$249+ Cheap flights from Chicago (CHI) to Midland (MAF)
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 12/19. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — MAF
Oct 29 — Nov 51
Round-trip
1 adult, Economy
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Find cheap flights from Chicago to Midland 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 Chicago to Midland
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Cheapest flights from Chicago to MidlandExplore the most affordable flight options available from Chicago to Midland. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 29, 2026.
Explore the most affordable flight options available from Chicago to Midland. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 29, 2026.
This American Airlines 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/712:02 pm -
1 stop7h 10m
Sat 11/148:03 am -
1 stop7h 57m
Deal found 9/27![American Airlines logo]()
$339
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.
Mon 10/265:15 am -
1 stop5h 15m
Mon 11/23:05 pm -
1 stop5h 55m
Deal found 9/26![Southwest logo]()
$339
This American Airlines deal was found by Cheapflights users on 9/24. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/245:00 am -
1 stop4h 59m
Fri 1/15:00 am -
1 stop5h 00m
Deal found 9/24![American Airlines logo]()
$364
This United Airlines 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/214:07 pm -
1 stop5h 51m
Tue 12/15:05 pm -
1 stop5h 51m
Deal found 9/28![United Airlines logo]()
$381
This American Airlines 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/243:50 pm -
1 stop6h 47m
Sun 10/255:00 am -
1 stop6h 09m
Deal found 9/29![American Airlines logo]()
$398
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.
Fri 12/47:05 am -
1 stop6h 15m
Sun 12/68:25 pm -
1 stop4h 40m
Deal found 9/27![Southwest logo]()
$413
This United Airlines 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/182:22 pm -
1 stop7h 36m
Tue 12/15:10 pm -
1 stop6h 49m
Deal found 9/28![United Airlines logo]()
$449
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 11/215:20 am -
1 stop4h 45m
Tue 12/14:05 pm -
1 stop6h 35m
Deal found 9/28![Southwest logo]()
$454
This American Airlines 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/1812:02 pm -
1 stop6h 11m
Fri 12/45:39 pm -
1 stop5h 25m
Deal found 9/28![American Airlines logo]()
$474
This United Airlines 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/244:07 pm -
1 stop5h 51m
Thu 12/35:00 am -
1 stop6h 15m
Deal found 9/28![United Airlines logo]()
$491
This American Airlines 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/265:16 pm -
1 stop5h 21m
Mon 11/28:03 am -
1 stop6h 09m
Deal found 9/26![American Airlines logo]()
$496
This United Airlines 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/207:00 am -
1 stop5h 37m
Thu 12/35:00 am -
1 stop6h 15m
Deal found 9/28![United Airlines logo]()
$498
Best flights from Chicago to MidlandDiscover carefully curated flight deals from Chicago to Midland that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated September 29, 2026.
Discover carefully curated flight deals from Chicago to Midland that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated September 29, 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.
Mon 10/265:15 am -
1 stop5h 15m
Mon 11/23:05 pm -
1 stop5h 55m
Deal found 9/26![Southwest logo]()
$339
This American Airlines deal was found by Cheapflights users on 9/24. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/245:00 am -
1 stop4h 59m
Fri 1/15:00 am -
1 stop5h 00m
Deal found 9/24![American Airlines logo]()
$364
This United Airlines 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/235:30 pm -
1 stop6h 13m
Mon 11/305:05 pm -
1 stop6h 21m
Deal found 9/28![United Airlines logo]()
$498
This Southwest deal was found by Cheapflights users on 9/24. 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.
Thu 1/217:50 am -
1 stop5h 00m
Sun 1/244:00 pm -
1 stop5h 00m
Deal found 9/24![Southwest logo]()
$388
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.
Fri 12/43:10 pm -
1 stop6h 45m
Sun 12/61:45 pm -
2 stops6h 45m
Deal found 9/27![Southwest logo]()
$418
This United Airlines 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/1912:40 pm -
1 stop5h 37m
Thu 12/35:00 am -
1 stop6h 15m
Deal found 9/28![United Airlines logo]()
$498
This United Airlines 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/269:44 pm -
2 stops25h 59m
Mon 11/211:58 am -
1 stop6h 32m
Deal found 9/26![United Airlines logo]()
$522
This American Airlines 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/93:50 pm -
1 stop6h 47m
Mon 10/125:00 am -
1 stop5h 00m
Deal found 9/26![American Airlines logo]()
$611
This United Airlines 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/205:30 am -
1 stop5h 44m
Fri 12/47:23 pm -
1 stop5h 22m
Deal found 9/28![United Airlines logo]()
$523
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.
Tue 10/136:25 am -
1 stop7h 00m
Sat 10/173:00 pm -
1 stop7h 20m
Deal found 9/28![Southwest logo]()
$537
This United Airlines 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/712:40 pm -
1 stop5h 37m
Sat 11/145:00 am -
2 stops15h 19m
Deal found 9/27![United Airlines logo]()
$530
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 10/103:10 pm -
1 stop6h 15m
Wed 10/146:15 pm -
1 stop5h 00m
Deal found 9/25![Southwest logo]()
$537
This United Airlines 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/135:53 pm -
1 stop5h 31m
Sat 10/172:13 pm -
1 stop6h 02m
Deal found 9/28![United Airlines logo]()
$537
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 10/102:40 pm -
1 stop6h 10m
Mon 10/125:50 pm -
1 stop7h 20m
Deal found 9/28![Southwest logo]()
$562
This United Airlines 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/105:53 pm -
1 stop5h 34m
Mon 10/125:00 pm -
1 stop6h 27m
Deal found 9/28![United Airlines logo]()
$562
This United Airlines 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/205:30 am -
1 stop5h 44m
Sun 11/297:15 pm -
1 stop5h 30m
Deal found 9/28![United Airlines logo]()
$597
This United Airlines deal was found by Cheapflights users on 9/24. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/246:50 am -
2 stops11h 19m
Fri 1/15:15 pm -
1 stop5h 27m
Deal found 9/24![United Airlines logo]()
$621
Last-minute flights from Chicago to MidlandDiscover last-minute flight deals from Chicago to Midland. Data last updated September 29, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to Midland. Data last updated September 29, 2026 and is based on user searches.
This American Airlines 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/45:00 am -
1 stop6h 20m
Tue 10/65:00 am -
1 stop6h 09m
Deal found 9/25![American Airlines logo]()
$636
This American Airlines 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/93:50 pm -
1 stop6h 47m
Mon 10/125:00 am -
1 stop5h 00m
Deal found 9/25![American Airlines logo]()
$537
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.
Fri 10/93:45 pm -
1 stop8h 25m
Mon 10/125:50 pm -
1 stop7h 20m
Deal found 9/25![Southwest logo]()
$568
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 10/103:10 pm -
1 stop6h 15m
Wed 10/146:15 pm -
1 stop5h 00m
Deal found 9/25![Southwest logo]()
$537
This United Airlines 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/105:30 am -
1 stop5h 19m
Tue 10/135:00 pm -
1 stop7h 23m
Deal found 9/29![United Airlines logo]()
$562
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.
Sat 10/102:40 pm -
1 stop6h 10m
Tue 10/132:05 pm -
1 stop4h 20m
Deal found 9/29![Southwest logo]()
$562
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.
Mon 10/1210:55 pm -
1 stop13h 40m
Fri 10/161:10 pm -
1 stop4h 35m
Deal found 9/26![Southwest logo]()
$595
This American Airlines 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/243:50 pm -
1 stop6h 47m
Sun 10/255:00 am -
1 stop6h 09m
Deal found 9/29![American Airlines logo]()
$398
This United Airlines 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/245:00 am -
1 stop7h 45m
Sun 10/252:20 pm -
2 stops16h 39m
Deal found 9/29![United Airlines logo]()
$548
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.
Mon 10/265:15 am -
1 stop5h 15m
Mon 11/23:05 pm -
1 stop5h 55m
Deal found 9/26![Southwest logo]()
$339
This American Airlines 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/265:16 pm -
1 stop5h 21m
Mon 11/28:03 am -
1 stop6h 09m
Deal found 9/26![American Airlines logo]()
$496
This United Airlines 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/269:44 pm -
2 stops25h 59m
Mon 11/211:58 am -
1 stop6h 32m
Deal found 9/26![United Airlines logo]()
$522
One-way flights from Chicago to MidlandSearch for one-way flight options from Chicago to Midland. Find affordable one-way fares based on user searches. Data last updated September 29, 2026.
Search for one-way flight options from Chicago to Midland. Find affordable one-way fares based on user searches. Data last updated September 29, 2026.
This American Airlines 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/197:01 pm -
1 stop4h 51m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/25![American Airlines logo]()
$249
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 12/195:20 am -
1 stop4h 45m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/25![Southwest logo]()
$287
This American Airlines 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/81:46 pm -
1 stop7h 48m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/29![American Airlines logo]()
$343
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 10/87:10 am -
1 stop6h 05m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/29![Southwest logo]()
$343
This United Airlines 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/125:53 pm -
1 stop5h 31m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/25![United Airlines logo]()
$447
This United Airlines 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/196:50 am -
2 stops16h 52m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/25![United Airlines logo]()
$476
This United Airlines 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/87:00 am -
2 stops9h 12m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/25![United Airlines logo]()
$621
This United Airlines 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/48:40 am -
2 stops14h 47m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/25![United Airlines logo]()
$768
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 10/45:30 pm -
3 stops48h 41m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/25![Multiple Airlines logo]()
$1,161
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.
Thu 10/83:20 pm -
3 stops52h 14m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/25![Multiple Airlines logo]()
$1,214
Find flight deals from Chicago to Midland
Discover tips and strategies to find the most affordable flight options for your journey from Chicago (CHI) to Midland (MAF). 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 29, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $339 (American Airlines) |
One-way from | $249 (American Airlines) |
Popular in | November |
Cheapest in | January |
Average price | $456 |
Cheapflights Fare Finder
Customize your flight search to find flights from Chicago to Midland 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 29, 2026.
Use the filters below to find and compare flights from Chicago to Midland that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
ChicagoMidland
ORD Chicago O'Hare Intl - MAF Midland Intl
ORDMAF
Chicago O'Hare Intl
Sat 12/19
7:01 pm-11:52 pm
1 stop4h 51m
Midland Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$249
Quickest round-trip
ChicagoMidland
MDW Chicago Midway - MAF Midland Intl
MDWMAF
Chicago Midway
Sat 12/19
5:20 am-10:05 am
1 stop4h 45m
Midland Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$287
ChicagoMidland
MDW Chicago Midway - MAF Midland Intl
MDWMAF
Chicago Midway
Mon 10/26
5:15 am-10:30 am
1 stop5h 15m
Midland Intl
Mon 11/2
3:05 pm-9:00 pm
1 stop5h 55m
$339
ChicagoMidland
ORD Chicago O'Hare Intl - MAF Midland Intl
ORDMAF
Chicago O'Hare Intl
Thu 10/8
1:46 pm-9:34 pm
1 stop7h 48m
Midland Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$343
ChicagoMidland
MDW Chicago Midway - MAF Midland Intl
MDWMAF
Chicago Midway
Thu 10/8
7:10 am-1:15 pm
1 stop6h 05m
Midland Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$343
ChicagoMidland
ORD Chicago O'Hare Intl - MAF Midland Intl
ORDMAF
Chicago O'Hare Intl
Thu 12/24
5:00 am-9:59 am
1 stop4h 59m
Midland Intl
Fri 1/1
5:00 am-10:00 am
1 stop5h 00m
$364
ChicagoMidland
MDW Chicago Midway - MAF Midland Intl
MDWMAF
Chicago Midway
Thu 1/21
7:50 am-12:50 pm
1 stop5h 00m
Midland Intl
Sun 1/24
4:00 pm-9:00 pm
1 stop5h 00m
$388
ChicagoMidland
MDW Chicago Midway - MAF Midland Intl
MDWMAF
Chicago Midway
Fri 12/4
3:10 pm-9:55 pm
1 stop6h 45m
Midland Intl
Sun 12/6
1:45 pm-8:30 pm
2 stops6h 45m
$418
ChicagoMidland
ORD Chicago O'Hare Intl - MAF Midland Intl
ORDMAF
Chicago O'Hare Intl
Mon 10/12
5:53 pm-11:24 pm
1 stop5h 31m
Midland Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$447
ChicagoMidland
ORD Chicago O'Hare Intl - MAF Midland Intl
ORDMAF
Chicago O'Hare Intl
Mon 11/23
5:30 pm-11:43 pm
1 stop6h 13m
Midland Intl
Mon 11/30
5:05 pm-11:26 pm
1 stop6h 21m
$498
Showing 1-10 of 24 resultsSorted by cheapest first
Compare providers for flights from Chicago to Midland
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 Chicago to Midland 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 Chicago-Midland flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Chicago-Midland flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Chicago-Midland flight searches over the past month and is updated monthly.
- Most trusted provider: When it comes to deals on Chicago-Midland 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-Midland 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 Chicago to Midland
Have a flexible travel schedule? Discover the best time to fly to Midland from Chicago with our price prediction graph.
CHI-MAF
ORD-MAF
MDW-MAF
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.
Cheapflights Insights
Everything you need to know about your flight from Chicago to Midland
CHI-MAF
ORD-MAF
MDW-MAF
No data available for this route at this time. Please check back soon.
Reviews of airlines servicing Midland
Get insights into the airlines that provide service to Midland. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Midland. Reviews last updated September 29, 2026.
Read reviews from past customers who have flown Southwest and United Airlines from Chicago to Midland. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
Comfort
8.0
Entertainment
7.5
Food
7.0
Crew
8.6
Overall
8.0
Boarding
8.1
Reviews
1 / 20
2.0
MediocreMike,Aug 2025
OKC - AUS
Comfort
8.0
Entertainment
7.5
Food
7.0
Crew
8.6
Overall
8.0
Boarding
8.1
Reviews
1 / 20
2.0
MediocreMike,Aug 2025
OKC - AUS
Comfort
8.0
Entertainment
7.5
Food
7.0
Crew
8.6
Overall
8.0
Boarding
8.1
Reviews
1 / 20
2.0
MediocreMike,Aug 2025
OKC - AUS
Related info for your journey
Find useful and relevant information for your journey from Chicago to Midland. 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 Midland?
Book flights to Midland if you plan to visit one of these locationsBig Spring
Barstow
Fort Stockton
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Other flights to Midland
Explore flights to Midland departing from other origins. Flights are based on user searches made on Cheapflights and were last updated on September 29, 2026.
Chicago and Midland flights
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Top 2 airlines flying from Chicago to Midland
Discover the top 2 airlines that operate flights from Chicago to Midland. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 7,457,451 searches. Data last updated September 29, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$347 | Average$473 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$379 | Average$434 | FlexibilityNo cancel fee | On-time71% |