$125 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 1/19. 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.
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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
In the last 7 days travelers have searched 41,299,237 times on KAYAK, and here is why:

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Best Illinois Flight Deals from Madison

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours

Chicago
Chicagononstop$249
St. Louis
St. Louis1 stop$228

Good to know

Low season

March

High season

July

Cheapest flight

$125
Best time to beat the crowds with an average 56% drop in price.
Most popular time to fly and prices are also 26% lower on average.
Flight from Madison to Chicago O'Hare Airport

FAQs - booking Illinois flights

  • How long is the flight to Illinois from Madison?

    Flights to Chicago1h 04m
  • What is the cheapest flight to Illinois from Madison?

    The cheapest ticket to Illinois from Madison found in the last 72 hours was $125 one-way, and $249 round-trip. The most popular route is from Madison Truax Field to Chicago O'Hare Intl, and the cheapest round-trip airline ticket found on this route in the last 72 hours was $155.

  • Which airlines fly to Illinois?

    United Airlines flies most frequently to Chicago O'Hare Intl from Madison Truax Field. In general, Air New Zealand, American Airlines and Alaska Airlines fly the most to Illinois.

  • 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.

See more FAQs

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 $250 one-way - $373 round-trip
  • High season is considered to be October, November and December. The cheapest month to fly from Madison is March.
  • Morning departure is around 19% more expensive than an evening flight, on average*.
*Average of the lowest prices shown in KAYAK’s search results for departures within the next 30 days

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 9041 reviews
8.1Crew
7.3Comfort
6.7Food
7.7Boarding
7.1Entertainment
Airline reviews

They canceled our flight and left us stranded to figure it out

2.0 MediocreMichael, Nov 2024MSY - ORD
Read more United Airlines reviews

They canceled our flight and left us stranded to figure it out

Everything was very good. Was able to change a make run flight leaving on direct earlier in the app -seamless!!! Well done

Being stick waiting for gate at ORD cause me to almost miss my connecting flight…being deaf United made no no effort to keep me updated as I couldn’t hear the PA

As usual, United scheduling is completely misleading. A 54-minute layover at O’Hare is too short to make a lot of connections, especially since the flight landed “on time” but had to wait on the taxiway 15 minutes for a gate to open up. Then it takes another 10 minutes to exit the plane before one can run to another concourse to catch a connecting flight.

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.

when you can say you don't remember being at any point upset during a flight, the airline is winning .

The staff was very friendly. The seats seemed quite small. Overall the flight was pleasant.

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!

Charging and entertainment didn't work. The meal was horrible. They only came by with the drink cart one time for the 8 hour flight. They did come by with water a couple times.

Exceptional, I’d like to specifically recognize Robert for his outstanding customer service. He is professional, pleasant, and personable.

Other than being delayed 5.5 hours and having to get a hotel because I missed my connecting flight, it was an okay flight. No in-flight Wi-Fi or entertainment.

It was nice being on a flight that had working wifi. The boarding was quick - why don’t all airlines have small boarding groups window to aisle? Makes so much sense!!! I was disappointed to be the first person stopped to have to gate check my carryon. Especially when there was plenty of overhead space at the back! But I get it…keeps it moving. Crew was nice.

The flight from Buffalo to Chicago was on an older and smaller plane. Seating was tight. Looking closely at the interior of the aircraft there were definitely signs of aging and wear.

The flight encountered a delay exceeding 4 hours. The food voucher issued was valued at $12, insufficient to cover our meal expenses. Consequently, I was unable to take my medication, leading to a drop in blood sugar levels and exacerbating my anxiety.

Airplane was cold. Flight attendants were rude. Phone charger did not work. No food available.

3hour delay In the last 3 months i had 3 flights and 2 of these had a more than 2:40 hrs delayed

My initial flight to ORD was extended without reason. We circled the airport a few time and then drove on the ground for at least 20 minutes. These kinds of delays are annoying but somewhat expected… it would be nice if the crew would make an announcement to give updates on how long we could expect to be delayed.

The flight was uneventful. What was a problem was I was delayed getting home one entire day because the flight from Sacramento was delayed. That made getting to my connecting flight impossible. I had to stay another night at the hotel and incur that expense as a result.

This flight was fine but had no time to breathe as the connection was late from Sea to ORD.. Super stressful. If we checked bags, the trip would have been very distressed.

Seats were very uncomfortable. I paid extra for a seat with more leg room, the seat was no different than a seat at the back of the plane. Flight attendant was rude.

Book cheap flights from Madison to Illinois

Recent round-trip flight deals

 
These are the cheapest round-trip flights from Madison to Illinois found on KAYAK in the last 72 hours.
2/21ו'
1 stopDelta
5h 10mMSN-STL
2/23א'
1 stopDelta
4h 18mSTL-MSN
$228
1/20ב'
nonstopAmerican Airlines
1h 08mMSN-ORD
1/25ש'
nonstopAmerican Airlines
1h 02mORD-MSN
$249
3/13ה'
nonstopAmerican Airlines
0h 59mMSN-ORD
3/21ו'
nonstopAmerican Airlines
1h 05mORD-MSN
$269
4/24ה'
nonstopAmerican Airlines
0h 59mMSN-ORD
5/11א'
nonstopAmerican Airlines
0h 59mORD-MSN
$283
3/20ה'
nonstopUnited Airlines
1h 07mMSN-ORD
3/30א'
nonstopUnited Airlines
1h 08mORD-MSN
$309
4/24ה'
nonstopAmerican Airlines
0h 59mMSN-ORD
5/10ש'
1 stopAmerican Airlines
5h 14mORD-MSN
$319
1/7ג'
nonstopAmerican Airlines
1h 11mMSN-ORD
1/11ש'
nonstopAmerican Airlines
1h 02mORD-MSN
$334
1/2ה'
nonstopUnited Airlines
1h 12mMSN-ORD
7/6א'
nonstopUnited Airlines
0h 58mORD-MSN
$362
1/12א'
1 stop
14h 59mMSN-ORD
1/15ד'
1 stop
9h 06mORD-MSN
$379
1/16ה'
1 stop
14h 54mMSN-ORD
1/23ה'
1 stop
12h 16mORD-MSN
$399

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Recent one-way flight deals

 
Only flying one-way? Below are some of the best one-way flight deals from Madison to Illinois found on KAYAK in the last 72 hours.
1/19א'
nonstopAmerican Airlines
1h 11mMSN-ORD
$125
1/17ו'
nonstopUnited Airlines
1h 12mMSN-ORD
$155
1/20ב'
nonstopUnited Airlines
1h 12mMSN-ORD
$189
3/16א'
nonstopUnited Airlines
1h 07mMSN-ORD
$200
1/20ב'
1 stopDelta
17h 50mMSN-ORD
$341
12/26ה'
1 stopUnited Airlines
5h 55mMSN-STL
$347
3/8ש'
1 stop
12h 41mMSN-ORD
$380
12/25ד'
1 stopAmerican Airlines
3h 36mMSN-STL
$396
1/18ש'
2 stopsDelta
14h 40mMSN-ORD
$462
3/8ש'
2 stops
23h 24mMSN-ORD
$498

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Last minute flights from Madison to Illinois

Last minute flight, train and bus deals

 
These last-minute flight deals are the cheapest flights found on KAYAK in the last 72 hours for flights from Madison to Illinois that are departing in the next 10 days.
12/23ב'
multi-stopDelta
5h 00mMSN-STL
1/18ש'
multi-stopDelta
4h 19mSTL-MSN
$258
12/23ב'
multi-stopDelta
5h 00mMSN-STL
1/17ו'
multi-stopDelta
4h 19mSTL-MSN
$288
12/22א'
multi-stopAmerican Airlines
3h 36mMSN-STL
1/17ו'
multi-stopAmerican Airlines
5h 21mSTL-MSN
$318
12/23ב'
multi-stopDelta
5h 00mMSN-STL
1/19א'
multi-stopDelta
4h 19mSTL-MSN
$389
12/24ג'
multi-stopAmerican Airlines
3h 36mMSN-STL
1/17ו'
multi-stopAmerican Airlines
5h 21mSTL-MSN
$393
12/22א'
multi-stopAmerican Airlines
3h 36mMSN-STL
1/18ש'
multi-stopAmerican Airlines
6h 18mSTL-MSN
$403
12/23ב'
multi-stopUnited Airlines
4h 27mMSN-STL
1/18ש'
multi-stopUnited Airlines
3h 54mSTL-MSN
$493
12/22א'
nonstopUnited Airlines
1h 13mMSN-ORD
1/13ב'
multi-stopUnited Airlines
19h 27mORD-MSN
$536
12/23ב'
multi-stop
8h 47mMSN-ORD
12/25ד'
multi-stop
11h 36mORD-MSN
$791
12/23ב'
multi-stop
17h 03mMSN-ORD
12/25ד'
multi-stop
11h 36mORD-MSN
$882

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

Information on your arrival and departure airports

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