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

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

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

August is typically the cheapest month to fly

From AU$258 - AU$586 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.
How do I find cheap flights from Chicago, IL (ORD) to Madison, WI (MSN)?
To find a cheap flight from Chicago, IL (ORD) to Madison, WI (MSN), 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) to Madison, WI (MSN) flight with Expedia?
It's easy to earn miles on a Chicago, IL (ORD) to Madison, WI (MSN) 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) to Madison, WI (MSN) at the last minute?
Typically, booking a last minute flight from Chicago, IL (ORD) to Madison, WI (MSN) 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) to Madison, WI (MSN) flight and hotel package?
Securing a Chicago, IL (ORD) to Madison, WI (MSN) 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) to Madison, WI (MSN)?
If you booked your Chicago, IL (ORD) to Madison, WI (MSN) 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
Distance
173 km
Average flight time
1 hour 9 mins

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Your quick guide to flights from Chicago to Madison

Pick up great flights from Chicago to Madison

With Expedia, you have your pick of flights a day with 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 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.

Your quick guide to flights from Chicago to Madison

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