$216+ 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 9/25. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — MSN
Oct 12 — Oct 191
Round-trip
1 adult, Economy
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Find cheap flights from Midway to Madison 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
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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 Midway to Madison
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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 12, 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 12, 2026.
This Delta deal was found by Cheapflights users on 9/8. 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 10/1512:27 pm -
1 stop6h 39m
Sun 10/186:00 am -
1 stop5h 47m
Deal found 9/8![Delta logo]()
$1,143
This Delta deal was found by Cheapflights users on 9/8. 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 10/65:31 pm -
1 stop5h 26m
Tue 10/137:59 am -
1 stop3h 48m
Deal found 9/8![Delta logo]()
$1,163
This Delta deal was found by Cheapflights users on 9/8. 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
Sun 11/1510:59 am -
1 stop5h 40m
Deal found 9/8![Delta logo]()
$1,173
This Delta deal was found by Cheapflights users on 9/10. 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 10/75:31 pm -
1 stop3h 24m
Mon 10/127:59 am -
1 stop3h 48m
Deal found 9/10![Delta logo]()
$1,295
This Delta deal was found by Cheapflights users on 9/10. 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 10/19:59 am -
1 stop4h 08m
Sun 10/41:21 pm -
1 stop5h 12m
Deal found 9/10![Delta logo]()
$1,368
This Delta deal was found by Cheapflights users on 9/7. 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
Thu 10/296:00 am -
1 stop5h 47m
Deal found 9/7![Delta logo]()
$1,380
This Delta deal was found by Cheapflights users on 9/10. 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 9/257:13 pm -
1 stop3h 48m
Tue 9/2912:00 pm -
1 stop6h 19m
Deal found 9/10![Delta logo]()
$1,405
This Delta deal was found by Cheapflights users on 9/10. 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 9/277:13 pm -
1 stop3h 48m
Wed 9/309:02 am -
1 stop4h 18m
Deal found 9/10![Delta logo]()
$1,423
This Delta deal was found by Cheapflights users on 9/8. 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 9/239:59 am -
1 stop4h 08m
Sun 9/2712:00 pm -
1 stop6h 19m
Deal found 9/8![Delta logo]()
$1,445
This Delta deal was found by Cheapflights users on 9/9. 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 9/209:59 am -
1 stop4h 08m
Wed 9/2312:00 pm -
1 stop6h 19m
Deal found 9/9![Delta logo]()
$1,473
This Delta deal was found by Cheapflights users on 9/7. 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 9/149:59 am -
1 stop4h 08m
Fri 9/259:02 am -
1 stop4h 18m
Deal found 9/7![Delta logo]()
$1,495
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 12, 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 12, 2026.
This Delta deal was found by Cheapflights users on 9/10. 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 10/2512:27 pm -
1 stop6h 39m
Sun 11/110:53 am -
1 stop5h 54m
Deal found 9/10![Delta logo]()
$1,143
This Delta deal was found by Cheapflights users on 9/8. 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 10/1512:27 pm -
1 stop6h 39m
Sun 10/186:00 am -
1 stop5h 47m
Deal found 9/8![Delta logo]()
$1,143
This Delta deal was found by Cheapflights users on 9/8. 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 10/75:31 pm -
1 stop3h 24m
Wed 10/147:59 am -
1 stop3h 48m
Deal found 9/8![Delta logo]()
$1,143
This Delta deal was found by Cheapflights users on 9/8. 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
Tue 10/136:00 am -
1 stop5h 47m
Deal found 9/8![Delta logo]()
$1,143
This Delta deal was found by Cheapflights users on 9/10. 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 12/95:30 pm -
1 stop4h 00m
Thu 12/1010:59 am -
1 stop5h 51m
Deal found 9/10![Delta logo]()
$1,143
This Delta deal was found by Cheapflights users on 9/8. 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 10/65:31 pm -
1 stop5h 26m
Tue 10/137:59 am -
1 stop3h 48m
Deal found 9/8![Delta logo]()
$1,163
This Delta deal was found by Cheapflights users on 9/8. 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
Sun 11/1510:59 am -
1 stop5h 40m
Deal found 9/8![Delta logo]()
$1,173
This Delta deal was found by Cheapflights users on 9/9. 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 10/85:31 pm -
1 stop3h 24m
Thu 10/1510:53 am -
1 stop5h 54m
Deal found 9/9![Delta logo]()
$1,295
This Delta deal was found by Cheapflights users on 9/9. 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
Mon 10/197:00 am -
1 stop5h 47m
Deal found 9/9![Delta logo]()
$1,368
This Delta deal was found by Cheapflights users on 9/9. 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 10/229:29 am -
1 stop3h 06m
Mon 11/96:30 am -
1 stop5h 20m
Deal found 9/9![Delta logo]()
$1,368
This Delta deal was found by Cheapflights users on 9/7. 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
Thu 10/296:00 am -
1 stop5h 47m
Deal found 9/7![Delta logo]()
$1,380
Last-minute flights from Midway to MadisonDiscover last-minute flight deals from Midway to Madison. Data last updated September 12, 2026 and is based on user searches.
Discover last-minute flight deals from Midway to Madison. Data last updated September 12, 2026 and is based on user searches.
This Delta deal was found by Cheapflights users on 9/7. 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 9/149:59 am -
1 stop4h 08m
Fri 9/259:02 am -
1 stop4h 18m
Deal found 9/7![Delta logo]()
$1,495
This Delta deal was found by Cheapflights users on 9/9. 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 9/209:59 am -
1 stop4h 08m
Wed 9/2312:00 pm -
1 stop6h 19m
Deal found 9/9![Delta logo]()
$1,473
This Delta deal was found by Cheapflights users on 9/8. 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 9/239:59 am -
1 stop4h 08m
Sun 9/2712:00 pm -
1 stop6h 19m
Deal found 9/8![Delta logo]()
$1,445
This Delta deal was found by Cheapflights users on 9/10. 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 9/257:13 pm -
1 stop3h 48m
Tue 9/2912:00 pm -
1 stop6h 19m
Deal found 9/10![Delta logo]()
$1,405
This Delta deal was found by Cheapflights users on 9/10. 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 9/277:13 pm -
1 stop3h 48m
Wed 9/309:02 am -
1 stop4h 18m
Deal found 9/10![Delta logo]()
$1,423
This Delta deal was found by Cheapflights users on 9/10. 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 10/19:59 am -
1 stop4h 08m
Sun 10/41:21 pm -
1 stop5h 12m
Deal found 9/10![Delta logo]()
$1,368
This Delta deal was found by Cheapflights users on 9/8. 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 10/65:31 pm -
1 stop5h 26m
Tue 10/137:59 am -
1 stop3h 48m
Deal found 9/8![Delta logo]()
$1,163
This Delta deal was found by Cheapflights users on 9/10. 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 10/75:31 pm -
1 stop3h 24m
Mon 10/127:59 am -
1 stop3h 48m
Deal found 9/10![Delta logo]()
$1,295
This Delta deal was found by Cheapflights users on 9/9. 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 10/1512:27 pm -
1 stop6h 39m
Sun 10/186:00 am -
1 stop5h 47m
Deal found 9/9![Delta logo]()
$1,143
This Delta deal was found by Cheapflights users on 9/7. 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
Thu 10/296:00 am -
1 stop5h 47m
Deal found 9/7![Delta logo]()
$1,380
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 12, 2026.
Search for one-way flight options from Midway to Madison. Find affordable one-way fares based on user searches. Data last updated September 12, 2026.
This Kiwi.com deal was found by Cheapflights users on 9/7. 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 9/256:25 am -
2 stops27h 28m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/7![Multiple Airlines logo]()
$216
This Delta deal was found by Cheapflights users on 9/10. 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 1/16:20 pm -
1 stop3h 48m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/10![Delta logo]()
$220
This Kiwi.com deal was found by Cheapflights users on 9/9. 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.
Sun 10/186:40 pm -
2 stops39h 10m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/9![Multiple Airlines logo]()
$222
This Kiwi.com deal was found by Cheapflights users on 9/8. 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 -
2 stops34h 55m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/8![Multiple Airlines logo]()
$245
This Kiwi.com deal was found by Cheapflights users on 9/8. 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 9/186:25 am -
2 stops27h 28m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/8![Multiple Airlines logo]()
$295
This Kiwi.com deal was found by Cheapflights users on 9/10. 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 9/236:25 am -
2 stops34h 55m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/10![Multiple Airlines logo]()
$325
This Kiwi.com deal was found by Cheapflights users on 9/11. 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 9/2412:54 pm -
3 stops44h 59m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/11![Multiple Airlines logo]()
$326
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 12, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $1,143 (Delta) |
One-way from | $216 (Kiwi.com) |
Popular in | June |
Cheapest in | October |
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 12, 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 9/25
6:25 am-9:53 am
2 stops27h 28m
Madison Truax Field
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$216
ChicagoMadison
MDW Chicago Midway - MSN Madison Truax Field
MDWMSN
Chicago Midway
Sun 10/18
6:40 pm-9:50 am
2 stops39h 10m
Madison Truax Field
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$222
ChicagoMadison
MDW Chicago Midway - MSN Madison Truax Field
MDWMSN
Chicago Midway
Fri 9/18
6:25 am-9:53 am
2 stops27h 28m
Madison Truax Field
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$295
ChicagoMadison
MDW Chicago Midway - MSN Madison Truax Field
MDWMSN
Chicago Midway
Thu 9/24
6:46 pm-9:53 am
2 stops39h 07m
Madison Truax Field
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$336
ChicagoMadison
MDW Chicago Midway - MSN Madison Truax Field
MDWMSN
Chicago Midway
Mon 9/21
6:46 pm-9:53 am
3 stops39h 07m
Madison Truax Field
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$383
ChicagoMadison
MDW Chicago Midway - MSN Madison Truax Field
MDWMSN
Chicago Midway
Wed 9/23
6:25 am-5:20 pm
3 stops34h 55m
Madison Truax Field
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$534
ChicagoMadison
MDW Chicago Midway - MSN Madison Truax Field
MDWMSN
Chicago Midway
Wed 10/7
10:12 am-2:11 pm
1 stop3h 59m
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
Sat 10/17
5:31 pm-9:23 pm
1 stop3h 52m
Madison Truax Field
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$592
Quickest round-trip
ChicagoMadison
MDW Chicago Midway - MSN Madison Truax Field
MDWMSN
Chicago Midway
Sun 10/18
5:31 pm-8:55 pm
1 stop3h 24m
Madison Truax Field
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$657
ChicagoMadison
MDW Chicago Midway - MSN Madison Truax Field
MDWMSN
Chicago Midway
Thu 10/22
1:27 pm-5:18 pm
1 stop3h 51m
Madison Truax Field
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$712
Showing 1-10 of 22 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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