$279+ 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 11/9. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — MAF
Nov 23 — Nov 301
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
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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 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 October 24, 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 October 24, 2026.
This American Airlines 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/114:53 pm -
1 stop7h 03m
Sat 11/148:03 am -
1 stop6h 09m
Deal found 10/22![American Airlines logo]()
$293
This Southwest deal was found by Cheapflights users on 10/19. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/86:40 am -
1 stop7h 20m
Tue 12/1511:00 am -
1 stop6h 10m
Deal found 10/19![Southwest logo]()
$293
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.
Tue 11/177:05 am -
1 stop6h 15m
Thu 11/194:05 pm -
2 stops6h 40m
Deal found 10/21![Southwest logo]()
$305
This American Airlines 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/1712:02 pm -
1 stop7h 10m
Thu 11/196:41 pm -
1 stop5h 39m
Deal found 10/21![American Airlines logo]()
$364
This United Airlines deal was found by Cheapflights users on 10/19. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/85:52 pm -
1 stop5h 52m
Tue 12/1511:50 am -
1 stop6h 29m
Deal found 10/19![United Airlines logo]()
$379
This United Airlines 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/175:30 pm -
1 stop6h 13m
Wed 11/181:21 pm -
1 stop8h 09m
Deal found 10/22![United Airlines logo]()
$403
This Southwest deal was found by Cheapflights users on 10/19. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/225:20 am -
1 stop4h 55m
Wed 12/2310:45 am -
2 stops7h 35m
Deal found 10/19![Southwest logo]()
$409
This United Airlines deal was found by Cheapflights users on 10/19. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/610:55 am -
1 stop5h 35m
Wed 11/115:00 am -
1 stop5h 10m
Deal found 10/19![United Airlines logo]()
$425
This Southwest deal was found by Cheapflights users on 10/19. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/65:20 pm -
1 stop6h 35m
Wed 11/116:20 pm -
1 stop4h 50m
Deal found 10/19![Southwest logo]()
$425
This American Airlines 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/155:59 pm -
1 stop4h 56m
Sun 12/2012:39 pm -
1 stop7h 20m
Deal found 10/20![American Airlines logo]()
$430
This Southwest deal was found by Cheapflights users on 10/19. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/612:45 pm -
2 stops9h 55m
Tue 11/104:05 pm -
1 stop6h 35m
Deal found 10/19![Southwest logo]()
$430
This American Airlines 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 American Airlines is selected, and click “Compare selected ” under the list of providers to see comparable flight deals.
Wed 10/286:00 am -
1 stop7h 57m
Sat 11/216:41 pm -
1 stop5h 39m
Deal found 10/20![American Airlines logo]()
$450
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 October 24, 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 October 24, 2026.
This Southwest deal was found by Cheapflights users on 10/19. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/86:40 am -
1 stop7h 20m
Tue 12/1511:00 am -
1 stop6h 10m
Deal found 10/19![Southwest logo]()
$293
This American Airlines 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/1712:02 pm -
1 stop7h 10m
Thu 11/196:41 pm -
1 stop5h 39m
Deal found 10/21![American Airlines logo]()
$364
This United Airlines 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/175:30 pm -
1 stop6h 13m
Wed 11/181:21 pm -
1 stop8h 09m
Deal found 10/22![United Airlines logo]()
$403
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.
Tue 11/177:05 am -
1 stop6h 15m
Thu 11/194:05 pm -
2 stops6h 40m
Deal found 10/21![Southwest logo]()
$305
This United Airlines 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/65:30 am -
1 stop5h 44m
Wed 11/117:00 am -
1 stop5h 29m
Deal found 10/21![United Airlines logo]()
$425
This American Airlines 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/63:00 pm -
1 stop7h 47m
Tue 11/106:48 pm -
1 stop5h 11m
Deal found 10/24![American Airlines logo]()
$425
This United Airlines 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/64:07 pm -
1 stop5h 51m
Tue 11/108:30 am -
1 stop6h 21m
Deal found 10/21![United Airlines logo]()
$425
This Southwest deal was found by Cheapflights users on 10/19. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/65:20 pm -
1 stop6h 35m
Wed 11/116:20 pm -
1 stop4h 50m
Deal found 10/19![Southwest logo]()
$425
This American Airlines 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/155:59 pm -
1 stop4h 56m
Sun 12/2012:39 pm -
1 stop7h 20m
Deal found 10/23![American Airlines logo]()
$438
This Southwest 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/612:25 pm -
1 stop5h 05m
Tue 11/104:05 pm -
1 stop6h 35m
Deal found 10/23![Southwest logo]()
$425
This American Airlines 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/65:00 am -
1 stop7h 08m
Wed 11/115:00 am -
1 stop5h 05m
Deal found 10/21![American Airlines logo]()
$470
This American Airlines 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/165:59 pm -
1 stop5h 53m
Thu 11/196:41 pm -
1 stop5h 39m
Deal found 10/23![American Airlines logo]()
$495
Last-minute flights from Chicago to MidlandDiscover last-minute flight deals from Chicago to Midland. Data last updated October 24, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to Midland. Data last updated October 24, 2026 and is based on user searches.
This American Airlines 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/286:00 am -
1 stop7h 57m
Sat 11/216:41 pm -
1 stop5h 39m
Deal found 10/20![American Airlines logo]()
$450
This Southwest 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/286:00 am -
1 stop5h 00m
Sat 11/216:30 pm -
1 stop6h 15m
Deal found 10/20![Southwest logo]()
$450
This United Airlines deal was found by Cheapflights users on 10/19. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/610:55 am -
1 stop5h 35m
Wed 11/115:00 am -
1 stop5h 10m
Deal found 10/19![United Airlines logo]()
$425
This Southwest deal was found by Cheapflights users on 10/19. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/65:20 pm -
1 stop6h 35m
Wed 11/116:20 pm -
1 stop4h 50m
Deal found 10/19![Southwest logo]()
$425
This Southwest deal was found by Cheapflights users on 10/19. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/612:45 pm -
2 stops9h 55m
Tue 11/104:05 pm -
1 stop6h 35m
Deal found 10/19![Southwest logo]()
$430
This American Airlines 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/65:00 am -
1 stop7h 08m
Wed 11/115:00 am -
1 stop5h 05m
Deal found 10/21![American Airlines logo]()
$470
This American Airlines 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/114:53 pm -
1 stop7h 03m
Sat 11/148:03 am -
1 stop6h 09m
Deal found 10/22![American Airlines logo]()
$293
This American Airlines 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/165:59 pm -
1 stop5h 53m
Thu 11/196:41 pm -
1 stop5h 39m
Deal found 10/23![American Airlines logo]()
$495
This Southwest 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/163:10 pm -
1 stop6h 50m
Thu 11/194:05 pm -
2 stops6h 40m
Deal found 10/23![Southwest logo]()
$501
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.
Tue 11/177:05 am -
1 stop6h 15m
Thu 11/194:05 pm -
2 stops6h 40m
Deal found 10/21![Southwest logo]()
$305
This American Airlines 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/1712:02 pm -
1 stop7h 10m
Thu 11/196:41 pm -
1 stop5h 39m
Deal found 10/21![American Airlines logo]()
$364
This United Airlines 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/175:30 pm -
1 stop6h 13m
Wed 11/181:21 pm -
1 stop8h 09m
Deal found 10/22![United Airlines logo]()
$403
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 October 24, 2026.
Search for one-way flight options from Chicago to Midland. Find affordable one-way fares based on user searches. Data last updated October 24, 2026.
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.
Mon 11/95:15 am -
1 stop6h 30m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/22![Southwest logo]()
$279
This United Airlines 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/99:35 pm -
1 stop26h 08m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/22![United Airlines logo]()
$338
This Qatar Airways deal was found by Cheapflights users on 10/19. 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 Qatar Airways is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 1/286:50 pm -
2 stops43h 28m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/19![Qatar Airways logo]()
$1,934
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 October 24, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $293 (American Airlines) |
One-way from | $279 (Southwest) |
Popular in | October |
Cheapest in | November |
Average price | $671 |
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 October 24, 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
Quickest round-trip
ChicagoMidland
MDW Chicago Midway - MAF Midland Intl
MDWMAF
Chicago Midway
Mon 11/9
5:15 am-11:45 am
1 stop6h 30m
Midland Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$279
ChicagoMidland
MDW Chicago Midway - MAF Midland Intl
MDWMAF
Chicago Midway
Tue 12/8
6:40 am-2:00 pm
1 stop7h 20m
Midland Intl
Tue 12/15
11:00 am-5:10 pm
1 stop6h 10m
$293
ChicagoMidland
MDW Chicago Midway - MAF Midland Intl
MDWMAF
Chicago Midway
Tue 11/17
7:05 am-1:20 pm
1 stop6h 15m
Midland Intl
Thu 11/19
4:05 pm-10:45 pm
2 stops6h 40m
$305
ChicagoMidland
ORD Chicago O'Hare Intl - MAF Midland Intl
ORDMAF
Chicago O'Hare Intl
Mon 11/9
9:35 pm-11:43 pm
1 stop26h 08m
Midland Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$338
ChicagoMidland
ORD Chicago O'Hare Intl - MAF Midland Intl
ORDMAF
Chicago O'Hare Intl
Tue 11/17
12:02 pm-7:12 pm
1 stop7h 10m
Midland Intl
Thu 11/19
6:41 pm-12:20 am
1 stop5h 39m
$364
ChicagoMidland
ORD Chicago O'Hare Intl - MAF Midland Intl
ORDMAF
Chicago O'Hare Intl
Tue 11/17
5:30 pm-11:43 pm
1 stop6h 13m
Midland Intl
Wed 11/18
1:21 pm-9:30 pm
1 stop8h 09m
$403
ChicagoMidland
ORD Chicago O'Hare Intl - MAF Midland Intl
ORDMAF
Chicago O'Hare Intl
Fri 11/6
5:30 am-11:14 am
1 stop5h 44m
Midland Intl
Wed 11/11
7:00 am-12:29 pm
1 stop5h 29m
$425
ChicagoMidland
ORD Chicago O'Hare Intl - MAF Midland Intl
ORDMAF
Chicago O'Hare Intl
Fri 11/6
3:00 pm-10:47 pm
1 stop7h 47m
Midland Intl
Tue 11/10
6:48 pm-11:59 pm
1 stop5h 11m
$425
ChicagoMidland
ORD Chicago O'Hare Intl - MAF Midland Intl
ORDMAF
Chicago O'Hare Intl
Fri 11/6
4:07 pm-9:58 pm
1 stop5h 51m
Midland Intl
Tue 11/10
8:30 am-2:51 pm
1 stop6h 21m
$425
ChicagoMidland
MDW Chicago Midway - MAF Midland Intl
MDWMAF
Chicago Midway
Fri 11/6
5:20 pm-11:55 pm
1 stop6h 35m
Midland Intl
Wed 11/11
6:20 pm-11:10 pm
1 stop4h 50m
$425
Showing 1-10 of 15 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 October.
| 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 October 24, 2026.
Read reviews from past customers who have flown Southwest,United Airlines, andAmerican 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.
Boarding
8.1
Comfort
8.0
Crew
8.6
Entertainment
7.4
Food
7.0
Overall
7.9
Reviews
1 / 20
2.0
MediocreMike,Aug 2025
OKC - AUS
Boarding
8.1
Comfort
8.0
Crew
8.6
Entertainment
7.4
Food
7.0
Overall
7.9
Reviews
1 / 20
2.0
MediocreMike,Aug 2025
OKC - AUS
Boarding
8.1
Comfort
8.0
Crew
8.6
Entertainment
7.4
Food
7.0
Overall
7.9
Reviews
1 / 20
2.0
MediocreMike,Aug 2025
OKC - AUS
Boarding
8.1
Comfort
8.0
Crew
8.6
Entertainment
7.4
Food
7.0
Overall
7.9
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 October 24, 2026.
Chicago and Midland flights
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Chicago to 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 October 24, 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% |