Cheap Flights from Madison to Chicago in 2019

Flight information Madison to Chicago

Cheapest roundtrip price last month


Non-stop airlines


Flights per week


Average flight time, total distance 101 miles

0h 47min

Most popular airline last month


Chicago O'Hare International, Chicago Midway, Chicago Pal-Waukee, Chicago Dupage County and others

5 airports

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!

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