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Illinois

$159+ 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 6/23. Fares are subject to change and may not be available on all flights or dates of travel.
MSN — ORD
May 27 — Jun 31
Wed 5/27
Wed 6/3
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 April 27, 2026.

This American Airlines deal was found by Cheapflights users on 4/22. 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 12/118:08 pm
MSN
-
ORD
Nonstop1h 21m
American Airlines
Sun 12/133:02 pm
ORD
-
MSN
Nonstop1h 07m
American Airlines
Deal found 4/22$239
This American Airlines deal was found by Cheapflights users on 4/27. 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.
Thu 5/218:19 am
MSN
-
ORD
Nonstop1h 24m
American Airlines
Sun 5/2410:28 am
ORD
-
MSN
Nonstop1h 08m
American Airlines
Deal found 4/27$241
This American Airlines deal was found by Cheapflights users on 4/23. 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 12/232:40 pm
MSN
-
ORD
Nonstop1h 18m
American Airlines
Fri 1/89:45 am
ORD
-
MSN
Nonstop1h 10m
American Airlines
Deal found 4/23$254
This American Airlines deal was found by Cheapflights users on 4/23. 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 5/88:24 pm
MSN
-
ORD
Nonstop1h 16m
American Airlines
Tue 5/1212:36 pm
ORD
-
MSN
Nonstop1h 12m
American Airlines
Deal found 4/23$269
This American Airlines deal was found by Cheapflights users on 4/26. 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.
Tue 5/55:30 am
MSN
-
ORD
Nonstop1h 17m
American Airlines
Thu 7/306:40 am
ORD
-
MSN
Nonstop1h 11m
American Airlines
Deal found 4/26$299
This United Airlines deal was found by Cheapflights users on 4/23. 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 5/308:10 am
MSN
-
STL
1 stop3h 57m
United Airlines
Sat 6/66:00 am
STL
-
MSN
1 stop3h 54m
United Airlines
Deal found 4/23$309
This American Airlines deal was found by Cheapflights users on 4/24. 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 5/202:18 pm
MSN
-
ORD
Nonstop1h 20m
American Airlines
Tue 6/96:40 am
ORD
-
MSN
Nonstop1h 05m
American Airlines
Deal found 4/24$309
This American Airlines deal was found by Cheapflights users on 4/24. 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 5/1311:50 am
MSN
-
STL
1 stop5h 31m
American Airlines
Wed 5/206:54 pm
STL
-
MSN
1 stop5h 00m
American Airlines
Deal found 4/24$314
This American Airlines deal was found by Cheapflights users on 4/26. 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.
Sun 5/37:45 am
MSN
-
ORD
Nonstop1h 18m
American Airlines
Sun 5/103:53 pm
ORD
-
MSN
Nonstop1h 13m
American Airlines
Deal found 4/26$314
This American Airlines deal was found by Cheapflights users on 4/23. 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 5/88:24 pm
MSN
-
STL
1 stop3h 32m
American Airlines
Tue 5/124:30 pm
STL
-
MSN
1 stop5h 41m
American Airlines
Deal found 4/23$319
This American Airlines deal was found by Cheapflights users on 4/24. 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 5/206:45 am
MSN
-
ORD
1 stop5h 51m
American Airlines
Fri 6/129:51 pm
ORD
-
MSN
Nonstop1h 10m
American Airlines
Deal found 4/24$319
This American Airlines deal was found by Cheapflights users on 4/27. 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 11/203:10 pm
MSN
-
STL
1 stop7h 19m
American Airlines
Sun 11/225:00 am
STL
-
MSN
1 stop5h 40m
American Airlines
Deal found 4/27$321

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 April 27, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$239
(American Airlines)

One-way from

$159
(Delta)

Popular in

February

Cheapest in

June

Average price

$239

Good round-trip deal

$378 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. 20% potential increase in price ($62 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 6% potential price decrease ($15 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in April 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 April 27, 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
Quickest round-trip

MadisonChicago

MSN - ORD

MSNORD

Madison Truax Field

Mon 5/25

5:00 am-6:09 am

Nonstop1h 09m

Chicago O'Hare Intl

Mon 6/1

10:50 pm-11:55 pm

Nonstop1h 05m

$239

MadisonSt. Louis

MSN - STL

MSNSTL

Madison Truax Field

Fri 6/5

8:10 am-12:11 pm

1 stop4h 01m

Lambert-St Louis

Sun 6/7

6:00 am-9:59 am

1 stop3h 59m

$309

MadisonSt. Louis

MSN - STL

MSNSTL

Madison Truax Field

Tue 5/26

6:44 pm-11:54 pm

1 stop5h 10m

Lambert-St Louis

Tue 6/2

7:50 pm-11:16 pm

1 stop3h 26m

$309

MadisonSt. Louis

MSN - STL

MSNSTL

Madison Truax Field

Sat 5/23

9:00 am-2:23 pm

1 stop5h 23m

Lambert-St Louis

Sat 5/30

7:05 pm-10:42 pm

1 stop3h 37m

$309

MadisonSt. Louis

MSN - STL

MSNSTL

Madison Truax Field

Thu 9/3

5:00 am-8:37 am

1 stop3h 37m

Lambert-St Louis

Sun 9/6

11:25 am-2:53 pm

1 stop3h 28m

$309

MadisonChicago

MSN - ORD

MSNORD

Madison Truax Field

Tue 6/30

8:10 am-9:20 am

Nonstop1h 10m

Chicago O'Hare Intl

Sat 7/4

9:47 pm-10:59 pm

Nonstop1h 12m

$309

MadisonSt. Louis

MSN - STL

MSNSTL

Madison Truax Field

Tue 7/28

9:32 am-1:02 pm

1 stop3h 30m

Lambert-St Louis

Sun 8/2

6:21 am-11:19 am

1 stop4h 58m

$323

MadisonChicago

MSN - ORD

MSNORD

Madison Truax Field

Tue 5/12

8:10 am-9:18 am

Nonstop1h 08m

Chicago O'Hare Intl

Sat 5/16

6:00 pm-7:07 pm

Nonstop1h 07m

$339

MadisonSt. Louis

MSN - STL

MSNSTL

Madison Truax Field

Tue 5/26

3:53 pm-9:21 pm

1 stop5h 28m

Lambert-St Louis

Sat 5/30

7:05 pm-10:42 pm

1 stop3h 37m

$379

MadisonSt. Louis

MSN - STL

MSNSTL

Madison Truax Field

Fri 5/8

3:56 pm-9:13 pm

1 stop5h 17m

Lambert-St Louis

Tue 5/12

8:46 am-2:16 pm

1 stop5h 30m

$439

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/26

Showing 1-10 of 43 resultsSorted by cheapest first
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5

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 July is currently the most expensive (average of $238). 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 April 27, 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 19% versus a flight in the evening.

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 April 25, 2026.

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

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 April 27, 2026.

The most flights from MSN to USIL are scheduled on a Monday (59 on average). You will have fewer flight options on Thursday, which is when the least amount of flights are scheduled (32 on average).

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 April 27, 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
9,665 reviews

Boarding

7.7

Entertainment

7.1

Crew

8.1

Food

6.6

Comfort

7.3

Overall

7.4

Reviews

1 / 20
8.0
Excellent

Anonymous,Apr 2026

DFW - EWR

The flight was on time. Crew was friendly. Will fly again. The seats was comfortable.
United Airlines
7.4
Good
9,665 reviews
United Airlines
7.4
Good
9,665 reviews

Boarding

7.7

Entertainment

7.1

Crew

8.1

Food

6.6

Comfort

7.3

Overall

7.4

Reviews

1 / 20
8.0
Excellent

Anonymous,Apr 2026

DFW - EWR

The flight was on time. Crew was friendly. Will fly again. The seats was comfortable.
American Airlines
7.1
Good
11,668 reviews
United Airlines
7.4
Good
9,665 reviews

Boarding

7.7

Entertainment

7.1

Crew

8.1

Food

6.6

Comfort

7.3

Overall

7.4

Reviews

1 / 20
8.0
Excellent

Anonymous,Apr 2026

DFW - EWR

The flight was on time. Crew was friendly. Will fly again. The seats was comfortable.

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 $323, American Airlines can have you in Illinois from Madison in 3h 30m. The distance between Madison and Illinois is about 307 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 Envoy Air (76%), Japan Airlines (75%) or ANA (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 $239 on average, our data indicates $1,097 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 July is currently the most expensive (average of $238). 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

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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 April 27, 2026.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$179Average$231FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$179Average$324FlexibilityNo cancel feeOn-time69%

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