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Cheap Flights from Madison to Chicago, IL, United States - MSN to CHI Last modified: May 31, 2016 7:34 PM

Popular flights from Madison to Chicago Last modified: May 31, 2016 7:34 PM

We’ve got the inside scoop on finding the best time to fly for the best price. Not sure when to travel for your next vacation? Find details below on when-to-fly and when-to-buy.

American Airlines
Departure Date Return Date Lowest Price
Aug 13, 2016 Aug 20, 2016 $318
United Airlines
Departure Date Return Date Lowest Price
Aug 13, 2016 Aug 20, 2016 $318

How Much Does it Cost to Fly from Madison to Chicago (MSN to CHI)?

We have collected flight cost data from across the web for travel from Madison to Chicago, and have found the average flight price for this trip to be $358.

When Can I Buy the Cheapest Flight from Madison to Chicago (MSN to CHI)?

Airlines can adjust prices for plane tickets from Madison to Chicago based on the day and time that you decide to book your flight. We have collected data from all airlines, and have discovered that the best days to book flights are Tuesdays, Wednesdays, and Saturdays. Read our article to find more information about the best time to buy airline tickets.

How far in advance should you book flights from Madison to Chicago

The chart below shows up-to-date information regarding how far in advance a flight from Madison to Chicago should be booked.

Non Stop versus 1-Stop
Advanced PurchaseNon StopOne Stop
< 7 days $0 $0
7-14 days $358 $477
14-21 days $358 $477
21-30 days $363 $501
30-60 days $363 $496
60-90 days $318 $487
90+ days $319 $455

Non-Stop vs Connecting Flights from Madison to Chicago (MSN to CHI)

Your Madison to Chicago flight can be significantly cheaper by choosing a multi-stop airline ticket. Although these connecting flights sacrifice some convenience, on average, travelers save 20%-60% when they choose to fly multi-stop versus a direct flight.

The average price for connecting flights from Madison to Chicago is $600.

The average price for non-stop flights from Madison to Chicago is $363.

The chart below shows up to date information regarding non-stop flights from Madison to Chicago.

Nonstop Flight Details from Madison to Chicago
CarrierMonTueWedThuFriSatSunEarliest FlightLatest Flight
American 5 5 5 5 5 4 5 06:35 18:11
United 7 9 9 9 8 5 6 05:40 19:10

Round Trip vs One Way Flights from Madison to Chicago (MSN to CHI)

We have found that there is often no price difference between buying a round trip flight versus a one way flight. Increased flexibility is the main benefit when it comes to buying a one way flight from Madison to Chicago. However, booking a round trip flight can be a simpler process. You can compare round trip and one way flights by using our flight comparison.

The average price for one way flights from Madison to Chicago is $317.

The average price for round trip flights from Madison to Chicago is $363.

Madison to Chicago Flight Questions

Below are some common questions that asked about this flight route:

Question: How long is a direct flight from Madison to Chicago?
Answer: The average Madison to Chicago flight time is 57 minutes.
Question: How many miles are there between Madison and Chicago?
Answer: The distance from Madison to Chicago is 108 miles.
Question: How common are direct flights from Madison to Chicago?
Answer: There are 77 direct flights from Madison to Chicago.
Question: What is the most popular airline for non-stop flights from Madison to Chicago?
Answer: United Airlines provides 58% of the non-stop flights between Madison and Chicago.

Airlines Flying from Madison to Chicago (MSN to CHI) Number of flights searched: 14Last modified: May 31, 2016 7:34 PM

Below are the different airlines that fly from Madison to Chicago with the average price of their plane tickets. Just remember that different airlines offer different levels of comfort and service, so consider convenience when choosing your airline.

Below is the full flight schedule summary of the next 30 days for flights from Madison to Chicago.

Madison to Chicago
Airline Connections Mon Tue Wed Thu Fri Sat Sun
American - X X X X X X X
United - X X X X X X X

Airports for Your Route

These pages contain information about the major airports in Madison and Chicago, so you can feel comfortable knowing how to get around whether you are about to take off or you just landed.

Cheap Domestic Flights to Chicago - CHI

FlightsAirlineLowest Price
Rochester to Chicago American $283
Grand Rapids to Chicago American, United $97
Eau Claire to Chicago United $186
Green Bay to Chicago American, United $295
Milwaukee to Chicago American, United $207
La Crosse to Chicago American $305
Moline to Chicago American, United $291
Peoria to Chicago American, United $291
Waterloo to Chicago American $287
Cedar Rapids to Chicago American, United $287
Appleton to Chicago United $473
Dubuque to Chicago American $287
South Bend to Chicago United $565
Wausau to ChicagoCheck Dates
Rhinelander to ChicagoCheck Dates
Bloomington - Normal to Chicago American $279
Chicago to New York American, Alaska, JetBlue, Spirit, United $81
Chicago to Minneapolis - St Paul American, Alaska, Frontier, Spirit, United $68
Chicago to Detroit American, United $174
Chicago to Las Vegas American, Alaska, Frontier, Spirit, United, Virgin America $118
Chicago to Orlando American, JetBlue, Frontier, Spirit, United $147
Chicago to Los Angeles American, Alaska, Frontier, Spirit, United, Virgin America $134
Chicago to Atlanta American, Spirit, United $81
Chicago to Dallas - Ft Worth American, Alaska, Frontier, Spirit, United $117
Chicago to Washington American, Alaska, Frontier, United $107
Chicago to Denver American, Alaska, Frontier, Spirit, United $117
Chicago to Houston American, Spirit, United $154
Chicago to Miami American, Alaska, Frontier, United $134
Chicago to Boston American, JetBlue, Spirit, United $105

Cheap International Flights to Chicago - CHI

FlightsAirlineLowest Price
Chicago to Toronto Air Choice One, American, Air Canada, Alaska, JetBlue, Frontier, Spirit, Public Charters, Porter, United, WestJet $197
Cheap Flights from Madison to Chicago, IL, United States, from $318 Round trip from MSN to CHI