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CA $332 Cheap Flights from Madison (MSN) to Chicago (ORD)

View CA $332 flight on Fri, Nov 13, 2026Opens in a new window

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

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

Prices were available within the past 7 days and start at CA $332 for one-way flights and CA $340 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

American Airlines
Fri, Nov 13 - Fri, Dec 4
MSN
Madison
ORD
Chicago
CA $340 Roundtrip, found 4 days ago
CA $340
Roundtrip
found 4 days ago
Select American Airlines flight, departing Fri, Nov 13 from Madison to Chicago, returning Fri, Dec 4, priced at CA $340 found 4 days ago
American Airlines
Fri, Nov 13 - Fri, Dec 4
MSN
Madison
ORD
Chicago
CA $361 Roundtrip, found 4 days ago
CA $361
Roundtrip
found 4 days ago
Select American Airlines flight, departing Fri, Nov 13 from Madison to Chicago, returning Fri, Dec 4, priced at CA $361 found 4 days ago
American Airlines
Fri, Nov 13 - Fri, Dec 4
MSN
Madison
ORD
Chicago
CA $417 Roundtrip, found 4 days ago
CA $417
Roundtrip
found 4 days ago
Select American Airlines flight, departing Fri, Nov 13 from Madison to Chicago, returning Fri, Dec 4, priced at CA $417 found 4 days ago
United
Fri, Nov 13 - Fri, Dec 4
MSN
Madison
ORD
Chicago
CA $439 Roundtrip, found 4 days ago
CA $439
Roundtrip
found 4 days ago
Select United flight, departing Fri, Nov 13 from Madison to Chicago, returning Fri, Dec 4, priced at CA $439 found 4 days ago
United
Fri, Nov 13 - Fri, Dec 4
MSN
Madison
ORD
Chicago
CA $451 Roundtrip, found 4 days ago
CA $451
Roundtrip
found 4 days ago
Select United flight, departing Fri, Nov 13 from Madison to Chicago, returning Fri, Dec 4, priced at CA $451 found 4 days ago
American Airlines
Fri, Nov 13 - Fri, Dec 4
MSN
Madison
ORD
Chicago
CA $460 Roundtrip, found 4 days ago
CA $460
Roundtrip
found 4 days ago
Select American Airlines flight, departing Fri, Nov 13 from Madison to Chicago, returning Fri, Dec 4, priced at CA $460 found 4 days ago
United
Fri, Nov 13 - Fri, Dec 4
MSN
Madison
ORD
Chicago
CA $485 Roundtrip, found 4 days ago
CA $485
Roundtrip
found 4 days ago
Select United flight, departing Fri, Nov 13 from Madison to Chicago, returning Fri, Dec 4, priced at CA $485 found 4 days ago
United
Fri, Nov 13 - Fri, Dec 4
MSN
Madison
ORD
Chicago
CA $497 Roundtrip, found 4 days ago
CA $497
Roundtrip
found 4 days ago
Select United flight, departing Fri, Nov 13 from Madison to Chicago, returning Fri, Dec 4, priced at CA $497 found 4 days ago
United
Fri, Nov 13 - Fri, Dec 4
MSN
Madison
ORD
Chicago
CA $500 Roundtrip, found 4 days ago
CA $500
Roundtrip
found 4 days ago
Select United flight, departing Fri, Nov 13 from Madison to Chicago, returning Fri, Dec 4, priced at CA $500 found 4 days ago
American Airlines
Fri, Nov 13 - Fri, Dec 4
MSN
Madison
ORD
Chicago
CA $508 Roundtrip, found 4 days ago
CA $508
Roundtrip
found 4 days ago
Select American Airlines flight, departing Fri, Nov 13 from Madison to Chicago, returning Fri, Dec 4, priced at CA $508 found 4 days ago

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

August is typically the cheapest month to fly

From CA $254 - CA $379 per traveller.

Frequently asked questions

How much does a flight from Madison, WI (MSN-Dane County Regional) to Chicago, IL (ORD-O'Hare Intl.) cost?
You can find one-way and return flights from MSN to ORD 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 MSN to ORD ticket fares go up or down.
What is the cheapest month to fly from Madison, WI (MSN-Dane County Regional) to Chicago, IL (ORD-O'Hare Intl.)?
July is typically the cheapest month to fly from Madison, WI (MSN-Dane County Regional) to Chicago, IL (ORD-O'Hare Intl.), with average return fares around CA$325. July sees lower prices because it falls after the spring travel rush, when demand drops and airlines compete for bookings. May and September are also good months to find deals on this route.
Which airlines fly direct from Madison, WI (MSN-Dane County Regional) to Chicago, IL (ORD-O'Hare Intl.)?
There are 2 airlines offering direct flights from Madison, WI (MSN-Dane County Regional) to Chicago, IL (ORD-O'Hare Intl.). These are:
  • United operates 86 direct flights from Madison, WI (MSN-Dane County Regional) to Chicago, IL (ORD-O'Hare Intl.) every week.
  • American Airlines operates 50 direct flights from Madison, WI (MSN-Dane County Regional) to Chicago, IL (ORD-O'Hare Intl.) every week.
What is the cheapest airline that flies from Madison, WI (MSN-Dane County Regional) to Chicago, IL (ORD-O'Hare Intl.)?
United is one of the cheapest airlines offering nonstop return flights from Madison, WI (MSN-Dane County Regional) to Chicago, IL (ORD-O'Hare Intl.), with tickets starting from around CA$260 for flights that can be booked for departure within the next year. American Airlines offers one of the cheapest connecting return flights on this route, with a layover in Charlotte-Douglas Intl. (CLT), starting from around CA$302. These prices are for economy/coach class per adult. 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 Madison, WI (MSN-Dane County Regional) to Chicago, IL (ORD-O'Hare Intl.)?
To find a cheap flight from Madison, WI (MSN-Dane County Regional) to Chicago, IL (ORD-O'Hare Intl.), 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 Madison, WI (MSN-Dane County Regional) to Chicago, IL (ORD-O'Hare Intl.)?
The best airline to fly with from Madison, WI (MSN-Dane County Regional) to Chicago, IL (ORD-O'Hare Intl.) 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 Madison, WI (MSN-Dane County Regional) to Chicago, IL (ORD-O'Hare Intl.), 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 Madison, WI (MSN) to Chicago, IL (ORD)?
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 Madison, WI (MSN-Dane County Regional) to Chicago, IL (ORD-O'Hare Intl.)?
You'll find approximately 19 nonstop flights per day from Madison, WI (MSN-Dane County Regional) to Chicago, IL (ORD-O'Hare Intl.). For even more choices, look at flights that include layovers, as there are around 24 connecting flights per day. Some common connection points include Minneapolis - St. Paul Intl. (MSP), Detroit Metropolitan Wayne County (DTW), and Hartsfield-Jackson Atlanta Intl. (ATL).
What is the earliest flight from Madison, WI (MSN-Dane County Regional) to Chicago, IL (ORD-O'Hare Intl.)?
The earliest flight from Madison, WI (MSN-Dane County Regional) to Chicago, IL (ORD-O'Hare Intl.) typically departs around 5:00 AM. This flight is operated by American Airlines. This is a seasonal service active in November 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 Madison, WI (MSN-Dane County Regional) to Chicago, IL (ORD-O'Hare Intl.)?
You'll typically find the most flights from Madison, WI (MSN-Dane County Regional) to Chicago, IL (ORD-O'Hare Intl.) on a Saturday, with around 28 flights available. This gives you plenty of options for your travel plans. Major airlines on this route include American Airlines, Delta, and United. Saturday offers notably more flight options compared to other days of the week, so if you're looking for the most choices, that's a great day to consider flying.
What are the most popular departure times for flights from Madison, WI (MSN-Dane County Regional) to Chicago, IL (ORD-O'Hare Intl.)?
The most popular departure times for flights from Madison, WI (MSN-Dane County Regional) to Chicago, IL (ORD-O'Hare Intl.) are in the early morning, from 6am to 9am. Many major carriers, including American Airlines, Delta and United, offer flights during this window. Many travellers prefer these times as it allows them to arrive in Chicago early, giving them a full day for business or leisure activities.
How long does it take to fly from Madison, WI (MSN-Dane County Regional) to Chicago, IL (ORD-O'Hare Intl.)?
A direct flight from Madison, WI (MSN-Dane County Regional) to Chicago, IL (ORD-O'Hare Intl.) typically takes around 1 hour 18 minutes, covering a distance of approximately 175 kilometers. If you opt for a flight with one stop, your travel time will be significantly longer, usually around 7 hours 18 minutes. Flights with two or more stops can take even longer, averaging about 7 hours 30 minutes. Keep in mind that actual flight times can vary due to factors like wind patterns and air traffic.
Can you fly business or first class from Madison, WI (MSN-Dane County Regional) to Chicago, IL (ORD-O'Hare Intl.)?
Yes, you can fly business class or first class between MSN and ORD. You can fly business class with Delta.First class cabins are available on Delta, United, and American Airlines.
How do I earn miles on a Madison, WI (MSN-Dane County Regional) to Chicago, IL (ORD-O'Hare Intl.) flight with Expedia?
It's easy to earn miles on a Madison, WI (MSN-Dane County Regional) to Chicago, IL (ORD-O'Hare Intl.) 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 Chicago, IL (ORD) from Madison, WI (MSN)?
If you're planning to travel to Chicago from Dane County Regional (MSN), you can fly directly into O'Hare Intl. (ORD). Some flights may connect through major hubs like Charlotte-Douglas Intl. (CLT), Dallas-Fort Worth Intl. (DFW), or Ronald Reagan Washington National (DCA) before reaching Chicago. 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 Madison, WI (MSN-Dane County Regional) to Chicago, IL (ORD-O'Hare Intl.) at the last minute?
Typically, booking a last minute flight from Madison, WI (MSN-Dane County Regional) to Chicago, IL (ORD-O'Hare Intl.) 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 Madison, WI (MSN-Dane County Regional) to Chicago, IL (ORD-O'Hare Intl.) flight and hotel package?
Securing a Madison, WI (MSN-Dane County Regional) to Chicago, IL (ORD-O'Hare Intl.) 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 Madison, WI (MSN-Dane County Regional) to Chicago, IL (ORD-O'Hare Intl.)?
If you booked your Madison, WI (MSN-Dane County Regional) to Chicago, IL (ORD-O'Hare Intl.) 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
Dane County Regional
Destination airport
O'Hare Intl.
Roundtrip price
CA $339
Distance
173 km
Average flight time
1 hour 12 mins

Book with confidence

Madison to Chicago Flights

The easy way to book your flights from Madison to Chicago 

With Expedia, it’s simple to find and book flights to Chicago from Madison 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 O'Hare Intl., 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 Madison to Chicago today, tomorrow, or this week.  

 

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

Sort your search results by price to find great deals on your flight from Madison to Chicago—you get all your cheapest options first. Grab yourself a bargain now—the lowest price on flights to Chicago from Madison currently is just CA $340 rising to CA $508.  

Here are more money-saving tips: 

  • Fly in November when flight prices are normally at their lowest 
  • Book about a month to 6 weeks before you travel for the best prices to Chicago  
  • 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 Chicago from Madison 

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 Chicago with Expedia today.

Madison to Chicago Flights

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