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Illinois

$115+ 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 1/18. Fares are subject to change and may not be available on all flights or dates of travel.
MSN — ORD
Jan 14 — Jan 211
Wed 1/14
Wed 1/21
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 December 15, 2025.

This American Airlines deal was found by Cheapflights users on 12/13. 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 12/268:10 pmMSN - ORD
Nonstop1h 20mAmerican Airlines
Tue 12/306:25 pmORD - MSN
Nonstop1h 15mAmerican Airlines
Deal found 12/13$224
This American Airlines deal was found by Cheapflights users on 12/13. 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 12/278:10 pmMSN - ORD
Nonstop1h 20mAmerican Airlines
Sun 12/286:25 pmORD - MSN
Nonstop1h 15mAmerican Airlines
Deal found 12/13$249
This American Airlines deal was found by Cheapflights users on 12/15. 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 12/298:10 pmMSN - STL
1 stop3h 34mAmerican Airlines
Thu 1/16:35 pmSTL - MSN
1 stop5h 24mAmerican Airlines
Deal found 12/15$259
This United Airlines deal was found by Cheapflights users on 12/14. 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 12/305:00 amMSN - ORD
Nonstop1h 21mUnited Airlines
Sat 1/38:57 amORD - MSN
Nonstop1h 13mUnited Airlines
Deal found 12/14$269
This American Airlines deal was found by Cheapflights users on 12/14. 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 12/208:10 pmMSN - ORD
Nonstop1h 20mAmerican Airlines
Thu 12/258:12 amORD - MSN
Nonstop1h 18mAmerican Airlines
Deal found 12/14$270
This Delta deal was found by Cheapflights users on 12/15. 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 12/305:01 pmMSN - STL
1 stop5h 15mDelta
Sat 1/36:05 amSTL - MSN
1 stop4h 05mDelta
Deal found 12/15$279
This American Airlines deal was found by Cheapflights users on 12/15. 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 12/199:51 amMSN - ORD
Nonstop1h 05mAmerican Airlines
Mon 12/226:25 pmORD - MSN
Nonstop1h 15mAmerican Airlines
Deal found 12/15$302
This United Airlines deal was found by Cheapflights users on 12/13. 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 12/198:15 amMSN - STL
1 stop6h 11mUnited Airlines
Sat 12/206:35 pmSTL - MSN
1 stop3h 55mUnited Airlines
Deal found 12/13$310
This United Airlines deal was found by Cheapflights users on 12/14. 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 12/183:46 pmMSN - ORD
Nonstop1h 21mUnited Airlines
Sat 12/201:55 pmORD - MSN
Nonstop1h 10mUnited Airlines
Deal found 12/14$320
This United Airlines deal was found by Cheapflights users on 12/15. 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 12/192:29 pmMSN - ORD
Nonstop1h 20mUnited Airlines
Sun 12/213:35 pmORD - MSN
Nonstop1h 10mUnited Airlines
Deal found 12/15$339
This United Airlines deal was found by Cheapflights users on 12/14. 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 12/298:15 amMSN - STL
1 stop6h 11mUnited Airlines
Fri 1/28:05 amSTL - MSN
1 stop3h 43mUnited Airlines
Deal found 12/14$393
This United Airlines deal was found by Cheapflights users on 12/12. 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 12/285:26 pmMSN - STL
1 stop4h 17mUnited Airlines
Thu 1/18:05 amSTL - MSN
1 stop3h 43mUnited Airlines
Deal found 12/12$411

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 December 15, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$179
(United Airlines)

One-way from

$115
(Delta)

Popular in

May

Cheapest in

June

Average price

$209

Good round-trip deal

$320 or less

Good one-way deal

$238 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. 5% potential increase in price ($12 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($10 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in December 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.
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 December 15, 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 1/29

6:00 am-7:21 am

Nonstop1h 21m

Chicago O'Hare Intl

Sat 2/14

8:15 am-9:15 am

Nonstop1h 00m

$179

MadisonChicago

MSN - ORD

MSNORD

Madison Truax Field

Thu 3/12

2:50 pm-4:02 pm

Nonstop1h 12m

Chicago O'Hare Intl

Thu 3/19

1:57 pm-2:58 pm

Nonstop1h 01m

$179

MadisonChicago

MSN - ORD

MSNORD

Madison Truax Field

Mon 1/5

6:18 pm-7:41 pm

Nonstop1h 23m

Chicago O'Hare Intl

Mon 1/12

9:45 am-10:55 am

Nonstop1h 10m

$179

MadisonChicago

MSN - ORD

MSNORD

Madison Truax Field

Wed 6/3

6:45 am-7:50 am

Nonstop1h 05m

Chicago O'Hare Intl

Mon 6/8

7:50 pm-8:54 pm

Nonstop1h 04m

$190

MadisonChicago

MSN - ORD

MSNORD

Madison Truax Field

Tue 2/17

6:30 am-7:42 am

Nonstop1h 12m

Chicago O'Hare Intl

Sat 2/21

1:55 pm-2:57 pm

Nonstop1h 02m

$239

MadisonSt. Louis

MSN - STL

MSNSTL

Madison Truax Field

Fri 2/27

5:51 pm-11:23 pm

1 stop5h 32m

Lambert-St Louis

Wed 3/4

5:29 pm-10:38 pm

1 stop5h 09m

$249

MadisonSt. Louis

MSN - STL

MSNSTL

Madison Truax Field

Tue 2/24

5:51 pm-11:23 pm

1 stop5h 32m

Lambert-St Louis

Sat 2/28

10:12 am-5:04 pm

1 stop6h 52m

$249

MadisonSt. Louis

MSN - STL

MSNSTL

Madison Truax Field

Thu 2/26

5:51 pm-11:23 pm

1 stop5h 32m

Lambert-St Louis

Tue 3/3

11:23 am-5:04 pm

1 stop5h 41m

$249

MadisonChicago

MSN - ORD

MSNORD

Madison Truax Field

Sat 12/27

8:10 pm-9:30 pm

Nonstop1h 20m

Chicago O'Hare Intl

Sun 12/28

6:25 pm-7:40 pm

Nonstop1h 15m

$249

MadisonSt. Louis

MSN - STL

MSNSTL

Madison Truax Field

Thu 2/26

5:51 pm-11:23 pm

1 stop5h 32m

Lambert-St Louis

Sun 3/1

6:10 am-10:19 am

1 stop4h 09m

$249

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/15

Showing 1-10 of 46 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, January is the cheapest month in which you can book a flight from Madison to Illinois (average of $179). Flying from Madison to Illinois in March is currently the most expensive (average of $209). 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 December 15, 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 33% 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 Thursday 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.

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 December 15, 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
9,092 reviews

Crew

8.1

Overall

7.4

Comfort

7.3

Entertainment

7.1

Food

6.6

Boarding

7.7

Reviews

1 / 20
10.0
Excellent

Sunderesh,Dec 2025

AUS - EWR

Smooth flight from Austin to Newark. The crew was friendly.
United Airlines
7.4
Good
9,092 reviews
United Airlines
7.4
Good
9,092 reviews

Crew

8.1

Overall

7.4

Comfort

7.3

Entertainment

7.1

Food

6.6

Boarding

7.7

Reviews

1 / 20
10.0
Excellent

Sunderesh,Dec 2025

AUS - EWR

Smooth flight from Austin to Newark. The crew was friendly.
American Airlines
7.2
Good
11,052 reviews
United Airlines
7.4
Good
9,092 reviews

Crew

8.1

Overall

7.4

Comfort

7.3

Entertainment

7.1

Food

6.6

Boarding

7.7

Reviews

1 / 20
10.0
Excellent

Sunderesh,Dec 2025

AUS - EWR

Smooth flight from Austin to Newark. The crew was friendly.

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, American Airlines can have you in Illinois from Madison in 1h 12m. 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 - 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 Copa Airlines (82%), Envoy Air (79%) or Air Canada (74%) 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 $157. While the most popular route (Madison Truax Field - Chicago O'Hare Intl) can be booked for $179 on average, our data indicates $901 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, January is the cheapest month in which you can book a flight from Madison to Illinois (average of $179). Flying from Madison to Illinois in March is currently the most expensive (average of $209). 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.

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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 December 15, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$179Average$249FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$179Average$284FlexibilityNo cancel feeOn-time69%

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