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$126+ 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 11/3. Fares are subject to change and may not be available on all flights or dates of travel.
MSN — ORD
Nov 28 — Dec 51
Fri 11/28
Fri 12/5
1 adult, Economy
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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 October 29, 2025.

This United Airlines deal was found by Cheapflights users on 10/28. 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.
Sat 11/226:20 amMSN - ORD
Nonstop1h 11mUnited Airlines
Tue 12/21:55 pmORD - MSN
Nonstop0h 58mUnited Airlines
Deal found 10/28$179
This American Airlines deal was found by Cheapflights users on 10/27. 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.
Wed 11/121:53 pmMSN - ORD
Nonstop1h 13mAmerican Airlines
Sun 11/168:15 amORD - MSN
Nonstop1h 03mAmerican Airlines
Deal found 10/27$189
This American Airlines deal was found by Cheapflights users on 10/29. 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.
Fri 12/198:10 pmMSN - ORD
Nonstop1h 20mAmerican Airlines
Mon 12/228:00 amORD - MSN
Nonstop1h 18mAmerican Airlines
Deal found 10/29$209
This American Airlines deal was found by Cheapflights users on 10/28. 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 11/64:35 pmMSN - ORD
Nonstop1h 17mAmerican Airlines
Mon 11/108:15 amORD - MSN
Nonstop1h 03mAmerican Airlines
Deal found 10/28$219
This Delta deal was found by Cheapflights users on 10/28. 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.
Sun 11/236:00 amMSN - STL
1 stop5h 59mDelta
Sun 12/76:39 amSTL - MSN
1 stop6h 11mDelta
Deal found 10/28$229
This American Airlines deal was found by Cheapflights users on 10/28. 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 11/77:00 amMSN - ORD
Nonstop1h 16mAmerican Airlines
Sun 11/98:15 amORD - MSN
Nonstop1h 03mAmerican Airlines
Deal found 10/28$239
This United Airlines deal was found by Cheapflights users on 10/27. 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.
Tue 11/116:50 pmMSN - ORD
Nonstop1h 14mUnited Airlines
Sat 11/157:35 pmORD - MSN
Nonstop1h 00mUnited Airlines
Deal found 10/27$249
This Delta deal was found by Cheapflights users on 10/27. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/251:30 pmMSN - STL
1 stop3h 39mDelta
Tue 12/26:39 amSTL - MSN
1 stop6h 11mDelta
Deal found 10/27$254
This American Airlines deal was found by Cheapflights users on 10/28. 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 11/78:12 pmMSN - STL
1 stop3h 44mAmerican Airlines
Sun 11/165:17 amSTL - MSN
1 stop5h 14mAmerican Airlines
Deal found 10/28$259
This Delta deal was found by Cheapflights users on 10/27. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/111:00 amMSN - STL
1 stop4h 31mDelta
Thu 1/86:10 amSTL - MSN
1 stop4h 09mDelta
Deal found 10/27$264
This United Airlines deal was found by Cheapflights users on 10/29. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/133:58 pmMSN - ORD
Nonstop1h 11mUnited Airlines
Mon 11/171:55 pmORD - MSN
Nonstop0h 59mUnited Airlines
Deal found 10/29$269
This United Airlines deal was found by Cheapflights users on 10/27. 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.
Fri 10/312:48 pmMSN - ORD
Nonstop1h 15mUnited Airlines
Sun 11/26:15 pmORD - MSN
Nonstop1h 06mUnited Airlines
Deal found 10/27$278

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 October 29, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$179
(United Airlines)

One-way from

$126
(Booking.com)

Popular in

November

Cheapest in

June

Average price

$182

Good round-trip deal

$299 or less

Good one-way deal

$228 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. 7% potential increase in price ($22 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 5% potential price decrease ($15 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in October 2025
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.
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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 October 29, 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

Sat 12/27

5:00 am-6:21 am

Nonstop1h 21m

Chicago O'Hare Intl

Sun 1/4

1:55 pm-3:05 pm

Nonstop1h 10m

$179

MadisonChicago

MSN - ORD

MSNORD

Madison Truax Field

Thu 12/18

8:00 pm-9:25 pm

Nonstop1h 25m

Chicago O'Hare Intl

Sun 2/1

3:49 pm-4:52 pm

Nonstop1h 03m

$179

MadisonChicago

MSN - ORD

MSNORD

Madison Truax Field

Sat 12/6

10:50 am-12:04 pm

Nonstop1h 14m

Chicago O'Hare Intl

Wed 12/10

7:47 pm-8:47 pm

Nonstop1h 00m

$179

MadisonChicago

MSN - ORD

MSNORD

Madison Truax Field

Sat 11/22

8:12 pm-9:30 pm

Nonstop1h 18m

Chicago O'Hare Intl

Tue 12/2

9:15 pm-10:23 pm

Nonstop1h 08m

$179

MadisonChicago

MSN - ORD

MSNORD

Madison Truax Field

Fri 2/13

8:15 am-9:27 am

Nonstop1h 12m

Chicago O'Hare Intl

Fri 3/13

9:35 pm-10:38 pm

Nonstop1h 03m

$179

MadisonChicago

MSN - ORD

MSNORD

Madison Truax Field

Sat 12/27

5:00 am-6:21 am

Nonstop1h 21m

Chicago O'Hare Intl

Sat 1/3

3:35 pm-4:45 pm

Nonstop1h 10m

$179

MadisonChicago

MSN - ORD

MSNORD

Madison Truax Field

Wed 11/12

1:53 pm-3:06 pm

Nonstop1h 13m

Chicago O'Hare Intl

Sun 11/16

8:15 am-9:18 am

Nonstop1h 03m

$189

MadisonSt. Louis

MSN - STL

MSNSTL

Madison Truax Field

Wed 4/8

2:00 pm-8:39 pm

1 stop6h 39m

Lambert-St Louis

Sat 4/11

3:50 pm-10:08 pm

1 stop6h 18m

$229

MadisonSt. Louis

MSN - STL

MSNSTL

Madison Truax Field

Tue 4/21

1:45 pm-8:31 pm

1 stop6h 46m

Lambert-St Louis

Sat 4/25

3:50 pm-9:57 pm

1 stop6h 07m

$229

MadisonSt. Louis

MSN - STL

MSNSTL

Madison Truax Field

Thu 1/8

11:14 am-4:39 pm

1 stop5h 25m

Lambert-St Louis

Sun 1/11

6:10 am-10:19 am

1 stop4h 09m

$229

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/29

Showing 1-10 of 43 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, February is the cheapest month in which you can book a flight from Madison to Illinois (average of $94). Flying from Madison to Illinois in June is currently the most expensive (average of $179). 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 October 29, 2025.

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 evening, which can drop the price by up to 35% versus a flight at noon.

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 December 8, 2024.

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

How much does it cost to fly round-trip from Madison to Illinois?

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 October 29, 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
8,999 reviews

Entertainment

7.1

Comfort

7.3

Boarding

7.7

Overall

7.4

Crew

8.1

Food

6.6

Reviews

1 / 20
2.0
Mediocre

Sebrena,Oct 2025

IAH - RSW

The worst that I have ever experienced in my life so bad if it was free I'm not ever going to use your Airline again I dont believe ..... very disappointed 😞 😔0000000000000
United Airlines
7.4
Good
8,999 reviews
United Airlines
7.4
Good
8,999 reviews

Entertainment

7.1

Comfort

7.3

Boarding

7.7

Overall

7.4

Crew

8.1

Food

6.6

Reviews

1 / 20
2.0
Mediocre

Sebrena,Oct 2025

IAH - RSW

The worst that I have ever experienced in my life so bad if it was free I'm not ever going to use your Airline again I dont believe ..... very disappointed 😞 😔0000000000000
American Airlines
7.2
Good
11,032 reviews
United Airlines
7.4
Good
8,999 reviews

Entertainment

7.1

Comfort

7.3

Boarding

7.7

Overall

7.4

Crew

8.1

Food

6.6

Reviews

1 / 20
2.0
Mediocre

Sebrena,Oct 2025

IAH - RSW

The worst that I have ever experienced in my life so bad if it was free I'm not ever going to use your Airline again I dont believe ..... very disappointed 😞 😔0000000000000

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 21m. 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 $126 on Frontier. Other airlines that offer cheap prices include United Airlines from $154 and American Airlines from $226 one-way.

  • 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 Avianca (93%), Copa Airlines (85%) or Japan Airlines (79%) 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 $175. While the most popular route (Madison Truax Field - Lambert-St Louis) can be booked for $229 on average, our data indicates $941 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, February is the cheapest month in which you can book a flight from Madison to Illinois (average of $94). Flying from Madison to Illinois in June is currently the most expensive (average of $179). 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 October 29, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$179Average$259FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$219Average$290FlexibilityNo cancel feeOn-time69%

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