$137 Cheap Flights from Madison (MSN) to Chicago (ORD)

View $137 flight on Sat, May 31, 2025Opens in a new window

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

Find available prices by choosing your travel dates.

Cheap Flights from Madison to Chicago (MSN-ORD)

Prices were available within the past 7 days and start at $137 for one-way flights and $179 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

American Airlines
Sat, May 24 - Fri, May 30
MSN
Madison
ORD
Chicago
$179 Roundtrip, found 1 hour ago
$179
Roundtrip
found 1 hour ago
Select American Airlines flight, departing Sat, May 24 from Madison to Chicago, returning Fri, May 30, priced at $179 found 1 hour ago
United
Mon, Aug 18 - Tue, Aug 26
MSN
Madison
ORD
Chicago
$179 Roundtrip, found 6 hours ago
$179
Roundtrip
found 6 hours ago
Select United flight, departing Mon, Aug 18 from Madison to Chicago, returning Tue, Aug 26, priced at $179 found 6 hours ago
United
Fri, Aug 29 - Mon, Sep 1
MSN
Madison
ORD
Chicago
$188 Roundtrip, found 4 days ago
$188
Roundtrip
found 4 days ago
Select United flight, departing Fri, Aug 29 from Madison to Chicago, returning Mon, Sep 1, priced at $188 found 4 days ago
United
Sat, May 24 - Fri, May 30
MSN
Madison
ORD
Chicago
$190 Roundtrip, found 1 hour ago
$190
Roundtrip
found 1 hour ago
Select United flight, departing Sat, May 24 from Madison to Chicago, returning Fri, May 30, priced at $190 found 1 hour ago
United
Fri, May 16 - Tue, May 20
MSN
Madison
ORD
Chicago
$191 Roundtrip, found 7 hours ago
$191
Roundtrip
found 7 hours ago
Select United flight, departing Fri, May 16 from Madison to Chicago, returning Tue, May 20, priced at $191 found 7 hours ago
United
Fri, May 16 - Tue, May 20
MSN
Madison
ORD
Chicago
$193 Roundtrip, found 7 hours ago
$193
Roundtrip
found 7 hours ago
Select United flight, departing Fri, May 16 from Madison to Chicago, returning Tue, May 20, priced at $193 found 7 hours ago
United
Sat, May 24 - Fri, May 30
MSN
Madison
ORD
Chicago
$194 Roundtrip, found 1 hour ago
$194
Roundtrip
found 1 hour ago
Select United flight, departing Sat, May 24 from Madison to Chicago, returning Fri, May 30, priced at $194 found 1 hour ago
United
Fri, Jun 6 - Sat, Jun 7
MSN
Madison
ORD
Chicago
$199 Roundtrip, found 2 days ago
$199
Roundtrip
found 2 days ago
Select United flight, departing Fri, Jun 6 from Madison to Chicago, returning Sat, Jun 7, priced at $199 found 2 days ago
United
Sun, May 4 - Sun, May 11
MSN
Madison
ORD
Chicago
$199 Roundtrip, found 3 days ago
$199
Roundtrip
found 3 days ago
Select United flight, departing Sun, May 4 from Madison to Chicago, returning Sun, May 11, priced at $199 found 3 days ago
Delta
Sat, Jun 7 - Mon, Jun 9
MSN
Madison
ORD
Chicago
$342 Roundtrip, found 1 day ago
$342
Roundtrip
found 1 day ago
Select Delta flight, departing Sat, Jun 7 from Madison to Chicago, returning Mon, Jun 9, priced at $342 found 1 day ago
Flights from Madison (MSN) to Chicago (ORD)
Origin airport
Dane County Regional
Destination airport
O'Hare Intl.
Airlines serving
American Airlines, Delta, United
Roundtrip price
$179
Distance
108 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 May. 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 $137 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 O'Hare Intl. Airport (ORD) cost?
Pick up cheap return flights starting at $179 from Dane County Regional Airport (MSN) to O’Hare Intl. Airport (ORD). 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 American Airlines flight leaving MSN on May 15 2025 and touching down at ORD. The price was last updated on April 23 2025 and has not changed since.
What is the cheapest month to fly from MSN to ORD?
The cheapest flights from MSN to ORD 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 Dane County Regional Airport (MSN) to O'Hare Intl. Airport (ORD)?
You can fly straight from Dane County Regional Airport (MSN) to O’Hare Intl. Airport (ORD) on a United Airlines flight.
What is the cheapest airline that flies from MSN to ORD?
Fly from MSN to ORD with United. This carrier currently offers the lowest one-way fare on this route, starting at $137. This fare is based on the lowest price found on Expedia departing within the next three months. The flight takes off from MSN on May 23 2025. Prices were last updated on April 23 2025 and have not changed since.
How many flights per day from Dane County Regional Airport (MSN) to O'Hare Intl. Airport (ORD)?
Each day on average, 10 nonstop flights take off from Dane County Regional Airport (MSN) to O’Hare Intl. Airport (ORD). Pick the departure time that best suits your plans.
What are the most popular departure times for flights from Dane County Regional Airport (MSN) to O'Hare Intl. Airport (ORD)?
The 3 PM departures from MSN to ORD see the highest demand. These flights can come with a higher price due to their popularity. If you’re hoping to save money, book during off-peak hours.
What day of the week has the most flights from MSN to ORD?
Monday offers the most flights from Dane County Regional Airport (MSN) to O’Hare Intl. Airport (ORD). Consider taking off on this day and you’ll have a greater chance of finding a departure that fits your plans.
What is the earliest flight from Dane County Regional Airport (MSN) to O'Hare Intl. Airport (ORD)?
Hop on the earliest flight at around 5:30AM UTC-6, departing from Dane County Regional Airport (MSN). You’ll be traveling for roughly 1h 11m, touching down at O’Hare Intl. Airport (ORD) at approximately 6:41AM UTC-6.
How long does it take to fly from Dane County Regional Airport (MSN) to O'Hare Intl. Airport (ORD)?
Flights from MSN to ORD have an average travel time of 1 hour and 11 minutes. The total distance between these two airports is 110 mi.
What airline has the least delays from MSN to ORD?
Consider traveling with Alaska Airlines if you’d like to go straight from Dane County Regional Airport (MSN) to O’Hare Intl. Airport (ORD) without any interruptions. This airline has the best track record for punctuality, with an on-time score of 92%. Want to be notified if anything changes? You can check your flight status using the Expedia App.
What is the best time to fly from Dane County Regional Airport (MSN) to O'Hare Intl. Airport (ORD)?
To avoid possible delays on the Dane County Regional Airport (MSN) to O’Hare Intl. Airport (ORD) route, travel before 3 PM. Departures after this time 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)?
If you’re on a direct flight from Dane County Regional Airport (MSN) to Chicago, O’Hare Intl. Airport (ORD) is the only airport you can touch down at.
Is it cheaper to buy a plane ticket from Dane County Regional Airport (MSN) to O'Hare Intl. Airport (ORD) last-minute?
Booking your flight from MSN to ORD just before your getaway is typically more expensive. But if you’re flexible with your travel dates and times, you could grab a cheap last-minute fare.
Is it cheaper to book a MSN to ORD flight and hotel package?
Securing a MSN to ORD flight and hotel package tends to be cheaper than booking separately. With Expedia, you can enjoy the convenience of organizing your trip all in one place. Pick from our wide range of hotels and then add car rentals, activities and flights 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 O'Hare Intl. Airport (ORD)?
It’s generally possible to reschedule or cancel your MSN to ORD flight. However, if it’s been more than 24 hours since booking, additional fees may apply. Refer to your airline’s policies in your itinerary to see what changes are allowed and if any costs are involved. You’ll also find further details on our Customer Service portal.

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*Available to One Key members.