$179+ Cheap flights from Madison (MSN) to Midway (MDW)
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 11/10. Fares are subject to change and may not be available on all flights or dates of travel.
MSN — MDW
Oct 23 — Oct 301
Round-trip
1 adult, Economy
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Find cheap flights from Madison to Midway 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
We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.3. Compare prices and book
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 Madison to Midway
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Cheapest flights from Madison to MidwayExplore the most affordable flight options available from Madison to Midway. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 23, 2026.
Explore the most affordable flight options available from Madison to Midway. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 23, 2026.
This Mytrip deal was found by Cheapflights users on 9/21. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/262:25 pm -
3 stops20h 57m
Wed 10/2812:27 pm -
2 stops24h 59m
Deal found 9/21![Multiple Airlines logo]()
$485
This Delta deal was found by Cheapflights users on 9/19. 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 11/266:30 am -
1 stop3h 55m
Tue 12/112:39 pm -
1 stop6h 37m
Deal found 9/19![Delta logo]()
$794
This Delta deal was found by Cheapflights users on 9/21. 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 11/266:30 am -
1 stop3h 55m
Sat 11/2810:34 am -
1 stop3h 16m
Deal found 9/21![Delta logo]()
$1,014
This Delta deal was found by Cheapflights users on 9/23. 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.
Sat 10/1710:53 am -
1 stop5h 54m
Wed 10/2112:27 pm -
1 stop6h 39m
Deal found 9/23![Delta logo]()
$1,163
This Delta deal was found by Cheapflights users on 9/21. 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 10/156:00 am -
1 stop5h 47m
Sat 10/175:31 pm -
1 stop3h 52m
Deal found 9/21![Delta logo]()
$1,183
This Delta deal was found by Cheapflights users on 9/18. 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.
Sat 10/39:02 am -
1 stop4h 18m
Wed 10/712:27 pm -
1 stop6h 39m
Deal found 9/18![Delta logo]()
$1,343
This Delta deal was found by Cheapflights users on 9/21. 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.
Mon 10/1910:53 am -
1 stop5h 54m
Mon 10/2612:27 pm -
1 stop6h 39m
Deal found 9/21![Delta logo]()
$1,363
This Delta deal was found by Cheapflights users on 9/21. 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.
Wed 10/76:00 am -
1 stop5h 47m
Sun 10/1112:27 pm -
1 stop6h 39m
Deal found 9/21![Delta logo]()
$1,365
This Delta deal was found by Cheapflights users on 9/20. 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 9/252:47 pm -
1 stop3h 32m
Sat 9/269:59 am -
1 stop4h 08m
Deal found 9/20![Delta logo]()
$1,445
This Delta deal was found by Cheapflights users on 9/22. 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 9/2612:00 pm -
1 stop5h 59m
Sun 9/277:13 pm -
1 stop3h 48m
Deal found 9/22![Delta logo]()
$1,456
Best flights from Madison to MidwayDiscover carefully curated flight deals from Madison to Midway that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated September 23, 2026.
Discover carefully curated flight deals from Madison to Midway that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated September 23, 2026.
This Mytrip deal was found by Cheapflights users on 9/21. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/262:25 pm -
3 stops20h 57m
Wed 10/2812:27 pm -
3 stops24h 59m
Deal found 9/21![Multiple Airlines logo]()
$538
This Delta deal was found by Cheapflights users on 9/21. 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 11/266:30 am -
1 stop3h 55m
Sat 11/2810:34 am -
1 stop3h 16m
Deal found 9/21![Delta logo]()
$1,014
This Delta deal was found by Cheapflights users on 9/23. 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.
Sat 10/1710:53 am -
1 stop5h 54m
Wed 10/2112:27 pm -
1 stop6h 39m
Deal found 9/23![Delta logo]()
$1,163
This Delta deal was found by Cheapflights users on 9/22. 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 10/246:00 am -
1 stop5h 47m
Mon 10/2612:27 pm -
1 stop6h 39m
Deal found 9/22![Delta logo]()
$1,183
This Delta deal was found by Cheapflights users on 9/19. 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 10/176:00 am -
1 stop5h 47m
Sat 10/2410:12 am -
1 stop3h 59m
Deal found 9/19![Delta logo]()
$1,183
This Delta deal was found by Cheapflights users on 9/22. 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.
Thu 10/1510:53 am -
1 stop5h 54m
Sun 10/185:31 pm -
1 stop5h 26m
Deal found 9/22![Delta logo]()
$1,183
This Delta deal was found by Cheapflights users on 9/21. 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 10/156:00 am -
1 stop5h 47m
Sat 10/175:31 pm -
1 stop3h 52m
Deal found 9/21![Delta logo]()
$1,183
This Delta deal was found by Cheapflights users on 9/19. 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 10/186:00 am -
1 stop5h 47m
Sun 10/2512:27 pm -
1 stop6h 39m
Deal found 9/19![Delta logo]()
$1,183
This Delta deal was found by Cheapflights users on 9/19. 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 10/1010:53 am -
1 stop5h 54m
Sun 10/115:31 pm -
1 stop3h 24m
Deal found 9/19![Delta logo]()
$1,183
Last-minute flights from Madison to MidwayDiscover last-minute flight deals from Madison to Midway. Data last updated September 23, 2026 and is based on user searches.
Discover last-minute flight deals from Madison to Midway. Data last updated September 23, 2026 and is based on user searches.
This Delta deal was found by Cheapflights users on 9/20. 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 9/252:47 pm -
1 stop3h 32m
Sat 9/269:59 am -
1 stop4h 08m
Deal found 9/20![Delta logo]()
$1,445
This Delta deal was found by Cheapflights users on 9/22. 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 9/2612:00 pm -
1 stop5h 59m
Sun 9/277:13 pm -
1 stop3h 48m
Deal found 9/22![Delta logo]()
$1,456
This Delta deal was found by Cheapflights users on 9/18. 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.
Mon 9/289:02 am -
1 stop4h 18m
Mon 9/287:13 pm -
1 stop3h 48m
Deal found 9/18![Delta logo]()
$1,503
This Delta deal was found by Cheapflights users on 9/18. 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.
Sat 10/39:02 am -
1 stop4h 18m
Wed 10/712:27 pm -
1 stop6h 39m
Deal found 9/18![Delta logo]()
$1,343
This Delta deal was found by Cheapflights users on 9/18. 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.
Sun 10/41:21 pm -
1 stop5h 12m
Thu 10/89:29 am -
1 stop3h 06m
Deal found 9/18![Delta logo]()
$1,533
This Delta deal was found by Cheapflights users on 9/21. 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.
Wed 10/76:00 am -
1 stop5h 47m
Sun 10/1112:27 pm -
1 stop6h 39m
Deal found 9/21![Delta logo]()
$1,365
This Delta deal was found by Cheapflights users on 9/21. 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 10/156:00 am -
1 stop5h 47m
Sat 10/175:31 pm -
1 stop3h 52m
Deal found 9/21![Delta logo]()
$1,183
This Delta deal was found by Cheapflights users on 9/23. 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.
Sat 10/1710:53 am -
1 stop5h 54m
Wed 10/2112:27 pm -
1 stop6h 39m
Deal found 9/23![Delta logo]()
$1,163
This Delta deal was found by Cheapflights users on 9/21. 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.
Mon 10/1910:53 am -
1 stop5h 54m
Mon 10/2612:27 pm -
1 stop6h 39m
Deal found 9/21![Delta logo]()
$1,363
This Mytrip deal was found by Cheapflights users on 9/21. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/262:25 pm -
3 stops20h 57m
Wed 10/2812:27 pm -
2 stops24h 59m
Deal found 9/21![Multiple Airlines logo]()
$485
One-way flights from Madison to MidwaySearch for one-way flight options from Madison to Midway. Find affordable one-way fares based on user searches. Data last updated September 23, 2026.
Search for one-way flight options from Madison to Midway. Find affordable one-way fares based on user searches. Data last updated September 23, 2026.
This Kiwi.com deal was found by Cheapflights users on 9/21. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/1010:30 am -
2 stops31h 17m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/21![Multiple Airlines logo]()
$179
This Kiwi.com deal was found by Cheapflights users on 9/21. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/1110:38 am -
2 stops13h 09m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/21![Multiple Airlines logo]()
$184
This Delta deal was found by Cheapflights users on 9/18. 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 11/2710:49 am -
1 stop5h 50m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/18![Delta logo]()
$230
This Kiwi.com deal was found by Cheapflights users on 9/21. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/126:00 pm -
3 stops47h 47m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/21![Multiple Airlines logo]()
$239
This Kiwi.com deal was found by Cheapflights users on 9/20. 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.
Wed 10/2110:38 am -
2 stops13h 05m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/20![Multiple Airlines logo]()
$244
This Kiwi.com deal was found by Cheapflights users on 9/22. 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 10/1410:38 am -
3 stops31h 07m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/22![Multiple Airlines logo]()
$256
This Kiwi.com deal was found by Cheapflights users on 9/18. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/86:00 pm -
2 stops28h 22m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/18![Multiple Airlines logo]()
$271
This Delta deal was found by Cheapflights users on 9/21. 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.
Tue 11/107:49 pm -
1 stop13h 01m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/21![Delta logo]()
$277
Find flight deals from Madison to Midway
Discover tips and strategies to find the most affordable flight options for your journey from Madison (MSN) to Midway (MDW). 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 23, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $485 (Mytrip) |
One-way from | $179 (Kiwi.com) |
Popular in | April |
Cheapest in | October |
Average price | $249 |
Cheapflights Fare Finder
Customize your flight search to find flights from Madison to Midway 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 23, 2026.
Use the filters below to find and compare flights from Madison to Chicago Midway Airport that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
Quickest round-trip
MadisonChicago
MSN Madison Truax Field - MDW Chicago Midway
MSNMDW
Madison Truax Field
Fri 11/27
10:49 am-4:39 pm
1 stop5h 50m
Chicago Midway
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$230
MadisonChicago
MSN Madison Truax Field - MDW Chicago Midway
MSNMDW
Madison Truax Field
Wed 11/11
10:38 am-5:47 pm
3 stops31h 09m
Chicago Midway
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$245
MadisonChicago
MSN Madison Truax Field - MDW Chicago Midway
MSNMDW
Madison Truax Field
Wed 10/14
10:38 am-5:45 pm
3 stops31h 07m
Chicago Midway
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$256
MadisonChicago
MSN Madison Truax Field - MDW Chicago Midway
MSNMDW
Madison Truax Field
Thu 10/8
6:00 pm-10:22 pm
2 stops28h 22m
Chicago Midway
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$271
MadisonChicago
MSN Madison Truax Field - MDW Chicago Midway
MSNMDW
Madison Truax Field
Tue 11/10
7:49 pm-8:50 am
1 stop13h 01m
Chicago Midway
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$277
MadisonChicago
MSN Madison Truax Field - MDW Chicago Midway
MSNMDW
Madison Truax Field
Wed 10/21
10:38 am-5:45 pm
3 stops31h 07m
Chicago Midway
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$280
MadisonChicago
MSN Madison Truax Field - MDW Chicago Midway
MSNMDW
Madison Truax Field
Sun 10/18
6:00 pm-2:35 pm
3 stops44h 35m
Chicago Midway
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$288
MadisonChicago
MSN Madison Truax Field - MDW Chicago Midway
MSNMDW
Madison Truax Field
Tue 10/20
10:30 am-11:43 pm
2 stops37h 13m
Chicago Midway
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$304
MadisonChicago
MSN Madison Truax Field - MDW Chicago Midway
MSNMDW
Madison Truax Field
Thu 11/12
11:35 am-10:54 pm
1 stop11h 19m
Chicago Midway
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$447
MadisonChicago
MSN Madison Truax Field - MDW Chicago Midway
MSNMDW
Madison Truax Field
Fri 11/27
2:40 pm-7:02 am
3 stops40h 22m
Chicago Midway
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$498
Showing 1-10 of 19 resultsSorted by cheapest first
Compare providers for flights from Madison to Midway
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 Madison to Midway in September.
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars |
- Most accurate provider: When it comes to deals on Madison-Chicago Midway Airport flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Madison-Chicago Midway Airport flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Madison-Chicago Midway Airport flight searches over the past month and is updated monthly.
- Most trusted provider: When it comes to deals on Madison-Chicago Midway Airport 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 Madison-Chicago Midway Airport 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 Madison to Midway
Have a flexible travel schedule? Discover the best time to fly to Midway from Madison with our price prediction graph.
MSN-MDW
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 Madison to Midway. 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 Chicago Midway Airport?
Book flights to Chicago Midway Airport if you plan to visit one of these locationsBenton Harbor
Lansing
Merrillville
Valparaiso
Hammond
Saint Joseph
Porter
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