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$161+ 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 9/1. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — MSN
Sep 3 — Sep 101
Thu 9/3
Thu 9/10
1 adult, Economy
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Cheap 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 August 4, 2026.

This Delta deal was found by Cheapflights users on 7/31. 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.
Thu 11/265:25 pm
MDW
-
MSN
1 stop4h 09m
Delta
Sun 11/296:30 am
MSN
-
MDW
1 stop5h 20m
Delta
Deal found 7/31$1,019
This Delta deal was found by Cheapflights users on 8/3. 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.
Thu 9/177:13 pm
MDW
-
MSN
1 stop3h 48m
Delta
Thu 9/2412:00 pm
MSN
-
MDW
1 stop6h 19m
Delta
Deal found 8/3$1,163
This Delta deal was found by Cheapflights users on 7/31. 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.
Thu 12/315:35 pm
MDW
-
MSN
1 stop5h 20m
Delta
Mon 1/411:00 am
MSN
-
MDW
1 stop5h 50m
Delta
Deal found 7/31$1,243
This KAYAK 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/49:24 am
MDW
-
MSN
1 stop3h 23m
Delta
Fri 8/79:06 am
MSN
-
MDW
1 stop4h 04m
Delta
Deal found 7/30$1,244
This Delta deal was found by Cheapflights users on 7/31. 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.
Fri 8/211:51 pm
MDW
-
MSN
1 stop3h 57m
Delta
Sun 8/239:06 am
MSN
-
MDW
1 stop4h 04m
Delta
Deal found 7/31$1,273
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.
Thu 8/271:51 pm
MDW
-
MSN
1 stop3h 57m
Delta
Thu 9/312:10 pm
MSN
-
MDW
1 stop5h 51m
Delta
Deal found 7/30$1,283
This Delta deal was found by Cheapflights users on 7/31. 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.
Thu 8/61:51 pm
MDW
-
MSN
1 stop3h 57m
Delta
Sun 8/91:35 pm
MSN
-
MDW
1 stop4h 58m
Delta
Deal found 7/31$1,601

Find 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 August 4, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$1,019
(Delta)

One-way from

$161
(Kiwi.com)

Popular in

June

Cheapest in

December

Average price

$470
Provider with most accurate pricing for Chicago Midway-Madison Truax Field flight deals.
Search Deals
Provider most trusted by Cheapflights users for Chicago Midway-Madison Truax Field flights.
Search Deals
From Chicago Midway to Madison Truax Field
Search Deals
One-way flight from Chicago Midway to Madison Truax Field
Search Deals
Highest demand for flights based on searches. 18% potential increase in price ($99 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 4% potential price decrease ($20 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in August 2026
Search Deals

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 August 4, 2026.
Use the filters below to find and compare flights from Chicago Midway Airport to Madison that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

ChicagoMadison

MDW - MSN

MDWMSN

Chicago Midway

Sat 9/19

9:59 am-2:07 pm

1 stop4h 08m

Madison Truax Field

Sun 9/20

2:47 pm-6:19 pm

1 stop3h 32m

$1,163

ChicagoMadison

MDW - MSN

MDWMSN

Chicago Midway

Thu 9/17

7:13 pm-11:01 pm

1 stop3h 48m

Madison Truax Field

Thu 9/24

12:00 pm-6:19 pm

1 stop6h 19m

$1,163

ChicagoMadison

MDW - MSN

MDWMSN

Chicago Midway

Tue 9/15

7:13 pm-11:01 pm

1 stop3h 48m

Madison Truax Field

Tue 9/22

9:02 am-1:20 pm

1 stop4h 18m

$1,163

ChicagoMadison

MDW - MSN

MDWMSN

Chicago Midway

Thu 9/24

2:00 pm-5:57 pm

1 stop3h 57m

Madison Truax Field

Sat 10/10

7:59 am-11:47 am

1 stop3h 48m

$1,163

ChicagoMadison

MDW - MSN

MDWMSN

Chicago Midway

Fri 10/23

12:27 pm-7:06 pm

1 stop6h 39m

Madison Truax Field

Sun 10/25

6:00 am-11:47 am

1 stop5h 47m

$1,163

ChicagoMadison

MDW - MSN

MDWMSN

Chicago Midway

Mon 8/31

9:59 am-2:11 pm

1 stop4h 12m

Madison Truax Field

Mon 9/7

12:10 pm-6:01 pm

1 stop5h 51m

$1,273

ChicagoMadison

MDW - MSN

MDWMSN

Chicago Midway

Fri 8/21

1:51 pm-5:48 pm

1 stop3h 57m

Madison Truax Field

Sun 8/23

9:06 am-1:10 pm

1 stop4h 04m

$1,273
Quickest round-trip

ChicagoMadison

MDW - MSN

MDWMSN

Chicago Midway

Sun 9/13

2:00 pm-5:57 pm

1 stop3h 57m

Madison Truax Field

Sun 9/20

2:47 pm-6:19 pm

1 stop3h 32m

$1,283

ChicagoMadison

MDW - MSN

MDWMSN

Chicago Midway

Thu 8/27

1:51 pm-5:48 pm

1 stop3h 57m

Madison Truax Field

Thu 9/3

12:10 pm-6:01 pm

1 stop5h 51m

$1,283

ChicagoMadison

MDW - MSN

MDWMSN

Chicago Midway

Thu 8/6

1:51 pm-5:48 pm

1 stop3h 57m

Madison Truax Field

Sun 8/9

1:35 pm-6:33 pm

1 stop4h 58m

$1,601

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/2

Showing 1-10 of 17 resultsSorted by cheapest first
1
2
  • Most accurate provider: When it comes to deals on Chicago Midway Airport-Madison flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Chicago Midway Airport-Madison flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Chicago Midway Airport-Madison flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Chicago Midway Airport-Madison flights, Cheapflights users trust FlightHub the most. FlightHub has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Chicago Midway Airport-Madison flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

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 $1,163, Delta can have you in Madison from Chicago Midway Airport in 4h 08m. 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.

See more FAQs

Traveling to a place near Madison?

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

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