$142 Find Cheap Flights from Madison to Illinois

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Madison to Illinois departing on 7/3. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
1 adult, Economy, 0 bags

KAYAK searches hundreds of travel sites at once for deals on flights to Illinois

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Madison to Illinois, as well as popular online travel agencies
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Madison to Illinois, as well as popular online travel agencies
Travelers love KAYAK
41 299 237 searches in the past 7 days on KAYAK

Save 24% or moreCompare multiple travel sites with one search.

Track pricesNot ready to book? Create a price alert for when prices drop.

Bundle and saveSave money when you bundle your flight + hotel.

Filter your dealsChoose cabin class, free Wi-Fi and more.

Flight Deals
Booking Insights
Flight Deals

Cheap Flights from Madison to Illinois

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
Chicago
Chicagononstop$239
St. Louis
St. Louis1 stop$289
Chicago
Chicagononstop$239
St. Louis
St. Louis1 stop$289

Book Cheap Madison to Illinois Plane Tickets

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Madison to Illinois that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Madison to Illinois

Tue, May 26 - Sun, May 31
United Airlines Logo
8:10 am - 9:20 am
MSN
-
ORD
1h 10mnonstop
United Airlines Logo
9:53 pm - 11:05 pm
ORD
-
MSN
1h 12mnonstop
$239United Airlines
Thu, May 21 - Sun, May 24
American Airlines Logo
3:03 pm - 4:17 pm
MSN
-
ORD
1h 14mnonstop
American Airlines Logo
6:40 am - 7:49 am
ORD
-
MSN
1h 09mnonstop
$241American Airlines
Thu, May 21 - Sun, May 24
American Airlines Logo
3:03 pm - 4:17 pm
MSN
-
ORD
1h 14mnonstop
American Airlines Logo
6:47 pm - 11:59 pm
ORD
-
MSN
5h 12m
1 stop
$250American Airlines
Mon, May 18 - Mon, May 25
American Airlines Logo
8:24 pm - 9:40 pm
MSN
-
ORD
1h 16mnonstop
American Airlines Logo
6:40 am - 7:49 am
ORD
-
MSN
1h 09mnonstop
$254American Airlines
Tue, May 12 - Sat, May 16
American Airlines Logo
8:24 pm - 9:40 pm
MSN
-
ORD
1h 16mnonstop
American Airlines Logo
8:40 am - 9:48 am
ORD
-
MSN
1h 08mnonstop
$269American Airlines
Thu, May 28 - Sun, May 31
United Airlines Logo
12:14 pm - 3:46 pm
MSN
-
STL
3h 32m
1 stop
United Airlines Logo
6:00 am - 9:59 am
STL
-
MSN
3h 59m
1 stop
$289United Airlines
Tue, May 26 - Tue, Jun 2
American Airlines Logo
5:11 pm - 11:59 pm
MSN
-
STL
6h 48m
1 stop
American Airlines Logo
5:25 am - 10:38 am
STL
-
MSN
5h 13m
1 stop
$309American Airlines
Tue, Jun 30 - Sat, Jul 4
United Airlines Logo
9:40 am - 10:56 am
MSN
-
ORD
1h 16mnonstop
United Airlines Logo
7:42 am - 8:55 am
ORD
-
MSN
1h 13mnonstop
$309United Airlines
Mon, May 25 - Tue, Jun 9
Delta Logo
2:33 pm - 8:42 am
MSN
-
MDW
18h 09m
1 stop
Delta Logo
9:54 am - 11:02 pm
MDW
-
MSN
13h 08m
1 stop
$425Delta
Wed, May 20 - Tue, Jun 9
Delta Logo
6:30 am - 5:56 pm
MSN
-
MDW
11h 26m
1 stop
Delta Logo
1:49 pm - 11:02 pm
MDW
-
MSN
9h 13m
1 stop
$445Delta
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.

How much is a round-trip flight from Madison to Illinois?

This analysis is based on the cheapest round-trip price found on KAYAK in the last 12 months by searching for a flight from Madison to Illinois departing in May.

What is the cheapest Madison to Illinois flight route?

Data is based on round-trip flight searches on KAYAK over the past month.

The cheapest ticket to Illinois from Madison found in the last 72 hours was to Chicago, at $290 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 72 hours was $290.

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

The average price for all round-trip flights from Madison to Illinois depending on the time of departure, clicked by users on KAYAK in the last 2 weeks.

The cheapest time of day to fly to Illinois is generally in the morning, when round-trip flights cost $428 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 $533.

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

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Madison to Illinois, removes the top 0.1% to account for outliers, and then takes the median of all values for each month.

The cheapest month for flights from Madison to Illinois is January, when tickets cost $179 (return) on average. On the other hand, the most expensive months are July and August, when the average cost of round-trip tickets is $238 and $226 respectively.

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

The average price of all round-trip flights from Madison to Illinois clicked on KAYAK for each day over the last 12 months.

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 seasonFebruary
Cheapest flight$142
Best time to beat the crowds but there is an average 32% increase in price.
Most popular time to fly with an average 46% increase in price.
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 $238 one-way - $378 round-trip

Reviews of the top airlines flying from Madison to Illinois

 
See real verified KAYAK customer reviews for airlines flying from Madison to Illinois. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
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 9677 reviews
7.7Boarding
8.1Crew
7.3Comfort
6.6Food
7.1Entertainment
Airline reviews

Standard flight with a drinks and a snack- overall very quick flight. The flight attendants were very strict, bordered on rude.

8.0 ExcellentWendi, Apr 2026
MSP - ORD
Read more United Airlines reviews

Standard flight with a drinks and a snack- overall very quick flight. The flight attendants were very strict, bordered on rude.

Delayed - weather wasn't bad at either end. Also sat on tarmac in ORD.

boarded early to only find out that flight would sit at gate for 45 min to an hour. Landed in chicago and sat on runway for over an hour before got to gate. Total delay was extensive for a 45 min flight door to door.

The flight was significantly delayed. The inbound flight from EWR was delayed departing because of mechanical problems. My original departure from CLT was 5:28 pm but due to the delay of the inbound flight, after arrival, deplaning, cleaning, boarding, we did not push back from the gate until 9:00 pm. Once in the air, the flight was smooth and what was originally supposed to be an arrival in ORD at 7:30 pm local time turned out to be 9:35 pm.

The flight I was supposed to be on was supposed to take off at 1:50 from State College. It was delayed over and over and over again until somehow I had to rebook on a flight that was supposed to have left State College at 8 am that morning but didn't end up taking off until almost 6 pm. Not only was this completely unacceptable, the "token from United" was a 15 dollar meal voucher that has to be used by today. I would personally like some miles added to my account for this inconvenience. I was in transit for 8 hours from the time I arrive at State College Aiport to when I got home. I was supposed to be home at 3 pm and I returned at 8 pm. Unacceptable. I have not been on an on Time united flight in nearly 5 years.

newer aircraft, ability to connect my headset via blue tooth for entertainment.

Very comfortable flight, snacks and drinks were good, good communication from crew. Could have used a little more information on timing of boarding for group 5

Great flight. Got to watch a movie. Smooth flight and early arrival at ORD.

It was better than excellent. The staff in Mason City were great. The young woman that pushed my wheelchair did more than could be expected of her. She came from India 17 years ago. I don't remember her name.

After arriving in Chicago, we were taxiing for 1.5 hours with infrequent and untruthful updates about the amount of time it would take to arrive at the gate. Minimally, the team could have provided timing expectations that were more truthful, especially one their original expectations were not met.

It was good, the staff was great, and the food, was as usual, tea and biscuit. Bathroom was clean, and the plane was clean as well.

Very good I can’t complain one bit. Thank you American Airlines for making my flight enjoyable and safe!

The staff and service on American Airlines were truly outstanding. I had requested wheelchair assistance for my mother due to her knee issues, and the team went above and beyond every step of the way—from boarding in Boston to our arrival in Chicago. Their care, professionalism, and attentiveness made the entire experience smooth and stress-free. I’m very grateful for the support they provided.

The new planes (American Eagle) are beautiful and especially comfortable. The flight attendants are consistently professional and courteous. And, while it may seem inconsequential, the new liquid tube of coffee creamer—in contrast to the powdered coffee creamer—makes all the difference in a cup of coffee.

Boarding was quick and efficient. We arrived at our destination early.

I'm not sure American is capable of on-time arrivals and departures. When you land at ORD, you almost always get held on the tarmac because your gate is still occupied. I may have missed my connection, but that ended up up being significantly delayed as well. Once again, I finally got home well after midnight.

Crew at the gate was very crabby and not at all polite. The plane was very hot the entire flight. And the seat cushion was very worn out.

The staff are very, very professional. It's what flying should feel like.

Flight was delayed half hour before boarding, but when I checked flight aware the plane that would Pick us up had a delay of more than an hour. AA should let us know in advance to avoid waiting several hours in the airport

Delays with no explanation. It could have been handled better.

Everything you need to know for your flight from Madison to Illinois

Information on your arrival and departure airports