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$181+ 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 4/16. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — MSN
Apr 29 — May 61
Wed 4/29
Wed 5/6
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 March 30, 2026.

This Kiwi.com deal was found by Cheapflights users on 3/25. 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.
Wed 4/226:15 am
MDW
-
MSN
2 stops11h 41m
Multiple Airlines
Wed 4/296:36 pm
MSN
-
MDW
1 stop12h 45m
Multiple Airlines
Deal found 3/25$340
This Kiwi.com deal was found by Cheapflights users on 3/29. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/29:14 am
MDW
-
MSN
1 stop8h 42m
Multiple Airlines
Wed 5/69:54 am
MSN
-
MDW
2 stops12h 08m
Multiple Airlines
Deal found 3/29$378
This Kiwi.com deal was found by Cheapflights users on 3/27. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/156:30 am
MDW
-
MSN
2 stops11h 26m
Multiple Airlines
Sat 4/186:36 pm
MSN
-
MDW
1 stop13h 23m
Multiple Airlines
Deal found 3/27$434
This Kiwi.com deal was found by Cheapflights users on 3/26. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 3/286:15 am
MDW
-
MSN
1 stop11h 41m
Multiple Airlines
Wed 4/16:36 pm
MSN
-
MDW
1 stop28h 37m
Multiple Airlines
Deal found 3/26$768

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 March 30, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$340
(Kiwi.com)

One-way from

$181
(Kiwi.com)

Popular in

April

Cheapest in

December

Average price

$449
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. 28% potential increase in price ($152 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 6% potential price decrease ($25 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in March 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 March 30, 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

Wed 4/22

6:15 am-5:56 pm

2 stops11h 41m

Madison Truax Field

Wed 4/29

6:36 pm-7:21 am

1 stop12h 45m

$340
Quickest round-trip

ChicagoMadison

MDW - MSN

MDWMSN

Chicago Midway

Sat 5/2

9:14 am-5:56 pm

1 stop8h 42m

Madison Truax Field

Wed 5/6

9:54 am-10:02 pm

2 stops12h 08m

$378

ChicagoMadison

MDW - MSN

MDWMSN

Chicago Midway

Wed 4/15

6:30 am-5:56 pm

2 stops11h 26m

Madison Truax Field

Sat 4/18

6:36 pm-7:59 am

1 stop13h 23m

$434
Cheapest one-way

ChicagoMadison

MDW - MSN

MDWMSN

Chicago Midway

Thu 4/16

4:15 pm-9:08 am

2 stops40h 53m

$181

ChicagoMadison

MDW - MSN

MDWMSN

Chicago Midway

Wed 6/3

3:07 pm-8:25 am

3 stops41h 18m

$215

ChicagoMadison

MDW - MSN

MDWMSN

Chicago Midway

Mon 5/11

3:07 pm-9:14 am

2 stops42h 07m

$215

ChicagoMadison

MDW - MSN

MDWMSN

Chicago Midway

Tue 4/7

2:56 pm-5:56 pm

2 stops27h 00m

$341

ChicagoMadison

MDW - MSN

MDWMSN

Chicago Midway

Fri 4/10

7:20 pm-10:05 am

1 stop14h 45m

$442

ChicagoMadison

MDW - MSN

MDWMSN

Chicago Midway

Mon 4/13

9:29 am-10:51 pm

1 stop13h 22m

$540

ChicagoMadison

MDW - MSN

MDWMSN

Chicago Midway

Thu 4/9

2:05 pm-10:58 pm

1 stop8h 53m

$641

Flights are sorted by cheapest round-trip flights first.

Deals found on 3/25

Showing 1-10 of 12 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.

  • 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
Portage
Middleton
Baraboo
Fitchburg

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