$147+ 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 1/9. Fares are subject to change and may not be available on all flights or dates of travel.
MAF — MDW
Nov 25 — Dec 21
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 October 26, 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 October 26, 2026.
This Southwest deal was found by Cheapflights users on 10/25. 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.
Mon 11/236:10 pm -
1 stop7h 00m
Wed 12/27:05 am -
1 stop6h 15m
Deal found 10/25![Southwest logo]()
$295
This Southwest 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/164:10 pm -
1 stop7h 00m
Sun 12/207:00 am -
1 stop7h 30m
Deal found 10/22![Southwest logo]()
$307
This Southwest deal was found by Cheapflights users on 10/26. 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.
Thu 11/2611:05 am -
1 stop5h 00m
Fri 12/47:05 am -
1 stop6h 15m
Deal found 10/26![Southwest logo]()
$315
This Southwest deal was found by Cheapflights users on 10/26. 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 11/276:15 pm -
1 stop6h 55m
Thu 12/37:05 am -
1 stop6h 15m
Deal found 10/26![Southwest logo]()
$414
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 October 26, 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 October 26, 2026.
This Southwest deal was found by Cheapflights users on 10/25. 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.
Mon 11/236:10 pm -
1 stop7h 00m
Wed 12/28:00 am -
2 stops7h 35m
Deal found 10/25![Southwest logo]()
$300
This Southwest deal was found by Cheapflights users on 10/26. 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 11/276:10 pm -
2 stops7h 00m
Thu 12/39:40 am -
2 stops5h 55m
Deal found 10/26![Southwest logo]()
$424
This Southwest 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/66:15 pm -
1 stop6h 55m
Tue 11/107:05 am -
1 stop6h 15m
Deal found 10/21![Southwest logo]()
$425
This Southwest deal was found by Cheapflights users on 10/26. 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 11/276:10 pm -
2 stops7h 00m
Fri 12/47:05 am -
1 stop6h 15m
Deal found 10/26![Southwest logo]()
$430
This Southwest deal was found by Cheapflights users on 10/25. 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.
Mon 11/236:10 pm -
1 stop7h 00m
Mon 11/306:40 pm -
1 stop5h 05m
Deal found 10/25![Southwest logo]()
$456
This Southwest 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/186:00 pm -
1 stop7h 00m
Sat 1/24:20 pm -
2 stops6h 50m
Deal found 10/24![Southwest logo]()
$479
This Southwest deal was found by Cheapflights users on 10/25. 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.
Mon 11/96:15 pm -
1 stop6h 55m
Fri 11/132:35 pm -
1 stop8h 05m
Deal found 10/25![Southwest logo]()
$557
Last-minute flights from Midland to MidwayDiscover last-minute flight deals from Midland to Midway. Data last updated October 26, 2026 and is based on user searches.
Discover last-minute flight deals from Midland to Midway. Data last updated October 26, 2026 and is based on user searches.
This Southwest 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/66:15 pm -
1 stop6h 55m
Tue 11/107:05 am -
1 stop6h 15m
Deal found 10/21![Southwest logo]()
$425
This Southwest deal was found by Cheapflights users on 10/25. 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.
Mon 11/236:10 pm -
1 stop7h 00m
Wed 12/27:05 am -
1 stop6h 15m
Deal found 10/25![Southwest logo]()
$295
This Southwest deal was found by Cheapflights users on 10/25. 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.
Mon 11/236:10 pm -
1 stop7h 00m
Mon 11/306:40 pm -
1 stop5h 05m
Deal found 10/25![Southwest logo]()
$456
This Southwest deal was found by Cheapflights users on 10/26. 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.
Thu 11/2611:05 am -
1 stop5h 00m
Fri 12/47:05 am -
1 stop6h 15m
Deal found 10/26![Southwest logo]()
$315
This Southwest deal was found by Cheapflights users on 10/26. 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 11/276:15 pm -
1 stop6h 55m
Thu 12/37:05 am -
1 stop6h 15m
Deal found 10/26![Southwest logo]()
$414
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 October 26, 2026.
Search for one-way flight options from Midland to Midway. Find affordable one-way fares based on user searches. Data last updated October 26, 2026.
This Southwest 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 1/93:35 pm -
1 stop4h 55m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/21![Southwest logo]()
$147
This Southwest 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/156:10 pm -
1 stop7h 00m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/24![Southwest logo]()
$217
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 October 26, 2026.
Most accurate provider | Expedia 1 star |
|---|---|
Most trusted provider | Expedia 3 stars |
Round-trip from | $295 (Southwest) |
One-way from | $147 (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 October 26, 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
Sat 1/9
5:55 am-11:25 am
2 stops5h 30m
Chicago Midway
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$152
MidlandChicago
MAF Midland Intl - MDW Chicago Midway
MAFMDW
Midland Intl
Sun 11/15
6:10 pm-1:10 am
1 stop7h 00m
Chicago Midway
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$217
MidlandChicago
MAF Midland Intl - MDW Chicago Midway
MAFMDW
Midland Intl
Mon 11/23
6:10 pm-1:10 am
1 stop7h 00m
Chicago Midway
Wed 12/2
8:00 am-3:35 pm
2 stops7h 35m
$300
MidlandChicago
MAF Midland Intl - MDW Chicago Midway
MAFMDW
Midland Intl
Fri 11/27
6:10 pm-1:10 am
2 stops7h 00m
Chicago Midway
Thu 12/3
9:40 am-3:35 pm
2 stops5h 55m
$424
MidlandChicago
MAF Midland Intl - MDW Chicago Midway
MAFMDW
Midland Intl
Fri 11/6
6:15 pm-1:10 am
1 stop6h 55m
Chicago Midway
Tue 11/10
7:05 am-1:20 pm
1 stop6h 15m
$425
MidlandChicago
MAF Midland Intl - MDW Chicago Midway
MAFMDW
Midland Intl
Fri 11/27
6:10 pm-1:10 am
2 stops7h 00m
Chicago Midway
Fri 12/4
7:05 am-1:20 pm
1 stop6h 15m
$430
MidlandChicago
MAF Midland Intl - MDW Chicago Midway
MAFMDW
Midland Intl
Mon 11/23
6:10 pm-1:10 am
1 stop7h 00m
Chicago Midway
Mon 11/30
6:40 pm-11:45 pm
1 stop5h 05m
$456
MidlandChicago
MAF Midland Intl - MDW Chicago Midway
MAFMDW
Midland Intl
Fri 12/18
6:00 pm-1:00 am
1 stop7h 00m
Chicago Midway
Sat 1/2
4:20 pm-11:10 pm
2 stops6h 50m
$479
MidlandChicago
MAF Midland Intl - MDW Chicago Midway
MAFMDW
Midland Intl
Mon 11/9
6:15 pm-1:10 am
1 stop6h 55m
Chicago Midway
Fri 11/13
2:35 pm-10:40 pm
1 stop8h 05m
$557
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
Merrillville
Lansing
Valparaiso
Hammond
Saint Joseph
Porter
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