$234+ 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 9/30. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — MSN
Sep 18 — Sep 251
Round-trip
1 adult, Economy
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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 19, 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 19, 2026.
This Delta deal was found by Cheapflights users on 8/18. 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
Tue 9/229:02 am -
1 stop4h 18m
Deal found 8/18![Delta logo]()
$1,163
This Delta deal was found by Cheapflights users on 8/15. 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 11/2510:22 am -
1 stop3h 28m
Mon 12/710:51 am -
1 stop5h 48m
Deal found 8/15![Delta logo]()
$1,203
This Delta deal was found by Cheapflights users on 8/16. 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 8/317:25 pm -
1 stop3h 35m
Sun 9/612:10 pm -
1 stop3h 47m
Deal found 8/16![Delta logo]()
$1,221
This Delta deal was found by Cheapflights users on 8/18. 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 9/27:25 pm -
1 stop3h 35m
Sun 9/612:10 pm -
1 stop3h 47m
Deal found 8/18![Delta logo]()
$1,269
This Delta deal was found by Cheapflights users on 8/17. 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 9/37:25 pm -
1 stop3h 35m
Sun 9/612:10 pm -
1 stop3h 47m
Deal found 8/17![Delta logo]()
$1,299
This Delta deal was found by Cheapflights users on 8/14. 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 8/14![Delta logo]()
$1,373
This Delta deal was found by Cheapflights users on 8/17. 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 9/109:59 am -
1 stop4h 08m
Sun 9/137:05 am -
1 stop5h 34m
Deal found 8/17![Delta logo]()
$1,428
This Delta deal was found by Cheapflights users on 8/17. 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 9/11:51 pm -
1 stop3h 57m
Sat 9/512:10 pm -
1 stop3h 47m
Deal found 8/17![Delta logo]()
$1,563
This Delta deal was found by Cheapflights users on 8/15. 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
Thu 9/39:06 am -
1 stop4h 04m
Deal found 8/15![Delta logo]()
$1,593
This Delta deal was found by Cheapflights users on 8/17. 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 8/171:25 pm -
1 stop4h 10m
Wed 8/191:35 pm -
1 stop4h 58m
Deal found 8/17![Delta logo]()
$1,601
This Delta deal was found by Cheapflights users on 8/16. 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 8/211:51 pm -
1 stop3h 57m
Mon 8/241:35 pm -
1 stop4h 58m
Deal found 8/16![Delta logo]()
$1,913
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 19, 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 19, 2026.
This Delta deal was found by Cheapflights users on 8/16. 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 9/307:13 pm -
1 stop3h 48m
Wed 10/76:00 am -
1 stop5h 47m
Deal found 8/16![Delta logo]()
$1,163
This Delta deal was found by Cheapflights users on 8/15. 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 10/2312:27 pm -
1 stop6h 39m
Sun 10/256:00 am -
1 stop5h 47m
Deal found 8/15![Delta logo]()
$1,163
This Delta deal was found by Cheapflights users on 8/18. 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
Tue 9/229:02 am -
1 stop4h 18m
Deal found 8/18![Delta logo]()
$1,163
This Delta deal was found by Cheapflights users on 8/18. 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 9/27:25 pm -
1 stop3h 35m
Sun 9/612:10 pm -
1 stop3h 47m
Deal found 8/18![Delta logo]()
$1,269
This Delta deal was found by Cheapflights users on 8/18. 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
Fri 10/910:53 am -
1 stop5h 54m
Deal found 8/18![Delta logo]()
$1,373
This Delta deal was found by Cheapflights users on 8/14. 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 9/177:13 pm -
1 stop3h 48m
Fri 9/182:47 pm -
1 stop3h 32m
Deal found 8/14![Delta logo]()
$1,373
This Delta deal was found by Cheapflights users on 8/14. 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 8/14![Delta logo]()
$1,373
This Delta deal was found by Cheapflights users on 8/17. 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 10/17:13 pm -
1 stop3h 48m
Thu 10/87:59 am -
1 stop3h 48m
Deal found 8/17![Delta logo]()
$1,373
Last-minute flights from Midway to MadisonDiscover last-minute flight deals from Midway to Madison. Data last updated August 19, 2026 and is based on user searches.
Discover last-minute flight deals from Midway to Madison. Data last updated August 19, 2026 and is based on user searches.
This Delta deal was found by Cheapflights users on 8/17. 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 8/189:59 am -
1 stop4h 12m
Tue 8/2512:10 pm -
1 stop5h 51m
Deal found 8/17![Delta logo]()
$1,601
This Delta deal was found by Cheapflights users on 8/16. 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 8/211:51 pm -
1 stop3h 57m
Mon 8/241:35 pm -
1 stop4h 58m
Deal found 8/16![Delta logo]()
$1,913
This Delta deal was found by Cheapflights users on 8/15. 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
Thu 9/39:06 am -
1 stop4h 04m
Deal found 8/15![Delta logo]()
$1,593
This Delta deal was found by Cheapflights users on 8/16. 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 8/317:25 pm -
1 stop3h 35m
Sun 9/612:10 pm -
1 stop3h 47m
Deal found 8/16![Delta logo]()
$1,221
This Delta deal was found by Cheapflights users on 8/17. 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 9/11:51 pm -
1 stop3h 57m
Sat 9/512:10 pm -
1 stop3h 47m
Deal found 8/17![Delta logo]()
$1,563
This Delta deal was found by Cheapflights users on 8/18. 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 9/27:25 pm -
1 stop3h 35m
Sun 9/612:10 pm -
1 stop3h 47m
Deal found 8/18![Delta logo]()
$1,269
This Delta deal was found by Cheapflights users on 8/17. 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 9/37:25 pm -
1 stop3h 35m
Sun 9/612:10 pm -
1 stop3h 47m
Deal found 8/17![Delta logo]()
$1,299
This Delta deal was found by Cheapflights users on 8/17. 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 9/109:59 am -
1 stop4h 08m
Sun 9/137:05 am -
1 stop5h 34m
Deal found 8/17![Delta logo]()
$1,428
This Delta deal was found by Cheapflights users on 8/18. 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
Tue 9/229:02 am -
1 stop4h 18m
Deal found 8/18![Delta logo]()
$1,163
This Delta deal was found by Cheapflights users on 8/14. 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 8/14![Delta logo]()
$1,373
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 19, 2026.
Search for one-way flight options from Midway to Madison. Find affordable one-way fares based on user searches. Data last updated August 19, 2026.
This Kiwi.com deal was found by Cheapflights users on 8/17. 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 9/306:25 am -
3 stops34h 55m
Deal found 8/17![Multiple Airlines logo]()
$234
This Delta deal was found by Cheapflights users on 8/14. 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 9/289:59 am -
1 stop4h 08m
Deal found 8/14![Delta logo]()
$582
This Delta deal was found by Cheapflights users on 8/17. 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 10/17:13 pm -
1 stop3h 48m
Deal found 8/17![Delta logo]()
$687
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 19, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $1,163 (Delta) |
One-way from | $234 (Kiwi.com) |
Popular in | June |
Cheapest in | December |
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 19, 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
Wed 9/30
7:13 pm-11:01 pm
1 stop3h 48m
Madison Truax Field
Wed 10/7
6:00 am-11:47 am
1 stop5h 47m
$1,163
ChicagoMadison
MDW Chicago Midway - MSN Madison Truax Field
MDWMSN
Chicago Midway
Fri 10/23
12:27 pm-7:06 pm
1 stop6h 39m
Madison Truax Field
Sun 10/25
6:00 am-11:47 am
1 stop5h 47m
$1,163
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
Tue 9/22
9:02 am-1:20 pm
1 stop4h 18m
$1,163
ChicagoMadison
MDW Chicago Midway - MSN Madison Truax Field
MDWMSN
Chicago Midway
Wed 9/2
7:25 pm-11:00 pm
1 stop3h 35m
Madison Truax Field
Sun 9/6
12:10 pm-3:57 pm
1 stop3h 47m
$1,269
ChicagoMadison
MDW Chicago Midway - MSN Madison Truax Field
MDWMSN
Chicago Midway
Fri 10/2
7:13 pm-11:01 pm
1 stop3h 48m
Madison Truax Field
Fri 10/9
10:53 am-4:47 pm
1 stop5h 54m
$1,373
Quickest round-trip
ChicagoMadison
MDW Chicago Midway - MSN Madison Truax Field
MDWMSN
Chicago Midway
Thu 9/17
7:13 pm-11:01 pm
1 stop3h 48m
Madison Truax Field
Fri 9/18
2:47 pm-6:19 pm
1 stop3h 32m
$1,373
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
$1,373
ChicagoMadison
MDW Chicago Midway - MSN Madison Truax Field
MDWMSN
Chicago Midway
Thu 10/1
7:13 pm-11:01 pm
1 stop3h 48m
Madison Truax Field
Thu 10/8
7:59 am-11:47 am
1 stop3h 48m
$1,373
Cheapest one-way
ChicagoMadison
MDW Chicago Midway - MSN Madison Truax Field
MDWMSN
Chicago Midway
Wed 9/30
6:25 am-5:20 pm
3 stops34h 55m
$234
ChicagoMadison
MDW Chicago Midway - MSN Madison Truax Field
MDWMSN
Chicago Midway
Mon 9/28
9:59 am-2:07 pm
1 stop4h 08m
$582
Showing 1-10 of 12 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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