
$125 Cheap flight deals from Madison (MSN) to Chicago (CHI)
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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 $125 One Way, $179 Round Trip from Madison to Chicago
Prices starting at $179 for return flights and $125 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

Sable at Navy Pier Chicago, Curio Collection by Hilton
Dec 5 - Dec 9
Madison (MSN) to Chicago (ORD)
Reviewed on Sep 16, 2025

Hotel Riu Plaza Chicago
Dec 5 - Dec 9
Madison (MSN) to Chicago (ORD)
Reviewed on Sep 2, 2025

LondonHouse Chicago, Curio Collection by Hilton
Dec 5 - Dec 9
Madison (MSN) to Chicago (ORD)
Reviewed on Sep 16, 2025
More About Flying To Chicago from Madison
Route Information for Flights from Madison to Chicago
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Destination Airport IATA Code | CHI |
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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
Flights to Chicago
- New York to Chicago
- Dallas to Chicago
- Houston to Chicago
- Phoenix to Chicago
- Toronto to Chicago
- Orlando to Chicago
- Las Vegas to Chicago
- San Francisco to Chicago
- Los Angeles to Chicago
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- New Orleans to Chicago
- Montreal to Chicago
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- Sacramento to Chicago
- Hartford to Chicago
- London to Chicago
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- Harrisburg - Hershey to Chicago
- Rome to Chicago
Flights from Madison
- Madison to Orlando
- Madison to New York
- Madison to San Francisco
- Madison to Los Angeles
- Madison to Dallas
- Madison to Houston
- Madison to Detroit
- Madison to Washington
- Madison to Chicago
- Madison to Hartford
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- Madison to Columbia
- Madison to Chattanooga
- Madison to Appleton
- Madison to Billings
- Madison to Eureka
- Madison to San Luis Obispo
- Madison to Accra
- Madison to Bristol
Madison Airports
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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.