S$279 Cheap Flights from Madison to Chicago

View S$279 flight on Sat, 9 May, 2026Opens 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$279 for one-way flights and S$305 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

American Airlines
Wed, 13 Aug - Wed, 20 Aug
MSN
Madison
ORD
Chicago
S$305 Return, found 5 days ago
S$305
Return
found 5 days ago
Select American Airlines flight, departing Wed, 13 Aug from Madison to Chicago, returning Wed, 20 Aug, priced at S$305 found 5 days ago
United
Wed, 13 Aug - Wed, 20 Aug
MSN
Madison
ORD
Chicago
S$305 Return, found 5 days ago
S$305
Return
found 5 days ago
Select United flight, departing Wed, 13 Aug from Madison to Chicago, returning Wed, 20 Aug, priced at S$305 found 5 days ago
American Airlines
Wed, 13 Aug - Wed, 20 Aug
MSN
Madison
ORD
Chicago
S$337 Return, found 5 days ago
S$337
Return
found 5 days ago
Select American Airlines flight, departing Wed, 13 Aug from Madison to Chicago, returning Wed, 20 Aug, priced at S$337 found 5 days ago
American Airlines
Wed, 13 Aug - Wed, 20 Aug
MSN
Madison
ORD
Chicago
S$363 Return, found 5 days ago
S$363
Return
found 5 days ago
Select American Airlines flight, departing Wed, 13 Aug from Madison to Chicago, returning Wed, 20 Aug, priced at S$363 found 5 days ago
American Airlines
Wed, 13 Aug - Wed, 20 Aug
MSN
Madison
ORD
Chicago
S$367 Return, found 5 days ago
S$367
Return
found 5 days ago
Select American Airlines flight, departing Wed, 13 Aug from Madison to Chicago, returning Wed, 20 Aug, priced at S$367 found 5 days ago
American Airlines
Wed, 13 Aug - Wed, 20 Aug
MSN
Madison
ORD
Chicago
S$376 Return, found 5 days ago
S$376
Return
found 5 days ago
Select American Airlines flight, departing Wed, 13 Aug from Madison to Chicago, returning Wed, 20 Aug, priced at S$376 found 5 days ago
American Airlines
Tue, 12 Aug - Tue, 19 Aug
MSN
Madison
ORD
Chicago
S$385 Return, found 5 days ago
S$385
Return
found 5 days ago
Select American Airlines flight, departing Tue, 12 Aug from Madison to Chicago, returning Tue, 19 Aug, priced at S$385 found 5 days ago
United
Tue, 12 Aug - Tue, 19 Aug
MSN
Madison
ORD
Chicago
S$389 Return, found 5 days ago
S$389
Return
found 5 days ago
Select United flight, departing Tue, 12 Aug from Madison to Chicago, returning Tue, 19 Aug, priced at S$389 found 5 days ago
American Airlines
Wed, 13 Aug - Wed, 20 Aug
MSN
Madison
ORD
Chicago
S$394 Return, found 5 days ago
S$394
Return
found 5 days ago
Select American Airlines flight, departing Wed, 13 Aug from Madison to Chicago, returning Wed, 20 Aug, priced at S$394 found 5 days ago
Delta
Tue, 12 Aug - Tue, 19 Aug
MSN
Madison
ORD
Chicago
S$467 Return, found 5 days ago
S$467
Return
found 5 days ago
Select Delta flight, departing Tue, 12 Aug from Madison to Chicago, returning Tue, 19 Aug, priced at S$467 found 5 days ago

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

September is typically the cheapest month to fly

From S$228 - S$559 per traveller.

Graph displaying average flight prices per month

Madison to Chicago route information
Origin airport
Dane County Regional
Destination airport
O'Hare Intl.
Return price
S$305
Distance
173 km
Average flight time
1 hour 6 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$279 and roundtrip prices from S$305*.
 

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$305. 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.

Explore a world of travel with Expedia

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