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$225+ 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 8/15. Fares are subject to change and may not be available on all flights or dates of travel.
MSN — MDW
Jul 21 — Jul 281
Tue 7/21
Tue 7/28
1 adult, Economy
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Cheap flight deals from Madison to Midway

One-way flights from Madison to Midway
Search for one-way flight options from Madison to Midway. Find affordable one-way fares based on user searches. Data last updated June 21, 2026.

This Kiwi.com deal was found by Cheapflights users on 6/16. 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 8/157:55 pm
MSN
-
MDW
2 stops26h 08m
Multiple Airlines
Deal found 6/16$225
This Kiwi.com deal was found by Cheapflights users on 6/16. 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 7/16:05 pm
MSN
-
MDW
2 stops28h 06m
Multiple Airlines
Deal found 6/16$251
This Kiwi.com deal was found by Cheapflights users on 6/18. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/36:50 pm
MSN
-
MDW
2 stops27h 21m
Multiple Airlines
Deal found 6/18$266
This Kiwi.com deal was found by Cheapflights users on 6/20. 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.
Thu 7/237:55 pm
MSN
-
MDW
2 stops26h 08m
Frontier
Deal found 6/20$353
This Kiwi.com deal was found by Cheapflights users on 6/16. 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 7/27:59 pm
MSN
-
MDW
2 stops43h 16m
Frontier
Deal found 6/16$388
This Kiwi.com deal was found by Cheapflights users on 6/20. 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.
Thu 7/237:55 pm
MSN
-
MDW
3 stops18h 43m
Multiple Airlines
Deal found 6/20$464
This Delta deal was found by Cheapflights users on 6/16. 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.
Wed 7/18:52 am
MSN
-
MDW
1 stop4h 17m
Delta
Deal found 6/16$792
This Delta deal was found by Cheapflights users on 6/16. 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.
Thu 7/29:30 am
MSN
-
MDW
1 stop3h 16m
Delta
Deal found 6/16$907

Find 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 June 21, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Popular in

April

Cheapest in

November

Average price

$239
Provider with most accurate pricing for Madison Truax Field-Chicago Midway flight deals.
Search Deals
Provider most trusted by Cheapflights users for Madison Truax Field-Chicago Midway flights.
Search Deals
Highest demand for flights based on searches. 26% potential increase in price ($134 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 13% potential price decrease ($46 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in June 2026
Search Deals

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 June 21, 2026.
Use the filters below to find and compare flights from Madison to Chicago Midway Airport that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest one-way

MadisonChicago

MSN - MDW

MSNMDW

Madison Truax Field

Sat 8/15

7:55 pm-10:03 pm

2 stops26h 08m

$225

MadisonChicago

MSN - MDW

MSNMDW

Madison Truax Field

Wed 7/1

6:05 pm-10:11 pm

2 stops28h 06m

$251

MadisonChicago

MSN - MDW

MSNMDW

Madison Truax Field

Fri 7/3

6:50 pm-10:11 pm

2 stops27h 21m

$266

MadisonChicago

MSN - MDW

MSNMDW

Madison Truax Field

Thu 7/23

7:55 pm-10:03 pm

2 stops26h 08m

$353

MadisonChicago

MSN - MDW

MSNMDW

Madison Truax Field

Thu 7/23

7:55 pm-2:38 pm

3 stops18h 43m

$464
Quickest one-way

MadisonChicago

MSN - MDW

MSNMDW

Madison Truax Field

Wed 7/1

8:52 am-1:09 pm

1 stop4h 17m

$792

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/16

Sorted by cheapest first

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 June.
ProviderPrice AccuracyTrust Score*
FlightHubPrice Accuracy3 starsTrust Score*3 stars
ExpediaPrice Accuracy1 starTrust 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.

  • 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
Benton Harbor
Lansing
Merrillville
Hammond
Porter

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