$269+ Cheap flights from Midland (MAF) 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 10/11. Fares are subject to change and may not be available on all flights or dates of travel.
MAF — MDW
Oct 30 — Nov 61
Round-trip
1 adult, Economy
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Find cheap flights from Midland 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 Midland to Midway
Cheapest
Best
Last-minute
One-way
Cheapest flights from Midland to MidwayExplore the most affordable flight options available from Midland to Midway. 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 Midland to Midway. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 30, 2026.
This Southwest 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/173:00 pm -
1 stop5h 00m
Sat 10/246:35 am -
1 stop7h 45m
Deal found 9/26![Southwest logo]()
$344
This Southwest 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/68:25 pm -
1 stop4h 45m
Mon 11/95:20 am -
1 stop5h 15m
Deal found 9/29![Southwest logo]()
$364
This Southwest 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/138:25 pm -
1 stop4h 45m
Sun 11/157:20 am -
1 stop5h 45m
Deal found 9/29![Southwest logo]()
$442
This Southwest 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/161:10 pm -
1 stop4h 35m
Mon 10/1910:55 pm -
1 stop13h 40m
Deal found 9/26![Southwest logo]()
$443
This Southwest 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/88:25 pm -
1 stop4h 45m
Mon 11/163:10 pm -
1 stop6h 50m
Deal found 9/25![Southwest logo]()
$454
Best flights from Midland to MidwayDiscover carefully curated flight deals from Midland to Midway 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 Midland to Midway that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated September 30, 2026.
This Southwest 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/173:00 pm -
1 stop5h 00m
Sat 10/246:35 am -
1 stop7h 45m
Deal found 9/26![Southwest logo]()
$344
This Southwest 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/61:45 pm -
2 stops6h 50m
Mon 11/95:20 am -
1 stop5h 15m
Deal found 9/29![Southwest logo]()
$369
This Southwest 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/161:10 pm -
1 stop4h 35m
Mon 10/1910:55 pm -
1 stop13h 40m
Deal found 9/26![Southwest logo]()
$443
This Southwest 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/88:25 pm -
1 stop4h 45m
Mon 11/163:10 pm -
1 stop6h 50m
Deal found 9/25![Southwest logo]()
$454
This Southwest 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/216:20 pm -
1 stop6h 30m
Mon 11/235:20 pm -
1 stop6h 35m
Deal found 9/28![Southwest logo]()
$466
This Southwest 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/195:50 am -
1 stop5h 10m
Tue 11/246:30 am -
1 stop5h 00m
Deal found 9/29![Southwest logo]()
$495
This Southwest 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/242:35 pm -
1 stop5h 20m
Sat 12/265:20 am -
1 stop4h 45m
Deal found 9/28![Southwest logo]()
$515
Last-minute flights from Midland to MidwayDiscover last-minute flight deals from Midland to Midway. Data last updated September 30, 2026 and is based on user searches.
Discover last-minute flight deals from Midland to Midway. Data last updated September 30, 2026 and is based on user searches.
This Southwest 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/103:00 pm -
1 stop7h 20m
Wed 10/1410:15 am -
1 stop7h 10m
Deal found 9/25![Southwest logo]()
$537
This Southwest 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/122:05 pm -
2 stops7h 05m
Fri 10/165:15 am -
2 stops8h 00m
Deal found 9/27![Southwest logo]()
$573
This Southwest 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/146:15 pm -
1 stop5h 00m
Sun 10/185:00 am -
1 stop6h 10m
Deal found 9/29![Southwest logo]()
$567
This Southwest 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/161:10 pm -
1 stop4h 35m
Mon 10/1910:55 pm -
1 stop13h 40m
Deal found 9/26![Southwest logo]()
$443
This Southwest 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/173:00 pm -
1 stop5h 00m
Sat 10/246:35 am -
1 stop7h 45m
Deal found 9/26![Southwest logo]()
$344
One-way flights from Midland to MidwaySearch for one-way flight options from Midland to Midway. Find affordable one-way fares based on user searches. Data last updated September 30, 2026.
Search for one-way flight options from Midland to Midway. Find affordable one-way fares based on user searches. Data last updated September 30, 2026.
This Southwest 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/117:30 pm -
1 stop5h 30m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/25![Southwest logo]()
$269
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.
Mon 10/122:27 pm -
3 stops48h 08m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/25![Multiple Airlines logo]()
$1,132
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.
Sun 10/112:27 pm -
3 stops48h 08m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/25![Multiple Airlines logo]()
$1,288
Find flight deals from Midland to Midway
Discover tips and strategies to find the most affordable flight options for your journey from Midland (MAF) 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 30, 2026.
Most accurate provider | Expedia 1 star |
|---|---|
Most trusted provider | Expedia 3 stars |
Round-trip from | $344 (Southwest) |
One-way from | $269 (Southwest) |
Cheapflights Fare Finder
Customize your flight search to find flights from Midland 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 30, 2026.
Use the filters below to find and compare flights from Midland to Chicago Midway Airport that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
Quickest round-trip
MidlandChicago
MAF Midland Intl - MDW Chicago Midway
MAFMDW
Midland Intl
Sun 10/11
7:30 pm-1:00 am
1 stop5h 30m
Chicago Midway
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$269
MidlandChicago
MAF Midland Intl - MDW Chicago Midway
MAFMDW
Midland Intl
Sat 10/17
3:00 pm-8:00 pm
1 stop5h 00m
Chicago Midway
Sat 10/24
6:35 am-2:20 pm
1 stop7h 45m
$344
MidlandChicago
MAF Midland Intl - MDW Chicago Midway
MAFMDW
Midland Intl
Fri 11/6
1:45 pm-8:35 pm
2 stops6h 50m
Chicago Midway
Mon 11/9
5:20 am-10:35 am
1 stop5h 15m
$369
MidlandChicago
MAF Midland Intl - MDW Chicago Midway
MAFMDW
Midland Intl
Fri 10/16
1:10 pm-5:45 pm
1 stop4h 35m
Chicago Midway
Mon 10/19
10:55 pm-12:35 pm
1 stop13h 40m
$443
MidlandChicago
MAF Midland Intl - MDW Chicago Midway
MAFMDW
Midland Intl
Sun 11/8
8:25 pm-1:10 am
1 stop4h 45m
Chicago Midway
Mon 11/16
3:10 pm-10:00 pm
1 stop6h 50m
$454
MidlandChicago
MAF Midland Intl - MDW Chicago Midway
MAFMDW
Midland Intl
Sat 11/21
6:20 pm-12:50 am
1 stop6h 30m
Chicago Midway
Mon 11/23
5:20 pm-11:55 pm
1 stop6h 35m
$466
MidlandChicago
MAF Midland Intl - MDW Chicago Midway
MAFMDW
Midland Intl
Thu 11/19
5:50 am-11:00 am
1 stop5h 10m
Chicago Midway
Tue 11/24
6:30 am-11:30 am
1 stop5h 00m
$495
MidlandChicago
MAF Midland Intl - MDW Chicago Midway
MAFMDW
Midland Intl
Thu 12/24
2:35 pm-7:55 pm
1 stop5h 20m
Chicago Midway
Sat 12/26
5:20 am-10:05 am
1 stop4h 45m
$515
Sorted by cheapest first
- Most accurate provider: When it comes to deals on Midland-Chicago Midway Airport flights, users find the pricing of Expedia to be most consistent on Cheapflights vs. Expedia Users can find the same prices on Midland-Chicago Midway Airport flight deals on Cheapflights vs. Expedia <90% of the time. Price accuracy is based on data collected from Midland-Chicago Midway Airport flight searches over the past month and is updated monthly.
- Most trusted provider: When it comes to deals on Midland-Chicago Midway Airport flights, Cheapflights users trust Expedia the most. Expedia 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 Midland-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 Midland to Midway
Have a flexible travel schedule? Discover the best time to fly to Midway from Midland with our price prediction graph.
MAF-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 Midland 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
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Valparaiso
Hammond
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Porter
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