S$280 Cheap Flights from Madison to Chicago

View S$280 flight on Thu, 4 Sep, 2025Opens in a new window

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

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Cheap Flights from Madison to Chicago (MSN-ORD)

Prices were available within the past 7 days and start at S$280 for one-way flights and S$306 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

American Airlines
Thu, 28 Aug - Thu, 4 Sep
MSN
Madison
ORD
Chicago
S$306 Return, found 11 hours ago
S$306
Return
found 11 hours ago
Select American Airlines flight, departing Thu, 28 Aug from Madison to Chicago, returning Thu, 4 Sep, priced at S$306 found 11 hours ago
United
Thu, 28 Aug - Thu, 4 Sep
MSN
Madison
ORD
Chicago
S$306 Return, found 11 hours ago
S$306
Return
found 11 hours ago
Select United flight, departing Thu, 28 Aug from Madison to Chicago, returning Thu, 4 Sep, priced at S$306 found 11 hours ago
United
Thu, 28 Aug - Thu, 4 Sep
MSN
Madison
ORD
Chicago
S$326 Return, found 11 hours ago
S$326
Return
found 11 hours ago
Select United flight, departing Thu, 28 Aug from Madison to Chicago, returning Thu, 4 Sep, priced at S$326 found 11 hours ago
American Airlines
Fri, 22 Aug - Fri, 29 Aug
MSN
Madison
ORD
Chicago
S$363 Return, found 6 days ago
S$363
Return
found 6 days ago
Select American Airlines flight, departing Fri, 22 Aug from Madison to Chicago, returning Fri, 29 Aug, priced at S$363 found 6 days ago
American Airlines
Thu, 28 Aug - Thu, 4 Sep
MSN
Madison
ORD
Chicago
S$365 Return, found 11 hours ago
S$365
Return
found 11 hours ago
Select American Airlines flight, departing Thu, 28 Aug from Madison to Chicago, returning Thu, 4 Sep, priced at S$365 found 11 hours ago
American Airlines
Fri, 22 Aug - Fri, 29 Aug
MSN
Madison
ORD
Chicago
S$372 Return, found 6 days ago
S$372
Return
found 6 days ago
Select American Airlines flight, departing Fri, 22 Aug from Madison to Chicago, returning Fri, 29 Aug, priced at S$372 found 6 days ago
American Airlines
Mon, 25 Aug - Mon, 1 Sep
MSN
Madison
ORD
Chicago
S$374 Return, found 3 days ago
S$374
Return
found 3 days ago
Select American Airlines flight, departing Mon, 25 Aug from Madison to Chicago, returning Mon, 1 Sep, priced at S$374 found 3 days ago
American Airlines
Fri, 22 Aug - Fri, 29 Aug
MSN
Madison
ORD
Chicago
S$376 Return, found 6 days ago
S$376
Return
found 6 days ago
Select American Airlines flight, departing Fri, 22 Aug from Madison to Chicago, returning Fri, 29 Aug, priced at S$376 found 6 days ago
American Airlines
Thu, 28 Aug - Thu, 4 Sep
MSN
Madison
ORD
Chicago
S$377 Return, found 11 hours ago
S$377
Return
found 11 hours ago
Select American Airlines flight, departing Thu, 28 Aug from Madison to Chicago, returning Thu, 4 Sep, priced at S$377 found 11 hours ago
Delta
Thu, 28 Aug - Thu, 4 Sep
MSN
Madison
ORD
Chicago
S$698 Return, found 11 hours ago
S$698
Return
found 11 hours ago
Select Delta flight, departing Thu, 28 Aug from Madison to Chicago, returning Thu, 4 Sep, priced at S$698 found 11 hours ago

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

November is typically the cheapest month to fly

From S$229 - S$562 per traveller.

Graph displaying average flight prices per month

Madison to Chicago route information
Origin airport
Dane County Regional
Destination airport
O'Hare Intl.
Airlines serving
American Airlines, Delta, United
Return price
S$306
Distance
173 km
Average flight time
1 hour 4 mins

Perfect flights from Madison to Chicago

Your Journey from Madison to Chicago

Start your unforgettable journey with Expedia. Our broad selection of flights from Madison to Chicago caters to every travel need. Whether you're yearning for a romantic escape, a solo adventure, or a cultural immersion, we've got you covered.
 

Choosing Your Ideal Flight

With Expedia, you have access to a wide range of airlines, including American Airlines, United, Delta. Our selection of flights from Dane County Regional to O'Hare Intl. caters to every traveler's requirements, ensuring your journey aligns with your schedule. With options from 20 airlines, you're bound to find the perfect flight.
 

Maximizing Value with Madison to Chicago Flights

Experience the joy of finding cheap flights from Dane County Regional to O'Hare Intl. that fit your budget. Keep an eye out for our special deals and discounts, and check our flexible one-way fares from S$280 and roundtrip prices from S$306*.
 

Pre-Flight Essentials

Ensure a smooth journey from Madison to Chicago with Expedia. From information about check-in times and in-flight amenities to guidance on baggage policies, we provide all the essentials to prepare you for your flight.
 

Experience the Vibrant Chicago

Picture yourself stepping off the plane in Chicago and immersing yourself in the unique atmosphere of . From local markets to cultural festivals, each city offers its distinct charm. Make the most of your trip by exploring local attractions and indulging in the local cuisine. With Expedia, explore all this and more, tailored to your budget.
 

Added Convenience on Your Madison to Chicago Flight

Traveling with Expedia is more than just a flight. We offer details about in-flight amenities, baggage policies, and more to ensure a smooth and hassle-free journey. Choose from our variety of airlines and embark on a memorable journey from Madison to Chicago.
 

Beyond the Flight – Exploring Chicago

With Expedia, your adventure extends beyond the flight. Explore Chicago at your own pace by renting a car or booking a hotel. Discover hidden gems off the beaten path and create unforgettable memories.
 

Book Your Flight from Madison to Chicago with Confidence

Planning your next great adventure is a breeze with Expedia. Our user-friendly platform, unbeatable prices, and round-the-clock customer support make your travel experience seamless and stress-free. Embark on your journey from Madison to Chicago with confidence. Book your travel arrangements with Expedia today.
 
*Note: Prices may vary based on availability and are subject to change.

Frequently asked questions

How much is a flight from Dane County Regional Airport (MSN) to O'Hare Intl. Airport (ORD)?
Within the past 7 days on Expedia, for flights departing within the next year, the lowest price listed for a round-trip journey between Dane County Regional Airport (MSN) and ORD was S$306. Fares this good don't hang around, so make sure you book yours today. Prices and availability are subject to change. Additional terms apply.
Do I need to pay a cancellation fee if I cancel my flight from Truax Field to O'Hare Airport?
The majority of flights can be cancelled online, but each air carrier has a different set of terms and conditions. If you do have to cancel your flight, check out our Customer Service Portal and follow the instructions.
How do I find cheap flights from Dane County Regional Airport (MSN) to O'Hare Intl. Airport (ORD) that have flexible change policies?
Many airlines offer the option to reschedule your flight without a change fee. All you pay is the difference between the original flight and the new flight. When you're searching for MSN to ORD flights, you'll see a "no change fees" filter for you to select.
How far is the flight from MSN to O'Hare Airport?
With a flight distance of 180 kilometres, it's only a hop from MSN to ORD. It might be a quick flight, but it's still worth bringing a good book to read.
Which airlines fly direct from MSN to ORD?
There are a few airlines that travel directly from MSN to O'Hare Intl. Airport (ORD). United Airlines (UA) is a popular choice, offering 182 flights a month. If you want more options, check out the fares from American Airlines (AA). This carrier offers 82 flights monthly between these airports.
Are Truax Field to O'Hare Intl. Airport (ORD) flight tickets cheaper when they're purchased at the last minute?
Tickets from MSN to O'Hare Airport are available up to 12 months before departure on Expedia. And although you may nab great last-minute deal, it's not something you should bank on. Also, booking your flights ahead of time means you'll have more options --- and you can avoid ending up with the dreaded middle seat! We're always updating our fares to bring you the best bargains, so check back often for all the latest specials.

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