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$170+ Cheap flights from Madison (MSN) to Midway (MDW)

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 11/1. Fares are subject to change and may not be available on all flights or dates of travel.
MSN — MDW
Oct 24 — Oct 311
Fri 10/24
Fri 10/31
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 September 24, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$349
(Kiwi.com)

One-way from

$170
(Kiwi.com)

Popular in

November

Cheapest in

June

Average price

$209
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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One-way flight from Madison Truax Field to Chicago Midway
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Highest demand for flights based on searches. 31% potential increase in price ($137 potential increase over avg. RT price).
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Cheapest flight prices on average. 14% potential price decrease ($38 potential savings vs. average RT price).
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Average for round-trip flights in September 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 September 24, 2025.

This Kiwi.com deal was found by Cheapflights users on 9/22. 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.
Thu 10/166:58 pmMSN - MDW
1 stop29h 26mFrontier
Thu 10/236:24 pmMDW - MSN
1 stop24h 50mFrontier
Deal found 9/22$349
This Kiwi.com deal was found by Cheapflights users on 9/23. 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.
Thu 10/308:00 pmMSN - MDW
1 stop15h 30mFrontier
Sun 11/26:06 pmMDW - MSN
2 stops25h 09mFrontier
Deal found 9/23$374
This Kiwi.com deal was found by Cheapflights users on 9/22. 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 10/67:59 pmMSN - MDW
2 stops17h 39mMultiple Airlines
Fri 10/109:45 amMDW - MSN
1 stop23h 23mMultiple Airlines
Deal found 9/22$377
This Kiwi.com deal was found by Cheapflights users on 9/24. 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.
Thu 10/97:59 pmMSN - MDW
1 stop28h 25mFrontier
Mon 10/1310:31 amMDW - MSN
1 stop8h 43mFrontier
Deal found 9/24$405
This Kiwi.com deal was found by Cheapflights users on 9/22. 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 10/67:59 pmMSN - MDW
2 stops17h 39mFrontier
Thu 10/96:24 pmMDW - MSN
1 stop24h 50mFrontier
Deal found 9/22$548

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 September 24, 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

Thu 10/16

6:58 pm-12:24 am

1 stop29h 26m

Chicago Midway

Thu 10/23

6:24 pm-7:14 pm

1 stop24h 50m

$349

MadisonChicago

MSN - MDW

MSNMDW

Madison Truax Field

Thu 10/30

8:00 pm-11:30 am

1 stop15h 30m

Chicago Midway

Sun 11/2

6:06 pm-7:15 pm

2 stops25h 09m

$374

MadisonChicago

MSN - MDW

MSNMDW

Madison Truax Field

Mon 10/6

7:59 pm-1:38 pm

2 stops17h 39m

Chicago Midway

Fri 10/10

9:45 am-9:08 am

1 stop23h 23m

$377

MadisonChicago

MSN - MDW

MSNMDW

Madison Truax Field

Thu 10/9

7:59 pm-12:24 am

1 stop28h 25m

Chicago Midway

Mon 10/13

10:31 am-7:14 pm

1 stop8h 43m

$405

MadisonChicago

MSN - MDW

MSNMDW

Madison Truax Field

Wed 3/4

6:15 am-1:08 pm

1 stop6h 53m

Chicago Midway

Sat 3/7

2:00 pm-10:08 pm

1 stop8h 08m

$419

MadisonChicago

MSN - MDW

MSNMDW

Madison Truax Field

Sat 11/1

9:48 am-11:26 am

2 stops25h 38m

$170

MadisonChicago

MSN - MDW

MSNMDW

Madison Truax Field

Sun 10/12

7:59 pm-9:31 am

1 stop13h 32m

$188

MadisonChicago

MSN - MDW

MSNMDW

Madison Truax Field

Fri 10/3

7:59 pm-9:23 am

2 stops37h 24m

$244

MadisonChicago

MSN - MDW

MSNMDW

Madison Truax Field

Thu 11/20

2:40 pm-6:12 pm

2 stops27h 32m

$276

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/23

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 September.
ProviderPrice AccuracyTrust Score*
FlightHubPrice Accuracy3 starsTrust Score*3 stars
ExpediaPrice Accuracy2 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 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 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 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 29h 26m. Fly via Frontier 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.

  • What is the cheapest month to book a flight from Madison to Chicago Midway Airport?

    Currently, April is the cheapest month in which you can book a flight from Madison to Chicago Midway Airport (average of $160). Flying from Madison to Chicago Midway Airport in November is currently the most expensive (average of $249). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

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
Merrillville
Lansing
Hammond
Benton Harbor
Porter
Chesterton

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