Cheap Flights from Madison (MSN) to Chicago (CHI)

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Flight deals from Madison to Chicago

Looking for a cheap last-minute deal or the best round-trip flight from Madison to Chicago? Find the lowest prices on one-way and round-trip tickets right here.

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Find the cheapest month to fly from Madison to Chicago

We’re always keeping an eye on fares, so you can find the best one in seconds. It looks like Madison to Chicago flights are currently cheapest in June.

Direct flights from Madison to Chicago

Alternative Madison to Chicago routes

Looking for the cheapest, fastest or easiest route from Madison to Chicago? You could fly into the following airports instead.

Madison to Chicago: Flight information

The things to know before you go.
Cheapest flight found$255
Cheapest month to flyJune
Average flight time1 hr, 4 mins
Most popular airlineAmerican Airlines
Average flights per week1,236

Finding cheap flights from Madison to Chicago: Frequently asked questions

There are 4 airports in Chicago: Chicago Midway, Chicago O'Hare International, Chicago Dupage County, and Chicago Rockford.
The best price we found for a round-trip flight from Madison to Chicago is $253. This is an estimate based on information collected from different airlines and travel providers over the last 4 days and is subject to change and availability.
1 hour and 4 minutes is the average flight time from Madison to Chicago.
American Airlines, United and Alaska Airlines fly direct from Madison to Chicago.
There are 412 flights per week flying from Madison to Chicago, as of May 2024.
The cheapest month to fly from Madison to Chicago is usually June.
If you're flying from Madison Airport, the cheapest airport near Chicago is Chicago O'Hare International – which is 15.8 miles away from the center of Chicago. We've found flights to this airport from $253.
After crunching the numbers on our flight calendar, we found that it's currently cheapest to fly from Madison Airport to Chicago on Thursday, June 27, 2024.
Yes – the average flight time is 1 hour and 4 minutes.
We show every price from over 1,200 airlines and travel agents, comparing them all so you don’t have to. If you know you want to fly to Chicago but you’re not ready to book, set up a Price Alert. We’ll track prices for you, and let you know when they rise or fall.
We crunched all the numbers in our flight calendar, and it looks like the cheapest time to book a flight to Chicago is around 40 days in advance, so don’t leave your flight to the last minute.
In May, the average temperature is usually around 56°F. July is typically the warmest month in Chicago, when it usually averages around 80°F. You can expect the least rain in January. The coldest month is January, with temperatures averaging 18°F. The rainiest month is August.
Currently, American Airlines offers the cheapest flight tickets to Chicago.

Wisconsin’s capital is only one of two cities (the other being Seattle) that is geographically located on an isthmus, and it is best recognized by the five main lakes that surround it. These are Kegonsa, Monona, Waubesa, Wingra, and Mendota.

Only minutes away from an extraordinary countryside and featuring a wide array of world-class eateries and shopping districts, Mad City is the tourist go-to spot that deserves a lot of appreciation! The much bigger Windy City is located 122 miles to the Southeast, with flight times averaging 57 minutes, although arrival delays at O’Hare can extend this a bit longer.

American Airlines, Continental Airlines, United Airlines, US Airways, and American Eagle all offer direct flights from Madison to Chicago, with the latter typically providing the quickest routes. Each city is a wonderful place to live and visit, but as is to be expected, Chi-Town is the sprawling, urban metropolis that Madison simply is not. Those who enjoy the big city life will find Chicago entertaining on all fronts!

 

Departing Dane County

The joint civil-military airport of Dane County Regional is based six miles northeast of the downtown center, and offers direct routes to 13 flight hubs throughout the United States, including Orlando, New York City, and Washington DC.

The facility has seen annual passenger traffic figures exceed the 1.5 million mark in recent years, and is equipped with three separate runways. One of Dane County Regional’s latest upgrades was the addition of 1,600 covered parking spaces and a new and improved instrument landing system; the cost for these projects was over $30 million.

 

Fun times in Chicago

There are certain cities where it is simply impossible to get bored, and Chi-Town is one of them. Far from just the third largest metropolis in the United States, Chicago is famously regarded for its top-notch attractions and entertainment value.

Tourists travel here from all parts of the world, and for good reason of course! Whether you are planning a weekend getaway or a lengthy vacation, there are a few sites to not miss during your time in The Windy City. The Magnificent Mile, City History Museum, a Cubs game at Wrigley Field, and Shedd Aquarium all provide a small taste of what this amazing city has to offer!

If you want to spend more time having fun in The Second City, do not hesitate to book cheap flights from Madison to Chicago with Skyscanner. Instant airfare savings are just seconds away!


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Prices shown on this page are estimated lowest prices only. Found in the last 45 days.