$149 Find Cheap Flights from Madison to Illinois - Compare and Save

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Cheap Flights from Madison to Illinois

Cheapest round-trip prices found by our users on KAYAK in the last 5 days
Chicago
Chicagononstop$289
Marion
Marion1 stop$570
Chicago
Chicagononstop$289
Marion
Marion1 stop$570
Booking Insights

KAYAK's insights & trends for Madison to Illinois flights

Get data-powered insights and trends into flights from Madison to Illinois to help you find the cheapest flights, the best time to fly and much more.

What is the cheapest Madison to Illinois flight route?

The cheapest ticket to Illinois from Madison found in the last 5 days was to Chicago, at $309 round-trip. The most popular route is from Madison (MSN) to Chicago O'Hare Intl Airport (ORD), and the cheapest round-trip airline ticket found on this route in the last 5 days was $309.

What is the cheapest time of day to fly to Illinois?

The cheapest time of day to fly to Illinois is generally in the morning, when round-trip flights cost $440 on average. Morning departures are around 12% cheaper than evening flights, on average. The most expensive time of day to fly to Illinois is generally at night, which is peak travel time and where the average cost of a ticket is $590.

Can I save money by flying with a layover from Madison to Illinois?

No, with an average price for the route of $400, prices are generally cheapest when you fly direct.

What is the cheapest month to fly from Madison to Illinois?

The cheapest month for flights from Madison to Illinois is March, when tickets cost $239 (return) on average. On the other hand, the most expensive months are April and May, when the average cost of round-trip tickets is $490 and $449 respectively.

What’s the cheapest day of the week to fly from Madison to Illinois?

If you are looking for a flight deal from Madison to Illinois, look for departures on Saturdays and avoid leaving on a Monday, as it's usually the priciest day. When flying back from Illinois, Friday is the cheapest day to fly and Tuesday is the most expensive.

Good to know

Low season

June

Cheapest flight

$149
Best time to beat the crowds with an average 34% drop in price.
Most popular time to fly and prices are also 13% lower on average.
Flight from Madison to Chicago O'Hare Airport

FAQs - booking Illinois flights

  • How does KAYAK find such low prices on flights from Madison to Illinois?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Madison to Illinois.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Madison to Illinois?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight from Madison to Illinois is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights from Madison to Illinois?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly from Madison to Illinois with an airline and back with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Madison to Illinois?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying from Madison to Illinois up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

Top tips for finding cheap flights to Illinois

  • Looking for a cheap flight? 25% of our users found tickets from Madison to the following destinations at these prices or less: Chicago $312 one-way - $376 round-trip

Reviews of the top airlines flying from Madison to Illinois

 
Need help choosing which airline to fly with from Madison to Illinois? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
7.4
United AirlinesOverall score based on 10283 reviews
8.1Crew
6.7Food
7.7Boarding
7.1Entertainment
7.3Comfort
Airline reviews

Raleigh to Chicago was OK. The problem was Chicago to Lincoln. Flight was delayed 4 hours. Give them credit for the updates and reason why it was delayed

2.0 MediocreAlejandro, Oct 2026
Read more United Airlines reviews

Raleigh to Chicago was OK. The problem was Chicago to Lincoln. Flight was delayed 4 hours. Give them credit for the updates and reason why it was delayed

Comfortable seats and good crew. There should be some breakfast options in menu for economy class to purchase Wifi was not working in the flight

On time. Accommodated carry on and personal bag in the plane. Good entertainment available and access without using own device. Gave a whole can of juice rather than a pour. Seat did not recline much.

Good, our flight was delayed but that was totally out of their control due to weather and a presidential visit.

The price. Omg $1100. Was crazy and it was not clear on the website.

Excellent. I had a medical emergency on flight SNA-ORD and the attendants were very helpful.

The seats on the aircraft are like sitting in a rock. During the boarding process they recognize Active Duty Military, why don’t they recognize Retired Military. I’ve always preferred Delta, this flight confirmed why I still prefer Delta.

It was literally one of the worst travel experiences ever. My flight got delayed by over an hour and there was no communication of this from the gate staff. I realized it by checking the screen periodically. Once on board the flight attendants continued to serve alcohol to a man who was clearly already drunk and that was making a bunch of commotion. Never again will I fly United!

At least the delays were short. Business class, even in the new planes is very crowded now with crappy tray tables

Flight cancelled due to fog. No other flights available for 36 hours. Directed by United to book passage on another carrier, and submit receipts for reimbursement. Did that. United now states they will not reimburse. Currently out 2 grand.

It would be helpful to be able to download an eticket from either American airlines or Cathay Pacific; not just Cathay Pacific.

Another American Airlines flight, another significant delay. At least this one wasn't canceled like many others have been. This time we sat on the runway at LaGuardia for 2.5 hours. By my count that is 7 American flights the last three months that have been delayed 2 hours or more or canceled entirely.

My luggage was lost at some point during my layover between Chicago and LHR. I landed Tuesday morning, and did not get it until Thursday night. Ironically, the people at the ticket desk had added a “priority” sticker to my tracking tag.

The flight was delayed multiple times. Breakfast was not served and only an apology given and statement that we could find better pastries in Paris. Seats were extremely narrow and uncomfortable.

The flight could have actually taken place. Canceled flight and no option to rebook that day.

Seating was horrible. Small seats. Access to flight information and extras very iser unfriendly. Kept losing internet after paying for it. Staff in madison was as unprofessional and unhelpful.

The counter/baggage counter was busy and so many people missed flights. We got stuck sitting on the plane over 2 hours at the gate while they were doing an inspection is wrong. Many of us missed our connecting flights because of it.

Our flight was changed from Madison to DC to Madison to Charlotte.

We were told we had no flights before our flight was continually delayed then cancelled.

Boarding was relatively fast and easy and the crew was attentive throughout.

More options for your flight from Madison to Illinois

Complete your trip to Illinois with a hotel stay or car rental