$125 Find Cheap Flights from Madison to Illinois - Compare and Save

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 9/2. 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

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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, Aug 11 - Tue, Aug 18
United Airlines Logo
2:47 pm - 4:00 pm
MSN
-
ORD
1h 13mnonstop
United Airlines Logo
4:00 pm - 5:13 pm
ORD
-
MSN
1h 13mnonstop
$239United Airlines
Thu, Aug 13 - Mon, Aug 17
American Airlines Logo
6:53 pm - 8:30 pm
MSN
-
ORD
1h 37mnonstop
American Airlines Logo
11:00 pm - 12:10 am
ORD
-
MSN
1h 10mnonstop
$240American Airlines
Fri, Dec 11 - Sun, Dec 13
American Airlines Logo
9:53 am - 11:10 am
MSN
-
ORD
1h 17mnonstop
American Airlines Logo
1:49 pm - 2:55 pm
ORD
-
MSN
1h 06mnonstop
$249American Airlines
Fri, Aug 7 - Mon, Aug 10
American Airlines Logo
7:47 am - 9:08 am
MSN
-
ORD
1h 21mnonstop
American Airlines Logo
9:09 pm - 10:18 pm
ORD
-
MSN
1h 09mnonstop
$254American Airlines
Sun, Aug 9 - Mon, Aug 17
American Airlines Logo
5:00 am - 6:12 am
MSN
-
ORD
1h 12mnonstop
American Airlines Logo
11:00 pm - 12:10 am
ORD
-
MSN
1h 10mnonstop
$264American Airlines
Wed, Aug 5 - Sun, Aug 9
United Airlines Logo
12:30 pm - 1:42 pm
MSN
-
ORD
1h 12mnonstop
United Airlines Logo
5:45 pm - 6:57 pm
ORD
-
MSN
1h 12mnonstop
$269United Airlines
Wed, Sep 2 - Fri, Sep 11
Multiple Airlines Logo
10:27 am - 12:50 pm
MSN
-
ORD
26h 23m
2 stops
Multiple Airlines Logo
11:06 am - 6:47 pm
ORD
-
MSN
7h 41m
1 stop
$274Multiple Airlines
Fri, Aug 7 - Tue, Aug 11
United Airlines Logo
6:41 am - 7:54 am
MSN
-
ORD
1h 13mnonstop
United Airlines Logo
1:55 pm - 2:59 pm
ORD
-
MSN
1h 04mnonstop
$279United Airlines
Fri, Nov 20 - Sun, Nov 22
Delta Logo
7:55 pm - 11:18 pm
MSN
-
STL
3h 23m
1 stop
Delta Logo
6:30 am - 10:15 am
STL
-
MSN
3h 45m
1 stop
$299Delta
Sat, Aug 29 - Mon, Aug 31
Delta Logo
6:05 am - 10:23 am
MSN
-
STL
4h 18m
1 stop
Delta Logo
5:34 pm - 11:00 pm
STL
-
MSN
5h 26m
1 stop
$309Delta
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?

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 5 days was to Chicago, at $288 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 $288.

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 $431 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 $565.

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

The average round-trip price for all non-stop flights, flights with one layover, and flights with two layovers for the route found by users searching on KAYAK in the last 2 weeks.

Yes, flying with a layover may cost you more time, but you can also save money on the route, with a 1 stop layover the cheapest option at $338 on average.

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 October, when tickets cost $199 (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?

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 season

February

Cheapest flight

$125
Best time to beat the crowds but there is an average 34% increase in price.
Most popular time to fly with an average 49% 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 $278 one-way - $352 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 10034 reviews
6.6Food
7.3Comfort
7.1Entertainment
7.7Boarding
8.1Crew
Airline reviews

I would have preferred a flight voucher and to hop on a different flight. Delayed over 6 hours.

2.0 MediocreEhrick, Jul 2026
BOS - ORD
Read more United Airlines reviews

I would have preferred a flight voucher and to hop on a different flight. Delayed over 6 hours.

I almost missed my connection in Chicago due to having to wait on a gate to be open I am assuming. Having to run from E terminal to C terminal and I barely made it there before they closed the door. This may not be the actual airline's fault it's crazy how there is so little time between flight especially when they are placed so far apart in the airport.

The Wi-Fi did not work, so you weren't able to watch entertainment on your own device. They did not have wired headphones so you couldn't watch it on the in-seat entertainment screen either. There was plenty of time to do a drink and snag service but the flight attendants chose not to.

Great experience, boarding was fast and efficient, so much so that we arrived to Chicago very early

The flight did not have its customary snacks during the flight. Apparently they were never loaded on the plane.

The seats on this flight weren’t as comfortable as we had expected. Even leaned back these seats left us feeling crappy in our backs. Also we had to use our own tablets for movies, but nothing in the seats in front of us to hold the tablets up.

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.

My seat had a worn out cushion, which made it a bit uncomfortable. Other than that, the flight was excellent.

Take this flight regularly. Every single week same thing. Departure delayed. Make up some time in the air. Land at ORD and then wait for gate in "L" concourse Terminal 3 for 30-40 min-which yields a very delayed final arrival. Plus I get to taxi around and see every runway and drive over the bridge (IFKYK) over the expressway 2-4 times in most cases. Change the sched of incoming plane/work with FAA to improve traffic flow at ORD/change the timing of these flights. Whatever it takes. But do better.

- flight was delayed several hours due to weather (understandable) - flight delayed further and we were told by attendants "we are not sure where the pilots are but they are on their way" as we have to find different pilots for the flight - announcements over the PA were somewhat unprofessional by the attendants, seems they need more training and were not reading off the script. They showed their young age and immaturity in their communications with the passengers. They were not clear and lacked professional communication language. - going from a hub to hub we were also parked at the tarmac at ohare for an additional hour and kept being told "few more minutes". Please just let the passengers know the real wait time instead of hiding the truth. We understand there is traffic and weather delays, but we just want transparency. There are several logistics of our lives that revolve around what the attendants and pilots are sharing with us but they are not being transparant.

Boarding and Delays The boarding process for my American Airlines flight from Copenhagen to Philadelphia was a bit tricky. We experienced a gate change that required a long walk to a new area of the airport. Additionally, boarding was not via a jet bridge; we had to take a shuttle bus to the plane and then carry our luggage up the stairs ourselves. Furthermore, the bag drop didn't open until about 12:20 PM, which was only three hours before our scheduled departure. This meant I couldn't drop my bag off early and had to wait outside of security in order to drop off my bag and use the kiosk. The bag drop self-service kiosks also didn't open until about 12:00 PM when an American Airlines employee unlocked them so that we could print out our boarding passes and bag tags, which further created a backlog. The flight was delayed by over an hour because we had to wait for one of the tires on the plane to be changed. Flight Attendant Professionalism On a positive note, the flight attendant was very professional when handling a passenger who was sitting in the wrong seat. Even though the passenger was persistent and reluctant to move, the flight attendant calmly ensured the assigned passenger could take their seat. Kudos to the flight attendant for keeping his calm and composure, not allowing the issue to escalate, and handling it well under pressure while a line of passengers waited in the aisle to board. In-Flight Service The in-flight service was also fast, prompt, and efficient, although service had to be suspended for the last two hours of the flight due to weather and turbulence, which was outside of the crew's control. Limited Flight Options Please note that American Airlines only operates one flight per day in and out of Copenhagen. This means there are limited options available if your flight is delayed or canceled, which is something to take into consideration when booking.

I will never but. through kayak again. and American Airlines. I will never fly again on. They're both thieves.

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.

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

Information on your arrival and departure airports