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$399+ Cheap flights from Madison (MSN) to Midway (MDW)

This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 12/31. Fares are subject to change and may not be available on all flights or dates of travel.
MSN — MDW
Dec 10 — Dec 171
Wed 12/10
Wed 12/17
1 adult, Economy
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Cheap flight deals from Madison to Midway

Discover tips and strategies to find the most affordable flight options for your journey from Madison (MSN) to Midway (MDW). 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 10, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

Expedia
3 stars

Round-trip from

$399
(Kiwi.com)

Popular in

May

Cheapest in

June

Average price

$179
Provider with most accurate pricing for Madison Truax Field-Chicago Midway flight deals.
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Provider most trusted by Cheapflights users for Madison Truax Field-Chicago Midway flights.
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From Madison Truax Field to Chicago Midway
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Highest demand for flights based on searches. 4% potential increase in price ($10 potential increase over avg. RT price).
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Cheapest flight prices on average. 4% potential price decrease ($10 potential savings vs. average RT price).
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Average for round-trip flights in November 2025
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Find flight deals from Madison to Midway

Cheapest flights from Madison to Midway
Explore the most affordable flight options available from Madison to Midway. Find the lowest fares from popular airlines and budget airlines, with prices last updated on November 10, 2025.

This Kiwi.com deal was found by Cheapflights users on 11/7. 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 12/316:08 pmMSN - MDW
2 stops23h 30mMultiple Airlines
Sun 1/410:50 pmMDW - MSN
1 stop15h 11mMultiple Airlines
Deal found 11/7$399
This Kiwi.com deal was found by Cheapflights users on 11/7. 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 12/512:10 pmMSN - MDW
2 stops25h 49mMultiple Airlines
Fri 12/123:52 pmMDW - MSN
1 stop25h 36mMultiple Airlines
Deal found 11/7$553
This Kiwi.com deal was found by Cheapflights users on 11/7. 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 11/86:08 pmMSN - MDW
1 stop15h 04mMultiple Airlines
Sun 11/912:30 pmMDW - MSN
1 stop6h 45mMultiple Airlines
Deal found 11/7$826
This Kiwi.com deal was found by Cheapflights users on 11/9. 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 11/108:00 pmMSN - MDW
2 stops15h 38mFrontier
Mon 11/1712:30 pmMDW - MSN
1 stop6h 45mFrontier
Deal found 11/9$886

Cheapflights Fare Finder

 
Customize your flight search to find flights from Madison to Midway 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 10, 2025.
Use the filters below to find and compare flights from Madison to Chicago Midway Airport that are best for you.

Fly from

Madison

Fly to

Midway

Route

Depart

Return

Price

MadisonChicago

MSN - MDW

MSNMDW

Madison Truax Field

Wed 3/4

10:54 am-6:37 pm

1 stop7h 43m

Chicago Midway

Sat 3/7

9:50 am-10:40 pm

1 stop12h 50m

$454

MadisonChicago

MSN - MDW

MSNMDW

Madison Truax Field

Fri 12/5

12:10 pm-1:59 pm

2 stops25h 49m

Chicago Midway

Fri 12/12

3:52 pm-5:28 pm

1 stop25h 36m

$553

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/7

Compare providers for flights from Madison to Midway

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 Madison to Midway in November.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy2 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 Madison-Chicago Midway Airport flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Madison-Chicago Midway Airport flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Madison-Chicago Midway Airport flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Madison-Chicago Midway Airport flights, Cheapflights users trust Expedia the most. Expedia 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 Madison-Chicago Midway Airport 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 Madison to Midway

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

    Located just 5.4 mi from the city center, Madison Truax Field is the airport most travelers will use when flying to Chicago Midway from Madison. Booking flights from Truax Field (MSN) to Chicago Midway should be relatively easy as there are 0 daily outbound flights to Chicago Midway from 0 different airlines.

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

    There are many flights that can get you from Madison to Chicago Midway Airport in 7h 43m. Fly via Delta to get the fastest option. Airlines will cover a distance of 123 mi.

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

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

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

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

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

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

Book flights to Chicago Midway Airport if you plan to visit one of these locations
Lansing
Hammond
Porter
Benton Harbor
Merrillville

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