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$264+ 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 10/23. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — MSN
Nov 19 — Nov 261
Wed 11/19
Wed 11/26
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 October 20, 2025.

This Delta deal was found by Cheapflights users on 10/18. 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 12/27:02 pmMDW - MSN
1 stop17h 40mDelta
Tue 12/96:00 amMSN - MDW
1 stop7h 08mDelta
Deal found 10/18$401
This Kiwi.com deal was found by Cheapflights users on 10/20. 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 11/1712:30 pmMDW - MSN
1 stop6h 45mFrontier
Mon 11/243:20 pmMSN - MDW
2 stops20h 10mFrontier
Deal found 10/20$440
This Kiwi.com deal was found by Cheapflights users on 10/19. 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 11/75:35 pmMDW - MSN
2 stops15h 33mMultiple Airlines
Sun 11/98:00 pmMSN - MDW
1 stop15h 30mMultiple Airlines
Deal found 10/19$455
This Kiwi.com deal was found by Cheapflights users on 10/19. 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 10/19$462
This KAYAK deal was found by Cheapflights users on 10/20. 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.
Mon 11/101:15 pmMDW - MSN
1 stop7h 11mDelta
Thu 11/131:30 pmMSN - MDW
1 stop4h 38mDelta
Deal found 10/20$898

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 October 20, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$393
(Kiwi.com)

One-way from

$264
(Kiwi.com)

Popular in

April

Cheapest in

December

Average price

$315
Provider with most accurate pricing for Chicago Midway-Madison Truax Field flight deals.
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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. 37% potential increase in price ($224 potential increase over avg. RT price).
Search Deals
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 October 2025
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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 October 20, 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 12/2

7:02 pm-12:42 pm

1 stop17h 40m

Madison Truax Field

Tue 12/9

6:00 am-1:08 pm

1 stop7h 08m

$401

ChicagoMadison

MDW - MSN

MDWMSN

Chicago Midway

Mon 11/17

12:30 pm-7:15 pm

1 stop6h 45m

Madison Truax Field

Mon 11/24

3:20 pm-11:30 am

2 stops20h 10m

$440

ChicagoMadison

MDW - MSN

MDWMSN

Chicago Midway

Fri 11/7

5:35 pm-9:08 am

2 stops15h 33m

Madison Truax Field

Sun 11/9

8:00 pm-11:30 am

1 stop15h 30m

$455

ChicagoMadison

MDW - MSN

MDWMSN

Chicago Midway

Fri 11/7

12:30 pm-7:15 pm

1 stop6h 45m

Madison Truax Field

Sun 11/9

8:00 pm-11:30 am

1 stop15h 30m

$462

ChicagoMadison

MDW - MSN

MDWMSN

Chicago Midway

Mon 11/10

1:15 pm-8:26 pm

1 stop7h 11m

Madison Truax Field

Thu 11/13

1:30 pm-6:08 pm

1 stop4h 38m

$898

ChicagoMadison

MDW - MSN

MDWMSN

Chicago Midway

Thu 10/23

9:26 pm-9:08 am

3 stops35h 42m

$264

ChicagoMadison

MDW - MSN

MDWMSN

Chicago Midway

Thu 10/23

10:49 am-7:14 pm

2 stops32h 25m

$355

ChicagoMadison

MDW - MSN

MDWMSN

Chicago Midway

Sun 11/2

9:35 am-8:27 pm

1 stop10h 52m

$517

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/18

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 October.
ProviderPrice AccuracyTrust Score*
FlightHubPrice Accuracy3 starsTrust Score*3 stars
eDreamsPrice Accuracy3 starsTrust Score*3 stars

*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 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 $440, Delta can have you in Madison from Chicago Midway Airport in 6h 45m. There are 123 mi between Chicago Midway Airport and Madison. Both multi-stop and nonstop flights can be found to your destination and back.

  • 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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