Cheap Flights 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 $342. Find the lowest prices on one-way and return tickets right here.

Madison.$293 per passenger.Departing Thu, 12 Mar, returning Fri, 27 Mar.Return flight with United.Outbound direct flight with United departs from Chicago O'Hare International on Thu, 12 Mar, arriving in Madison.Inbound direct flight with United departs from Madison on Fri, 27 Mar, arriving in Chicago O'Hare International.Price includes taxes and charges.From $293, select.

Madison.$293 per passenger.Departing Sun, 24 May, returning Sun, 31 May.Return flight with United.Outbound direct flight with United departs from Chicago O'Hare International on Sun, 24 May, arriving in Madison.Inbound direct flight with United departs from Madison on Sun, 31 May, arriving in Chicago O'Hare International.Price includes taxes and charges.From $293, select.

Madison.$318 per passenger.Departing Thu, 2 Apr, returning Mon, 6 Apr.Return flight with United.Outbound direct flight with United departs from Chicago O'Hare International on Thu, 2 Apr, arriving in Madison.Inbound direct flight with United departs from Madison on Mon, 6 Apr, arriving in Chicago O'Hare International.Price includes taxes and charges.From $318, select.

Madison.$342 per passenger.Departing Sat, 14 Feb, returning Mon, 16 Feb.Return flight with United.Outbound direct flight with United departs from Chicago O'Hare International on Sat, 14 Feb, arriving in Madison.Inbound direct flight with United departs from Madison on Mon, 16 Feb, arriving in Chicago O'Hare International.Price includes taxes and charges.From $342, select.

Madison.$344 per passenger.Departing Mon, 30 Mar, returning Sun, 5 Apr.Return flight with United.Outbound direct flight with United departs from Chicago O'Hare International on Mon, 30 Mar, arriving in Madison.Inbound direct flight with United departs from Madison on Sun, 5 Apr, arriving in Chicago O'Hare International.Price includes taxes and charges.From $344, select.

Madison.$353 per passenger.Departing Fri, 27 Feb, returning Sun, 1 Mar.Return flight with United.Outbound direct flight with United departs from Chicago O'Hare International on Fri, 27 Feb, arriving in Madison.Inbound direct flight with United departs from Madison on Sun, 1 Mar, arriving in Chicago O'Hare International.Price includes taxes and charges.From $353, select.

Madison.$766 per passenger.Departing Mon, 28 Sep, returning Sun, 4 Oct.Return flight with United.Outbound direct flight with United departs from Chicago O'Hare International on Mon, 28 Sep, arriving in Madison.Inbound direct flight with United departs from Madison on Sun, 4 Oct, arriving in Chicago O'Hare International.Price includes taxes and charges.From $766, select.

Madison.$771 per passenger.Departing Tue, 2 Jun, returning Fri, 5 Jun.Return flight with United.Outbound direct flight with United departs from Chicago O'Hare International on Tue, 2 Jun, arriving in Madison.Inbound direct flight with United departs from Madison on Fri, 5 Jun, arriving in Chicago O'Hare International.Price includes taxes and charges.From $771, select.

Madison.$776 per passenger.Departing Wed, 20 May, returning Fri, 5 Jun.Return flight with United.Outbound direct flight with United departs from Chicago O'Hare International on Wed, 20 May, arriving in Madison.Inbound direct flight with United departs from Madison on Fri, 5 Jun, arriving in Chicago O'Hare International.Price includes taxes and charges.From $776, select.

Madison.$832 per passenger.Departing Fri, 30 Oct, returning Thu, 5 Nov.Return flight with United.Outbound direct flight with United departs from Chicago O'Hare International on Fri, 30 Oct, arriving in Madison.Inbound direct flight with United departs from Madison on Thu, 5 Nov, arriving in Chicago O'Hare International.Price includes taxes and charges.From $832, select.

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 March.

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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.

Madison

9km from central Madison

ClosestCheapest

from $293

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Chicago to Madison: Flight information

The things to know before you go.

Cheapest flight found	$293
Cheapest month to fly	May
Average flight time	1 hr, 6 mins
Most popular airline	American Airlines
Average flights per week	636

Finding cheap flights from Chicago to Madison: Frequently asked questions

How much are return flights from Chicago to Madison?

The best price we found for a return flight from Chicago to Madison is $293. 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.

How long does it take to fly from Chicago to Madison?

1 hour and 6 minutes is the average flight time from Chicago to Madison.

Which airlines fly direct from Chicago to Madison?

American Airlines, United and Alaska Airlines fly direct from Chicago to Madison.

How many flights are there a week from Chicago to Madison?

As of January 2026, there are 1,272 flights per week flying from Chicago to Madison.

When is the cheapest time to fly from Chicago to Madison?

The cheapest month to fly from Chicago to Madison is usually May.

Which upcoming date is cheapest to fly from Chicago to Madison Airport on?

After crunching the numbers on our flight calendar, we found that it is currently cheapest to fly from Chicago to Madison Airport on Sunday, 24 May 2026.

Can I get a direct flight from Chicago to Madison Airport?

Yes – the average flight time is 1 hour and 6 minutes.

How can I find the best flight deal to Madison?

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.

When is the best time to book flights to Madison?

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.

Which is the cheapest airline to fly from Chicago to Madison with?

The cheapest airline that flies to Madison is United .

Flying 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) leaving from either of these.
Expect to be travelling for 1 hour 5 minutes. That's the average duration of a direct Chicago to Dane County Regional Airport flight.
Madison (where Dane County Regional Airport is located) and Chicago share the UTC-5 timezone. Easily coordinate travel plans without worrying about time differences.
O'Hare International Airport (ORD) to Dane County Regional Airport (MSN) is the most popular route. There are 77 direct weekly departures to choose from. If you prefer starting your day later, take the last flight with American Airlines at 10:26pm. Opt for the first ORD to MSN departure operated by American Airlines at 7am if you're aiming for an earlier start.
Arriving two hours before an international flight and one hour ahead of a domestic departure are travel rules to live by. Get to the airport on time to catch your flight from Chicago to MSN.
Peak season means busier airports, so plan to arrive even earlier. Give yourself at least two hours before a domestic flight and four hours for an international journey to stay on schedule.

Airports in Chicago

O'Hare International Airport (ORD)

O'Hare International Airport (ORD) is a convenient option for travelling directly to your destination. Nonstop flights from Chicago to Dane County Regional Airport (MSN) can be booked from this terminal.
United Airlines is a well-known airline that offers direct flights from Chicago to Dane County Regional Airport taking off from ORD.
United Airlines is the airline with the highest number of bookings for flights from ORD to MSN.
With 71.71% of its services landing as planned, American Airlines is the top performer for punctuality on this route.
ORD is around 40 kilometres from central Chicago. If you're driving, catching a cab or ride-sharing from the centre, it'll take you 35 minutes or so to get there, depending on traffic. If you're taking public transport, expect the trip time to be around 55 minutes.
Have an early flight from Chicago to Dane County Regional Airport? Avoid the stress of rushing to the terminal (and enjoy a few extra z's) by staying at one of these stays close to O'Hare International Airport:
Of the departures from O'Hare International Airport, 74.85% arrive on time at their destination.
The address for ORD is 10000 West O'Hare.

Chicago Midway International Airport (MDW)

MDW is around 19 kilometres from central Chicago. It'll take you 20 minutes or so to get to the airport in a car from the city centre. Public transport takes roughly 45 minutes.
Want to treat yourself to an extra night away before catching your Chicago to MSN flight? Unwind in a hotel near Chicago Midway International Airport before your trip officially begins. These stays are calling your name:
Chicago Midway International Airport has an on-time performance of 77.88%. This figure highlights how frequently flights departing from this airport arrive on time.
You'll find MDW at 5700 South Cicero.

Chicago Rockford International Airport (RFD)

From the centre of Chicago, RFD is around 137 kilometres away. It takes roughly 1 hour 25 minutes to reach the airport by car and 4 hours 15 minutes or so if you're on public transport.
Make catching an early Chicago to Dane County Regional Airport flight the easiest part of your journey. Book a room at one of these hotels near Chicago Rockford International Airport and get to your check-in counter feeling relaxed and unhurried:
Flights departing from RFD touch down at their destination as scheduled 76.19% of the time.
Chicago Rockford International Airport is located at 2 Airport Cir.

About Dane County Regional Airport (MSN)

Book a hotel close to MSN if you have a late flight from Chicago to Dane County Regional Airport. Pick one of these accommodation options and be under the covers in no time flat:
Follow your own route with a Dane County Regional Airport rental car. Pick up your wheels from Hertz, Alamo or Enterprise and chase adventure across Madison and beyond.
Get the best deal by booking your vehicle around two weeks ahead of your Chicago to Dane County Regional Airport flight.
MSN is located at 4000 International Lane.

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

Dane County Regional Airport is roughly 10 kilometres from central Madison. How long it takes to get to the centre by cab or car hire depends on the time of day. Do a little research before you go.
If you're travelling by public transport, expect a journey of around 1 hour 10 minutes.

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

$334 is the best price for a one-way ticket from Chicago to Dane County Regional Airport. A return flight starts at $293. These prices may change depending on availability and demand.
Book one month before your departure date. Pricing trends show that this is the ideal window for finding cheap flights from Chicago to MSN.
The best month for finding cheap Chicago to Dane County Regional Airport tickets is June. Use the 'Whole month' tool to compare prices, then select the dates that offer the lowest fares.
Finding a cheap flight ticket from Chicago to MSN is easy with Price Alerts. Simply set up one of these automatic alerts and we'll let you know as soon as there's a better deal.
Chase down a great fare on a flight from Chicago to Dane County Regional Airport with the help of the filters. Choose your ideal departure and arrival times, number of stops and airlines. You can also sort your results by 'Best,' 'Fastest' or 'Cheapest.'

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

Think about the kind of experience you want when deciding the best time to fly. February is the quietest month to visit Madison. August is when most people book flights from Chicago to Dane County Regional Airport (MSN), which may be perfect if you're chasing more excitement.
Book a Chicago to MSN flight ticket departing in July if you want to explore the city during its warmest month. Expect temperatures in Madison to range from 13ºC to 29ºC.
Look for cheap tickets from Chicago to Dane County Regional Airport in January if you'd rather travel during cooler conditions. Temperatures are at their lowest then, ranging between -18ºC and 0ºC.

More about Madison

Start your Madison trip right by choosing the ideal place to stay. After booking your flight from Chicago to Dane County Regional Airport, check out our selection of hotels including:
Your Madison trip wouldn't be complete without a bit of sightseeing. Top attractions you can't miss include Olbrich Botanical Gardens, Chazen Museum of Art and Madison Museum of Contemporary Art.

Explore more of the United States

You've done Madison, now it's time to discover more of the United States. Travel about 193 kilometres south-east to Chicago to check off its leading sights. From Millennium Park to Lollapalooza and Art Institute of Chicago, you've got a jam-packed schedule ahead.
If there's time to check out another major destination in the United States, head for Milwaukee, roughly 121 kilometres east of Madison. Richards Duplex Apartments by Frank Lloyd Wright, Miller Park and Milwaukee County Zoo are key highlights.