Cheap Flight Deals From Madison (MSN) to Chicago (CHI) Starting at $153

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This Weekend's Flight Deals from Madison 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.

Airfares from $153 One Way, $128 Round Trip from Madison to Chicago

Prices starting at $128 for return flights and $153 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.

Chicago economy flight packages

Waldorf Astoria Chicago
Kimpton Gray Hotel, an IHG Hotel
The Langham, Chicago
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More About Flying To Chicago from Madison

Route Information for Flights from Madison to Chicago

Origin Airport IATA Code MSN
Destination Airport IATA Code CHI
Distance 108 mi
Direct Flight Airlines American Airlines, Qatar Airways, JAL, Alaska Airlines, Air Canada, Aer Lingus, Iberia, ANA, Air New Zealand, Lufthansa, United Airlines, British Airways
Earliest Flight Arrival 1:06PM UTC
Latest Flight Arrival 12:50AM UTC

Cheap Flights from Madison to Chicago

Dane County Regional Airport

Planning a trip can often be a challenge, especially for travelers on a budget. Orbitz.com 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

Orbitz.com 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. Orbitz.com 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. Orbitz.com 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, Orbitz.com 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 Orbitz.com and schedule your trip during the off-peak travel season, it's easy to find cheap flights to Chicago.

Highlights and Attractions

Orbitz.com 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.

Frequently asked questions

Am I able to catch a flight from Madison to Chicago now?
Go right to the Covid-19 Travel Advisor for the most useful info on travel restrictions and quarantine requirements when getting a flight from Madison to Chicago.
Are there non-stop flights from Madison to Chicago?
Get ready to book, because there are two airlines that operate nonstop flights from MSN to ORD. Lock in a fantastic deal with United Airlines or American Airlines.
What is the shortest flight from Madison to Chicago?
Leave that epic movie for another occasion, because the trip from Madison, WI (MSN-Dane County Regional) to O’Hare Airport can take as little as 59 minutes.
What airlines fly from Madison to Chicago most frequently?
The airlines that have the most frequent flights between Dane County Regional Airport (MSN) and O’Hare Airport include United Airlines (UA). This popular option operates 173 flights on the route each month. If you can’t find the right flight there, look into the airfares with American Airlines (AA). This airline is a terrific alternative and has 134 flights between Madison and Chicago 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 2021 shows that Monday is the cheapest day to depart, followed by Tuesday. 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 from 2021, the cheapest month to fly is February. Perfect for those who need a weekend getaway, or just a break from it all in the shortest month of the year. Be aware that the most expensive time to fly is during the height of summer in July, and in the holiday month of December.*According to flight demand on Orbitz.com from January to December 2021. Savings are subject to change based on departure location, date and destination.

Fare, taxes & fees: Fares include all taxes and fees, except baggage fees. Rates shown reflect fares found by other Orbitz users over the past 7 days. Due to rapidly changing airline prices & seat availability, these fares may no longer be available.

Refunds/changes/cancellations: Itinerary changes, if permitted for the fare, will have a $30 service fee charged by Orbitz. Additional airline charges may apply.

Other conditions: Schedules, fares and rules are subject to change without notice. Seats are limited and may not be available on all flights/dates or in all markets. Lower fares may be available. Fares will not be honored retroactively or in exchange for any wholly/partially unused ticket. Tickets are non-transferable and non-refundable. Fare rules are provided for the selected itinerary before booking.