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Illinois

$124+ 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 9/23. Fares are subject to change and may not be available on all flights or dates of travel.
MSN — ORD
Aug 30 — Sep 61
Sun 8/30
Sun 9/6
1 adult, Economy
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Cheap 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 July 31, 2026.

This American Airlines deal was found by Cheapflights users on 7/26. 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.
Fri 12/117:05 pm
MSN
-
ORD
Nonstop1h 25m
American Airlines
Sun 12/1311:00 pm
ORD
-
MSN
Nonstop1h 12m
American Airlines
Deal found 7/26$249
This American Airlines deal was found by Cheapflights users on 7/30. 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.
Sun 9/1312:56 pm
MSN
-
ORD
Nonstop1h 24m
American Airlines
Sun 9/207:03 am
ORD
-
MSN
Nonstop1h 11m
American Airlines
Deal found 7/30$251
This American Airlines deal was found by Cheapflights users on 7/30. 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 8/205:00 am
MSN
-
ORD
Nonstop1h 12m
American Airlines
Sun 8/238:15 am
ORD
-
MSN
Nonstop1h 07m
American Airlines
Deal found 7/30$266
This United Airlines deal was found by Cheapflights users on 7/26. 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.
Sun 8/26:41 am
MSN
-
ORD
Nonstop1h 13m
United Airlines
Tue 8/187:45 pm
ORD
-
MSN
Nonstop1h 08m
United Airlines
Deal found 7/26$279
This American Airlines deal was found by Cheapflights users on 7/29. 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.
Wed 8/59:48 am
MSN
-
ORD
Nonstop1h 13m
American Airlines
Wed 8/128:10 am
ORD
-
MSN
Nonstop1h 07m
American Airlines
Deal found 7/29$294
This American Airlines deal was found by Cheapflights users on 7/29. 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.
Wed 8/266:53 pm
MSN
-
STL
1 stop5h 21m
American Airlines
Wed 9/28:07 pm
STL
-
MSN
1 stop4h 03m
American Airlines
Deal found 7/29$298
This United Airlines deal was found by Cheapflights users on 7/27. 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 8/265:00 am
MSN
-
STL
1 stop3h 39m
United Airlines
Wed 9/210:53 am
STL
-
MSN
1 stop4h 06m
United Airlines
Deal found 7/27$299
This American Airlines deal was found by Cheapflights users on 7/30. 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 8/276:53 pm
MSN
-
STL
1 stop5h 21m
American Airlines
Thu 9/39:32 am
STL
-
MSN
1 stop4h 33m
American Airlines
Deal found 7/30$300
This American Airlines deal was found by Cheapflights users on 7/27. 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.
Fri 8/77:47 am
MSN
-
ORD
Nonstop1h 21m
American Airlines
Sun 8/911:00 pm
ORD
-
MSN
Nonstop1h 10m
American Airlines
Deal found 7/27$309
This American Airlines deal was found by Cheapflights users on 7/26. 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.
Fri 11/205:00 am
MSN
-
STL
1 stop5h 51m
American Airlines
Sun 11/2211:32 am
STL
-
MSN
1 stop3h 32m
American Airlines
Deal found 7/26$314
This Delta deal was found by Cheapflights users on 7/30. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/107:49 pm
MSN
-
STL
1 stop3h 34m
Delta
Wed 11/186:20 am
STL
-
MSN
1 stop3h 51m
Delta
Deal found 7/30$319
This American Airlines deal was found by Cheapflights users on 7/29. 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.
Mon 12/219:53 am
MSN
-
ORD
Nonstop1h 17m
American Airlines
Tue 1/59:30 pm
ORD
-
MSN
Nonstop1h 16m
American Airlines
Deal found 7/29$319

Find flight deals from Madison to Illinois

Keep the following information in mind while searching for Madison to Illinois flight deals. Data was last updated July 31, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$249
(United Airlines)

One-way from

$124
(Kiwi.com)

Popular in

April

Cheapest in

November

Average price

$314

Good round-trip deal

$350 or less

Good one-way deal

$279 or less
Provider with most accurate pricing for Madison Truax Field-Chicago (CHI) flight deals.
Search Deals
Provider most trusted by Cheapflights users for Madison Truax Field-Chicago (CHI) flights.
Search Deals
From Madison Truax Field to Illinois
Search Deals
One-way flight from Madison Truax Field to Illinois
Search Deals
Highest demand for flights based on searches. 27% potential increase in price ($139 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 13% potential price decrease ($42 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in July 2026
Search Deals
Price to beat on a round-trip flight from Madison Truax Field to Illinois.
Search Deals
Price to beat on a one-way flight from Madison Truax Field to Illinois.
Search Deals

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 July 31, 2026.
Use the filters below to find and compare flights from Madison to Illinois that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

MadisonChicago

MSN - ORD

MSNORD

Madison Truax Field

Fri 9/18

12:56 pm-2:20 pm

Nonstop1h 24m

Chicago O'Hare Intl

Mon 9/21

11:17 am-12:26 pm

Nonstop1h 09m

$249

MadisonChicago

MSN - ORD

MSNORD

Madison Truax Field

Fri 8/28

12:34 pm-1:53 pm

Nonstop1h 19m

Chicago O'Hare Intl

Sat 8/29

8:50 am-10:04 am

Nonstop1h 14m

$249
Quickest round-trip

MadisonChicago

MSN - ORD

MSNORD

Madison Truax Field

Sat 9/12

5:00 am-6:15 am

Nonstop1h 15m

Chicago O'Hare Intl

Sat 9/26

12:40 pm-1:37 pm

Nonstop0h 57m

$249

MadisonChicago

MSN - ORD

MSNORD

Madison Truax Field

Wed 9/30

4:10 pm-5:29 pm

Nonstop1h 19m

Chicago O'Hare Intl

Wed 11/4

8:45 am-9:50 am

Nonstop1h 05m

$249

MadisonChicago

MSN - ORD

MSNORD

Madison Truax Field

Fri 8/28

9:48 am-11:01 am

Nonstop1h 13m

Chicago O'Hare Intl

Fri 9/4

11:00 pm-12:10 am

Nonstop1h 10m

$251

MadisonChicago

MSN - ORD

MSNORD

Madison Truax Field

Fri 8/14

6:30 am-7:43 am

Nonstop1h 13m

Chicago O'Hare Intl

Sat 8/15

1:49 pm-2:51 pm

Nonstop1h 02m

$279

MadisonChicago

MSN - ORD

MSNORD

Madison Truax Field

Sat 8/8

10:35 am-11:52 am

Nonstop1h 17m

Chicago O'Hare Intl

Mon 8/10

7:45 pm-8:57 pm

Nonstop1h 12m

$294

MadisonSt. Louis

MSN - STL

MSNSTL

Madison Truax Field

Thu 9/24

8:05 pm-12:27 am

1 stop4h 22m

Lambert-St Louis

Sat 9/26

7:27 am-12:26 pm

1 stop4h 59m

$299

MadisonSt. Louis

MSN - STL

MSNSTL

Madison Truax Field

Wed 8/26

6:53 pm-12:14 am

1 stop5h 21m

Lambert-St Louis

Wed 9/2

8:07 pm-12:10 am

1 stop4h 03m

$299

MadisonSt. Louis

MSN - STL

MSNSTL

Madison Truax Field

Fri 9/11

5:00 am-10:20 am

1 stop5h 20m

Lambert-St Louis

Mon 9/14

7:21 am-12:26 pm

1 stop5h 05m

$299

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/26

Showing 1-10 of 54 resultsSorted by cheapest first
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6

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, October is the cheapest month in which you can book a flight from Madison to Illinois (average of $199). Flying from Madison to Illinois in April is currently the most expensive (average of $490). 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 July 31, 2026.

When flying from Madison to Illinois, the time of day you fly usually plays a role in the price. Save by searching for a flight in the morning, which can drop the price by up to 23% versus a flight in the evening.

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 July 31, 2026.

The most flights from MSN to USIL are scheduled on a Thursday (44 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (4 on average).

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

Use this chart to determine the cheapest time to fly round-trip from Madison to Illinois. Price data was last updated on July 25, 2026.

Travelers seeking maximum savings on their Madison to Illinois flight should consider departing on Saturday mornings when fares are most often at their lowest. Wednesday evenings flights should be avoided if possible as fares are typically the most expensive at this time.

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 July 31, 2026.
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
10,053 reviews

Crew

8.1

Boarding

7.7

Overall

7.4

Entertainment

7.1

Food

6.7

Comfort

7.3

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
10,053 reviews
United Airlines
7.4
Good
10,053 reviews

Crew

8.1

Boarding

7.7

Overall

7.4

Entertainment

7.1

Food

6.7

Comfort

7.3

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
7.1
Good
11,846 reviews
United Airlines
7.4
Good
10,053 reviews

Crew

8.1

Boarding

7.7

Overall

7.4

Entertainment

7.1

Food

6.7

Comfort

7.3

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 $249, American Airlines can have you in Illinois from Madison in 1h 19m. 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 most popular routes from Madison to Illinois?

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

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

    Consider Envoy Air (87%), Copa Airlines (84%) or Japan Airlines (84%) 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 $190. While the most popular route (Madison Truax Field - Lambert-St Louis) can be booked for $276 on average, our data indicates $1,318 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, October is the cheapest month in which you can book a flight from Madison to Illinois (average of $199). Flying from Madison to Illinois in April is currently the most expensive (average of $490). 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 July 31, 2026.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$179Average$231FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$179Average$389FlexibilityNo cancel feeOn-time69%

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