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

View AU$434 flight on Sat, 16 Aug. 2025Opens in a new window

Popular airlines from Chicago O'Hare International 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 35% 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 (ORD) to Madison (MSN)

Prices were available within the past 7 days for one-way flights and round trip tickets for the period specified. Prices and availability are subject to change. Additional terms apply.

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

July is typically the cheapest month to fly

From AU$277 - AU$629 per traveller.

Graph displaying average flight prices per month

Flight from Chicago to Madison route information
Origin airport
O'Hare Intl.
Destination airport
Dane County Regional
Distance
173 km
Average flight time
1 hour 4 mins

Your quick guide to flights from Chicago to Madison

Pick up great flights from Chicago to Madison

With Expedia, you have your pick of 42 flights a day with 20 airlines covering flights from Chicago to Madison. Whether you’re on a business trip, a family holiday or a luxury break, just enter your travel dates, hit search then check out your choice of flights. Select from return, one way or multi-city flights, and use the advance search tool if you want a direct or refundable flight. You can narrow your search to show you just your preferred cabin class and airline, too. It’s all easy. You can book direct flights from Chicago to Madison that take around 0 hours.

Find cheap flights from Chicago to Madison

From the great flight deals with prices currently ranging from to , you can choose to see the cheapest flights first. Generally, you can book the cheapest flights from Chicago to Madison around 4 to 6 weeks in advance. If your travel dates are flexible, try to avoid weekends and peak seasons – when you are more likely to grab the lowest prices. Even last minute, there are some impressive deals. The cheapest time to fly to Madison is normally in .

Reasons to book your flight from Chicago to Madison with Expedia

Expedia makes it easy to find, book, and travel, with everything you need all in one place. When you enter your travel details, find fantastic deals just for you on flight tickets from Chicago to Madison across all the main airline carriers, so you can save time, dollars, and hassle finding the perfect flight. If you think your plans could change, choose refundable flights so any changes won’t cost you more. Book your flight to Madison right now and, if you join Expedia Rewards, you earn points this time and every time you travel with Expedia.

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 . 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

*Available to Expedia members.