S$281 Cheap Flights from Chicago to Madison

View S$281 flight on Wed, 12 Nov, 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 S$281 for one-way flights and S$310 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

United
Sun, 23 Nov - Sun, 30 Nov
ORD
Chicago
MSN
Madison
S$310 Return, found 23 hours ago
S$310
Return
found 23 hours ago
Select United flight, departing Sun, 23 Nov from Chicago to Madison, returning Sun, 30 Nov, priced at S$310 found 23 hours ago
United
Sun, 23 Nov - Sun, 30 Nov
ORD
Chicago
MSN
Madison
S$330 Return, found 23 hours ago
S$330
Return
found 23 hours ago
Select United flight, departing Sun, 23 Nov from Chicago to Madison, returning Sun, 30 Nov, priced at S$330 found 23 hours ago
United
Sun, 23 Nov - Sun, 30 Nov
ORD
Chicago
MSN
Madison
S$368 Return, found 23 hours ago
S$368
Return
found 23 hours ago
Select United flight, departing Sun, 23 Nov from Chicago to Madison, returning Sun, 30 Nov, priced at S$368 found 23 hours ago
United
Sun, 23 Nov - Sun, 30 Nov
ORD
Chicago
MSN
Madison
S$394 Return, found 23 hours ago
S$394
Return
found 23 hours ago
Select United flight, departing Sun, 23 Nov from Chicago to Madison, returning Sun, 30 Nov, priced at S$394 found 23 hours ago
United
Sun, 23 Nov - Sun, 30 Nov
ORD
Chicago
MSN
Madison
S$401 Return, found 23 hours ago
S$401
Return
found 23 hours ago
Select United flight, departing Sun, 23 Nov from Chicago to Madison, returning Sun, 30 Nov, priced at S$401 found 23 hours ago
United
Sun, 23 Nov - Sun, 30 Nov
ORD
Chicago
MSN
Madison
S$414 Return, found 23 hours ago
S$414
Return
found 23 hours ago
Select United flight, departing Sun, 23 Nov from Chicago to Madison, returning Sun, 30 Nov, priced at S$414 found 23 hours ago
United
Sun, 23 Nov - Sun, 30 Nov
ORD
Chicago
MSN
Madison
S$420 Return, found 23 hours ago
S$420
Return
found 23 hours ago
Select United flight, departing Sun, 23 Nov from Chicago to Madison, returning Sun, 30 Nov, priced at S$420 found 23 hours ago
United
Sun, 23 Nov - Sun, 30 Nov
ORD
Chicago
MSN
Madison
S$438 Return, found 23 hours ago
S$438
Return
found 23 hours ago
Select United flight, departing Sun, 23 Nov from Chicago to Madison, returning Sun, 30 Nov, priced at S$438 found 23 hours ago
United
Sun, 23 Nov - Sun, 30 Nov
ORD
Chicago
MSN
Madison
S$452 Return, found 23 hours ago
S$452
Return
found 23 hours ago
Select United flight, departing Sun, 23 Nov from Chicago to Madison, returning Sun, 30 Nov, priced at S$452 found 23 hours ago
American Airlines
Sun, 23 Nov - Sun, 30 Nov
ORD
Chicago
MSN
Madison
S$497 Return, found 23 hours ago
S$497
Return
found 23 hours ago
Select American Airlines flight, departing Sun, 23 Nov from Chicago to Madison, returning Sun, 30 Nov, priced at S$497 found 23 hours ago

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

July is typically the cheapest month to fly

From S$231 - S$525 per traveller.

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$310. 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.

Travel information

Travel information

Origin airport
O'Hare Intl.
Destination airport
Dane County Regional
Airlines serving
American Airlines, United
Return price
S$310
Distance
173 km
Average flight time
1 hour 2 mins

Book with confidence

Book with confidence

Perfect flights from Chicago to Madison

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*Note: Prices may vary based on availability and are subject to change.
Perfect flights from Chicago to Madison

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