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Madison to Chicago Flights

Flight only Hotel only Flight + Hotel

Flight type

Round-trip One-way
Age of children at time of trip

We will search for applicable airfare discounts. Must have 1 adult for each infant in lap

Selected fares from Madison to Chicago

Departure Arrival Travel dates Round-trip
MSN CHI Thu, Nov 27 - Sat, Nov 29 $315
MSN CHI Thu, Nov 27 - Sat, Nov 29 $315
MSN CHI Thu, Nov 27 - Sat, Nov 29 $315
MSN CHI Fri, Nov 7 - Tue, Nov 11 $449
MSN CHI Thu, Nov 27 - Sat, Nov 29 $573

Madison and Chicago airports and terminals

Airports in Madison WI, US
map of airports in Madison
  • 1

    Dane County Regional (MSN)

    Distance from City Center: 4.4 miles

    Carriers for flights from MSN to CHI

    Carriers
    American Airlines, Qatar Airways, US Airways, United Airlines
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Airports in Chicago IL, US
map of airports in Chicago
  • 1

    Midway Airport (MDW)

    Distance from City Center: 9.5 miles

  • 2

    O'Hare Airport (ORD)

    Distance from City Center: 15.1 miles

    Terminals and carriers for flights from MSN to ORD

    Terminal Carriers
    Terminal 1 US Airways, United Airlines
    Terminal 2 US Airways, United Airlines
    Terminal 3 American Airlines, Qatar Airways, US Airways
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Cheap flights from Madison to Chicago

Sun Mon Tue Wed Thu Fri Sat
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$315
28 29
30

Highlighted price = Cheapest round-trip flights

Prices are round trip per person (conditions apply)

Featured Chicago Airport Hotels

Hotel only $119

Hilton Chicago O'Hare Airport

4 stars
3.9 / 5 125 reviews

O'Hare International Airport Map

Rate Includes Breakfast

...This O'Hare airport hotel is located in Terminal 2 and is within walking distance to all O'Hare Airport's domestic terminals.... More

Hotel only $137

Holiday Inn Express & Suites CHICAGO-MIDWAY AIRPORT

3 stars
4.1 / 5 43 reviews

6500 South Cicero Avenue Map

Exceptional Hotel Near Chicago Midway Airport Searching for hotels near the best sights in downtown Chicago?... More

Hotel only $144

Hilton Garden Inn Chicago/Midway Airport

3 stars
3.7 / 5 15 reviews

6530 S. Cicero Avenue Map

Complimentary wired and Wi-Fi Internet Access

...Advance Purchase Rate online!The Hilton Garden Inn Chicago Midway Airport in Chicago is located on the Midway Hotel Center campus just two blocks south of the Chicago Midway Airport and the... More

Hotel only $127

Hampton Inn Chicago-Midway Airport

2 stars
3.8 / 5 17 reviews

6540 S. Cicero Ave. Map

Free On The HouseT hot breakfast, Wi-Fi

...And no matter what time your flight got in or is going out, we're here to pick you up or drop you off.... land here and let your vacation take off...welcome to the Hampton Inn Chicago-Midway... More

Hotel only $179

Chicago Marriott Midway

3 stars
3.7 / 5 7 reviews

6520 South Cicero Avenue Map

Rate includes breakfast

...WiFi-equipped guest rooms at our Chicago Midway Airport hotel are recently renovated and offer soundproof windows, 32" flat-screen TVs and room service.... Perfect for business travel and... More

Hotel only $109

Sheraton Chicago O’Hare Airport Hotel

4 stars
4.0 / 5 112 reviews

6501 N. Mannheim Road Map

Save 40% on your stay

...Complimentary shuttle service to and from O'Hare Airport is available 24 hours a day.... Our all-suite hotel is conveniently located minutes from O'Hare International Airport, Donald E. Stephens... More

November

Cheapest weekend flights in November from Madison to Chicago

Travel dates Departure Arrival Stops: Round-trip
Leave Thu, Nov 27 Madison (MSN) Chicago (ORD) United Airlines $315
Earn $3.15
Return Sat, Nov 29 Chicago (ORD) Madison (MSN) United Airlines

Lowest roundtrip airfare in November from Madison to Chicago

Travel dates Departure Arrival Stops: Round-trip
Leave Thu, Nov 27 Madison (MSN) Chicago (ORD) United Airlines $315
Earn $3.15
Return Sat, Nov 29 Chicago (ORD) Madison (MSN) United Airlines
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January

Lowest roundtrip airfare in January from Madison to Chicago

Travel dates Departure Arrival Stops: Round-trip
Leave Sat, Jan 24 Madison (MSN) Chicago (ORD) United Airlines $295
Earn $2.95
Return Sun, Feb 1 Chicago (ORD) Madison (MSN) United Airlines
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Flights 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.

Interesting facts about flights from Madison to Chicago

    • 21 direct flights are operating from Madison to Chicago today.
    • Today's average time for a direct flight is 0h 57m.
    • US Airways flight 8768 (12:50 AM GMT, Canadair Regional Jet) is today's earliest available flight from Madison to Chicago.
    • United Airlines flight 3679 (12:55 PM GMT, Canadair Regional Jet 700) is today's latest available flight from Madison to Chicago.
    • Today's shortest direct flight from Madison to Chicago (United Airlines flight 3611, Canadair Regional Jet 700) takes 0h 48m.
    • Today's longest direct flight from Madison to Chicago (US Airways flight 8615, Embraer RJ135/RJ140/RJ145) takes 1h 6m.
    • Flights from Dane County Regional (MSN) to Midway Airport (MDW), O'Hare Airport (ORD) are available for this route.