CA $319 Cheap Flights from Madison (MSN) to Chicago (ORD)

View CA $319 flight on Sat, May 30, 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 $319 for one-way flights and for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Frequently asked questions

How much does a flight from Madison, WI (MSN-Dane County Regional) to Chicago, IL (ORD-O'Hare Intl.) cost?
One-way flights typically cost between $665 and $2,977 and return flights often range between $665 and $2,977. 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 Anaa (AAA) to Toronto, ON (YYZ-Pearson Intl.) 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 round-trip fares around 569 CAD. This is about 26% lower than the average price throughout the year. July often sees lower prices for this route as it can be a shoulder season for business travel, and airlines may offer deals to fill seats. Other cheap months to fly from Madison, WI (MSN-Dane County Regional) to Chicago, IL (ORD-O'Hare Intl.) include May and September.
Which airlines fly direct from Madison, WI (MSN-Dane County Regional) to Chicago, IL (ORD-O'Hare Intl.)?
Enter MSN to ORD and your travel dates, then apply the 'Nonstop' filter to see only direct flights.
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, AA offers early morning flights. If price is the most important factor, UA typically offers the lowest fares. DL 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-Dane County Regional) to Chicago, IL (ORD-O'Hare Intl.)?
Based on booking data from the past year, the cheapest months to fly from Madison, WI (MSN-Dane County Regional) to Chicago, IL (ORD-O'Hare Intl.) are typically July and May, with average prices around 569 CAD for a round-trip flight. However, the most popular months for this route are December and November, which means you'll find plenty of flight options during those times. If you're looking for the best value, aiming for July or May could save you money, but if flexibility and a wide selection of flights are your priority, consider traveling in December or November.
How many flights per day from Madison, WI (MSN-Dane County Regional) to Chicago, IL (ORD-O'Hare Intl.)?
When flying from Madison, WI (MSN-Dane County Regional) to Chicago, IL (ORD-O'Hare Intl.), you'll find approximately 19 nonstop flights per day. For even more choice, look at flights that include layovers, as there are around 20 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) (MSN) to Chicago, IL (ORD-O'Hare Intl.) (ORD) typically departs at approximately 5:00 AM local time, operated by American Airlines. This is a seasonal service active in November and December. An early departure like this can help maximize 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 Dane County Regional (MSN) to O'Hare Intl. (ORD) on a Wednesday, with around 25 flights available. This gives you plenty of options for your travel plans. Major airlines on this route include American Airlines, Delta Air Lines, and United Airlines.
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. About 35% of passengers prefer this time window. Many major carriers, including American Airlines and Delta, offer flights during this window. These times work well because you can get an early start to your day in Chicago, whether you're traveling for business or leisure.
How long does it take to fly from Madison, WI (MSN-Dane County Regional) to Chicago, IL (ORD-O'Hare Intl.)?
Direct flights from MSN to ORD usually take about 1 hour 20 minutes, traveling roughly 109 miles. If you opt for a connecting flight, expect to add around 6 hours to your journey. 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 Madison, WI (MSN-Dane County Regional) to Chicago, IL (ORD-O'Hare Intl.)?
Select the "Business class" and "First class" filters when looking for MSN to ORD 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 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 from Dane County Regional (MSN)?
From Dane County Regional (MSN), you can fly directly into O'Hare Intl. (ORD) to reach Chicago. Some flights may connect through major hubs like Charlotte-Douglas Intl. (CLT), Dallas-Fort Worth Intl. (DFW), 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 $638
Distance
173 km
Average flight time
1 hour 9 mins

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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 rising to .  

Here are more money-saving tips: 

  • Fly in 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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