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This Weekend's Flight Deals to Chicago

This weekend's flight prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.

Fares from $171 One Way, $262 Round Trip from Madison to Chicago

Prices starting at $262 for return flights and $171 for one-way flights to Chicago were the cheapest prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.

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More About Flying To Chicago from Madison

Route Information for Flights from Madison to Chicago

Origin Airport IATA CodeMSN
Destination Airport IATA CodeCHI
Distance108 mi
Direct Flight AirlinesAer Lingus, ANA, Lufthansa, Air New Zealand, United Airlines
Earliest Flight Arrival1:03PM UTC
Latest Flight Arrival10:00PM UTC

Flights Review

Dec 11, 2019

With all the missing of connections American did very well accommodating me to get where going in shorter time yet.

Nov 7, 2019

Loved online check in and tickets displayed on device

Sep 8, 2019

Flight landed 1/2 hour early.

Aug 17, 2019

The staff on the flight were hilarious. They were the entertainment. Excellent flight.

Jul 8, 2019

I paid 82.00 to upgrade my seat to better class but was still squished. Not sure what I paid for, otherwise all good.

Jan 21, 2019

We had mechanical issues. And flight was delayed - before I could talk to the agent I recurved a text and email with a rebooked flight for the swim s leg of my flight - gate agent in Madison was exceptional - efficient and great personality keeping everyone I in great spurts - Brian G ? He was awesome -

Jan 21, 2019

Would have been nice to be allowed a carryon bag like other airlines.

Dec 23, 2018

Lots of room in economy! I was impressed!

Dec 7, 2018

I was pleasantly surprised that we arrived on Cincinnati on time, despite the fact that we were only able to board our plane 25 min. after the scheduled time.

Oct 7, 2018

Will definitely use Orbitz again!

Cheap Flights from Madison to Chicago

Dane County Regional Airport

Planning a trip can often be a challenge, especially for travelers on a budget. allows you to search many different airlines at once in order to locate cheap flights from Madison. The Dane County Regional Airport is located approximately 10 miles from downtown Madison on International Lane. It is served by seven airlines, including Continental, Delta, Northwest and United Airlines. Orbitz provides bookings for nearly all of these airlines.

Parking at the AirportThere are several surface lots across the street from the airport. Fees are charged hourly or by the day, and shuttle services are provided to and from the terminal. A long-term economy lot is available approximately ten minutes away. Discount rates are available at this lot for those planning to park for more than a few days. Shuttle services are not provided to the economy lot.

Transportation to the Airport can assist in locating discount car rental services to and from the airport. Rental car booths are located in the baggage claim areas for convenience. Many hotels offer free shuttle services for their guests to the airport, and the Madison Metro bus is available for a flat rate fee. The airport provides courtesy shuttles to several hotels in the area.

Restaurants at Dane County Regional Airport

Travelers who arrive at the airport early may wish to grab a bite to eat before flying. Several restaurants are available for breakfast. The Great Dane provides excellent pub fare, and Ancora Coffee Roasters is a Madison-based specialty coffee shop that offers espresso, coffee and fresh bakery items. The Café Ritazza also offers a variety of blended coffees and pastries. can help you find cheap flights from Madison.

Airports in Chicago

Chicago O'Hare International Airport is located on West O'Hare, approximately 18 miles from downtown Chicago. It has hubs for every major airline that offers flights to Chicago, including American Airlines, British Airways and JetBlue. The Chicago Midway International Airport is located on South Cicero Avenue, approximately 12 miles from downtown Chicago. Seven airlines service Midway airport, including Air Tran, Delta and Southwest Airlines. searches flights arriving at both airports so you get the best prices.

Transportation from the Airport

Both airports offer public transportation via Chicago's elevated train system. The tickets cost $2.25, or you can purchase an all-day pass for $5.75. Taxi services are also available from both airports. Cab fares to downtown Chicago range from $35 to $45. If you want to rent a car for the duration of your stay, can reserve a vehicle for you. Both airports have onsite rental car facilities.

Weather in Chicago

Summer temperatures in Chicago range from 66 to 84 degrees Fahrenheit, and the temperatures during the winter months range from 18 to 35 degrees Fahrenheit. Chicago is prone to heavy snowfall during the winter months, so most vacationers travel to Chicago during the summer. However, if you use and schedule your trip during the off-peak travel season, it's easy to find cheap flights to Chicago.

Highlights and Attractions not only helps you find cheap flights to Chicago, but can also help you purchase tickets to the Sears Tower or make reservations for guided city tours.

Flights from Madison to Chicago - Frequently Asked Questions

Are there non-stop flights from Madison to Chicago?

Yes, you'll be pleased to hear that you can fly straight from Madison, WI (MSN-Dane County Regional) to Chicago, IL (ORD-O'Hare Intl.). Direct flights are offered by United Airlines and American Airlines.

What is the shortest flight from Madison to Chicago?

If the weather is good and all goes as planned, you could be disembarking at Chicago, IL (ORD-O'Hare Intl.) from Madison, WI (MSN-Dane County Regional) in only 54 minutes. With such a brief flight time, consider traveling with just hand luggage.

What airlines fly from Madison (and vicinity) to Chicago (and vicinity) most frequently?

The airlines that offer the most frequent flights between Madison, WI Airport (MSN-Dane County Regional) and Chicago, IL Airport (ORD-OHare Intl.) include United Airlines (UA). This well-known option offers 205 flights on the route every month. American Airlines (AA) also operates services from Madison (and vicinity) to Chicago (and vicinity). It's another excellent choice and has 124 flights each month.

If I am not able to travel due to COVID-19, can I cancel my flight to Chicago?

We get that traveling right now has its challenges, so it's good to know that many reservations booked through us are able to be cancelled or changed. If your travel plans to Chicago have been affected by COVID-19, a lot of airlines are making things easier by offering credits to use at a later date. Just sign in to your account and you'll quickly see what options are available. Our Customer Service Portal is the place to go for more information.

Are there flights to Chicago with flexible change policies?

In most cases you'll have the option to reschedule your flight to Chicago without a change fee. All you have to do then is pay the difference between the old flight and the new one. Look for the "no change fees" filter and book with confidence.

What is the cheapest day of the week to fly?

Consider flying out early in the week to save on your airfare. Orbitz data from 2019 shows that Tuesday is the cheapest day to depart, followed by Monday. Saturday showed the highest average ticket prices likely because many travelers prefer to start their vacation on a weekend.

What is the cheapest month to fly?

We won't keep you guessing, according to Orbitz data the cheapest month to fly is February. Perfect for those who need a weekend getaway, or just a fresh start to the new year. Be aware that the most expensive time to fly isn't the height of summer, as most people assume, but the festive month of December.

How can I save money on flights?

To really save big on your next vacation, think outside the box. Select two different airlines or fare types for your return trip and you'll generally get a much better deal. Those who tried this on Orbitz in 2019 saved over 50% on their airfares. Get mixing and matching today!

*According to flight demand on from January to December 2019. Savings are subject to change based on departure location, date and destination.

^Savings based on all package bookings with Flight + Hotel made on from January 1, 2019 to December 31, 2019 as compared to the price of the same components booked separately. Savings will vary based on origin/destination, length of trip, stay dates and selected travel supplier(s). Savings not available on all packages.