C$233 Cheap Flights from Madison (MSN) to Chicago (CHIA)

Compare Madison to Chicago flight deals

Find the cheapest month or even day of the year to fly to Chicago

Book the best Chicago fare with no extra fees

Flight deals from Madison Airport to Chicago

Looking for a cheap last-minute deal or the best return flight from Madison Airport to Chicago? If you want to travel next month, return fares start from C$432. Find the lowest prices on one-way and return tickets right here.

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 May.

Which airlines fly from Madison to Chicago?

Madison to Chicago: Flight information

The things to know before you go.
Cheapest flight foundC$233
Cheapest month to flyMay
Average flight time1 hr, 14 mins
Most popular airlineAmerican Airlines
Average flights per week583

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 return flight from Madison to Chicago is C$333. 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 14 minutes is the average flight time from Madison to Chicago.
American Airlines, United and Alaska Airlines fly direct from Madison to Chicago.
As of April 2026, there are 583 flights per week flying from Madison to Chicago.
The cheapest month to fly from Madison to Chicago is usually April.
If you're flying from Madison Airport, the cheapest airport near Chicago is Chicago O'Hare International – which is 25.4 km away from the centre of Chicago. We've found flights into this airport from C$333.
After crunching the numbers on our flight calendar, we found that it's currently cheapest to fly from Madison Airport to Chicago on Wednesday, April 22, 2026.
Yes – the average flight time is 1 hour and 14 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 April, the average temperature is usually around 8°C. July is typically the warmest month in Chicago, when it usually averages around 26°C. You can expect the least rain in January. The coldest month is January, with temperatures averaging -8°C. The rainiest month is August.
Currently, United offers the cheapest flight tickets to Chicago.

Travelling from Dane County Regional Airport (MSN) to Chicago: what you need to know

  • Expect to be travelling for 1 hour 2 minutes. On average, that's the duration of a direct flight from Dane County Regional Airport to Chicago.

  • Madison (the location of Dane County Regional Airport) and Chicago share the same timezone — UTC-5.

  • With 97 flights a week between the two airports, Dane County Regional Airport (MSN) to O'Hare International Airport (ORD) is the most popular route. American Airlines operates the earliest flight at 05:30. If you'd like to get more out of your day before you fly, the latest flight from MSN to ORD is with American Airlines at 20:52.

  • Give yourself plenty of time to make your flight from MSN to Chicago. It's generally best to arrive two hours before international departures and an hour ahead for domestic flights.

  • If you're going away during a popular month like August, make your way to the airport even earlier. It's smart to arrive up to four hours before an international flight and two hours ahead of domestic departures. Security lines will be longer during high seasons like summer, Christmas and New Year.

  • Nonstop flights from Dane County Regional Airport (MSN) to Chicago are available for booking. O'Hare International Airport (ORD) will be your arrival point.

  • Take to the skies with United. This well-known carrier offers direct flights from Dane County Regional Airport to Chicago.

  • When flying within United States, you don't need a visa or passport. However, you'll have to bring another form of identification, like an ID card or driver's licence. Once you've booked flight tickets from Dane County Regional Airport to Chicago, make sure your ID is up to date.

  • Located around 14 kilometres from central Madison, MSN can be reached in approximately 20 minutes by car, depending on traffic. The journey by public transport takes roughly 1 hour and 9 minutes.

  • Planning to catch an early flight from Dane County Regional Airport to Chicago? Avoid the last-minute rush to the airport (and sneak in some extra precious sleep) by picking one of these hotels close to MSN:

How to find the cheapest flights from Dane County Regional Airport (MSN) to Chicago

  • C$233 is the lowest price we've found for a one-way ticket from Dane County Regional Airport to Chicago. For a return flight on this route, the best price is C$333. Depending on when you want to go and the availability, these fares may change.

  • Book 10 months before you want to fly. After crunching the numbers on our calendar, this is how far you should book ahead to find cheap tickets from MSN to Chicago.

  • June is the cheapest month for tickets from Dane County Regional Airport to Chicago. If you'd like to travel during a different time of year, the 'Whole month' tool will show you the lowest prices across every month.

  • Log into your online account or use the app to create a Price Alert. We'll notify you straight away if there's a better deal on this route. It's easy to do, and it'll save you time looking for cheap tickets from MSN to Chicago every day.

  • Tailor your flights with filters. Pick your preferred arrival and departure times, airlines and total journey duration. You can also sort your results by 'Best,' 'Fastest' or 'Cheapest' flights from Dane County Regional Airport to Chicago.

Airports in Chicago

O'Hare International Airport (ORD)

Chicago Midway International Airport (MDW)

Best time to go to Chicago

  • It's time to figure out your trip dates for your flight from Dane County Regional Airport to Chicago. August is the busiest month for a trip to Chicago. If you want a quieter atmosphere, go in February.

  • Before booking a flight from Dane County Regional Airport to Chicago, think about the kind of weather you enjoy. July is the warmest month in Chicago, with the temperature ranging from 15ºC to 29ºC.

  • If you want to travel in cooler conditions, search for a cheap flight from MSN to Chicago in January when temperatures average between -12ºC and 3ºC.

More about Chicago

  • When it comes to searching for somewhere to rest your head, you'll find the best stays in Chicago right here. Explore these options once you've booked your flight from Dane County Regional Airport to Chicago:

  • There are so many things to discover in this city it can be difficult to know where to start. Millennium Park, Art Institute of Chicago and LandShark Beer Garden at Navy Pier are leading attractions which should be on every Chicago itinerary.

Complete your Chicago trip with a car rental

  • Select one of our car rentals in Chicago and see the sights on your own terms. Easily compare rates in one go to find your ideal ride after booking your hotel and cheap flights from Dane County Regional Airport to Chicago.

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