$173+ Cheap flights from Midway (MDW) to Madison (MSN)
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 10/30. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — MSN
Oct 30 — Nov 61
Round-trip
1 adult, Economy
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Find cheap flights from Midway to Madison with Cheapflights
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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
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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 September 30, 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 September 30, 2026.
This Kiwi.com deal was found by Cheapflights users on 9/25. 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 12/1612:28 pm -
2 stops29h 02m
Thu 12/316:10 pm -
1 stop24h 52m
Deal found 9/25![Multiple Airlines logo]()
$578
This Delta deal was found by Cheapflights users on 9/29. 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.
Wed 11/2512:30 pm -
1 stop6h 37m
Fri 11/2710:49 am -
1 stop5h 50m
Deal found 9/29![Delta logo]()
$851
This Delta deal was found by Cheapflights users on 9/26. 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 10/175:31 pm -
1 stop3h 52m
Sun 10/186:00 am -
1 stop5h 47m
Deal found 9/26![Delta logo]()
$1,163
This Delta deal was found by Cheapflights users on 9/28. 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.
Thu 10/2212:27 pm -
1 stop6h 39m
Mon 10/267:59 am -
1 stop3h 48m
Deal found 9/28![Delta logo]()
$1,373
This Delta deal was found by Cheapflights users on 9/30. 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.
Fri 10/301:27 pm -
1 stop3h 45m
Sat 10/3110:53 am -
1 stop5h 54m
Deal found 9/30![Delta logo]()
$1,428
This Delta deal was found by Cheapflights users on 9/29. 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 10/1712:27 pm -
1 stop6h 39m
Tue 10/206:00 am -
1 stop5h 47m
Deal found 9/29![Delta logo]()
$1,469
This Delta deal was found by Cheapflights users on 9/25. 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 10/145:31 pm -
1 stop3h 24m
Thu 10/226:00 am -
1 stop5h 47m
Deal found 9/25![Delta logo]()
$1,479
This Delta deal was found by Cheapflights users on 9/27. 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 10/12:00 pm -
1 stop3h 57m
Sun 10/42:47 pm -
1 stop3h 32m
Deal found 9/27![Delta logo]()
$1,565
This Delta deal was found by Cheapflights users on 9/26. 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.
Sun 10/119:29 am -
1 stop3h 10m
Thu 10/151:29 pm -
1 stop4h 31m
Deal found 9/26![Delta logo]()
$1,612
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 September 30, 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 September 30, 2026.
This Delta deal was found by Cheapflights users on 9/29. 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.
Wed 11/2512:30 pm -
1 stop6h 37m
Fri 11/2710:49 am -
1 stop5h 50m
Deal found 9/29![Delta logo]()
$851
This Delta deal was found by Cheapflights users on 9/26. 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 10/245:31 pm -
1 stop3h 52m
Sat 10/317:59 am -
1 stop3h 48m
Deal found 9/26![Delta logo]()
$1,163
This Delta deal was found by Cheapflights users on 9/26. 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.
Tue 11/105:29 pm -
1 stop3h 48m
Tue 11/1710:59 am -
1 stop5h 40m
Deal found 9/26![Delta logo]()
$1,163
This Delta deal was found by Cheapflights users on 9/30. 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 10/285:31 pm -
1 stop5h 26m
Wed 11/46:00 am -
1 stop5h 47m
Deal found 9/30![Delta logo]()
$1,163
This Delta deal was found by Cheapflights users on 9/28. 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.
Tue 10/2010:12 am -
1 stop3h 59m
Thu 10/2210:53 am -
1 stop5h 54m
Deal found 9/28![Delta logo]()
$1,163
This Delta deal was found by Cheapflights users on 9/25. 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 12/1612:39 pm -
1 stop6h 37m
Thu 12/316:40 am -
1 stop4h 21m
Deal found 9/25![Delta logo]()
$1,163
This Delta deal was found by Cheapflights users on 9/28. 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.
Thu 10/2212:27 pm -
1 stop6h 39m
Mon 10/267:59 am -
1 stop3h 48m
Deal found 9/28![Delta logo]()
$1,373
This Delta deal was found by Cheapflights users on 9/29. 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 10/1712:27 pm -
1 stop6h 39m
Tue 10/206:00 am -
1 stop5h 47m
Deal found 9/29![Delta logo]()
$1,469
This Delta deal was found by Cheapflights users on 9/25. 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 10/145:31 pm -
1 stop3h 24m
Thu 10/226:00 am -
1 stop5h 47m
Deal found 9/25![Delta logo]()
$1,479
This Delta deal was found by Cheapflights users on 9/26. 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.
Sun 10/119:29 am -
1 stop3h 10m
Thu 10/151:29 pm -
1 stop4h 31m
Deal found 9/26![Delta logo]()
$1,612
Last-minute flights from Midway to MadisonDiscover last-minute flight deals from Midway to Madison. Data last updated September 30, 2026 and is based on user searches.
Discover last-minute flight deals from Midway to Madison. Data last updated September 30, 2026 and is based on user searches.
This Delta deal was found by Cheapflights users on 9/27. 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 10/12:00 pm -
1 stop3h 57m
Sun 10/42:47 pm -
1 stop3h 32m
Deal found 9/27![Delta logo]()
$1,565
This Delta deal was found by Cheapflights users on 9/26. 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.
Sun 10/119:29 am -
1 stop3h 10m
Thu 10/151:29 pm -
1 stop4h 31m
Deal found 9/26![Delta logo]()
$1,612
This Delta deal was found by Cheapflights users on 9/25. 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 10/145:31 pm -
1 stop3h 24m
Thu 10/226:00 am -
1 stop5h 47m
Deal found 9/25![Delta logo]()
$1,479
This Delta deal was found by Cheapflights users on 9/26. 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 10/175:31 pm -
1 stop3h 52m
Sun 10/186:00 am -
1 stop5h 47m
Deal found 9/26![Delta logo]()
$1,163
This Delta deal was found by Cheapflights users on 9/29. 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 10/1712:27 pm -
1 stop6h 39m
Tue 10/206:00 am -
1 stop5h 47m
Deal found 9/29![Delta logo]()
$1,469
This Delta deal was found by Cheapflights users on 9/28. 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.
Thu 10/2212:27 pm -
1 stop6h 39m
Mon 10/267:59 am -
1 stop3h 48m
Deal found 9/28![Delta logo]()
$1,373
This Delta deal was found by Cheapflights users on 9/30. 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.
Fri 10/301:27 pm -
1 stop3h 45m
Sat 10/3110:53 am -
1 stop5h 54m
Deal found 9/30![Delta logo]()
$1,428
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 September 30, 2026.
Search for one-way flight options from Midway to Madison. Find affordable one-way fares based on user searches. Data last updated September 30, 2026.
This Kiwi.com deal was found by Cheapflights users on 9/30. 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.
Fri 10/306:16 am -
3 stops27h 42m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/30![Multiple Airlines logo]()
$173
This Kiwi.com deal was found by Cheapflights users on 9/29. 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.
Mon 12/73:50 pm -
2 stops42h 08m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/29![Multiple Airlines logo]()
$209
This Mytrip deal was found by Cheapflights users on 9/27. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/2812:27 pm -
2 stops24h 59m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/27![Multiple Airlines logo]()
$213
This Mytrip deal was found by Cheapflights users on 9/26. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/213:30 pm -
2 stops21h 56m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/26![Multiple Airlines logo]()
$219
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 September 30, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $578 (Kiwi.com) |
One-way from | $207 (Kiwi.com) |
Popular in | June |
Cheapest in | December |
Average price | $562 |
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 September 30, 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
Fri 10/30
6:16 am-9:58 am
2 stops27h 42m
Madison Truax Field
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$184
ChicagoMadison
MDW Chicago Midway - MSN Madison Truax Field
MDWMSN
Chicago Midway
Wed 10/21
3:30 pm-1:26 pm
2 stops21h 56m
Madison Truax Field
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$219
ChicagoMadison
MDW Chicago Midway - MSN Madison Truax Field
MDWMSN
Chicago Midway
Mon 12/7
9:37 pm-9:58 am
3 stops36h 21m
Madison Truax Field
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$232
ChicagoMadison
MDW Chicago Midway - MSN Madison Truax Field
MDWMSN
Chicago Midway
Wed 10/28
6:16 am-1:26 pm
3 stops31h 10m
Madison Truax Field
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$273
ChicagoMadison
MDW Chicago Midway - MSN Madison Truax Field
MDWMSN
Chicago Midway
Sun 10/11
6:40 pm-9:50 am
2 stops39h 10m
Madison Truax Field
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$313
ChicagoMadison
MDW Chicago Midway - MSN Madison Truax Field
MDWMSN
Chicago Midway
Sat 10/24
6:21 am-5:20 pm
2 stops34h 59m
Madison Truax Field
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$399
ChicagoMadison
MDW Chicago Midway - MSN Madison Truax Field
MDWMSN
Chicago Midway
Fri 10/16
6:15 am-9:58 am
2 stops27h 43m
Madison Truax Field
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$446
Quickest round-trip
ChicagoMadison
MDW Chicago Midway - MSN Madison Truax Field
MDWMSN
Chicago Midway
Wed 12/16
12:39 pm-7:16 pm
1 stop6h 37m
Madison Truax Field
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$582
ChicagoMadison
MDW Chicago Midway - MSN Madison Truax Field
MDWMSN
Chicago Midway
Wed 11/25
12:30 pm-7:07 pm
1 stop6h 37m
Madison Truax Field
Fri 11/27
10:49 am-4:39 pm
1 stop5h 50m
$851
ChicagoMadison
MDW Chicago Midway - MSN Madison Truax Field
MDWMSN
Chicago Midway
Sat 10/24
5:31 pm-9:23 pm
1 stop3h 52m
Madison Truax Field
Sat 10/31
7:59 am-11:47 am
1 stop3h 48m
$1,163
Showing 1-10 of 18 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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