Cheap flights from Madison 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 Airport to Chicago? If you want to travel next month, return fares start from $308. 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 June.

Direct flights from Madison to Chicago

Madison to Chicago: Flight information

The things to know before you go.
Cheapest flight found$298
Cheapest month to flyJune
Average flight time1 hr, 16 mins
Most popular airlineAmerican Airlines
Average flights per week524

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 $304. 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 16 minutes is the average flight time from Madison to Chicago.
American Airlines, Alaska Airlines and United fly direct from Madison to Chicago.
As of June 2026, there are 524 flights per week flying from Madison to Chicago.
The cheapest month to fly from Madison to Chicago is usually August.
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 $304.
After crunching the numbers on our flight calendar, we found that it's currently cheapest to fly from Madison Airport to Chicago on Monday, 10 August 2026.
Yes – the average flight time is 1 hour and 16 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 June, the average temperature is usually around 19°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 5 minutes. On average, that's the time it takes for a direct flight from Dane County Regional Airport to Chicago.

  • Chicago's timezone is UTC-6, which is the same as Madison (the location of Dane County Regional Airport).

  • The most popular route is from Dane County Regional Airport (MSN) to Chicago O'Hare International Airport (ORD). Take your pick of 88 weekly services between these two airports. If you want to get on your way as soon as possible, the earliest flight from MSN to ORD is the 05:00 American Airlines option. If you prefer to leave later in the day, the final departure is at 20:16 with American Airlines.

  • For a stress-free journey, arrive at the airport two hours ahead of international flights and one hour before domestic departures. This will give you plenty of time to board your MSN to Chicago flight.

  • You'll likely experience bigger queues during popular months like October. Arriving up to four hours ahead of an international flight and two hours for a domestic departure is a good idea.

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

  • Book your ticket with United Airlines. This popular airline offers direct flights from Dane County Regional Airport to Chicago.

  • MSN is about 10 kilometres from central Madison. If you're ride-sharing, driving or catching a taxi from the centre, it'll take 20 minutes or so to get there, depending on traffic. If you're using public transport, expect the journey time to be around 40 minutes.

  • Have an early flight from Dane County Regional Airport to Chicago? Avoid rushing to the airport (and catch some extra z's) by choosing one of these hotels close to MSN:

  • Of the flights that depart from Dane County Regional Airport, 75% arrive on time at their destination.

  • You'll find MSN at 4000 International Lane.

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

  • The best price we've found for a one-way Dane County Regional Airport to Chicago flight is $298. The cheapest price for a return flight is $304. Bear in mind fares may change due to demand at the time of booking.

  • Book one month before travelling. Pricing trends suggest that this is the ideal window for finding cheap flights from MSN to Chicago.

  • Schedule your trip for June. That's the best month for landing a bargain on Dane County Regional Airport to Chicago tickets. If your travel dates are flexible, use the 'Whole month' tool to access the cheapest price across every month.

  • Picking up a cheap flight from MSN to Chicago is easy with Price Alerts. All you need to do is create one of these automatic notifications and we'll notify you when there's a better deal.

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

Airports in Chicago

Chicago O'Hare International Airport (ORD)

  • Chicago O'Hare International Airport (ORD) is around 27 kilometres from the centre of Chicago. If you're catching a taxi or a ride-share, the drive takes roughly 30 minutes.

  • If you're travelling by public transport, expect a journey time of about 45 minutes.

  • Consider booking a hotel close to ORD if you're coming in on a late flight from Dane County Regional Airport to Chicago. Choose one of these accommodation options and skip the long transfer:

  • To lock in the lowest price, reserve your vehicle from Chicago O'Hare International Airport about four weeks ahead of your flight from MSN to Chicago.

  • You'll find ORD at 10000 West O'Hare.

Chicago Midway International Airport (MDW)

  • Chicago Midway International Airport (MDW) is around 16 kilometres from the centre of Chicago. Once you've disembarked your flight from Dane County Regional Airport to Chicago, it'll take you around 25 minutes to get to the heart of the city in a ride-share or taxi.

  • The journey will take roughly 30 minutes on public transport.

  • Place the 'Do not disturb' sign on your door and rest at a hotel close to MDW. Here are a few options where you can tuck yourself in after your MSN to Chicago flight:

  • Get first dibs on the best options. Securing your ride from MDW four weeks in advance often means better deals and a bigger choice of vehicles.

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

Chicago Rockford International Airport (RFD)

  • Step off your flight from Dane County Regional Airport to Chicago and head straight for your hotel or start taking in the sights right away. Central Chicago is around 145 kilometres from Chicago Rockford International Airport (RFD) and usually takes 1 hour 40 minutes to reach driving.

  • Public transport will take you there in roughly 2 hours.

  • If you don't want to make your way into the centre, find a hotel near RFD. Check in to one of these options after your MSN to Chicago flight:

  • If you're hoping for a particular model or make, booking early increases your chances of snagging what you want. Reserve your ride from RFD a couple of weeks ahead of your flight from Dane County Regional Airport to Chicago.

  • The address for Chicago Rockford International Airport is 2 Airport Cir.

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. July is the most popular month for a trip to Chicago. If you prefer a more peaceful vibe, go in January.

  • The warmest month in Chicago is July, with temperatures ranging between 16ºC (61ºF) and 28ºC (82ºF). Lock in your Dane County Regional Airport to Chicago plane ticket then if that's your idea of comfortable weather.

  • For cooler conditions, search for a cheap ticket from MSN to Chicago in January when temperatures average between -12ºC (10ºF) and 3ºC (37ºF).

More about Chicago

Explore more of the United States

  • Columbus is just one of the many cities in the United States waiting to be discovered once you've taken in the sights of Chicago. Around 451 kilometres away to the southeast, well-known attractions include Franklin Park Conservatory and Botanical Gardens, Whetstone Park / Park of Roses and Ohio Theatre.

  • If you're eager to discover another great destination in the United States, head for Indianapolis, about 257 kilometres southeast of Chicago. Lucas Oil Stadium, Eiteljorg Museum and The Children's Museum of Indianapolis are the start of reasons to visit.

Prices shown on this page are estimated lowest prices only. Found in the last 12 days.