day ago
Select United flight, departing Sat, Aug 30 from Chicago to Madison, returning Mon, Sep 1, priced at $190 found 1 day ago
United
Wed, Nov 26 - Sun, Nov 30
ORD
Chicago
MSN
Madison
$191 Roundtrip, found 1 day ago
$191
Roundtrip
found 1 day ago
Select United flight, departing Wed, Nov 26 from Chicago to Madison, returning Sun, Nov 30, priced at $191 found 1 day ago
United
Sat, Aug 30 - Mon, Sep 1
ORD
Chicago
MSN
Madison
$194 Roundtrip, found 1 day ago
$194
Roundtrip
found 1 day ago
Select United flight, departing Sat, Aug 30 from Chicago to Madison, returning Mon, Sep 1, priced at $194 found 1 day ago
United
Sat, Aug 9 - Sun, Aug 10
ORD
Chicago
MSN
Madison
$197 Roundtrip, found 1 day ago
$197
Roundtrip
found 1 day ago
Select United flight, departing Sat, Aug 9 from Chicago to Madison, returning Sun, Aug 10, priced at $197 found 1 day ago
United
Sat, Aug 9 - Sun, Aug 10
ORD
Chicago
MSN
Madison
$199 Roundtrip, found 1 day ago
$199
Roundtrip
found 1 day ago
Select United flight, departing Sat, Aug 9 from Chicago to Madison, returning Sun, Aug 10, priced at $199 found 1 day ago
American Airlines
Wed, Jul 30 - Sun, Aug 3
ORD
Chicago
MSN
Madison
$199 Roundtrip, found 22 hours ago
$199
Roundtrip
found 22 hours ago
Select American Airlines flight, departing Wed, Jul 30 from Chicago to Madison, returning Sun, Aug 3, priced at $199 found 22 hours ago
Delta
Tue, Oct 14 - Sat, Oct 18
ORD
Chicago
MSN
Madison
$375 Roundtrip, just found
$375
Roundtrip
just found
Select Delta flight, departing Tue, Oct 14 from Chicago to Madison, returning Sat, Oct 18, priced at $375 just found

Find the cheapest month to fly from Chicago (ORD) to Madison (MSN)

June is typically the cheapest month to fly

From $179 - $407 per traveler.

Graph displaying average flight prices per month

Flights from Chicago (ORD) to Madison (MSN)
Origin airport
O'Hare Intl.
Destination airport
Dane County Regional
Airlines serving
American Airlines, Delta, United
Roundtrip price
$179
Distance
108 mi
Average flight time
1 hour 4 mins

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 August. 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 2025. You can also book with separate airlines for your outbound and return journeys, from $129 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.

 

Frequently asked questions

How much does a flight from O'Hare Intl. Airport (ORD) to Dane County Regional Airport (MSN) cost?
Score cheap return flights from O'Hare Intl. Airport (ORD) to Dane County Regional Airport (MSN) starting at $179. Book a seat and start your adventure. This information is based on the cheapest price found on Expedia for this return journey departing within the next three months. This airfare is for a United flight leaving ORD on August 6 2025 and touching down at MSN. The price was last updated on July 11 2025 and has not changed since.
What is the cheapest month to fly from ORD to MSN?
The cheapest flights from ORD to MSN are usually during off-peak season, when demand is lower. To save money, avoid flying during public holidays, school breaks and major local events.
Which airlines fly direct from O'Hare Intl. Airport (ORD) to Dane County Regional Airport (MSN)?
You can fly nonstop from O'Hare Intl. Airport (ORD) to Dane County Regional Airport (MSN) on a United Airlines flight.
What is the cheapest airline that flies from ORD to MSN?
Jet off from ORD to MSN with United. This carrier currently has the lowest one-way fare for this route, starting at $174. This fare is based on the lowest price found on Expedia departing within the next three months. The flight takes off from ORD on September 3 2025. Prices were last updated on July 11 2025 and have not changed since.
How many flights per day from O'Hare Intl. Airport (ORD) to Dane County Regional Airport (MSN)?
When departing from O'Hare Intl. Airport (ORD), you can choose from an average of 10 daily direct flights to Dane County Regional Airport (MSN).
What are the most popular departure times for flights from O'Hare Intl. Airport (ORD) to Dane County Regional Airport (MSN)?
The 10 AM departures from ORD to MSN are the most sought after. They can also be more expensive. If you want to save on your trip, pick a less crowded time to fly.
What day of the week has the most flights from ORD to MSN?
Fly on a Tuesday if you're looking for the best selection of flights from O'Hare Intl. Airport (ORD) to Dane County Regional Airport (MSN).
What is the earliest flight from O'Hare Intl. Airport (ORD) to Dane County Regional Airport (MSN)?
The first flight of the day leaving O'Hare Intl. Airport (ORD) is at around 8:52AM UTC-6. Board this plane and you'll land at Dane County Regional Airport (MSN) at approximately 10:09AM UTC-6. The overall travel time is 1h 17m.
How long does it take to fly from O'Hare Intl. Airport (ORD) to Dane County Regional Airport (MSN)?
The average flight time from ORD to MSN is 1 hour and 6 minutes, covering a total distance of 110 mi.
What airline has the least delays from ORD to MSN?
Consider booking with Alaska Airlines if you'd like to fly straight from O'Hare Intl. Airport (ORD) to Dane County Regional Airport (MSN) without any interruptions. This airline has the best track record for punctuality, with an on-time performance of 85%. Want to be notified if anything changes? You can keep an eye on your flight status using the Expedia App.
What is the best time to fly from O'Hare Intl. Airport (ORD) to Dane County Regional Airport (MSN)?
To land at Dane County Regional Airport (MSN) on schedule, choose a flight that leaves O'Hare Intl. Airport (ORD) before 3 PM. The likelihood of cancellations is 22% higher, on average, for departures after this hour.**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 Madison from O'Hare Intl. Airport (ORD)?
If you're on a direct flight from O'Hare Intl. Airport (ORD) to Madison, Dane County Regional Airport (MSN) is the only airport you can touch down at.
Is it cheaper to buy a plane ticket from O'Hare Intl. Airport (ORD) to Dane County Regional Airport (MSN) last-minute?
Last-minute fares from ORD to MSN are generally more expensive. To lock in the cheapest rates, start looking for flights ahead of time. That being said, if you're flexible with your travel dates, it's possible to score a cheap fare right before your trip.
Is it cheaper to book an ORD to MSN flight and hotel package?
You'll typically save money by securing an ORD to MSN flight and hotel package compared to booking separately. In fact, you could save hundreds of dollars by bundling with Expedia. And it's simple to manage everything in one place. Once you've chosen your ideal flights and accommodations, consider adding extras like tours, car rentals and activities.
Can I cancel or change the date of my flight from O'Hare Intl. Airport (ORD) to Dane County Regional Airport (MSN)?
If you reserved your ORD to MSN flight within the last 24 hours, you may be able to cancel or modify it without fees. Depending on the airline and the ticket type you purchased, additional charges may apply for changes after that time. Airline policies and contact information can be found in your itinerary or confirmation email. Or, visit our Customer Service portal for more details.

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