Flight tickets from Chicago to Madison

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Flight deals from Chicago to Madison

Looking for a cheap last-minute deal or the best return flight from Chicago to Madison? 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 found₹ 16,963
Cheapest month to flyApril
Average flight time1 hr, 6 mins
Most popular airlineAlaska Airlines
Average flights per week415

Finding cheap flights from Chicago to Madison: Frequently asked questions

The best price we found for a return flight from Chicago to Madison is ₹ 15,624. 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 6 minutes is the average flight time from Chicago to Madison.
Alaska Airlines, American Airlines and United fly direct from Chicago to Madison.
As of April 2025, there are 415 flights per week flying from Chicago to Madison.
The cheapest month to fly from Chicago to Madison is usually April 2025.
After crunching the numbers on our flight calendar, we found that it is currently cheapest to fly from Chicago to Madison Airport on Saturday, 17 May 2025.
Yes – the average flight time is 1 hour and 6 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

  • Begin your journey at one of Chicago's main airports, O'Hare International Airport (ORD) or Chicago Midway International Airport (MDW). Explore your options for booking a flight from Chicago to Dane County Regional Airport (MSN) jetting off from either of these.

  • Take a direct flight from Chicago to Dane County Regional Airport and you'll be travelling for an average of 1 hour 2 minutes.

  • Madison (where Dane County Regional Airport is located) and Chicago share the UTC-5 timezone. You can plan your trip without factoring in timezone differences.

  • The most popular route is from O'Hare International Airport (ORD) to Dane County Regional Airport (MSN), with 97 direct weekly services. If you'd like to get going as soon as possible, the earliest flight from ORD to MSN is the 06:20 American Airlines service. If you prefer to travel later, the last departure is at 21:40 with United.

  • For stress-free travel, turn up at the airport two hours ahead of international flights and one hour before domestic departures. This will give you enough time to catch your flight from Chicago to MSN.

  • Hopping on a plane during a peak time like August? High seasons (like Thanksgiving, Christmas/New Year and spring break) can add another hour at check-in and security. Play things extra safe and arrive up to four hours ahead of international flights and two hours before a domestic departure.

Airports in Chicago

O'Hare International Airport (ORD)

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

  • You can book a direct flight from Chicago to Dane County Regional Airport with American Airlines. This leading airline operates departures from ORD.

  • The distance from central Chicago to ORD is around 40 kilometres. Use Google Maps for the best way to get there, whether you prefer to drive or use public transport.

  • Searching for a convenient hotel near O'Hare International Airport? If you're boarding an early flight from Chicago to Dane County Regional Airport, these stays will have you moments from your departure lounge:

Chicago Midway International Airport (MDW)

  • Chicago Midway International Airport (MDW) offers direct flights from Chicago to Dane County Regional Airport (MSN).

  • From MDW, direct flights from Chicago to MSN are available with United.

  • You can get to MDW from central Chicago in about 21 minutes by car (depending on traffic). The ride by public transport takes roughly 46 minutes to travel the 19 kilometres or so.

  • Want to treat yourself to an extra night away before boarding your flight from Chicago to MSN? Check in to a hotel near Chicago Midway International Airport before your break officially begins. Check out these accommodation options:

About Dane County Regional Airport (MSN)

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

  • Dane County Regional Airport is approximately 14 kilometres from the centre of Madison. With your own car rental or if you take a cab, the drive is about 20 minutes.

  • If you're travelling on public transport, expect a journey of around 1 hour and 9 minutes.

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

  • The best price we've seen for a one-way ticket from Chicago to Dane County Regional Airport is ₹ 16,963. The cheapest price for a return flight is ₹ 15,624. Remember fares may change due to availability at the time of booking.

  • You're more likely to find flight tickets from Chicago to MSN when you book 9 months ahead of takeoff. We crunched the flight price data and found that's when fares for this route tend to be at their lowest.

  • June is the cheapest month for tickets from Chicago to Dane County Regional Airport. If you'd like to travel at a different time of year, use the 'Whole month' search feature to see the lowest prices for each month.

  • Set up a Price Alert for flight tickets from Chicago to MSN. You don't need to check every day to find out if prices have dropped. We'll notify you when the price changes.

  • Play around with the filters to find your ideal trip. To see the 'Cheapest,' 'Fastest' or 'Best' flights from Chicago to Dane County Regional Airport, use the 'Sort by' function. You can also filter by arrival and departure times, airline, and number of stops.

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

  • It's time to figure out your trip dates for your flight from Chicago to Dane County Regional Airport. August is the most popular month to visit Madison. If you want a more peaceful vibe, go in February.

  • Book your flight from Chicago to MSN for July if you're eager to explore the city during its warmest month. Expect temperatures in Madison to range from 13ºC to 29ºC.

  • If you want cooler conditions, look for a cheap flight from Chicago to Dane County Regional Airport in January when temperatures average between -18ºC and 0ºC.

More about Madison

  • When it comes to looking for somewhere to lay your head, you'll find the most popular stays in Madison right here. Explore these options once you've locked in your flight from Chicago to Dane County Regional Airport:

  • One of the best ways to get to know Madison is to explore its top attractions. Some highlights include University of Wisconsin-Madison Atmospheric & Oceanic Sceinces, Capitol Square and Olbrich Botanical Gardens.

Complete your Madison trip with a car rental

  • Get behind the wheel of one of our car rentals in Madison and explore the city at your own pace. Easily compare prices from trusted providers in one place after booking your hotel and cheap flights from Chicago to Dane County Regional Airport.

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