$241+ Cheap flights from Midway (MDW) to Madison (MSN)
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 10/22. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — MSN
Sep 30 — Oct 71
Round-trip
1 adult, Economy
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Find cheap flights from Midway to Madison with Cheapflights
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Cheapest flights from Midway to MadisonExplore the most affordable flight options available from Midway to Madison. Find the lowest fares from popular airlines and budget airlines, with prices last updated on August 31, 2026.
Explore the most affordable flight options available from Midway to Madison. Find the lowest fares from popular airlines and budget airlines, with prices last updated on August 31, 2026.
This Delta deal was found by Cheapflights users on 8/29. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/199:59 am -
1 stop4h 08m
Sun 9/202:47 pm -
1 stop3h 32m
Deal found 8/29![Delta logo]()
$1,183
This Delta deal was found by Cheapflights users on 8/27. 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.
Fri 10/27:13 pm -
1 stop3h 48m
Sun 10/49:02 am -
1 stop4h 18m
Deal found 8/27![Delta logo]()
$1,295
This Delta deal was found by Cheapflights users on 8/28. 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 9/272:00 pm -
1 stop3h 57m
Mon 9/282:47 pm -
1 stop3h 32m
Deal found 8/28![Delta logo]()
$1,303
This Delta deal was found by Cheapflights users on 8/26. 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 10/37:13 pm -
1 stop3h 21m
Fri 10/910:53 am -
1 stop5h 54m
Deal found 8/26![Delta logo]()
$1,343
This Delta deal was found by Cheapflights users on 8/31. 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.
Tue 9/157:13 pm -
1 stop3h 48m
Sat 9/1912:00 pm -
1 stop5h 59m
Deal found 8/31![Delta logo]()
$1,405
This Delta deal was found by Cheapflights users on 8/28. 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 9/139:59 am -
1 stop4h 08m
Thu 9/1712:00 pm -
1 stop6h 19m
Deal found 8/28![Delta logo]()
$1,413
This Delta deal was found by Cheapflights users on 8/30. 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.
Mon 9/77:25 pm -
1 stop3h 35m
Sat 9/1212:00 pm -
1 stop4h 00m
Deal found 8/30![Delta logo]()
$1,505
This Delta deal was found by Cheapflights users on 8/26. 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 9/99:59 am -
1 stop4h 08m
Sat 9/1212:00 pm -
1 stop4h 00m
Deal found 8/26![Delta logo]()
$1,563
This Delta deal was found by Cheapflights users on 8/29. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/301:51 pm -
1 stop3h 57m
Tue 9/19:06 am -
1 stop4h 04m
Deal found 8/29![Delta logo]()
$1,601
Best flights from Midway to MadisonDiscover carefully curated flight deals from Midway to Madison that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated August 31, 2026.
Discover carefully curated flight deals from Midway to Madison that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated August 31, 2026.
This Delta deal was found by Cheapflights users on 8/29. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/1310:12 am -
1 stop3h 59m
Tue 10/206:00 am -
1 stop5h 47m
Deal found 8/29![Delta logo]()
$1,183
This Delta deal was found by Cheapflights users on 8/27. 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 9/249:59 am -
1 stop4h 08m
Thu 10/19:02 am -
1 stop4h 18m
Deal found 8/27![Delta logo]()
$1,183
This Delta deal was found by Cheapflights users on 8/27. 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.
Sun 10/115:31 pm -
1 stop3h 24m
Sun 10/186:00 am -
1 stop5h 47m
Deal found 8/27![Delta logo]()
$1,183
This Delta deal was found by Cheapflights users on 8/29. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/199:59 am -
1 stop4h 08m
Sun 9/202:47 pm -
1 stop3h 32m
Deal found 8/29![Delta logo]()
$1,183
This Delta deal was found by Cheapflights users on 8/28. 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 10/165:31 pm -
1 stop5h 26m
Sun 10/186:00 am -
1 stop5h 47m
Deal found 8/28![Delta logo]()
$1,183
This Delta deal was found by Cheapflights users on 8/29. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/282:00 pm -
1 stop3h 57m
Mon 10/512:00 pm -
1 stop6h 19m
Deal found 8/29![Delta logo]()
$1,183
This Delta deal was found by Cheapflights users on 8/28. 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 10/1210:01 am -
1 stop4h 10m
Mon 10/196:00 am -
1 stop5h 47m
Deal found 8/28![Delta logo]()
$1,295
This Delta deal was found by Cheapflights users on 8/28. 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 9/272:00 pm -
1 stop3h 57m
Mon 9/282:47 pm -
1 stop3h 32m
Deal found 8/28![Delta logo]()
$1,303
This Delta deal was found by Cheapflights users on 8/26. 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 10/37:13 pm -
1 stop3h 21m
Fri 10/910:53 am -
1 stop5h 54m
Deal found 8/26![Delta logo]()
$1,343
This Delta deal was found by Cheapflights users on 8/31. 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.
Tue 9/157:13 pm -
1 stop3h 48m
Sat 9/1912:00 pm -
1 stop5h 59m
Deal found 8/31![Delta logo]()
$1,405
Last-minute flights from Midway to MadisonDiscover last-minute flight deals from Midway to Madison. Data last updated August 31, 2026 and is based on user searches.
Discover last-minute flight deals from Midway to Madison. Data last updated August 31, 2026 and is based on user searches.
This Delta deal was found by Cheapflights users on 8/29. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/301:51 pm -
1 stop3h 57m
Tue 9/19:06 am -
1 stop4h 04m
Deal found 8/29![Delta logo]()
$1,601
This Delta deal was found by Cheapflights users on 8/30. 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.
Mon 9/77:25 pm -
1 stop3h 35m
Sat 9/1212:00 pm -
1 stop4h 00m
Deal found 8/30![Delta logo]()
$1,505
This Delta deal was found by Cheapflights users on 8/26. 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 9/99:59 am -
1 stop4h 08m
Sat 9/1212:00 pm -
1 stop4h 00m
Deal found 8/26![Delta logo]()
$1,563
This Delta deal was found by Cheapflights users on 8/28. 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 9/139:59 am -
1 stop4h 08m
Thu 9/1712:00 pm -
1 stop6h 19m
Deal found 8/28![Delta logo]()
$1,413
This Delta deal was found by Cheapflights users on 8/31. 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.
Tue 9/157:13 pm -
1 stop3h 48m
Sat 9/1912:00 pm -
1 stop5h 59m
Deal found 8/31![Delta logo]()
$1,405
This Delta deal was found by Cheapflights users on 8/29. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/199:59 am -
1 stop4h 08m
Sun 9/202:47 pm -
1 stop3h 32m
Deal found 8/29![Delta logo]()
$1,183
This Delta deal was found by Cheapflights users on 8/28. 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 9/272:00 pm -
1 stop3h 57m
Mon 9/282:47 pm -
1 stop3h 32m
Deal found 8/28![Delta logo]()
$1,303
One-way flights from Midway to MadisonSearch for one-way flight options from Midway to Madison. Find affordable one-way fares based on user searches. Data last updated August 31, 2026.
Search for one-way flight options from Midway to Madison. Find affordable one-way fares based on user searches. Data last updated August 31, 2026.
This Kiwi.com deal was found by Cheapflights users on 8/27. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/226:40 pm -
3 stops39h 13m
Deal found 8/27![Multiple Airlines logo]()
$241
This Kiwi.com deal was found by Cheapflights users on 8/30. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/136:21 am -
2 stops27h 32m
Deal found 8/30![Multiple Airlines logo]()
$248
This Kiwi.com deal was found by Cheapflights users on 8/26. 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 9/166:25 am -
2 stops34h 55m
Deal found 8/26![Multiple Airlines logo]()
$250
This Kiwi.com deal was found by Cheapflights users on 8/30. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/191:06 pm -
2 stops28h 14m
Deal found 8/30![Multiple Airlines logo]()
$292
This Kiwi.com deal was found by Cheapflights users on 8/28. 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 9/146:46 pm -
3 stops39h 07m
Deal found 8/28![Multiple Airlines logo]()
$295
This Kiwi.com deal was found by Cheapflights users on 8/27. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/311:50 am -
2 stops20h 35m
Deal found 8/27![Multiple Airlines logo]()
$457
This Delta deal was found by Cheapflights users on 8/30. 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.
Tue 10/1312:27 pm -
1 stop6h 39m
Deal found 8/30![Delta logo]()
$592
This Delta deal was found by Cheapflights users on 8/30. 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.
Wed 9/92:00 pm -
1 stop7h 30m
Deal found 8/30![Delta logo]()
$642
Find flight deals from Midway to Madison
Discover tips and strategies to find the most affordable flight options for your journey from Midway (MDW) to Madison (MSN). 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 August 31, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $1,183 (Delta) |
One-way from | $241 (Kiwi.com) |
Popular in | June |
Cheapest in | October |
Average price | $470 |
Cheapflights Fare Finder
Customize your flight search to find flights from Midway to Madison 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 August 31, 2026.
Use the filters below to find and compare flights from Chicago Midway Airport to Madison that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
ChicagoMadison
MDW Chicago Midway - MSN Madison Truax Field
MDWMSN
Chicago Midway
Tue 10/13
10:12 am-2:11 pm
1 stop3h 59m
Madison Truax Field
Tue 10/20
6:00 am-11:47 am
1 stop5h 47m
$1,183
ChicagoMadison
MDW Chicago Midway - MSN Madison Truax Field
MDWMSN
Chicago Midway
Thu 9/24
9:59 am-2:07 pm
1 stop4h 08m
Madison Truax Field
Thu 10/1
9:02 am-1:20 pm
1 stop4h 18m
$1,183
ChicagoMadison
MDW Chicago Midway - MSN Madison Truax Field
MDWMSN
Chicago Midway
Sun 10/11
5:31 pm-8:55 pm
1 stop3h 24m
Madison Truax Field
Sun 10/18
6:00 am-11:47 am
1 stop5h 47m
$1,183
ChicagoMadison
MDW Chicago Midway - MSN Madison Truax Field
MDWMSN
Chicago Midway
Sat 9/19
9:59 am-2:07 pm
1 stop4h 08m
Madison Truax Field
Sun 9/20
2:47 pm-6:19 pm
1 stop3h 32m
$1,183
ChicagoMadison
MDW Chicago Midway - MSN Madison Truax Field
MDWMSN
Chicago Midway
Fri 10/16
5:31 pm-10:57 pm
1 stop5h 26m
Madison Truax Field
Sun 10/18
6:00 am-11:47 am
1 stop5h 47m
$1,183
ChicagoMadison
MDW Chicago Midway - MSN Madison Truax Field
MDWMSN
Chicago Midway
Mon 9/28
2:00 pm-5:57 pm
1 stop3h 57m
Madison Truax Field
Mon 10/5
12:00 pm-6:19 pm
1 stop6h 19m
$1,183
ChicagoMadison
MDW Chicago Midway - MSN Madison Truax Field
MDWMSN
Chicago Midway
Mon 10/12
10:01 am-2:11 pm
1 stop4h 10m
Madison Truax Field
Mon 10/19
6:00 am-11:47 am
1 stop5h 47m
$1,295
Quickest round-trip
ChicagoMadison
MDW Chicago Midway - MSN Madison Truax Field
MDWMSN
Chicago Midway
Sun 9/27
2:00 pm-5:57 pm
1 stop3h 57m
Madison Truax Field
Mon 9/28
2:47 pm-6:19 pm
1 stop3h 32m
$1,303
ChicagoMadison
MDW Chicago Midway - MSN Madison Truax Field
MDWMSN
Chicago Midway
Sat 10/3
7:13 pm-10:34 pm
1 stop3h 21m
Madison Truax Field
Fri 10/9
10:53 am-4:47 pm
1 stop5h 54m
$1,343
ChicagoMadison
MDW Chicago Midway - MSN Madison Truax Field
MDWMSN
Chicago Midway
Tue 9/15
7:13 pm-11:01 pm
1 stop3h 48m
Madison Truax Field
Sat 9/19
12:00 pm-5:59 pm
1 stop5h 59m
$1,405
Showing 1-10 of 20 resultsSorted by cheapest first
- Most accurate provider: When it comes to deals on Chicago Midway Airport-Madison flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Chicago Midway Airport-Madison flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Chicago Midway Airport-Madison flight searches over the past month and is updated monthly.
- Most trusted provider: When it comes to deals on Chicago Midway Airport-Madison 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 Chicago Midway Airport-Madison 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 Midway to Madison
Have a flexible travel schedule? Discover the best time to fly to Madison from Midway with our price prediction graph.
MDW-MSN
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 Midway to Madison. 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 Madison?
Book flights to Madison if you plan to visit one of these locationsSun Prairie
Middleton
Fitchburg
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