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$164+ Cheap flights from Midway (MDW) to Madison (MSN)

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 10/14. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — MSN
Oct 15 — Oct 221
Wed 10/15
Wed 10/22
1 adult, Economy
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Cheap flight deals from Midway to Madison

Discover tips and strategies to find the most affordable flight options for your journey from Midway (MDW) to Madison (MSN). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated September 15, 2025.

Round-trip from

$291
(Kiwi.com)

One-way from

$164
(Kiwi.com)

Popular in

April

Cheapest in

December

Average price

$285
From Chicago Midway to Madison Truax Field
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One-way flight from Chicago Midway to Madison Truax Field
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Highest demand for flights based on searches. 37% potential increase in price ($224 potential increase over avg. RT price).
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Cheapest flight prices on average. 12% potential price decrease ($40 potential savings vs. average RT price).
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Average for round-trip flights in September 2025
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Find flight deals from Midway to Madison

Cheapest flights from Midway to Madison
Explore the most affordable flight options available from Midway to Madison. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 15, 2025.

This Kiwi.com deal was found by Cheapflights users on 9/13. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/286:30 amMDW - MSN
2 stops36h 44mFrontier
Thu 10/27:59 pmMSN - MDW
1 stop19h 54mFrontier
Deal found 9/13$282
This Kiwi.com deal was found by Cheapflights users on 9/14. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/302:32 pmMDW - MSN
2 stops18h 36mMultiple Airlines
Sat 10/49:48 amMSN - MDW
1 stop26h 56mMultiple Airlines
Deal found 9/14$291
This Kiwi.com deal was found by Cheapflights users on 9/15. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/2710:51 amMDW - MSN
2 stops32h 23mMultiple Airlines
Sat 10/49:48 amMSN - MDW
1 stop26h 56mMultiple Airlines
Deal found 9/15$369
This Kiwi.com deal was found by Cheapflights users on 9/14. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/712:14 pmMDW - MSN
2 stops20h 54mMultiple Airlines
Sun 11/98:00 pmMSN - MDW
1 stop15h 30mMultiple Airlines
Deal found 9/14$432
This Kiwi.com deal was found by Cheapflights users on 9/14. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/118:35 amMDW - MSN
1 stop8h 53mMultiple Airlines
Sun 10/127:59 pmMSN - MDW
1 stop13h 32mMultiple Airlines
Deal found 9/14$475
This Kiwi.com deal was found by Cheapflights users on 9/14. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/712:30 pmMDW - MSN
1 stop6h 45mFrontier
Sun 11/98:00 pmMSN - MDW
1 stop15h 30mFrontier
Deal found 9/14$511
This Kiwi.com deal was found by Cheapflights users on 9/13. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/1310:31 amMDW - MSN
1 stop8h 43mFrontier
Mon 10/207:59 pmMSN - MDW
2 stops27h 21mFrontier
Deal found 9/13$546

Cheapflights Fare Finder

 
Customize your flight search to find flights from Midway to Madison 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 15, 2025.
Use the filters below to find and compare flights from Chicago Midway Airport to Madison that are best for you.

Fly from

Midway

Fly to

Madison

Route

Depart

Return

Price

ChicagoMadison

MDW - MSN

MDWMSN

Chicago Midway

Sun 9/28

6:30 am-7:14 pm

2 stops36h 44m

Madison Truax Field

Thu 10/2

7:59 pm-3:53 pm

1 stop19h 54m

$282

ChicagoMadison

MDW - MSN

MDWMSN

Chicago Midway

Tue 9/30

2:32 pm-9:08 am

2 stops18h 36m

Madison Truax Field

Sat 10/4

9:48 am-12:44 pm

1 stop26h 56m

$291

ChicagoMadison

MDW - MSN

MDWMSN

Chicago Midway

Sat 9/27

10:51 am-7:14 pm

2 stops32h 23m

Madison Truax Field

Sat 10/4

9:48 am-12:44 pm

1 stop26h 56m

$369

ChicagoMadison

MDW - MSN

MDWMSN

Chicago Midway

Fri 11/7

12:14 pm-9:08 am

2 stops20h 54m

Madison Truax Field

Sun 11/9

8:00 pm-11:30 am

1 stop15h 30m

$432

ChicagoMadison

MDW - MSN

MDWMSN

Chicago Midway

Sat 10/11

8:35 am-5:28 pm

1 stop8h 53m

Madison Truax Field

Sun 10/12

7:59 pm-9:31 am

1 stop13h 32m

$475

ChicagoMadison

MDW - MSN

MDWMSN

Chicago Midway

Mon 10/13

10:31 am-7:14 pm

1 stop8h 43m

Madison Truax Field

Mon 10/20

7:59 pm-11:20 pm

2 stops27h 21m

$546

ChicagoMadison

MDW - MSN

MDWMSN

Chicago Midway

Sat 3/14

2:00 pm-10:08 pm

1 stop8h 08m

Madison Truax Field

Tue 3/17

10:55 am-6:08 pm

1 stop7h 13m

$572

ChicagoMadison

MDW - MSN

MDWMSN

Chicago Midway

Tue 10/14

8:05 am-5:28 pm

2 stops33h 23m

$164

ChicagoMadison

MDW - MSN

MDWMSN

Chicago Midway

Sat 10/11

8:35 am-5:28 pm

1 stop8h 53m

$193

ChicagoMadison

MDW - MSN

MDWMSN

Chicago Midway

Sun 9/21

6:21 am-7:14 pm

2 stops36h 53m

$207

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/14

Showing 1-10 of 13 results
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Best time to book a flight from Midway to Madison

Have a flexible travel schedule? Discover the best time to fly to Madison from Midway 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.

Related info for your journey

Find useful and relevant information for your journey from Midway to Madison. 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 into for flights to Madison from Chicago Midway?

    Madison Truax Field (MSN) is the airport you will fly into if you book a flight from Chicago Midway to Madison. You should not have trouble finding flights to Truax Field from Chicago Midway; the airport handles an average of 0 inbound flights from Chicago Midway per day. You should also have plenty of airline options to choose from since 0 airlines have flights to the Madison airport from Chicago Midway. It is only a 5.4 mi journey from Truax Field (MSN) to Madison’s city center.

  • How long is the flight from Chicago Midway Airport to Madison?

    For as low as $282, Frontier can have you in Madison from Chicago Midway Airport in 36h 44m. There are 123 mi between Chicago Midway Airport and Madison.

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

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

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

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

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

    Yes. Cheapflights offers flight deals from Midway to Madison 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 Chicago Midway Airport to Madison?

    Currently, January is the cheapest month in which you can book a flight from Chicago Midway Airport to Madison (average of $338). Flying from Chicago Midway Airport to Madison in March is currently the most expensive (average of $422). 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

Traveling to a place near Madison?

Book flights to Madison if you plan to visit one of these locations
Portage
Middleton
Baraboo
Fitchburg

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