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$189 Cheap Flights from Madison (MSN) to Chicago (ORD)

View $189 flight on Thu, Nov 12, 2026Opens in a new window

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

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Cheap Flights from Madison to Chicago (MSN-ORD)

Prices were available within the past 7 days and start at $189 for one-way flights and $289 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

United
Wed, Dec 16 - Sat, Dec 19
MSN
Madison
ORD
Chicago
$289 Roundtrip, found 1 hour ago
$289
Roundtrip
found 1 hour ago
Select United flight, departing Wed, Dec 16 from Madison to Chicago, returning Sat, Dec 19, priced at $289 found 1 hour ago
United
Wed, Feb 17 - Fri, Feb 26
MSN
Madison
ORD
Chicago
$301 Roundtrip, found 6 days ago
$301
Roundtrip
found 6 days ago
Select United flight, departing Wed, Feb 17 from Madison to Chicago, returning Fri, Feb 26, priced at $301 found 6 days ago
American Airlines
Wed, Oct 14 - Wed, Oct 21
MSN
Madison
ORD
Chicago
$304 Roundtrip, found 16 hours ago
$304
Roundtrip
found 16 hours ago
Select American Airlines flight, departing Wed, Oct 14 from Madison to Chicago, returning Wed, Oct 21, priced at $304 found 16 hours ago
United
Thu, Feb 4 - Mon, Feb 8
MSN
Madison
ORD
Chicago
$306 Roundtrip, found 1 day ago
$306
Roundtrip
found 1 day ago
Select United flight, departing Thu, Feb 4 from Madison to Chicago, returning Mon, Feb 8, priced at $306 found 1 day ago
United
Sun, Dec 20 - Sun, Jan 17
MSN
Madison
ORD
Chicago
$308 Roundtrip, found 5 days ago
$308
Roundtrip
found 5 days ago
Select United flight, departing Sun, Dec 20 from Madison to Chicago, returning Sun, Jan 17, priced at $308 found 5 days ago
United
Wed, Dec 2 - Sun, Dec 6
MSN
Madison
ORD
Chicago
$309 Roundtrip, found 18 hours ago
$309
Roundtrip
found 18 hours ago
Select United flight, departing Wed, Dec 2 from Madison to Chicago, returning Sun, Dec 6, priced at $309 found 18 hours ago
United
Fri, Oct 16 - Sun, Oct 18
MSN
Madison
ORD
Chicago
$311 Roundtrip, found 3 days ago
$311
Roundtrip
found 3 days ago
Select United flight, departing Fri, Oct 16 from Madison to Chicago, returning Sun, Oct 18, priced at $311 found 3 days ago
United
Fri, Oct 23 - Mon, Oct 26
MSN
Madison
ORD
Chicago
$312 Roundtrip, found 22 hours ago
$312
Roundtrip
found 22 hours ago
Select United flight, departing Fri, Oct 23 from Madison to Chicago, returning Mon, Oct 26, priced at $312 found 22 hours ago
United
Tue, Jul 20 - Sun, Aug 1
MSN
Madison
ORD
Chicago
$316 Roundtrip, found 5 days ago
$316
Roundtrip
found 5 days ago
Select United flight, departing Tue, Jul 20 from Madison to Chicago, returning Sun, Aug 1, priced at $316 found 5 days ago
Delta
Sat, Jan 30 - Wed, Feb 10
MSN
Madison
ORD
Chicago
$405 Roundtrip, found 19 hours ago
$405
Roundtrip
found 19 hours ago
Select Delta flight, departing Sat, Jan 30 from Madison to Chicago, returning Wed, Feb 10, priced at $405 found 19 hours 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 $637
ORD
O'Hare Intl.
Cheapest
Average driving time to city center23 min
Flights from $637

What you need to know for your flight from Dane County Regional to O'Hare Intl.

Madison (MSN) to Chicago (ORD) at a glance

Explore a range of options for flights from Madison (MSN) to Chicago (ORD) on this domestic short-haul route. You can choose from various airlines to find the best fit for your budget and schedule while planning your visit to Chicago's iconic attractions and vibrant neighborhoods. Check out the essential details for your journey from Dane County Regional Airport to O'Hare International Airport.

  • Fastest flight duration: around 1h 15m non-stop
  • Route distance: roughly 100 miles (160 km)
  • Flights per week: around 8 departures on average
  • Typical fares (one-way): economy tickets often range from $95–$345, depending on seasonality and how far ahead you book

Flights from Dane County Regional Airport (MSN) to O'Hare International Airport (ORD)

According to recent traveler bookings, the top airlines favored for non-stop flights from Madison to Chicago offer flexibility in selecting the best itinerary. You can easily compare prices, travel times, and cabin classes to find the perfect combination that suits your needs.

  • United: This full-service airline provides non-stop flights, holding a significant share of roughly 58% of departures on this route. One-way ticket prices generally fall between $105 and $345, with a flight duration of 1 hour and 15 minutes.
  • American Airlines: Another full-service option, American Airlines offers non-stop services and represents about 42% of the flights on this route. Expect one-way fares to range from $95 to $345, with a total travel time of 1 hour and 15 minutes.

Travelers flying from Madison to Chicago can opt for an upgrade, as United provides first-class service on this route for a more comfortable journey.

How to find the best prices for flights from Madison (MSN) to Chicago (ORD)

Getting some of the best deals on flights from Madison to Chicago is all about timing and flexibility. Here are some key tips to help you save:

  1. Best times to book and fly: cheaper fares are usually found when booking 2-8 weeks in advance, which coincides with when most travelers make their reservations. Evening departures (6pm-12am) often come at lower prices, while morning flights (5am-12pm) are the most favored. Additionally, flying on Saturday tends to be cheaper, although Friday remains the most popular travel day.
  2. Set up price alerts: stay updated on price changes by using Expedia's Price Tracker. Receive alerts when fares drop for your selected route.
  3. Bundle and save: bundle your flight and hotel to save on Expedia, or unlock a hotel deal after booking your flight.*
  4. Compare flight options: use Expedia's search tool to compare airlines, routes, direct vs. non-direct flights, and flight times. You can also sort by price to find the most affordable options.
  5. Stay flexible with dates: being open to different travel days can sometimes help you find better prices on flights and hotels.
  6. Think about luggage: nowadays, it's important to check the airline's baggage policies to find the best value. That may be paying for an additional carry-on bag or booking a ticket with checked luggage included. Either way, double-check your allowance before confirming your booking to avoid excess baggage fees at the airport.

*Members only. Savings vary and are not available on all bundles. Select hotels.

Arriving at O'Hare International Airport from Dane County Regional Airport

Chicago welcomes travelers from Madison with a range of transport options based on price, convenience, and proximity. Here's how to reach Chicago efficiently:

  • Hotel transfer: Transfers offer a convenient way to reach your hotel in Chicago, with private rides that can be arranged in advance.
  • Car rental: Renting a car from O'Hare International Airport is a great option if you plan to explore and sightsee beyond the city. Browse cheap car rentals at O'Hare International Airport on Expedia.
  • Taxi/ride-hailing: Taxis and ride-hailing services may be available from designated pickup areas outside the terminal, check locally on arrival.
  • Public transportation: From O'Hare International Airport, O'Hare Station, a metro station, is located just 0.1 miles away on foot, while Rosemont Station, a train station, is about 2.2 miles from the airport and typically reached by car.

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 from $189 and cheap return flights from $289 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
$283
Distance
108 mi
Average flight time
1 hour 13 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 December. 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 $189 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.

 

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