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$81+ Cheap flights from Madison (MSN) to Illinois

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 11/10. Fares are subject to change and may not be available on all flights or dates of travel.
MSN — ORD
Oct 11 — Oct 181
Sat 10/11
Sat 10/18
1 adult, Economy
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Cheap flight deals from Madison to Illinois

Keep the following information in mind while searching for Madison to Illinois flight deals. Data was last updated September 11, 2025.

Round-trip from

$179
(United Airlines)

One-way from

$81
(Kiwi.com)

Popular in

November

Cheapest in

June

Average price

$456

Good round-trip deal

$317 or less

Good one-way deal

$211 or less
From Madison Truax Field to Illinois
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One-way flight from Madison Truax Field to Illinois
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Highest demand for flights based on searches. 24% potential increase in price ($105 potential increase over avg. RT price).
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Cheapest flight prices on average. 11% potential price decrease ($35 potential savings vs. average RT price).
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Average for round-trip flights in September 2025
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Price to beat on a round-trip flight from Madison Truax Field to Illinois.
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Price to beat on a one-way flight from Madison Truax Field to Illinois.
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Find flight deals from Madison to Illinois

Cheapest flights from Madison to Illinois
Explore the most affordable flight options available from Madison to Illinois. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 11, 2025.

This United Airlines deal was found by Cheapflights users on 9/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/1612:26 pmMSN - ORD
Nonstop1h 12mUnited Airlines
Sun 10/198:52 amORD - MSN
Nonstop1h 03mUnited Airlines
Deal found 9/10$179
This United Airlines deal was found by Cheapflights users on 9/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/295:45 pmMSN - ORD
Nonstop1h 10mUnited Airlines
Wed 10/159:25 pmORD - MSN
Nonstop1h 03mUnited Airlines
Deal found 9/10$184
This United Airlines deal was found by Cheapflights users on 9/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/910:51 amMSN - ORD
Nonstop1h 07mUnited Airlines
Thu 10/168:52 amORD - MSN
Nonstop1h 03mUnited Airlines
Deal found 9/11$190
This American Airlines deal was found by Cheapflights users on 9/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/236:41 pmMSN - ORD
Nonstop1h 11mAmerican Airlines
Thu 10/28:47 amORD - MSN
Nonstop1h 12mAmerican Airlines
Deal found 9/11$194
This United Airlines deal was found by Cheapflights users on 9/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/1712:19 pmMSN - ORD
Nonstop1h 11mUnited Airlines
Thu 9/2512:50 pmORD - MSN
Nonstop1h 00mUnited Airlines
Deal found 9/9$199
This American Airlines deal was found by Cheapflights users on 9/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/209:35 amMSN - ORD
Nonstop1h 08mAmerican Airlines
Tue 9/238:35 amORD - MSN
Nonstop1h 05mAmerican Airlines
Deal found 9/11$209
This American Airlines deal was found by Cheapflights users on 9/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/28:18 pmMSN - ORD
Nonstop1h 09mAmerican Airlines
Sun 10/51:23 pmORD - MSN
Nonstop1h 01mAmerican Airlines
Deal found 9/11$224
This American Airlines deal was found by Cheapflights users on 9/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/28:18 pmMSN - STL
1 stop3h 31mAmerican Airlines
Sun 10/55:18 amSTL - MSN
1 stop5h 13mAmerican Airlines
Deal found 9/9$229
This American Airlines deal was found by Cheapflights users on 9/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/98:25 pmMSN - ORD
Nonstop1h 05mAmerican Airlines
Thu 10/1612:40 pmORD - MSN
Nonstop1h 04mAmerican Airlines
Deal found 9/11$231
This American Airlines deal was found by Cheapflights users on 9/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/258:18 pmMSN - STL
1 stop3h 30mAmerican Airlines
Mon 9/296:05 amSTL - MSN
1 stop3h 54mAmerican Airlines
Deal found 9/10$239
This United Airlines deal was found by Cheapflights users on 9/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/26:30 amMSN - ORD
Nonstop1h 07mUnited Airlines
Sun 10/55:55 pmORD - MSN
Nonstop1h 04mUnited Airlines
Deal found 9/10$239
This United Airlines deal was found by Cheapflights users on 9/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/106:30 amMSN - STL
1 stop4h 19mUnited Airlines
Sun 10/126:30 amSTL - MSN
1 stop3h 25mUnited Airlines
Deal found 9/9$241

Cheapflights Fare Finder

 
Customize your flight search to find flights from Madison to Illinois that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated September 11, 2025.
Use the filters below to find and compare flights from Madison to Illinois that are best for you.

Fly from

Madison

Fly to

Illinois

Route

Depart

Return

Price

MadisonChicago

MSN - ORD

MSNORD

Madison Truax Field

Thu 10/23

6:30 am-7:37 am

Nonstop1h 07m

Chicago O'Hare Intl

Sun 10/26

6:15 pm-7:21 pm

Nonstop1h 06m

$179

MadisonChicago

MSN - ORD

MSNORD

Madison Truax Field

Fri 11/21

7:00 am-8:16 am

Nonstop1h 16m

Chicago O'Hare Intl

Sun 11/23

9:20 pm-10:28 pm

Nonstop1h 08m

$179

MadisonChicago

MSN - ORD

MSNORD

Madison Truax Field

Sat 10/4

6:30 am-7:37 am

Nonstop1h 07m

Chicago O'Hare Intl

Mon 10/6

12:50 pm-1:50 pm

Nonstop1h 00m

$179

MadisonChicago

MSN - ORD

MSNORD

Madison Truax Field

Tue 11/11

1:56 pm-3:09 pm

Nonstop1h 13m

Chicago O'Hare Intl

Sun 11/16

10:55 pm-11:58 pm

Nonstop1h 03m

$179

MadisonChicago

MSN - ORD

MSNORD

Madison Truax Field

Thu 10/16

12:26 pm-1:38 pm

Nonstop1h 12m

Chicago O'Hare Intl

Sun 10/19

8:52 am-9:55 am

Nonstop1h 03m

$179

MadisonChicago

MSN - ORD

MSNORD

Madison Truax Field

Thu 10/16

8:25 pm-9:30 pm

Nonstop1h 05m

Chicago O'Hare Intl

Fri 10/31

9:09 am-10:24 am

Nonstop1h 15m

$179

MadisonChicago

MSN - ORD

MSNORD

Madison Truax Field

Mon 9/29

5:45 pm-6:55 pm

Nonstop1h 10m

Chicago O'Hare Intl

Wed 10/15

9:25 pm-10:28 pm

Nonstop1h 03m

$184

MadisonChicago

MSN - ORD

MSNORD

Madison Truax Field

Thu 10/9

10:51 am-11:58 am

Nonstop1h 07m

Chicago O'Hare Intl

Thu 10/16

8:52 am-9:55 am

Nonstop1h 03m

$190

MadisonChicago

MSN - ORD

MSNORD

Madison Truax Field

Thu 10/2

8:18 pm-9:27 pm

Nonstop1h 09m

Chicago O'Hare Intl

Sun 10/5

1:23 pm-2:24 pm

Nonstop1h 01m

$224

MadisonChicago

MSN - ORD

MSNORD

Madison Truax Field

Thu 10/9

2:14 pm-3:23 pm

Nonstop1h 09m

Chicago O'Hare Intl

Thu 10/16

8:59 am-10:15 am

Nonstop1h 16m

$224

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/9

Showing 1-10 of 37 results
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Best time to book a flight from Madison to Illinois

Have a flexible travel schedule? Discover the best time to fly to Illinois from Madison with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

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

What is the cheapest month to book a flight from Madison to Illinois?

Currently, August is the cheapest month in which you can book a flight from Madison to Illinois (average of $245). Flying from Madison to Illinois in March is currently the most expensive (average of $321). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

What is the cheapest time of day to fly from MSN to IL?

Find hourly flight availability from Madison to Illinois. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated September 11, 2025.

Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Madison to Illinois as you normally would.

Weekly flight availability from Madison to Illinois

Explore weekly flight availability from Madison to Illinois. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated September 11, 2025.

The most flights from MSN to USIL are scheduled on a Thursday (50 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (18 on average).

Reviews of airlines servicing Illinois

Get insights into the airlines that provide service to Illinois. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Illinois. Reviews last updated September 11, 2025.
Get a feel of what it's like to fly with United Airlines and American Airlines from Madison to Illinois by reading reviews from past customers. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
United Airlines
7.4
Good
8,937 reviews

Comfort

7.3

Entertainment

7.1

Overall

7.4

Food

6.6

Crew

8.1

Boarding

7.7

Reviews

1 / 20
2.0
Mediocre

Deb,Jan 2025

MKE - ORD

It was terrible! So much to say, but in a nutshell we used vouchers from United because our last trip with them was awful with many mishaps and errors made. Unfortunately, this trip was even worse!
United Airlines
7.4
Good
8,937 reviews
United Airlines
7.4
Good
8,937 reviews

Comfort

7.3

Entertainment

7.1

Overall

7.4

Food

6.6

Crew

8.1

Boarding

7.7

Reviews

1 / 20
2.0
Mediocre

Deb,Jan 2025

MKE - ORD

It was terrible! So much to say, but in a nutshell we used vouchers from United because our last trip with them was awful with many mishaps and errors made. Unfortunately, this trip was even worse!
American Airlines
7.2
Good
10,000 reviews
United Airlines
7.4
Good
8,937 reviews

Comfort

7.3

Entertainment

7.1

Overall

7.4

Food

6.6

Crew

8.1

Boarding

7.7

Reviews

1 / 20
2.0
Mediocre

Deb,Jan 2025

MKE - ORD

It was terrible! So much to say, but in a nutshell we used vouchers from United because our last trip with them was awful with many mishaps and errors made. Unfortunately, this trip was even worse!

Related info for your journey

Find useful and relevant information for your journey from Madison to Illinois. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What airport do you fly from for flights from Madison to Illinois?

    Madison Truax Field (MSN) is the airport you will fly out of if you book a flight from Madison to Illinois. It is only a 5.4 mi journey to Truax Field (MSN) from Madison’s city center.

  • How long is the flight from Madison to Illinois?

    For as low as $179, United Airlines can have you in Illinois from Madison in 1h 07m. The distance between Madison and Illinois is about 108 mi. Both multi-stop and nonstop flights can be found to your destination and back.

  • What are the cheapest airlines to fly from Madison to Illinois one-way?

    One-way options have recently been found by users for as low as $124 on United Airlines. Other airlines that offer cheap prices include Frontier from $125 and American Airlines from $127 one-way.

  • What are the most popular routes from Madison to Illinois?

    While some choose either Madison Truax Field - Lambert-St Louis or Madison Truax Field - Chicago Midway, Madison Truax Field - Chicago O'Hare Intl is the most popular route from Madison to Illinois.

  • What are the most reliable airlines from Madison to Illinois?

    Consider Avianca (85%), Copa Airlines (84%) or Japan Airlines (77%) when booking your flight. These represent the most reliable airlines when flying from Madison to Illinois.

  • What are the cheapest flights from Madison to Illinois?

    Looking at all options, your cheapest flight can be booked for $130. While the most popular route (Madison Truax Field - Chicago O'Hare Intl) can be booked for $179 on average, our data indicates $857 when flying from Madison to Illinois.

  • Can I find deals for flights from Madison to Illinois that include hotel bookings?

    Yes. In addition to deals on Madison to Illinois flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Madison to Illinois?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Madison to Illinois.

  • Can I find deals for business class flights from Madison to Illinois?

    Yes. Cheapflights offers flight deals from Madison to Illinois by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Madison to Illinois?

    Currently, August is the cheapest month in which you can book a flight from Madison to Illinois (average of $245). Flying from Madison to Illinois in March is currently the most expensive (average of $321). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

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Alternative routes for Madison to Illinois

See prices for flight routes from nearby airports that may be better suited for you.
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Top 2 airlines flying from Madison to Illinois

Discover the top 2 airlines that operate flights from Madison to Illinois. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated September 11, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$184Average$279FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$219Average$290FlexibilityNo cancel feeOn-time69%

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