$153+ 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 1/11. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — MSN
Nov 24 — Dec 11
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 October 25, 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 October 25, 2026.
This Delta deal was found by Cheapflights users on 10/22. 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 12/239:30 am -
1 stop6h 44m
Tue 12/2910:58 am -
1 stop6h 26m
Deal found 10/22![Delta logo]()
$567
This Kiwi.com deal was found by Cheapflights users on 10/22. 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 12/238:35 pm -
1 stop20h 55m
Tue 12/295:04 pm -
2 stops30h 57m
Deal found 10/22![Multiple Airlines logo]()
$572
This Kiwi.com deal was found by Cheapflights users on 10/24. 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 11/218:42 pm -
1 stop20h 38m
Sat 11/2810:38 am -
2 stops45h 36m
Deal found 10/24![Multiple Airlines logo]()
$1,084
This Delta deal was found by Cheapflights users on 10/23. 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 11/2012:30 pm -
1 stop6h 37m
Sun 11/2210:59 am -
1 stop5h 40m
Deal found 10/23![Delta logo]()
$1,120
This Delta deal was found by Cheapflights users on 10/22. 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 11/2010:34 am -
1 stop3h 16m
Fri 11/276:30 am -
1 stop3h 55m
Deal found 10/22![Delta logo]()
$1,130
This KAYAK deal was found by Cheapflights users on 10/20. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/265:31 pm -
1 stop3h 24m
Thu 10/297:59 am -
1 stop3h 48m
Deal found 10/20![Delta logo]()
$1,297
This Delta deal was found by Cheapflights users on 10/20. 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 11/910:34 am -
1 stop3h 16m
Wed 11/1110:59 am -
1 stop5h 40m
Deal found 10/20![Delta logo]()
$1,331
This Delta deal was found by Cheapflights users on 10/23. 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 11/135:29 pm -
1 stop3h 48m
Sun 11/156:30 am -
1 stop5h 20m
Deal found 10/23![Delta logo]()
$1,429
This Delta deal was found by Cheapflights users on 10/20. 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
Sat 10/247:59 am -
1 stop3h 48m
Deal found 10/20![Delta logo]()
$1,465
This KAYAK deal was found by Cheapflights users on 10/21. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/239:29 am -
1 stop3h 06m
Thu 10/299:27 am -
1 stop3h 20m
Deal found 10/21![Delta logo]()
$1,467
This Delta deal was found by Cheapflights users on 10/21. 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 11/125:29 pm -
1 stop3h 48m
Sun 11/1510:59 am -
1 stop5h 40m
Deal found 10/21![Delta logo]()
$1,483
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 October 25, 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 October 25, 2026.
This Kiwi.com deal was found by Cheapflights users on 10/24. 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 11/218:42 pm -
1 stop20h 38m
Sat 11/2810:38 am -
2 stops45h 36m
Deal found 10/24![Multiple Airlines logo]()
$1,084
This Delta deal was found by Cheapflights users on 10/22. 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 11/2010:34 am -
1 stop3h 16m
Fri 11/276:30 am -
1 stop3h 55m
Deal found 10/22![Delta logo]()
$1,130
This Delta deal was found by Cheapflights users on 10/20. 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 11/910:34 am -
1 stop3h 16m
Wed 11/1110:59 am -
1 stop5h 40m
Deal found 10/20![Delta logo]()
$1,331
This Delta deal was found by Cheapflights users on 10/23. 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 11/135:29 pm -
1 stop3h 48m
Sun 11/156:30 am -
1 stop5h 20m
Deal found 10/23![Delta logo]()
$1,429
This Delta deal was found by Cheapflights users on 10/20. 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 12/1110:24 am -
1 stop3h 46m
Sat 12/1210:59 am -
1 stop5h 51m
Deal found 10/20![Delta logo]()
$1,483
This Delta deal was found by Cheapflights users on 10/21. 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 12/55:30 pm -
1 stop3h 59m
Sat 12/126:32 am -
1 stop5h 27m
Deal found 10/21![Delta logo]()
$1,483
This Delta deal was found by Cheapflights users on 10/21. 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 11/125:29 pm -
1 stop3h 48m
Sun 11/1510:59 am -
1 stop5h 40m
Deal found 10/21![Delta logo]()
$1,483
This Delta deal was found by Cheapflights users on 10/22. 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 11/612:27 pm -
1 stop6h 39m
Tue 11/106:30 am -
1 stop5h 20m
Deal found 10/22![Delta logo]()
$1,519
This Delta deal was found by Cheapflights users on 10/22. 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 11/710:12 am -
1 stop3h 59m
Wed 11/1110:59 am -
1 stop5h 40m
Deal found 10/22![Delta logo]()
$1,519
This Delta deal was found by Cheapflights users on 10/23. 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 12/85:30 pm -
1 stop3h 59m
Thu 12/1010:59 am -
1 stop5h 51m
Deal found 10/23![Delta logo]()
$1,693
This Delta deal was found by Cheapflights users on 10/23. 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 12/65:30 pm -
1 stop3h 59m
Sat 12/1210:59 am -
1 stop5h 51m
Deal found 10/23![Delta logo]()
$1,693
Last-minute flights from Midway to MadisonDiscover last-minute flight deals from Midway to Madison. Data last updated October 25, 2026 and is based on user searches.
Discover last-minute flight deals from Midway to Madison. Data last updated October 25, 2026 and is based on user searches.
This KAYAK deal was found by Cheapflights users on 10/21. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/239:29 am -
1 stop3h 06m
Thu 10/299:27 am -
1 stop3h 20m
Deal found 10/21![Delta logo]()
$1,467
This KAYAK deal was found by Cheapflights users on 10/20. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/265:31 pm -
1 stop3h 24m
Thu 10/297:59 am -
1 stop3h 48m
Deal found 10/20![Delta logo]()
$1,297
This Delta deal was found by Cheapflights users on 10/22. 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 11/612:27 pm -
1 stop6h 39m
Tue 11/106:30 am -
1 stop5h 20m
Deal found 10/22![Delta logo]()
$1,519
This Delta deal was found by Cheapflights users on 10/20. 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 11/910:34 am -
1 stop3h 16m
Wed 11/1110:59 am -
1 stop5h 40m
Deal found 10/20![Delta logo]()
$1,331
This Delta deal was found by Cheapflights users on 10/21. 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 11/125:29 pm -
1 stop3h 48m
Sun 11/1510:59 am -
1 stop5h 40m
Deal found 10/21![Delta logo]()
$1,483
This Delta deal was found by Cheapflights users on 10/23. 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 11/135:29 pm -
1 stop3h 48m
Sun 11/156:30 am -
1 stop5h 20m
Deal found 10/23![Delta logo]()
$1,429
This Delta deal was found by Cheapflights users on 10/23. 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 11/2012:30 pm -
1 stop6h 37m
Sun 11/2210:59 am -
1 stop5h 40m
Deal found 10/23![Delta logo]()
$1,120
This Delta deal was found by Cheapflights users on 10/22. 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 11/2010:34 am -
1 stop3h 16m
Fri 11/276:30 am -
1 stop3h 55m
Deal found 10/22![Delta logo]()
$1,130
This Kiwi.com deal was found by Cheapflights users on 10/24. 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 11/218:42 pm -
1 stop20h 38m
Sat 11/2810:38 am -
2 stops45h 36m
Deal found 10/24![Multiple Airlines logo]()
$1,084
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 October 25, 2026.
Search for one-way flight options from Midway to Madison. Find affordable one-way fares based on user searches. Data last updated October 25, 2026.
This Kiwi.com deal was found by Cheapflights users on 10/20. 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 1/115:21 pm -
2 stops40h 37m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/20![Multiple Airlines logo]()
$153
This Kiwi.com deal was found by Cheapflights users on 10/24. 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 11/126:42 pm -
2 stops39h 16m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/24![Multiple Airlines logo]()
$178
This Kiwi.com deal was found by Cheapflights users on 10/23. 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 12/218:35 pm -
1 stop19h 49m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/23![Multiple Airlines logo]()
$235
This Kiwi.com deal was found by Cheapflights users on 10/20. 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 -
2 stops27h 42m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/20![Multiple Airlines logo]()
$357
This Kiwi.com deal was found by Cheapflights users on 10/20. 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 10/317:25 am -
2 stops34h 55m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/20![Multiple Airlines logo]()
$444
This Kiwi.com deal was found by Cheapflights users on 10/22. 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 12/261:11 pm -
2 stops28h 19m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/22![Multiple Airlines logo]()
$525
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 October 25, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $567 (Delta) |
One-way from | $153 (Kiwi.com) |
Popular in | June |
Cheapest in | December |
Average price | $289 |
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 October 25, 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
Mon 1/11
5:21 pm-9:58 am
3 stops40h 37m
Madison Truax Field
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$177
ChicagoMadison
MDW Chicago Midway - MSN Madison Truax Field
MDWMSN
Chicago Midway
Thu 11/12
6:42 pm-9:58 am
2 stops39h 16m
Madison Truax Field
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$178
ChicagoMadison
MDW Chicago Midway - MSN Madison Truax Field
MDWMSN
Chicago Midway
Mon 12/21
8:35 pm-4:24 pm
1 stop19h 49m
Madison Truax Field
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$235
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
$357
ChicagoMadison
MDW Chicago Midway - MSN Madison Truax Field
MDWMSN
Chicago Midway
Sat 12/26
1:11 pm-5:30 pm
2 stops28h 19m
Madison Truax Field
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$525
ChicagoMadison
MDW Chicago Midway - MSN Madison Truax Field
MDWMSN
Chicago Midway
Tue 4/6
5:35 pm-10:55 pm
1 stop5h 20m
Madison Truax Field
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$662
Quickest round-trip
ChicagoMadison
MDW Chicago Midway - MSN Madison Truax Field
MDWMSN
Chicago Midway
Sat 10/31
10:12 am-2:11 pm
1 stop3h 59m
Madison Truax Field
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$712
ChicagoMadison
MDW Chicago Midway - MSN Madison Truax Field
MDWMSN
Chicago Midway
Fri 10/30
5:31 pm-10:57 pm
1 stop5h 26m
Madison Truax Field
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$712
ChicagoMadison
MDW Chicago Midway - MSN Madison Truax Field
MDWMSN
Chicago Midway
Thu 11/12
12:30 pm-7:07 pm
1 stop6h 37m
Madison Truax Field
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$745
ChicagoMadison
MDW Chicago Midway - MSN Madison Truax Field
MDWMSN
Chicago Midway
Sat 11/21
8:42 pm-5:20 pm
1 stop20h 38m
Madison Truax Field
Sat 11/28
10:38 am-8:14 am
2 stops45h 36m
$1,084
Showing 1-10 of 20 resultsSorted by cheapest first
Compare providers for flights from Midway to Madison
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 Midway to Madison in October.
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy2 stars | Trust Score*3 stars |
- 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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