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$171+ 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 12/4. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — MSN
Dec 13 — Dec 201
Sat 12/13
Sat 12/20
1 adult, Economy
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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 November 13, 2025.

This Delta deal was found by Cheapflights users on 11/11. 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 12/166:40 pmMDW - MSN
1 stop18h 10mDelta
Thu 12/257:00 amMSN - MDW
1 stop10h 26mDelta
Deal found 11/11$405
This Delta deal was found by Cheapflights users on 11/11. 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.
Mon 12/156:40 pmMDW - MSN
1 stop14h 20mDelta
Thu 12/257:00 amMSN - MDW
1 stop10h 26mDelta
Deal found 11/11$432
This Delta deal was found by Cheapflights users on 11/11. 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 12/161:50 pmMDW - MSN
1 stop9h 07mDelta
Tue 12/236:31 amMSN - MDW
1 stop10h 48mDelta
Deal found 11/11$434
This Delta deal was found by Cheapflights users on 11/11. 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 12/166:40 pmMDW - MSN
1 stop14h 20mDelta
Wed 12/247:00 amMSN - MDW
1 stop10h 26mDelta
Deal found 11/11$445
This Delta deal was found by Cheapflights users on 11/11. 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 12/161:50 pmMDW - MSN
1 stop9h 07mDelta
Sun 12/285:01 pmMSN - MDW
1 stop18h 05mDelta
Deal found 11/11$454
This Kiwi.com deal was found by Cheapflights users on 11/11. 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 12/2110:50 pmMDW - MSN
1 stop15h 11mFrontier
Mon 12/292:56 pmMSN - MDW
1 stop28h 59mFrontier
Deal found 11/11$463
This Delta deal was found by Cheapflights users on 11/11. 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.
Mon 12/159:34 amMDW - MSN
1 stop8h 04mDelta
Wed 12/247:00 amMSN - MDW
1 stop10h 26mDelta
Deal found 11/11$472
This Delta deal was found by Cheapflights users on 11/11. 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 12/169:59 amMDW - MSN
1 stop12h 58mDelta
Mon 12/225:01 pmMSN - MDW
1 stop18h 05mDelta
Deal found 11/11$474
This Kiwi.com deal was found by Cheapflights users on 11/11. 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 11/145:57 pmMDW - MSN
1 stop15h 11mMultiple Airlines
Sun 11/168:00 pmMSN - MDW
2 stops21h 01mMultiple Airlines
Deal found 11/11$678
This Kiwi.com deal was found by Cheapflights users on 11/11. 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 12/2110:50 pmMDW - MSN
1 stop15h 11mFrontier
Sun 12/287:17 pmMSN - MDW
2 stops18h 04mFrontier
Deal found 11/11$758

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 November 13, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$405
(Delta)

One-way from

$171
(Kiwi.com)

Popular in

April

Cheapest in

December

Average price

$413
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. 35% potential increase in price ($211 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 12% potential price decrease ($43 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in November 2025
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 November 13, 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

Tue 12/16

6:40 pm-12:50 pm

1 stop18h 10m

Madison Truax Field

Thu 12/25

7:00 am-5:26 pm

1 stop10h 26m

$405

ChicagoMadison

MDW - MSN

MDWMSN

Chicago Midway

Wed 12/17

1:14 pm-8:30 pm

1 stop7h 16m

Madison Truax Field

Thu 12/25

7:00 am-5:26 pm

1 stop10h 26m

$405

ChicagoMadison

MDW - MSN

MDWMSN

Chicago Midway

Mon 12/15

6:40 pm-9:00 am

1 stop14h 20m

Madison Truax Field

Thu 12/25

7:00 am-5:26 pm

1 stop10h 26m

$432

ChicagoMadison

MDW - MSN

MDWMSN

Chicago Midway

Wed 12/17

1:50 pm-10:57 pm

1 stop9h 07m

Madison Truax Field

Tue 12/23

6:31 am-5:19 pm

1 stop10h 48m

$434

ChicagoMadison

MDW - MSN

MDWMSN

Chicago Midway

Tue 12/16

1:50 pm-10:57 pm

1 stop9h 07m

Madison Truax Field

Tue 12/23

6:31 am-5:19 pm

1 stop10h 48m

$434

ChicagoMadison

MDW - MSN

MDWMSN

Chicago Midway

Wed 12/17

1:14 pm-9:00 am

1 stop19h 46m

Madison Truax Field

Wed 12/24

7:00 am-5:26 pm

1 stop10h 26m

$445

ChicagoMadison

MDW - MSN

MDWMSN

Chicago Midway

Tue 12/16

6:40 pm-9:00 am

1 stop14h 20m

Madison Truax Field

Wed 12/24

7:00 am-5:26 pm

1 stop10h 26m

$445

ChicagoMadison

MDW - MSN

MDWMSN

Chicago Midway

Sat 3/14

2:00 pm-10:08 pm

1 stop8h 08m

Madison Truax Field

Tue 3/17

6:15 am-6:08 pm

1 stop11h 53m

$454

ChicagoMadison

MDW - MSN

MDWMSN

Chicago Midway

Wed 12/17

1:50 pm-10:57 pm

1 stop9h 07m

Madison Truax Field

Mon 12/29

6:31 am-5:19 pm

1 stop10h 48m

$454

ChicagoMadison

MDW - MSN

MDWMSN

Chicago Midway

Wed 12/17

1:50 pm-10:57 pm

1 stop9h 07m

Madison Truax Field

Sun 12/28

5:01 pm-11:06 am

1 stop18h 05m

$454

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/12

Showing 1-10 of 11 results
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Compare providers for flights from Midway to Madison

Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Midway to Madison in November.
ProviderPrice AccuracyTrust Score*
eDreamsPrice Accuracy3 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*1 star

*The Trust Score is based on feedback from users after their booking experience. It measures overall satisfaction, helping us identify issues like hidden fees, problems during the ticketing process, and the quality of customer service. This score is our best indicator of the provider's quality and reliability.

  • Most accurate provider: When it comes to deals on Chicago Midway Airport-Madison flights, users find the pricing of eDreams to be most consistent on Cheapflights vs. eDreams Users can find the same prices on Chicago Midway Airport-Madison flight deals on Cheapflights vs. eDreams >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 eDreams the most. eDreams 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 $405, Delta can have you in Madison from Chicago Midway Airport in 18h 10m. 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
Portage
Middleton
Baraboo
Fitchburg

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