$179+ 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 12/16. Fares are subject to change and may not be available on all flights or dates of travel.
MSN — MDW
Dec 3 — Dec 101
Round-trip
1 adult, Economy
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Find cheap flights from Madison to Midway with Cheapflights
1. Tell us where you want to go
Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”2. Select your favorite providers
We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.3. Compare prices and book
Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.Cheap flight deals from Madison to Midway
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Cheapest flights from Madison to MidwayExplore 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 November 3, 2026.
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 November 3, 2026.
This Mytrip deal was found by Cheapflights users on 11/2. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/1710:40 am -
3 stops32h 50m
Thu 12/246:43 am -
3 stops31h 17m
Deal found 11/2![Multiple Airlines logo]()
$852
This Expedia deal was found by Cheapflights users on 10/29. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/76:00 am -
1 stop10h 47m
Wed 11/1112:30 pm -
1 stop8h 47m
Deal found 10/29![Delta logo]()
$995
This Expedia deal was found by Cheapflights users on 10/30. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/76:00 am -
1 stop10h 47m
Thu 11/1211:27 am -
1 stop11h 23m
Deal found 10/30![Delta logo]()
$1,107
This Delta deal was found by Cheapflights users on 10/31. 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.
Sun 11/156:30 am -
1 stop5h 20m
Sun 11/225:29 pm -
1 stop3h 48m
Deal found 10/31![Delta logo]()
$1,220
This Delta deal was found by Cheapflights users on 10/31. 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.
Sun 11/2210:59 am -
1 stop5h 40m
Sun 11/295:29 pm -
1 stop3h 48m
Deal found 10/31![Delta logo]()
$1,370
This Delta deal was found by Cheapflights users on 11/2. 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.
Fri 11/2010:59 am -
1 stop5h 40m
Sun 11/225:29 pm -
1 stop3h 48m
Deal found 11/2![Delta logo]()
$1,422
This Delta deal was found by Cheapflights users on 11/1. 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.
Fri 12/1110:59 am -
1 stop5h 51m
Sat 12/125:30 pm -
1 stop3h 59m
Deal found 11/1![Delta logo]()
$1,453
Best flights from Madison to MidwayDiscover carefully curated flight deals from Madison to Midway that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated November 3, 2026.
Discover carefully curated flight deals from Madison to Midway that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated November 3, 2026.
This Delta deal was found by Cheapflights users on 10/31. 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.
Sun 11/156:30 am -
1 stop5h 20m
Sun 11/225:29 pm -
1 stop3h 48m
Deal found 10/31![Delta logo]()
$1,220
This Delta deal was found by Cheapflights users on 10/31. 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.
Sun 11/2210:59 am -
1 stop5h 40m
Sun 11/295:29 pm -
1 stop3h 48m
Deal found 10/31![Delta logo]()
$1,370
This Delta deal was found by Cheapflights users on 11/2. 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.
Fri 11/2010:59 am -
1 stop5h 40m
Sun 11/225:29 pm -
1 stop3h 48m
Deal found 11/2![Delta logo]()
$1,422
This Delta deal was found by Cheapflights users on 11/2. 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.
Sat 12/1210:59 am -
1 stop5h 51m
Sun 12/1312:39 pm -
1 stop6h 37m
Deal found 11/2![Delta logo]()
$1,453
This Delta deal was found by Cheapflights users on 11/1. 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.
Fri 12/1110:59 am -
1 stop5h 51m
Sat 12/125:30 pm -
1 stop3h 59m
Deal found 11/1![Delta logo]()
$1,453
This Delta deal was found by Cheapflights users on 11/1. 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.
Fri 12/410:59 am -
1 stop5h 51m
Sun 12/612:39 pm -
1 stop6h 37m
Deal found 11/1![Delta logo]()
$1,453
This Delta deal was found by Cheapflights users on 10/30. 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.
Sun 11/156:30 am -
1 stop5h 20m
Mon 11/1610:34 am -
1 stop3h 16m
Deal found 10/30![Delta logo]()
$1,643
This Delta deal was found by Cheapflights users on 10/30. 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.
Sat 11/1410:49 am -
1 stop5h 50m
Wed 11/1810:34 am -
1 stop3h 16m
Deal found 10/30![Delta logo]()
$1,643
This Delta deal was found by Cheapflights users on 11/1. 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.
Mon 11/1610:59 am -
1 stop5h 40m
Fri 11/205:29 pm -
1 stop3h 50m
Deal found 11/1![Delta logo]()
$1,723
This Delta deal was found by Cheapflights users on 11/1. 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.
Sat 11/146:30 am -
1 stop5h 20m
Sat 11/145:29 pm -
1 stop3h 48m
Deal found 11/1![Delta logo]()
$1,783
Last-minute flights from Madison to MidwayDiscover last-minute flight deals from Madison to Midway. Data last updated November 3, 2026 and is based on user searches.
Discover last-minute flight deals from Madison to Midway. Data last updated November 3, 2026 and is based on user searches.
This Expedia deal was found by Cheapflights users on 10/29. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/76:00 am -
1 stop10h 47m
Wed 11/1112:30 pm -
1 stop8h 47m
Deal found 10/29![Delta logo]()
$995
This Expedia deal was found by Cheapflights users on 10/30. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/76:00 am -
1 stop10h 47m
Thu 11/1211:27 am -
1 stop11h 23m
Deal found 10/30![Delta logo]()
$1,107
This Delta deal was found by Cheapflights users on 10/31. 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.
Sun 11/156:30 am -
1 stop5h 20m
Sun 11/225:29 pm -
1 stop3h 48m
Deal found 10/31![Delta logo]()
$1,220
This Delta deal was found by Cheapflights users on 11/2. 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.
Fri 11/2010:59 am -
1 stop5h 40m
Sun 11/225:29 pm -
1 stop3h 48m
Deal found 11/2![Delta logo]()
$1,422
This Delta deal was found by Cheapflights users on 10/31. 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.
Sun 11/2210:59 am -
1 stop5h 40m
Sun 11/295:29 pm -
1 stop3h 48m
Deal found 10/31![Delta logo]()
$1,370
This Delta deal was found by Cheapflights users on 11/1. 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.
Fri 12/1110:59 am -
1 stop5h 51m
Sat 12/125:30 pm -
1 stop3h 59m
Deal found 11/1![Delta logo]()
$1,453
This Mytrip deal was found by Cheapflights users on 11/2. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/1710:40 am -
3 stops32h 50m
Thu 12/246:43 am -
3 stops31h 17m
Deal found 11/2![Multiple Airlines logo]()
$852
One-way flights from Madison to MidwaySearch for one-way flight options from Madison to Midway. Find affordable one-way fares based on user searches. Data last updated November 3, 2026.
Search for one-way flight options from Madison to Midway. Find affordable one-way fares based on user searches. Data last updated November 3, 2026.
This Kiwi.com deal was found by Cheapflights users on 11/1. 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 12/1610:38 am -
2 stops36h 39m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/1![Multiple Airlines logo]()
$179
This Kiwi.com deal was found by Cheapflights users on 11/3. 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.
Tue 1/2611:05 am -
2 stops36h 41m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/3![Multiple Airlines logo]()
$185
This Delta deal was found by Cheapflights users on 10/31. 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 11/266:30 am -
1 stop3h 55m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/31![Delta logo]()
$213
This Kiwi.com deal was found by Cheapflights users on 10/31. 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 11/302:40 pm -
2 stops42h 46m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/31![Multiple Airlines logo]()
$237
This Kiwi.com deal was found by Cheapflights users on 11/3. 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 2/1710:38 am -
2 stops13h 08m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/3![Multiple Airlines logo]()
$259
This Kiwi.com deal was found by Cheapflights users on 10/29. 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 12/33:55 pm -
3 stops43h 38m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/29![Multiple Airlines logo]()
$271
This Kiwi.com deal was found by Cheapflights users on 10/31. 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 11/132:50 pm -
3 stops32h 57m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/31![Multiple Airlines logo]()
$388
This Delta deal was found by Cheapflights users on 10/31. 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.
Mon 11/306:16 pm -
1 stop18h 45m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/31![Delta logo]()
$397
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 November 3, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $852 (Mytrip) |
One-way from | $179 (Kiwi.com) |
Popular in | April |
Cheapest in | March |
Average price | $289 |
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 7,457,451 searches. Data last updated November 3, 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
Cheapest round-trip
MadisonChicago
MSN Madison Truax Field - MDW Chicago Midway
MSNMDW
Madison Truax Field
Wed 12/16
10:38 am-11:17 pm
2 stops36h 39m
Chicago Midway
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$179
Quickest round-trip
MadisonChicago
MSN Madison Truax Field - MDW Chicago Midway
MSNMDW
Madison Truax Field
Thu 11/26
6:30 am-10:25 am
1 stop3h 55m
Chicago Midway
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$213
MadisonChicago
MSN Madison Truax Field - MDW Chicago Midway
MSNMDW
Madison Truax Field
Fri 11/27
6:30 am-10:25 am
1 stop3h 55m
Chicago Midway
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$213
MadisonChicago
MSN Madison Truax Field - MDW Chicago Midway
MSNMDW
Madison Truax Field
Thu 12/3
3:55 pm-11:33 am
3 stops43h 38m
Chicago Midway
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$271
MadisonChicago
MSN Madison Truax Field - MDW Chicago Midway
MSNMDW
Madison Truax Field
Wed 2/17
10:38 am-7:42 pm
3 stops33h 04m
Chicago Midway
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$307
MadisonChicago
MSN Madison Truax Field - MDW Chicago Midway
MSNMDW
Madison Truax Field
Fri 11/13
2:50 pm-11:47 pm
3 stops32h 57m
Chicago Midway
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$388
MadisonChicago
MSN Madison Truax Field - MDW Chicago Midway
MSNMDW
Madison Truax Field
Fri 11/27
2:40 pm-7:37 am
2 stops16h 57m
Chicago Midway
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$470
MadisonChicago
MSN Madison Truax Field - MDW Chicago Midway
MSNMDW
Madison Truax Field
Sun 11/29
3:40 pm-12:21 pm
2 stops20h 41m
Chicago Midway
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$499
MadisonChicago
MSN Madison Truax Field - MDW Chicago Midway
MSNMDW
Madison Truax Field
Wed 2/17
10:56 am-4:41 pm
1 stop5h 45m
Chicago Midway
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$727
MadisonChicago
MSN Madison Truax Field - MDW Chicago Midway
MSNMDW
Madison Truax Field
Sun 11/15
6:30 am-11:50 am
1 stop5h 20m
Chicago Midway
Sun 11/22
5:29 pm-9:17 pm
1 stop3h 48m
$1,220
Showing 1-10 of 19 resultsSorted 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 November.
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy2 stars | Trust Score*3 stars |
- 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.
MSN-MDW
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.
Traveling to a place near Chicago Midway Airport?
Book flights to Chicago Midway Airport if you plan to visit one of these locationsBenton Harbor
Merrillville
Lansing
Valparaiso
Hammond
Saint Joseph
Porter
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