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CA $335 Cheap Flights from Chicago (ORD) to Madison (MSN)

View CA $335 flight on Mon, Sep 28, 2026Opens in a new window

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

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

Prices were available within the past 7 days and start at CA $335 for one-way flights and CA $350 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

American Airlines
Mon, Sep 28 - Sat, Oct 3
ORD
Chicago
MSN
Madison
CA $350 Roundtrip, found 4 days ago
CA $350
Roundtrip
found 4 days ago
Select American Airlines flight, departing Mon, Sep 28 from Chicago to Madison, returning Sat, Oct 3, priced at CA $350 found 4 days ago
American Airlines
Mon, Sep 28 - Sat, Oct 3
ORD
Chicago
MSN
Madison
CA $370 Roundtrip, found 4 days ago
CA $370
Roundtrip
found 4 days ago
Select American Airlines flight, departing Mon, Sep 28 from Chicago to Madison, returning Sat, Oct 3, priced at CA $370 found 4 days ago
American Airlines
Mon, Sep 28 - Sat, Oct 3
ORD
Chicago
MSN
Madison
CA $383 Roundtrip, found 4 days ago
CA $383
Roundtrip
found 4 days ago
Select American Airlines flight, departing Mon, Sep 28 from Chicago to Madison, returning Sat, Oct 3, priced at CA $383 found 4 days ago
American Airlines
Mon, Sep 28 - Sat, Oct 3
ORD
Chicago
MSN
Madison
CA $392 Roundtrip, found 4 days ago
CA $392
Roundtrip
found 4 days ago
Select American Airlines flight, departing Mon, Sep 28 from Chicago to Madison, returning Sat, Oct 3, priced at CA $392 found 4 days ago
American Airlines
Mon, Sep 28 - Sat, Oct 3
ORD
Chicago
MSN
Madison
CA $404 Roundtrip, found 4 days ago
CA $404
Roundtrip
found 4 days ago
Select American Airlines flight, departing Mon, Sep 28 from Chicago to Madison, returning Sat, Oct 3, priced at CA $404 found 4 days ago
American Airlines
Mon, Sep 28 - Sat, Oct 3
ORD
Chicago
MSN
Madison
CA $420 Roundtrip, found 4 days ago
CA $420
Roundtrip
found 4 days ago
Select American Airlines flight, departing Mon, Sep 28 from Chicago to Madison, returning Sat, Oct 3, priced at CA $420 found 4 days ago
American Airlines
Mon, Sep 28 - Sat, Oct 3
ORD
Chicago
MSN
Madison
CA $440 Roundtrip, found 4 days ago
CA $440
Roundtrip
found 4 days ago
Select American Airlines flight, departing Mon, Sep 28 from Chicago to Madison, returning Sat, Oct 3, priced at CA $440 found 4 days ago
United
Mon, Sep 28 - Sat, Oct 3
ORD
Chicago
MSN
Madison
CA $448 Roundtrip, found 4 days ago
CA $448
Roundtrip
found 4 days ago
Select United flight, departing Mon, Sep 28 from Chicago to Madison, returning Sat, Oct 3, priced at CA $448 found 4 days ago
American Airlines
Thu, Sep 3 - Thu, Sep 10
ORD
Chicago
MSN
Madison
CA $449 Roundtrip, found 1 day ago
CA $449
Roundtrip
found 1 day ago
Select American Airlines flight, departing Thu, Sep 3 from Chicago to Madison, returning Thu, Sep 10, priced at CA $449 found 1 day ago
Delta
Thu, Sep 3 - Thu, Sep 10
ORD
Chicago
MSN
Madison
CA $949 Roundtrip, found 1 day ago
CA $949
Roundtrip
found 1 day ago
Select Delta flight, departing Thu, Sep 3 from Chicago to Madison, returning Thu, Sep 10, priced at CA $949 found 1 day ago

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

February is typically the cheapest month to fly

From CA $254 - CA $578 per traveller.

Frequently asked questions

How much does a flight from Chicago, IL (ORD-O'Hare Intl.) to Madison, WI (MSN-Dane County Regional) cost?
You can find one-way and return flights from ORD to MSN with Expedia. Flight prices vary based on the month and day of the week you want to travel, as well as the airline and how far in advance you book your ticket. Filter your search on Expedia by "Price (lowest to highest)" to see our cheapest fares first, and use the Price Tracking tool to receive alerts when ORD to MSN ticket fares go up or down.
What is the cheapest month to fly from Chicago, IL (ORD-O'Hare Intl.) to Madison, WI (MSN-Dane County Regional)?
The cheapest months to fly from ORD to MSN are typically during off-peak season when demand is low. Traveling in off-peak or shoulder months is usually a good way to secure cheap tickets, just remember to avoid flying during holidays if you are able to. Use the calendar view in your search to see which months have low fares on this route.
Which airlines fly direct from Chicago, IL (ORD-O'Hare Intl.) to Madison, WI (MSN-Dane County Regional)?
There are 2 airlines that offer direct flights from Chicago, IL (ORD-O'Hare Intl.) to Madison, WI (MSN-Dane County Regional):
  • United operates 106 direct flights from ORD to MSN every week.
  • American Airlines operates 48 direct flights from ORD to MSN every week.
What is the cheapest airline that flies from Chicago, IL (ORD-O'Hare Intl.) to Madison, WI (MSN-Dane County Regional)?
United is one of the cheapest airlines offering nonstop return flights from Chicago O'Hare International Airport (ORD) to Madison Dane County Regional (MSN), with tickets starting from around CA$247 for flights that can be booked for departure within the next year. American Airlines is one of the cheapest airlines offering connecting return flights from Chicago O'Hare International Airport (ORD) to Madison Dane County Regional (MSN), with tickets starting from around CA$302. These prices are per adult for economy/coach class. Use Expedia's search tool to compare the prices and schedules of airlines that fly this route to find the best option for your plans and budget.
How do I find cheap flights from Chicago, IL (ORD-O'Hare Intl.) to Madison, WI (MSN-Dane County Regional)?
To find a cheap flight from Chicago, IL (ORD-O'Hare Intl.) to Madison, WI (MSN-Dane County Regional), be flexible with your dates. Traveling outside of peak vacation months and booking a mid-week flight can help you save. Early morning and late night flights are often more affordable, too. Expedia allows you to compare flight times, airlines and routes all in one place to find low fares. You can also set up Price Tracking and receive alerts when fares go up or down.
What is the best airline to fly with from Chicago, IL (ORD-O'Hare Intl.) to Madison, WI (MSN-Dane County Regional)?
The best airline to fly with from Chicago, IL (ORD-O'Hare Intl.) to Madison, WI (MSN-Dane County Regional) will differ from traveler to traveler. If you like to fly early, American Airlines offers early morning flights. If price is the most important factor, American Airlines typically offers the lowest fares. Delta offers the most daily flights from Chicago, IL (ORD-O'Hare Intl.) to Madison, WI (MSN-Dane County Regional), which is great if flexibility is what you value most. The best carrier for this journey could also be the one you have a loyalty membership with, as flying with that airline or another airline within the same alliance could help you collect points or enjoy lounge access.
What is the best time to fly from Chicago, IL (ORD-O'Hare Intl.) to Madison, WI (MSN-Dane County Regional)?
The best time to fly is usually mid-week (Tuesday or Wednesday) and during early morning hours as flights tend to be cheaper, less crowded, and generally more on-time. Avoid major holidays and peak vacation seasons for smoother travel. Combining off-peak days and hours often gives the best combination of cost, comfort, and convenience.
How many flights per day from Chicago, IL (ORD-O'Hare Intl.) to Madison, WI (MSN-Dane County Regional)?
You'll find approximately 22 nonstop flights per day from Chicago, IL (ORD-O'Hare Intl.) to Madison, WI (MSN-Dane County Regional). For even more choices, look at flights that include layovers, as there are around 48 connecting flights per day. Some common connection points include Detroit Metropolitan Wayne County (DTW), Minneapolis - St. Paul Intl. (MSP), and Hartsfield-Jackson Atlanta Intl. (ATL).
What is the earliest flight from Chicago, IL (ORD-O'Hare Intl.) to Madison, WI (MSN-Dane County Regional)?
The earliest flight from Chicago, IL (ORD-O'Hare Intl.) to Madison, WI (MSN-Dane County Regional) typically departs around 5:00 AM local time. This flight is operated by American Airlines. This is a seasonal service, active in January, February, March, and December. An early departure like this can help you make the most of your time at your destination. To compare early flights on Expedia, select the "Early Morning" and "Morning" filters in your search.
What day of the week has the most flights from Chicago, IL (ORD-O'Hare Intl.) to Madison, WI (MSN-Dane County Regional)?
You'll typically find the most flights from Chicago, IL (ORD-O'Hare Intl.) to Madison, WI (MSN-Dane County Regional) on a Wednesday, with around 47 flights available. This gives you a good selection of options for your travel plans. Major airlines on this route include American Airlines, Delta, and United. Flight schedules are fairly consistent throughout the week, so you should find suitable options on other days as well.
What are the most popular departure times for flights from Chicago, IL (ORD-O'Hare Intl.) to Madison, WI (MSN-Dane County Regional)?
The most popular departure times for flights from Chicago O'Hare International Airport (ORD) to Madison (MSN) are between 9am and 12pm. Many major carriers, including American Airlines, Delta and United, offer flights during this window. Many travellers prefer these times as they allow for a productive morning before heading to the airport, and you'll arrive in Madison with plenty of time for afternoon activities.
How long does it take to fly from Chicago, IL (ORD-O'Hare Intl.) to Madison, WI (MSN-Dane County Regional)?
A non-stop flight from Chicago, IL (ORD-O'Hare Intl.) to Madison, WI (MSN-Dane County Regional) typically takes around 1 hour 18 minutes, covering a distance of about 175 kilometres. If you opt for a one-stop flight, your travel time will be longer, usually around 8 hours. Flights with two or more stops generally take about 6 hours 48 minutes. Keep in mind that these are average times, and your actual flight duration can vary due to factors like wind patterns and specific routing.
Can you fly business or first class from Chicago, IL (ORD-O'Hare Intl.) to Madison, WI (MSN-Dane County Regional)?
Select the "Business class" and "First class" filters when looking for ORD to MSN flights on Expedia. This is the easiest way to compare prices, routes and flight times for your trip.
How do I earn miles on a Chicago, IL (ORD-O'Hare Intl.) to Madison, WI (MSN-Dane County Regional) flight with Expedia?
It's easy to earn miles on a Chicago, IL (ORD-O'Hare Intl.) to Madison, WI (MSN-Dane County Regional) flight when you book with Expedia. Before you confirm your booking, simply select your frequent flyer program and enter your program number. As a member of One Key™, you can also earn OneKeyCash™* on top of your airline miles when you book with Expedia.*Excludes taxes and fees. OneKeyCash is not redeemable for cash and can only be used on Expedia and other participating brands.
What airports do you fly into for Madison, WI (MSN) from Chicago, IL (ORD)?
If you're planning to travel to Madison from O'Hare Intl. (ORD), you can fly directly into Dane County Regional (MSN) which offers domestic flights and connections. Some flights may connect through major hubs like Indianapolis Intl. (IND), Hopkins Intl. (CLE), or John Glenn Columbus Intl. (CMH) before reaching Madison. Compare routes and airports on Expedia to find the best flight options for your travel plans.
Is it cheaper to buy a plane ticket from Chicago, IL (ORD-O'Hare Intl.) to Madison, WI (MSN-Dane County Regional) at the last minute?
Typically, booking a last minute flight from Chicago, IL (ORD-O'Hare Intl.) to Madison, WI (MSN-Dane County Regional) will be more expensive than booking in advance. As the departure date approaches, there are usually fewer seats available which can drive up the cost. However, if there's some wiggle room with your travel dates and times, you could bag a cheap last-minute fare.
Is it cheaper to book a Chicago, IL (ORD-O'Hare Intl.) to Madison, WI (MSN-Dane County Regional) flight and hotel package?
Securing a Chicago, IL (ORD-O'Hare Intl.) to Madison, WI (MSN-Dane County Regional) flight and hotel package is usually cheaper than booking separately. With Expedia, you can enjoy the ease of organizing your travels all in one place. Select from our extensive range of stays and then add flights, activities and car rentals to your booking. Bundle everything together, and you could save hundreds of dollars.
Can I cancel or change the date of my flight from Chicago, IL (ORD-O'Hare Intl.) to Madison, WI (MSN-Dane County Regional)?
If you booked your Chicago, IL (ORD-O'Hare Intl.) to Madison, WI (MSN-Dane County Regional) flight within the last 24 hours, you may be able to modify or cancel it without any fees. Depending on the airline and the type of ticket you have, additional charges may apply for changes beyond this timeframe. Airline policies and contact information can be found in your itinerary or confirmation email. Or, head to our Customer Service portal if you'd like more information.

Travel information

Origin airport
O'Hare Intl.
Destination airport
Dane County Regional
Roundtrip price
CA $350
Distance
173 km
Average flight time
1 hour 6 mins

Book with confidence

Chicago to Madison Flights

The easy way to book your flights from Chicago to Madison 

With Expedia, it’s simple to find and book flights to Madison from Chicago whether you’re traveling for business or pleasure. Enter your travel dates, hit search, and choose your flight from 20 airlines that cover this route. There are nonstop flights to Dane County Regional, too.  

Choose your preferred carrier and cabin class with the advanced search tool and select your ideal departure time. Then, if you want, you can see just nonstop or refundable flights. And if you’re traveling last minute, just enter the date to check out flights from Chicago to Madison today, tomorrow, or this week.  

 

Save dollars with cheap flights from O'Hare Intl., ORD to Dane County Regional, MSN 

Sort your search results by price to find great deals on your flight from Chicago to Madison—you get all your cheapest options first. Grab yourself a bargain now—the lowest price on flights to Madison from Chicago currently is just CA $350 rising to CA $949.  

Here are more money-saving tips: 

  • Fly in September when flight prices are normally at their lowest 
  • Book about a month to 6 weeks before you travel for the best prices to Madison  
  • Avoid peak season and weekends when flights can cost more
  • Early morning and late-night flights are sometimes cheaper, so try varying your travel times 
  • One surefire way to save money on your flight is to book your flight and hotel together with Expedia. Sometimes, the savings are so large that the flight is basically free! 

 

Reasons to choose Expedia for your flight to Madison from Chicago 

Whatever your destination, budget, or reason to travel, in just one quick search, you can choose from loads of flights, airlines, and cabin classes. The filters make it quick and easy to find your ideal flights, and if you choose one of the flexible options, you won’t be charged to change your flight. So book your flight to Madison with Expedia today.

Chicago to Madison Flights

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