Cheap flight tickets from Chicago to Madison

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Flight deals from Chicago to Madison Airport

Looking for a cheap last-minute deal or the best return flight from Chicago to Madison Airport? If you want to travel next month, return fares start from RM937. Find the lowest prices on one-way and return tickets right here.

Find the cheapest month to fly from Chicago to Madison

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

Direct flights from Chicago to Madison

Chicago to Madison: Alternative routes

Compare routes from Chicago to Madison below. You may find an airport to fly into that's cheaper, faster, or easier than Madison.

Chicago to Madison: Flight information

The things to know before you go.
Cheapest flight foundRM937
Cheapest month to flyApril
Average flight time1 hr, 8 mins
Most popular airlineUnited
Average flights per week537

Finding cheap flights from Chicago to Madison: Frequently asked questions

The best price we found for a return flight from Chicago to Madison is RM937. 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 8 minutes is the average flight time from Chicago to Madison.
United, American Airlines and Alaska Airlines fly direct from Chicago to Madison.
As of March 2026, there are 537 flights per week flying from Chicago to Madison.
The cheapest month to fly from Chicago to Madison is usually April.
After crunching the numbers on our flight calendar, we found that it is currently cheapest to fly from Chicago to Madison Airport on Thursday, 9 April 2026.
Yes – the average flight time is 1 hour and 8 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 Madison 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 Madison is around 40 days in advance, so don’t leave your flight to the last minute.
The cheapest airline that flies to Madison is United .

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

  • Chicago's main airport is Chicago O'Hare International Airport (ORD). Check out your options for leaving from here when searching for your flights from Chicago to Dane County Regional Airport (MSN).

  • Around 1 hour 5 minutes is how long you can expect to be in the air on a direct Chicago to Dane County Regional Airport flight.

  • Madison (where Dane County Regional Airport is located) and Chicago share the UTC-6 timezone. You can fly without needing to calculate any time difference.

  • Chicago O'Hare International Airport (ORD) to Dane County Regional Airport (MSN) is the most popular route. There are 88 direct weekly flights to pick from. If you prefer starting your day later, hop on the last flight with American Airlines at 10:26pm. Go for the first ORD to MSN departure operated by American Airlines at 7am if you'd rather get going earlier.

  • Get to the airport on time so you don't miss your flight from Chicago to MSN. Be there at least two hours ahead for international flights and an hour early for domestic departures to avoid the stress of rushing.

  • With more people on the move during busy months like July, be at your terminal even earlier. Two hours for domestic flights and as much as four for international journeys will help you stay ahead of the crowds. Remember things also get busy during major holidays like July Fourth.

Airports in Chicago

Chicago O'Hare International Airport (ORD)

  • You can jump on a direct flight from Chicago to Dane County Regional Airport (MSN) departing from Chicago O'Hare International Airport (ORD).

  • United Airlines is a well-known airline that operates direct flights from Chicago to Dane County Regional Airport leaving from ORD.

  • The majority of passengers prefer to fly with United between ORD and MSN.

  • The carrier with the most consistent on-time arrival rate on this route is United.

  • ORD is about 27 kilometres from central Chicago. If you're catching a taxi, driving or ride-sharing from the centre, it'll take you 30 minutes or so to get there, depending on traffic conditions. If you're taking public transport, expect the travel time to be around 45 minutes.

  • Want a relaxed start to your holiday? Stay near Chicago O'Hare International Airport. Whether you're catching an early flight from Chicago to Dane County Regional Airport or prefer not to feel hurried, these hotels have you covered:

  • Of the departures from Chicago O'Hare International Airport, 70% arrive on time at their destination.

  • ORD's address is 10000 West O'Hare.

Chicago Midway International Airport (MDW)

  • You can reach MDW from central Chicago in about 25 minutes by car, depending on traffic. The ride by public transport will take roughly 30 minutes to travel the 16 kilometres or so.

  • Flying off with the first light? Think about staying at one of these accommodation options near Chicago Midway International Airport the day before your Chicago to MSN flight:

  • When it comes to keeping flights on track, Chicago Midway International Airport has an on-time arrival performance of 76%.

  • You'll find MDW at 5700 South Cicero.

Chicago Rockford International Airport (RFD)

  • RFD is roughly 145 kilometres from central Chicago. The drive from the city centre to the terminal takes about 1 hour 40 minutes. If you're thinking about taking public transport, expect a journey of around 2 hours.

  • Skip the morning rush on departure day — stay close to Chicago Rockford International Airport and know you'll make it to the terminal with time to spare. Get comfy at one of these hotels the day before if you've booked an early Chicago to Dane County Regional Airport flight:

  • Flights departing from RFD arrive at their destination as scheduled 71% of the time.

  • Chicago Rockford International Airport is located at 2 Airport Cir.

About Dane County Regional Airport (MSN)

Getting from Dane County Regional Airport (MSN) to central Madison

  • Dane County Regional Airport is around 13 kilometres from central Madison. It takes around 20 minutes or so to get to the city by car.

  • It takes around 40 minutes if you're travelling on public transport.

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

  • The lowest price we've found for a one-way ticket from Chicago to Dane County Regional Airport is RM807. For a return flight on this route, the best price is RM937. Depending on how early you book and the availability, these fares could change.

  • Book one month before you want to travel. Pricing trends show that this is the ideal window for finding cheap flights from Chicago to MSN.

  • June is when you're most likely to find a bargain on a Chicago to Dane County Regional Airport ticket. 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.

  • You don't need to search every day to find out if prices have dropped when you set up a Price Alert. We'll notify you the moment a better deal is available on plane tickets from Chicago to MSN.

  • Find an affordable flight from Chicago to Dane County Regional Airport by using filters. Select your ideal duration, number of stops and airlines, then sort the results by 'Cheapest' for the best deals.

The best time to fly from Chicago to Dane County Regional Airport (MSN)

  • October is the most popular month for flights from Chicago to Dane County Regional Airport (MSN). Visit Madison in January if you'd rather be there when it's quieter.

  • When booking your Chicago to MSN plane ticket, consider the kind of weather forecast you're hoping for. July is the warmest month in Madison, with temperatures ranging from 13ºC (55ºF) to 29ºC (84ºF).

  • January has temperatures of between -18ºC (0ºF) and 0ºC (32ºF). Look for cheap tickets from Chicago to Dane County Regional Airport around that time if you like travelling in cooler conditions.

More about Madison

  • When it comes to looking for somewhere to rest your head, you'll find the top stays in Madison right here. Check out these hotels once you've booked your flight from Chicago to Dane County Regional Airport:

  • Olbrich Botanical Gardens and Chazen Museum of Art are just the start of the top attractions to put on your Madison to-do list. Keep the momentum going by heading to Madison Museum of Contemporary Art.

Explore more of the United States

  • Chicago is just one of the many places in the United States waiting to be discovered once you've taken in the sights of Madison. Around 193 kilometres away to the southeast, its best attractions include Millennium Park, Art Institute of Chicago and Willis Tower.

  • Around 121 kilometres east of Madison, Milwaukee is another essential stop in the United States. No visit is complete without checking out Richards Duplex Apartments by Frank Lloyd Wright, Miller Park and Milwaukee County Zoo.

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