Cheap flights from Madison to Chicago

Compare Madison to Chicago flight deals

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

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Flight deals from Madison to Chicago

Looking for a cheap last-minute deal or the best return flight from Madison to Chicago? 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.

Direct flights from Madison to Chicago

Madison to Chicago: Flight information

The things to know before you go.
Cheapest flight found$257
Cheapest month to flyMay
Average flight time1 hr, 13 mins
Most popular airlineAmerican Airlines
Average flights per week561

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 $227. 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 13 minutes is the average flight time from Madison to Chicago.
American Airlines, United and Alaska Airlines fly direct from Madison to Chicago.
As of February 2026, there are 561 flights per week flying from Madison to Chicago.
The cheapest month to fly from Madison to Chicago is usually March.
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 $227.
After crunching the numbers on our flight calendar, we found that it's currently cheapest to fly from Madison Airport to Chicago on Thursday, 26 March 2026.
Yes – the average flight time is 1 hour and 13 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 February, the average temperature is usually around -2°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.

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

  • Book a direct flight from Dane County Regional Airport to Chicago and you'll be in the air for around 1 hour 5 minutes.

  • Chicago's timezone is UTC-5, which is the same as Madison (the location of Dane County Regional Airport).

  • Dane County Regional Airport (MSN) to O'Hare International Airport (ORD) is the most popular route, with 77 weekly departures to choose from. If you have things to do before heading off, the last flight from MSN to ORD is with American Airlines at 20:16. Opt for the first departure operated by American Airlines at 05:00 if you want to get on your way earlier.

  • To avoid rushing for your MSN to Chicago flight, leave enough time for things like check-in and baggage drop. Turning up two hours before international departures and one hour before domestic flights is the general rule.

  • Heading off during a peak time like school or public holidays? Expect longer lines at security and check-in. For peace of mind, arrive up to four hours before international flights and two hours before domestic departures.

  • Start your trip at MSN and travel straight to O'Hare International Airport (ORD). That will be your arrival point when searching for Dane County Regional Airport to Chicago tickets.

  • Book your favourite seat with United Airlines. This leading carrier operates direct flights from Dane County Regional Airport to Chicago.

  • Travelling from central Madison to MSN takes around 1 hour 10 minutes by public transport. If you ride-share, drive or get a cab, you'll cover the 10 kilometres in 20 minutes or so, depending on traffic conditions.

  • Want a leisurely start to your trip? Stay near MSN. Whether you have an early flight from Dane County Regional Airport to Chicago or just don't like being rushed, these hotels have you covered:

  • When it comes to Dane County Regional Airport's on-time performance, data shows 77.89% of flights arrive within the expected time frame.

  • MSN's address is 4000 International Lane.

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

  • $257 is the lowest price we've seen for a one-way Dane County Regional Airport to Chicago flight. A round-trip ticket right now is $227. Depending on when you book and the availability, these fares may change.

  • Book two months before your departure date. Pricing trends suggest that this is the ideal window for finding cheap flights from MSN to Chicago.

  • June is the best month for landing a fantastic deal on Dane County Regional Airport to Chicago tickets. If you'd like to travel at a different time of year, the 'Whole month' tool will give you the lowest prices for each month.

  • There's no need to check in daily to find out if fares have dropped when you set up a Price Alert. We'll notify you when there's an even bigger deal on cheap flights from MSN to Chicago.

  • Pick your ideal arrival and departure times, airlines and number of stops with our filters. Then, sort the results for your flight from Dane County Regional Airport to Chicago by 'Cheapest,' 'Best' or 'Fastest.'

Airports in Chicago

O'Hare International Airport (ORD)

  • The distance from O'Hare International Airport (ORD) to central Chicago is roughly 40 kilometres. It takes about 35 minutes to reach the centre driving.

  • Getting there by public transport takes around 55 minutes.

  • The last thing you need is a long journey to your hotel if you're landing late on a flight from Dane County Regional Airport to Chicago. Book one of these accommodation options near ORD instead:

  • Begin your adventure by picking up an O'Hare International Airport rental car. Grab a set of wheels from Routes Car Rentals, Dollar or Budget and explore beyond Chicago's main sights.

  • Reserving your vehicle from O'Hare International Airport around four weeks ahead of your flight from MSN to Chicago can help you lock in the best possible rate.

  • ORD is located at 10000 West O'Hare.

Chicago Midway International Airport (MDW)

  • Once your flight from Dane County Regional Airport to Chicago has arrived, you can make your way to the city centre in about 20 minutes by car. Central Chicago is roughly 19 kilometres from Chicago Midway International Airport (MDW).

  • If you travel by public transport, the journey will take you 45 minutes or so.

  • You'll find some comfortable places ready to welcome you near MDW. Unwind and get cosy after your MSN to Chicago flight at one of these well-located options:

  • Forget about public transport schedules or slow-moving cab lines. Pick up a Chicago Midway International Airport rental car and take your journey in whatever direction you like. Check out the availability and rates from Dollar, Hertz and Budget.

  • Get what you want, not just what's left over. Securing your ride from MDW four weeks ahead of time often means better prices and a greater selection of vehicles.

  • You'll find Chicago Midway International Airport at 5700 South Cicero.

Chicago Rockford International Airport (RFD)

  • Make tracks for the city centre after your flight from Dane County Regional Airport to Chicago has arrived. Central Chicago is around 137 kilometres from Chicago Rockford International Airport (RFD) and takes roughly 1 hour 25 minutes to reach by cab or ride-share.

  • Public transport will get you there in around 4 hours 15 minutes.

  • Reserve a hotel near RFD and get from baggage claim to your bed in a snap. Whether you're arriving on a late MSN to Chicago flight or just want to simplify your travel plans, these stays will have you settling in quickly:

  • Stay in control of the next leg of your journey by picking up a Chicago Rockford International Airport rental car. Budget, Alamo and National are dependable companies for booking.

  • Booking at least a few weeks in advance of your flight from Dane County Regional Airport to Chicago is a smart way to go. Along with better deals, you'll get a better selection of vehicle makes and models at RFD.

  • Chicago Rockford International Airport's street address is 2 Airport Cir.

Best time to go to Chicago

  • Before you book your flights from Dane County Regional Airport to Chicago, consider which time of year is best for you. High season in Chicago offers a lively atmosphere and plenty of activities, while low season brings better hotel deals and smaller crowds.

  • Lock in a Dane County Regional Airport to Chicago plane ticket with a departure in July to explore the city during its warmest month. You can expect temperatures to range from 15ºC (59ºF) to 29ºC (84ºF).

  • Search for cheap tickets from MSN to Chicago in January if you'd rather travel when it's cooler. Temperatures are at their lowest then, ranging between -12ºC (10ºF) and 3ºC (37ºF) on average.

More about Chicago

Explore more of United States

  • Columbus is just one of the many cities in United States waiting to be explored once you've taken in the sights of Chicago. Around 451 kilometres away to the south-east, popular attractions include Franklin Park Conservatory and Botanical Gardens, Ohio Statehouse and German Village.

  • Around 257 kilometres south-east of Chicago, Indianapolis is another essential stop in United States. Experience the best of this destination with a visit to The Children's Museum of Indianapolis, Indianapolis Museum of Art and Indianapolis Zoo.

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