$164 Cheap Flights from Chicago (ORD) to Madison (MSN)

View $164 flight on Sat, Jun 6, 2026Opens 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 $164 for one-way flights and $239 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

American Airlines
Tue, Sep 1 - Sat, Sep 5
ORD
Chicago
MSN
Madison
$239 Roundtrip, just found
$239
Roundtrip
just found
Select American Airlines flight, departing Tue, Sep 1 from Chicago to Madison, returning Sat, Sep 5, priced at $239 just found
United
Fri, May 15 - Tue, May 19
ORD
Chicago
MSN
Madison
$239 Roundtrip, found 1 hour ago
$239
Roundtrip
found 1 hour ago
Select United flight, departing Fri, May 15 from Chicago to Madison, returning Tue, May 19, priced at $239 found 1 hour ago
United
Fri, May 22 - Mon, May 25
ORD
Chicago
MSN
Madison
$246 Roundtrip, found 1 hour ago
$246
Roundtrip
found 1 hour ago
Select United flight, departing Fri, May 22 from Chicago to Madison, returning Mon, May 25, priced at $246 found 1 hour ago
United
Fri, May 22 - Mon, May 25
ORD
Chicago
MSN
Madison
$248 Roundtrip, found 1 hour ago
$248
Roundtrip
found 1 hour ago
Select United flight, departing Fri, May 22 from Chicago to Madison, returning Mon, May 25, priced at $248 found 1 hour ago
American Airlines
Tue, Sep 1 - Sat, Sep 5
ORD
Chicago
MSN
Madison
$249 Roundtrip, just found
$249
Roundtrip
just found
Select American Airlines flight, departing Tue, Sep 1 from Chicago to Madison, returning Sat, Sep 5, priced at $249 just found
United
Thu, Apr 30 - Thu, May 7
ORD
Chicago
MSN
Madison
$254 Roundtrip, found 1 day ago
$254
Roundtrip
found 1 day ago
Select United flight, departing Thu, Apr 30 from Chicago to Madison, returning Thu, May 7, priced at $254 found 1 day ago
United
Fri, Jun 12 - Mon, Jun 15
ORD
Chicago
MSN
Madison
$256 Roundtrip, found 1 day ago
$256
Roundtrip
found 1 day ago
Select United flight, departing Fri, Jun 12 from Chicago to Madison, returning Mon, Jun 15, priced at $256 found 1 day ago
American Airlines
Tue, Sep 1 - Sat, Sep 5
ORD
Chicago
MSN
Madison
$259 Roundtrip, just found
$259
Roundtrip
just found
Select American Airlines flight, departing Tue, Sep 1 from Chicago to Madison, returning Sat, Sep 5, priced at $259 just found
American Airlines
Tue, Jun 30 - Sat, Jul 4
ORD
Chicago
MSN
Madison
$263 Roundtrip, just found
$263
Roundtrip
just found
Select American Airlines flight, departing Tue, Jun 30 from Chicago to Madison, returning Sat, Jul 4, priced at $263 just found
Delta
Tue, Jun 2 - Sat, Jun 6
ORD
Chicago
MSN
Madison
$435 Roundtrip, found 17 hours ago
$435
Roundtrip
found 17 hours ago
Select Delta flight, departing Tue, Jun 2 from Chicago to Madison, returning Sat, Jun 6, priced at $435 found 17 hours ago

Alternative airports near Madison

Prices were available within the past 7 days. Prices and availability are subject to change.

Select flight to Dane County Regional MSN. Cheapest and Closest option available. Average driving time to city center is 11 minutes. Flights from $254
MSN
Dane County Regional
CheapestClosest
Average driving time to city center11 min
Flights from $254

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 cheap one-way flights from $164 and cheap return flights from $239 Chicago, IL (ORD-O'Hare Intl.) to Madison, WI (MSN-Dane County Regional) with Expedia. One-way flights usually range from $192 to $862, and return flights typically cost between $238 and $1033. 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 the cheapest fares first, and use the Price Tracking tool to receive alerts when Chicago, IL (ORD-O'Hare Intl.) to Madison, WI (MSN-Dane County Regional) ticket fares go up or down.*Typical price ranges based on flights available on Expedia in the last year. Prices include multi-airline options.
What is the cheapest month to fly from Chicago, IL (ORD-O'Hare Intl.) to Madison, WI (MSN-Dane County Regional)?
The cheapest month to fly from ORD to MSN is September 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're 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)?
2 airlines operate nonstop service from ORD to MSN:

  • United operates around 94 direct flights from ORD to MSN every week
  • American Airlines operates around 44 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)?
American Airlines is one of the cheapest airlines offering connecting flights from ORD to MSN, with round-trip tickets starting from around $541. 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.*Prices based on flights available on Expedia in the last year.
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) to Madison, WI (MSN) will differ from traveler to traveler. If you like to fly early, United offers early morning flights. If price is the most important factor, United typically offers the lowest fares. Delta offers the most daily flights from Chicago to Madison, 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 can find approximately 20 nonstop flights per day from O'Hare Intl. (ORD) to Dane County Regional (MSN). For more options, look at flights that include layovers.
What is the earliest flight from Chicago, IL (ORD-O'Hare Intl.) to Madison, WI (MSN-Dane County Regional)?
The earliest flight from O'Hare International (ORD) to Dane County Regional (MSN) typically departs at around 5:00 AM, operated by American Airlines. This seasonal service is available in January and December, allowing you to start your day early and make the most of your time in Madison. To compare early flights on Expedia, select the "Early Morning" and "Morning" filters in your search.
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, IL (ORD) to Madison, WI (MSN) are in the late morning, from 9am to noon. This accounts for around 25% of total traffic. Many major carriers, including Delta Airlines and American Airlines, offer flights during this window. This timing is favored because it allows travelers to start their day early and arrive in Madison with ample time for their plans.
How long does it take to fly from Chicago, IL (ORD-O'Hare Intl.) to Madison, WI (MSN-Dane County Regional)?
Flying nonstop from ORD to MSN takes around 1 hour, with the route covering approximately 109 miles. Flights with a layover typically take 7 hours longer than direct options. Keep in mind that actual flight times can vary due to wind patterns, weather, and air traffic.
Can you fly business or first class from Chicago, IL (ORD-O'Hare Intl.) to Madison, WI (MSN-Dane County Regional)?
You can fly first class between ORD and MSN. First class cabins are available on:

  • Delta Air Lines
  • American Airlines
  • United Airlines

How much is a business class flight from Chicago, IL (ORD-O'Hare Intl.) to Madison, WI (MSN-Dane County Regional)?
A non-stop, one-way business class flight from Chicago O'Hare International Airport (ORD) to Dane County Regional Airport (MSN) is usually around $313 - $593. Prices often fluctuate based on seasonality and how early you book. You may also be able to find a cheaper business class journey between Chicago, IL (ORD-O'Hare Intl.) to Madison, WI (MSN-Dane County Regional) if you opt for a connecting flight.*Prices based on flights available on Expedia in the last year.
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 from O'Hare Intl. (ORD)?
If you're planning to travel to Madison from O'Hare Intl. (ORD), you can fly into Dane County Regional (MSN) Some flights may connect through major hubs like Indianapolis Intl. (IND), Hopkins Intl. (CLE), Pittsburgh Intl. (PIT) 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) Madison Vacation Packages 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
Airlines serving
American Airlines, Delta, United
Roundtrip price
$239
Distance
108 mi
Average flight time
1 hour 4 mins

Book with confidence

Chicago to Madison Flights

The cheapest times to fly from Chicago to Madison

On average, Thursday can be the cheapest time to fly, according to data from the Airlines Reporting Corporation (ARC), one of the world's biggest databases for global airline sales. The data reveals that you could save up to 16% by flying on a Thursday—the cheapest day to travel on average—instead of a Sunday—the most expensive. Some of the most affordable flights from Chicago to Madison are during the month of September. You can find some of the cheapest flights from Chicago to Madison with Expedia's search tool and vast selection of airlines.

 

The best time to book a flight from Chicago to Madison

Sunday is one of the best days to book for cheap flights from Chicago to Madison: Tickets reserved on a Sunday cost between 6% and 13% less than those reserved on a Friday, according to ARC data. The data also suggests booking early can also lead to cheaper airfares. You could save 24% by buying your tickets for domestic flights at least a month in advance and 10% by booking international flights 2 months in advance.

 

How to find cheap round-trip tickets from Chicago to Madison

Being flexible with your dates and using Expedia's Price Drop Protection and Price Tracking features are some of the best ways of finding a cheap ticket from Chicago to Madison in 2026. You can also book with separate airlines for your outbound and return journeys, from $164 one-way. Expedia also offers Price Drop Protection, so if the cost of your airfare goes down after booking, you'll receive a credit for the difference*. This is available for a small fee, and is free to One Key Gold and Platinum tier members.

 

Expedia's Price Tracking feature means you can stay on top of airfares without manually checking every day. It sends you automated price alerts for cheap Chicago to Madison flights and uses historical data to indicate when the best time to book is. Download Expedia's free app to activate this handy tool in a few easy taps.

 

You could also save big by booking one of Expedia's vacation packages. Bundling together your Chicago to Madison airfare with your accommodations and car rental is often cheaper than booking everything separately. There’s also One Key, Expedia's generous rewards program. Join for free and you could earn One Key cash on most bookings to save on future adventures.

 

*Terms apply.

 

Disclaimer: ARC The statistics are based on average round-trip ticket prices between January and August 2023. The percentages you see are averages.

 

Chicago to Madison Flights

*Flight schedules are subject to change.

*Available to One Key members.

 

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