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

View $164 flight on Tue, May 19, 2026Opens in a new window

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

  • Be in the know

    Get alerts if flight prices drop or rise*

  • Book smarter

    Save up to 30% on select hotels after you book a flight*

  • Earn twice

    Earn your airline miles on top of our OneKeyCash
    Learn about One Key

Cheap Flights from Madison to Chicago (MSN-ORD)

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
Sun, May 31 - Sat, Jun 6
MSN
Madison
ORD
Chicago
$239 Roundtrip, just found
$239
Roundtrip
just found
Select American Airlines flight, departing Sun, May 31 from Madison to Chicago, returning Sat, Jun 6, priced at $239 just found
United
Sun, May 31 - Sat, Jun 6
MSN
Madison
ORD
Chicago
$239 Roundtrip, just found
$239
Roundtrip
just found
Select United flight, departing Sun, May 31 from Madison to Chicago, returning Sat, Jun 6, priced at $239 just found
United
Fri, May 22 - Sat, May 23
MSN
Madison
ORD
Chicago
$244 Roundtrip, found 5 days ago
$244
Roundtrip
found 5 days ago
Select United flight, departing Fri, May 22 from Madison to Chicago, returning Sat, May 23, priced at $244 found 5 days ago
United
Sat, May 23 - Sun, May 24
MSN
Madison
ORD
Chicago
$245 Roundtrip, found 4 days ago
$245
Roundtrip
found 4 days ago
Select United flight, departing Sat, May 23 from Madison to Chicago, returning Sun, May 24, priced at $245 found 4 days ago
United
Mon, Jun 29 - Sat, Jul 11
MSN
Madison
ORD
Chicago
$246 Roundtrip, just found
$246
Roundtrip
just found
Select United flight, departing Mon, Jun 29 from Madison to Chicago, returning Sat, Jul 11, priced at $246 just found
United
Mon, Jun 8 - Sat, Jun 13
MSN
Madison
ORD
Chicago
$247 Roundtrip, found 1 day ago
$247
Roundtrip
found 1 day ago
Select United flight, departing Mon, Jun 8 from Madison to Chicago, returning Sat, Jun 13, priced at $247 found 1 day ago
United
Sat, Nov 7 - Sun, Nov 8
MSN
Madison
ORD
Chicago
$248 Roundtrip, found 4 days ago
$248
Roundtrip
found 4 days ago
Select United flight, departing Sat, Nov 7 from Madison to Chicago, returning Sun, Nov 8, priced at $248 found 4 days ago
United
Sun, May 31 - Sat, Jun 6
MSN
Madison
ORD
Chicago
$249 Roundtrip, just found
$249
Roundtrip
just found
Select United flight, departing Sun, May 31 from Madison to Chicago, returning Sat, Jun 6, priced at $249 just found
American Airlines
Sun, May 31 - Sat, Jun 6
MSN
Madison
ORD
Chicago
$249 Roundtrip, just found
$249
Roundtrip
just found
Select American Airlines flight, departing Sun, May 31 from Madison to Chicago, returning Sat, Jun 6, priced at $249 just found
Delta
Wed, Sep 2 - Tue, Sep 15
MSN
Madison
ORD
Chicago
$425 Roundtrip, found 2 days ago
$425
Roundtrip
found 2 days ago
Select Delta flight, departing Wed, Sep 2 from Madison to Chicago, returning Tue, Sep 15, priced at $425 found 2 days ago

Alternative airports near Chicago

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

Select flight to O'Hare Intl. ORD. Cheapest option available. Average driving time to city center is 23 minutes. Flights from $324
ORD
O'Hare Intl.
Cheapest
Average driving time to city center23 min
Flights from $324

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 cheap one-way flights and cheap return flights from $239 Madison, WI (MSN-Dane County Regional) to Chicago, IL (ORD-O'Hare Intl.) with Expedia. One-way flights usually range from $204 to $803, and return flights typically cost between $260 and $1166. 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 Madison, WI (MSN-Dane County Regional) to Chicago, IL (ORD-O'Hare Intl.) 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 Madison, WI (MSN-Dane County Regional) to Chicago, IL (ORD-O'Hare Intl.)?
July is the cheapest month to fly from Madison (MSN) to Chicago (ORD), with average round-trip fares around $234. This is about 26% lower than the average price throughout the year, as summer travel often leads to increased competition among airlines. Other economical months to consider are May and September.*Averages based on flights available on Expedia in the last year.
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 MSN to ORD:

  • United operates around 69 direct flights from MSN to ORD every week
  • American Airlines operates around 43 direct flights from MSN to ORD 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 flights from Dane County Regional (MSN) to O'Hare Intl. (ORD), with round-trip tickets starting from around $394. 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 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) to Chicago, IL (ORD) 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 MSN to ORD, 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.)?
The ideal months to fly from Madison, WI (MSN) to Chicago, IL (ORD) are July and May. Return flights during these months average around $234, providing a good balance of affordability and convenience. July is popular for summer travel, while May offers pleasant spring weather, making both months great choices for your trip.*Prices based on flights available on Expedia in the last year.
How many flights per day from Madison, WI (MSN-Dane County Regional) to Chicago, IL (ORD-O'Hare Intl.)?
There are approximately 16 nonstop flights per day from Dane County Regional (MSN) to O'Hare Intl. (ORD). For more options, look at flights that include layovers.
What is the earliest flight from Madison, WI (MSN-Dane County Regional) to Chicago, IL (ORD-O'Hare Intl.)?
The earliest flight from Dane County Regional Airport (MSN) to O'Hare International Airport (ORD) usually departs at around 5:00 AM, operated by American Airlines. This seasonal service is available in November and December, giving you an early start to your trip to Chicago. 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 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 31% of passengers prefer this time window. Many major carriers, including American Airlines, Delta and United, offer flights during this window. This timing works well because it allows you to start your day early and make the most of your time in Chicago.
How long does it take to fly from Madison, WI (MSN-Dane County Regional) to Chicago, IL (ORD-O'Hare Intl.)?
A nonstop flight from MSN to ORD typically takes around 1 hour 20 minutes, covering approximately 109 miles. Connecting flights on this route usually add 5 hours 40 minutes to your travel time. 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.)?
You can fly first class between MSN and ORD. First class cabins are available on:

  • Delta Air Lines
  • American Airlines
  • United 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 from Dane County Regional (MSN)?
From Dane County Regional (MSN), you can fly into O'Hare Intl. (ORD) to reach Chicago. Some flights may connect through major hubs like Dallas-Fort Worth Intl. (DFW), Charlotte-Douglas Intl. (CLT), Minneapolis - St. Paul Intl. (MSP) 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.) Chicago 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 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.
Airlines serving
American Airlines, Delta, United
Roundtrip price
$239
Distance
108 mi
Average flight time
1 hour 9 mins

Book with confidence

Madison to Chicago Flights

The cheapest times to fly from Madison to Chicago

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 Madison to Chicago are during the month of May. You can find some of the cheapest flights from Madison to Chicago with Expedia's search tool and vast selection of airlines.

 

The best time to book a flight from Madison to Chicago

Sunday is one of the best days to book for cheap flights from Madison to Chicago: 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 Madison to Chicago

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 Madison to Chicago 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 Madison to Chicago 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 Madison to Chicago 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.

 

Madison to Chicago Flights

*Flight schedules are subject to change.

*Available to One Key members.

 

Explore a world of travel with Expedia