$143 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 10/6. 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

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
$239American Airlines
Thu, Jul 30 - Sun, Aug 2
American Airlines Logo
5:00 am - 6:15 am
MSN
-
ORD
1h 15mnonstop
American Airlines Logo
11:00 pm - 12:10 am
ORD
-
MSN
1h 10mnonstop
$240American Airlines
Mon, Aug 3 - Mon, Aug 10
American Airlines Logo
1:18 pm - 2:30 pm
MSN
-
ORD
1h 12mnonstop
American Airlines Logo
5:06 pm - 6:19 pm
ORD
-
MSN
1h 13mnonstop
$241American Airlines
Fri, Jul 24 - Mon, Jul 27
United Airlines Logo
5:00 am - 6:17 am
MSN
-
ORD
1h 17mnonstop
United Airlines Logo
10:00 pm - 11:12 pm
ORD
-
MSN
1h 12mnonstop
$254United Airlines
Sat, Jul 18 - Tue, Jul 21
United Airlines Logo
8:10 am - 9:20 am
MSN
-
ORD
1h 10mnonstop
United Airlines Logo
5:45 pm - 6:57 pm
ORD
-
MSN
1h 12mnonstop
$269United 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
$289Delta
Thu, Jul 30 - Sun, Aug 2
American Airlines Logo
5:00 am - 8:31 am
MSN
-
STL
3h 31m
1 stop
American Airlines Logo
5:58 pm - 12:10 am
STL
-
MSN
6h 12m
1 stop
$304American Airlines
Wed, Aug 19 - Wed, Aug 26
United Airlines Logo
2:44 pm - 3:57 pm
MSN
-
ORD
1h 13mnonstop
United Airlines Logo
10:40 am - 11:58 am
ORD
-
MSN
1h 18mnonstop
$309United Airlines
Wed, Sep 9 - Mon, Sep 14
Multiple Airlines Logo
10:33 am - 9:40 am
MSN
-
STL
23h 07m
2 stops
Multiple Airlines Logo
8:34 pm - 2:20 pm
STL
-
MSN
17h 46m
1 stop
$364Multiple Airlines
Mon, Sep 7 - Fri, Sep 11
Delta Logo
6:05 am - 10:23 am
MSN
-
STL
4h 18m
1 stop
Delta Logo
6:15 am - 11:20 am
STL
-
MSN
5h 05m
1 stop
$425Delta
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 $432 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 $542.

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.

No, with an average price for the route of $357, prices are generally cheapest when you fly direct.

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 August and May, when the average cost of round-trip tickets is $249 and $239 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$143
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 $270 one-way - $357 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 9948 reviews
6.7Food
7.1Entertainment
7.7Boarding
7.3Comfort
8.1Crew
Airline reviews

Horrible experience. They delayed our flight 7 hours!! We had to seat at the airport with kids on 4th July all day!

2.0 MediocreBarbara, Jul 2026
PNS - ORD
Read more United Airlines reviews

Horrible experience. They delayed our flight 7 hours!! We had to seat at the airport with kids on 4th July all day!

1 flight cancelled Had to fly out of different city Flight at new departure city was delayed 3 hours causing us to miss connecting flights. By the time we did make it to Prague our luggage did not. Had to wait day and a half for luggage to be delivered. Customer service was not good. Agents did not arrive at gate until 5-10 minutes before boarding

Awful. Delayed flights, missed connection to Toronto. Hotel vouchers were for already booked hotels x3. Giant waste of my time

Boarding was great, and the crew were very friendly. The seats must have been a bit on the older side and you could feel some of the seat components through the padding. Also, the plugs did not work on the row's entertainment screen or charging ports. Checked bag was transferred for connecting flight, and we appreciated how early we had the connecting gate information.

Very easy ! Use the kiosk and bag drop and right to security within 10 min

Over 5 hour delay with minimal updates or ability to standby for alternative flights. During boarding and 1 hr+ wait for takeoff, seats were drenched w water from air conditioning condensation and always leftover crumbs on carpet and seats

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.

Nothing, I wont be flying American Airlines again and will not be recommending anyone to fly American Airlines. It was the worst experience flying I've ever had.

My luggage was not sent with us. Not sure if this is Envoy Air responsibility but that was a very BAD experience

The planes can use an actual cleaning. The armrest and seats do not appear to be cleaned on this one and most other planes.

Flight was delayed…once landed at ORD, no gates were available so made us wait for 56 minutes after we landed to let us out of the aircraft!

The flight de-boarded after being informed of a 3 hour delay. The gate agent said we could go to lounge. The flight ended up boarding 20 minutes later and I missed it.

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