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$811+ 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 8/28. Fares are subject to change and may not be available on all flights or dates of travel.
MSN — MDW
Aug 3 — Aug 101
Sun 8/3
Sun 8/10
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 July 29, 2025.

Round-trip from

$811
(Delta)

Popular in

November

Cheapest in

June

Average price

$479
From Madison Truax Field to Chicago Midway
Search Deals
Highest demand for flights based on searches. 23% potential increase in price ($107 potential increase over avg. RT price).
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Cheapest flight prices on average. 10% potential price decrease ($33 potential savings vs. average RT price).
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Average for round-trip flights in July 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 July 29, 2025.

This Delta deal was found by Cheapflights users on 7/27. 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 8/289:28 amMSN - MDW
1 stop9h 09mDelta
Sun 8/319:31 amMDW - MSN
1 stop12h 43mDelta
Deal found 7/27$811

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 July 29, 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 8/28

9:28 am-6:37 pm

1 stop9h 09m

Chicago Midway

Sun 8/31

9:31 am-10:14 pm

1 stop12h 43m

$811

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/27

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.

Reviews of airlines servicing Midway

Get insights into the airlines that provide service to Midway. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Midway. Reviews last updated July 29, 2025.
Read reviews from past customers who have flown Delta from Madison to Chicago Midway Airport. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
Delta
8.0
Very good
7,979 reviews

Food

7.3

Comfort

7.9

Overall

8.0

Crew

8.5

Boarding

8.2

Entertainment

7.9

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
Delta
8.0
Very good
7,979 reviews
Delta
8.0
Very good
7,979 reviews

Food

7.3

Comfort

7.9

Overall

8.0

Crew

8.5

Boarding

8.2

Entertainment

7.9

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!

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.

  • 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
Valparaiso
Chesterton

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