S$279 Cheap Flights from Chicago to Madison

View S$279 flight on Fri, 3 Oct, 2025Opens in a new window

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

  • Plan, book, fly with confidence

  • trending down icon
    Be in the know
    Get alerts if flight prices drop or rise*
  • bex rewards loyalty icon
    Book smarter
    Save up to 40% on select hotels after you book a flight*
  • payments icon
    Earn twice
    Earn your airline miles on top of our rewards
    Sign in

Cheap Flights from Chicago to Madison (ORD-MSN)

Prices were available within the past 7 days and start at S$279 for one-way flights and S$308 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

American Airlines
Sun, 10 Aug - Sun, 17 Aug
ORD
Chicago
MSN
Madison
S$308 Return, found 4 days ago
S$308
Return
found 4 days ago
Select American Airlines flight, departing Sun, 10 Aug from Chicago to Madison, returning Sun, 17 Aug, priced at S$308 found 4 days ago
United
Sun, 10 Aug - Sun, 17 Aug
ORD
Chicago
MSN
Madison
S$308 Return, found 4 days ago
S$308
Return
found 4 days ago
Select United flight, departing Sun, 10 Aug from Chicago to Madison, returning Sun, 17 Aug, priced at S$308 found 4 days ago
American Airlines
Thu, 7 Aug - Thu, 14 Aug
ORD
Chicago
MSN
Madison
S$309 Return, found 6 days ago
S$309
Return
found 6 days ago
Select American Airlines flight, departing Thu, 7 Aug from Chicago to Madison, returning Thu, 14 Aug, priced at S$309 found 6 days ago
United
Sun, 10 Aug - Sun, 17 Aug
ORD
Chicago
MSN
Madison
S$327 Return, found 4 days ago
S$327
Return
found 4 days ago
Select United flight, departing Sun, 10 Aug from Chicago to Madison, returning Sun, 17 Aug, priced at S$327 found 4 days ago
United
Sun, 10 Aug - Sun, 17 Aug
ORD
Chicago
MSN
Madison
S$365 Return, found 4 days ago
S$365
Return
found 4 days ago
Select United flight, departing Sun, 10 Aug from Chicago to Madison, returning Sun, 17 Aug, priced at S$365 found 4 days ago
American Airlines
Thu, 7 Aug - Thu, 14 Aug
ORD
Chicago
MSN
Madison
S$367 Return, found 6 days ago
S$367
Return
found 6 days ago
Select American Airlines flight, departing Thu, 7 Aug from Chicago to Madison, returning Thu, 14 Aug, priced at S$367 found 6 days ago
American Airlines
Sun, 10 Aug - Sun, 17 Aug
ORD
Chicago
MSN
Madison
S$374 Return, found 4 days ago
S$374
Return
found 4 days ago
Select American Airlines flight, departing Sun, 10 Aug from Chicago to Madison, returning Sun, 17 Aug, priced at S$374 found 4 days ago
American Airlines
Thu, 7 Aug - Thu, 14 Aug
ORD
Chicago
MSN
Madison
S$375 Return, found 6 days ago
S$375
Return
found 6 days ago
Select American Airlines flight, departing Thu, 7 Aug from Chicago to Madison, returning Thu, 14 Aug, priced at S$375 found 6 days ago
American Airlines
Sun, 10 Aug - Sun, 17 Aug
ORD
Chicago
MSN
Madison
S$377 Return, found 4 days ago
S$377
Return
found 4 days ago
Select American Airlines flight, departing Sun, 10 Aug from Chicago to Madison, returning Sun, 17 Aug, priced at S$377 found 4 days ago
Delta
Sun, 17 Aug - Thu, 21 Aug
ORD
Chicago
MSN
Madison
S$1,276 Return, found 2 days ago
S$1,276
Return
found 2 days ago
Select Delta flight, departing Sun, 17 Aug from Chicago to Madison, returning Thu, 21 Aug, priced at S$1,276 found 2 days ago

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

June is typically the cheapest month to fly

From S$229 - S$521 per traveller.

Graph displaying average flight prices per month

Chicago to Madison route information
Origin airport
O'Hare Intl.
Destination airport
Dane County Regional
Return price
S$307
Distance
173 km
Average flight time
1 hour 4 mins

Perfect flights from Chicago to Madison

Your Journey from Chicago to Madison

Start your unforgettable journey with Expedia. Our broad selection of flights from Chicago to Madison 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 O'Hare Intl. to Dane County Regional 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 Chicago to Madison Flights

Experience the joy of finding cheap flights from O'Hare Intl. to Dane County Regional 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$308*.
 

Pre-Flight Essentials

Ensure a smooth journey from Chicago to Madison 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 Madison

Picture yourself stepping off the plane in Madison 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 Chicago to Madison 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 Chicago to Madison.
 

Beyond the Flight – Exploring Madison

With Expedia, your adventure extends beyond the flight. Explore Madison 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 Chicago to Madison 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 Chicago to Madison 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 ORD to Dane County Regional Airport (MSN)?
Round-trip tickets between O'Hare Airport and Truax Field start from S$308. This price is based on fares advertised within the last 7 days on Expedia for flights departing within the next year --- book now to avoid missing out. Prices and availability are subject to change. Additional terms apply.
Do I need to pay a cancellation fee if I cancel my flight from O'Hare Intl. Airport (ORD) to Truax Field?
Most flights can be cancelled online, but each airline has its own 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 ORD to Truax Field 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 O'Hare Intl. Airport (ORD) to Truax Field flights, you'll see a "no change fees" filter for you to select.
How far is the flight from O'Hare Airport to Dane County Regional Airport (MSN)?
You won't need a lengthy novel for this flight --- it's only 180 kilometres from Chicago to Madison. Find your seat, enjoy the in-flight service and you'll be in Madison before long.
Which airlines fly direct from ORD to Dane County Regional Airport (MSN)?
United Airlines (UA) is one of the preferred choices for travellers jetting between O'Hare Airport and Dane County Regional Airport (MSN). Select from the 182 flights it operates on this route each month. Like more options? Check out the seats available with American Airlines (AA). This carrier offers 82 flights every month between these airports.
Are O'Hare Intl. Airport (ORD) to Truax Field flight tickets cheaper when they're purchased at the last minute?
Late planners can sometimes pick up a bargain, with some of the cheapest fares from O'Hare Intl. Airport (ORD) to Truax Field appearing a few weeks before the departure date. If you'd rather plan ahead of time, Expedia compares and updates the best flight deals frequently --- as early as a year in advance in some cases. It depends on the carrier though, as not all airlines quote prices so far in advance.

Explore a world of travel with Expedia

Chicago Airports

Chicago

*Available to Expedia members.