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$263+ 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 4/2. Fares are subject to change and may not be available on all flights or dates of travel.
MSN — MDW
Apr 24 — May 11
Fri 4/24
Fri 5/1
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 March 25, 2026.

This Kiwi.com deal was found by Cheapflights users on 3/21. 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 4/186:36 pm
MSN
-
MDW
1 stop13h 23m
Multiple Airlines
Sat 4/259:14 am
MDW
-
MSN
1 stop8h 42m
Multiple Airlines
Deal found 3/21$367
This Kiwi.com deal was found by Cheapflights users on 3/24. 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.
Fri 5/86:50 pm
MSN
-
MDW
2 stops16h 14m
Multiple Airlines
Fri 5/154:52 pm
MDW
-
MSN
1 stop26h 23m
Multiple Airlines
Deal found 3/24$397
This Kiwi.com deal was found by Cheapflights users on 3/24. 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.
Wed 4/156:36 pm
MSN
-
MDW
1 stop13h 28m
Multiple Airlines
Fri 4/176:00 am
MDW
-
MSN
2 stops27h 08m
Multiple Airlines
Deal found 3/24$426
This Kiwi.com deal was found by Cheapflights users on 3/22. 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.
Wed 4/156:36 pm
MSN
-
MDW
2 stops24h 55m
Multiple Airlines
Sat 4/189:14 am
MDW
-
MSN
1 stop8h 42m
Multiple Airlines
Deal found 3/22$453
This Kiwi.com deal was found by Cheapflights users on 3/21. 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 4/1010:10 am
MSN
-
MDW
2 stops36h 19m
Multiple Airlines
Sat 4/189:14 am
MDW
-
MSN
1 stop8h 42m
Multiple Airlines
Deal found 3/21$592
This Kiwi.com deal was found by Cheapflights users on 3/22. 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 3/262:45 pm
MSN
-
MDW
1 stop30h 51m
Multiple Airlines
Sat 3/286:15 am
MDW
-
MSN
1 stop11h 41m
Multiple Airlines
Deal found 3/22$821

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 March 25, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$367
(Kiwi.com)

One-way from

$263
(Kiwi.com)

Popular in

February

Cheapest in

June

Average price

$344
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.
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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. 26% potential increase in price ($88 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 6% potential price decrease ($15 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in March 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 March 25, 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 round-trip
Quickest round-trip

MadisonChicago

MSN - MDW

MSNMDW

Madison Truax Field

Sat 4/18

6:36 pm-7:59 am

1 stop13h 23m

Chicago Midway

Sat 4/25

9:14 am-5:56 pm

1 stop8h 42m

$367

MadisonChicago

MSN - MDW

MSNMDW

Madison Truax Field

Fri 5/8

6:50 pm-11:04 am

2 stops16h 14m

Chicago Midway

Fri 5/15

4:52 pm-7:15 pm

1 stop26h 23m

$397

MadisonChicago

MSN - MDW

MSNMDW

Madison Truax Field

Wed 4/15

6:36 pm-8:04 am

1 stop13h 28m

Chicago Midway

Fri 4/17

6:00 am-9:08 am

2 stops27h 08m

$426

MadisonChicago

MSN - MDW

MSNMDW

Madison Truax Field

Wed 4/15

6:36 pm-7:31 pm

2 stops24h 55m

Chicago Midway

Sat 4/18

9:14 am-5:56 pm

1 stop8h 42m

$453

MadisonChicago

MSN - MDW

MSNMDW

Madison Truax Field

Sat 4/4

6:36 pm-11:57 pm

1 stop29h 21m

Chicago Midway

Wed 4/8

6:00 am-5:56 pm

2 stops11h 56m

$581

MadisonChicago

MSN - MDW

MSNMDW

Madison Truax Field

Fri 4/10

10:10 am-10:29 pm

2 stops36h 19m

Chicago Midway

Sat 4/18

9:14 am-5:56 pm

1 stop8h 42m

$592
Cheapest one-way

MadisonChicago

MSN - MDW

MSNMDW

Madison Truax Field

Thu 4/2

2:40 pm-10:19 pm

2 stops31h 39m

$263
Quickest one-way

MadisonChicago

MSN - MDW

MSNMDW

Madison Truax Field

Tue 3/31

6:01 pm-9:58 pm

1 stop27h 57m

$267

MadisonChicago

MSN - MDW

MSNMDW

Madison Truax Field

Mon 4/20

10:10 am-7:31 pm

3 stops33h 21m

$293

MadisonChicago

MSN - MDW

MSNMDW

Madison Truax Field

Mon 6/15

6:50 pm-11:09 am

3 stops40h 19m

$333

Flights are sorted by cheapest round-trip flights first.

Deals found on 3/23

Showing 1-10 of 11 resultsSorted by cheapest first
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 March.
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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