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$199+ 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 3/4. Fares are subject to change and may not be available on all flights or dates of travel.
MSN — MDW
Mar 7 — Mar 141
Sat 3/7
Sat 3/14
1 adult, Economy
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Cheap 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 February 5, 2026.

This Kiwi.com deal was found by Cheapflights users on 2/3. 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 2/186:36 pm
MSN
-
MDW
1 stop19h 50m
Multiple Airlines
Fri 2/206:48 pm
MDW
-
MSN
2 stops23h 08m
Multiple Airlines
Deal found 2/3$384
This Kiwi.com deal was found by Cheapflights users on 2/3. 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 3/46:36 pm
MSN
-
MDW
1 stop19h 50m
Multiple Airlines
Fri 3/132:41 pm
MDW
-
MSN
2 stops18h 27m
Multiple Airlines
Deal found 2/3$459
This Kiwi.com deal was found by Cheapflights users on 2/5. 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 3/146:36 pm
MSN
-
MDW
1 stop21h 16m
Multiple Airlines
Tue 3/176:00 am
MDW
-
MSN
2 stops11h 21m
Multiple Airlines
Deal found 2/5$530
This Kiwi.com deal was found by Cheapflights users on 2/5. 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 2/76:36 pm
MSN
-
MDW
1 stop25h 16m
Multiple Airlines
Sat 2/148:00 am
MDW
-
MSN
1 stop9h 56m
Multiple Airlines
Deal found 2/5$629
This Kiwi.com deal was found by Cheapflights users on 2/3. 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 2/186:36 pm
MSN
-
MDW
1 stop19h 50m
Multiple Airlines
Sun 2/229:04 pm
MDW
-
MSN
2 stops20h 28m
Multiple Airlines
Deal found 2/3$703
This Kiwi.com deal was found by Cheapflights users on 2/4. 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 2/192:45 pm
MSN
-
MDW
1 stop8h 56m
Multiple Airlines
Sun 2/229:04 pm
MDW
-
MSN
2 stops20h 28m
Multiple Airlines
Deal found 2/4$802
This Delta deal was found by Cheapflights users on 2/5. 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 2/1210:59 am
MSN
-
MDW
1 stop7h 41m
Delta
Sat 2/1411:45 am
MDW
-
MSN
1 stop11h 03m
Delta
Deal found 2/5$873

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 February 5, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$384
(Kiwi.com)

One-way from

$199
(Kiwi.com)

Popular in

March

Cheapest in

June

Average price

$283
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
From Madison Truax Field to Chicago Midway
Search Deals
One-way flight from Madison Truax Field to Chicago Midway
Search Deals
Highest demand for flights based on searches. 22% potential increase in price ($73 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 7% potential price decrease ($19 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in February 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 February 5, 2026.
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 2/18

6:36 pm-2:26 pm

1 stop19h 50m

Chicago Midway

Fri 2/20

6:48 pm-5:56 pm

2 stops23h 08m

$384

MadisonChicago

MSN - MDW

MSNMDW

Madison Truax Field

Wed 3/4

6:36 pm-2:26 pm

1 stop19h 50m

Chicago Midway

Fri 3/13

2:41 pm-9:08 am

2 stops18h 27m

$459

MadisonChicago

MSN - MDW

MSNMDW

Madison Truax Field

Sat 3/14

6:36 pm-3:52 pm

1 stop21h 16m

Chicago Midway

Tue 3/17

6:00 am-5:21 pm

2 stops11h 21m

$530

MadisonChicago

MSN - MDW

MSNMDW

Madison Truax Field

Wed 2/18

6:36 pm-2:26 pm

1 stop19h 50m

Chicago Midway

Sun 2/22

9:04 pm-5:32 pm

2 stops20h 28m

$703

MadisonChicago

MSN - MDW

MSNMDW

Madison Truax Field

Thu 2/19

2:45 pm-11:41 pm

1 stop8h 56m

Chicago Midway

Sun 2/22

9:04 pm-5:32 pm

2 stops20h 28m

$802

MadisonChicago

MSN - MDW

MSNMDW

Madison Truax Field

Wed 3/4

6:36 pm-2:26 pm

1 stop19h 50m

$199

MadisonChicago

MSN - MDW

MSNMDW

Madison Truax Field

Tue 6/16

9:00 am-6:05 pm

1 stop9h 05m

$326

MadisonChicago

MSN - MDW

MSNMDW

Madison Truax Field

Thu 2/19

2:45 pm-11:41 pm

1 stop8h 56m

$344

MadisonChicago

MSN - MDW

MSNMDW

Madison Truax Field

Sun 6/14

6:15 am-1:07 pm

1 stop6h 52m

$345

MadisonChicago

MSN - MDW

MSNMDW

Madison Truax Field

Wed 3/11

6:00 am-1:25 pm

1 stop7h 25m

$348

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/5

Showing 1-10 of 14 results
1
2

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 February.
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
Lansing
Merrillville
Hammond
Porter
Benton Harbor

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