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Midland

$214+ Cheap flights from Chicago (CHI) to Midland (MAF)

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 2/13. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — MAF
Feb 20 — Feb 271
Fri 2/20
Fri 2/27
1 adult, Economy
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Cheap flight deals from Chicago to Midland

Cheapest flights from Chicago to Midland
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 January 21, 2026.

This Southwest deal was found by Cheapflights users on 1/19. 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 2/172:15 pm
ORD
-
MAF
1 stop8h 00m
Southwest
Tue 2/243:00 pm
MAF
-
ORD
1 stop7h 35m
Southwest
Deal found 1/19$337
This American Airlines deal was found by Cheapflights users on 1/21. 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.
Thu 2/266:10 am
ORD
-
MAF
1 stop5h 42m
American Airlines
Tue 3/35:00 am
MAF
-
ORD
1 stop4h 45m
American Airlines
Deal found 1/21$347
This American Airlines deal was found by Cheapflights users on 1/18. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/289:46 am
ORD
-
MAF
1 stop7h 42m
American Airlines
Tue 5/52:15 pm
MAF
-
ORD
1 stop7h 41m
American Airlines
Deal found 1/18$359
This Southwest deal was found by Cheapflights users on 1/19. 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.
Mon 5/113:45 pm
ORD
-
MAF
2 stops7h 25m
Southwest
Mon 5/186:00 am
MAF
-
ORD
2 stops7h 15m
Southwest
Deal found 1/19$370
This Southwest deal was found by Cheapflights users on 1/19. 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.
Sat 2/143:05 pm
ORD
-
MAF
1 stop7h 00m
Southwest
Fri 2/206:20 am
MAF
-
ORD
1 stop7h 45m
Southwest
Deal found 1/19$372
This American Airlines deal was found by Cheapflights users on 1/19. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/129:29 am
ORD
-
MAF
1 stop7h 52m
American Airlines
Tue 2/176:42 pm
MAF
-
ORD
1 stop4h 54m
American Airlines
Deal found 1/19$380
This United Airlines deal was found by Cheapflights users on 1/20. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 3/710:48 am
ORD
-
MAF
1 stop5h 35m
United Airlines
Sun 3/157:03 pm
MAF
-
ORD
1 stop5h 23m
United Airlines
Deal found 1/20$383

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 January 21, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

Expedia
3 stars

Round-trip from

$337
(Southwest)

One-way from

$214
(American Airlines)

Popular in

February

Cheapest in

September

Average price

$316
Provider with most accurate pricing for Chicago (CHI)-Midland Intl flight deals.
Search Deals
Provider most trusted by Cheapflights users for Chicago (CHI)-Midland Intl flights.
Search Deals
From Chicago (CHI) to Midland Intl
Search Deals
One-way flight from Chicago (CHI) to Midland Intl
Search Deals
Highest demand for flights based on searches. 0% potential increase in price ($2 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 4% potential price decrease ($20 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in January 2026
Search Deals

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 2,558,603 searches. Data last updated January 21, 2026.
Use the filters below to find and compare flights from Chicago to Midland that are best for you.

Fly from

Chicago

Fly to

Midland

Route

Depart

Return

Price

ChicagoMidland

ORD - MAF

ORDMAF

Chicago O'Hare Intl

Tue 2/17

2:15 pm-10:35 pm

2 stops8h 20m

Midland Intl

Tue 2/24

3:00 pm-10:35 pm

1 stop7h 35m

$342

ChicagoMidland

ORD - MAF

ORDMAF

Chicago O'Hare Intl

Thu 2/26

6:10 am-11:52 am

1 stop5h 42m

Midland Intl

Tue 3/3

5:00 am-9:45 am

1 stop4h 45m

$347

ChicagoMidland

ORD - MAF

ORDMAF

Chicago O'Hare Intl

Sat 2/14

1:15 pm-8:11 pm

1 stop6h 56m

Midland Intl

Fri 2/20

5:51 pm-12:55 am

1 stop7h 04m

$372

ChicagoMidland

ORD - MAF

ORDMAF

Chicago O'Hare Intl

Sat 2/14

3:45 pm-11:15 pm

2 stops7h 30m

Midland Intl

Fri 2/20

6:20 am-2:05 pm

1 stop7h 45m

$377

ChicagoMidland

ORD - MAF

ORDMAF

Chicago O'Hare Intl

Thu 2/12

9:29 am-5:21 pm

1 stop7h 52m

Midland Intl

Tue 2/17

6:42 pm-11:36 pm

1 stop4h 54m

$380

ChicagoMidland

ORD - MAF

ORDMAF

Chicago O'Hare Intl

Sat 3/7

10:48 am-4:23 pm

1 stop5h 35m

Midland Intl

Sun 3/15

7:03 pm-12:26 am

1 stop5h 23m

$383

ChicagoMidland

ORD - MAF

ORDMAF

Chicago O'Hare Intl

Mon 5/11

4:15 pm-11:10 pm

1 stop6h 55m

Midland Intl

Mon 5/18

6:00 am-1:15 pm

2 stops7h 15m

$388

ChicagoMidland

ORD - MAF

ORDMAF

Chicago O'Hare Intl

Fri 2/13

6:49 pm-11:59 pm

1 stop5h 10m

$214

ChicagoMidland

ORD - MAF

ORDMAF

Chicago O'Hare Intl

Fri 2/13

8:13 pm-1:50 pm

2 stops17h 37m

$347

ChicagoMidland

ORD - MAF

ORDMAF

Chicago O'Hare Intl

Thu 1/29

6:54 am-12:11 pm

1 stop5h 17m

$399

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/19

Showing 1-10 of 13 results
1
2

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 January.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy2 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*1 star

*The Trust Score is based on feedback from users after their booking experience. It measures overall satisfaction, helping us identify issues like hidden fees, problems during the ticketing process, and the quality of customer service. This score is our best indicator of the provider's quality and reliability.

  • 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 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 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.
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

How much does it cost to fly round-trip from Chicago to Midland?

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 January 21, 2026.
Read reviews from past customers who have flown Southwest, United Airlines, and American 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.
Southwest
8.0
Very good
4,266 reviews

Boarding

8.1

Overall

8.0

Entertainment

7.5

Comfort

8.0

Crew

8.6

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Southwest
8.0
Very good
4,266 reviews
Southwest
8.0
Very good
4,266 reviews

Boarding

8.1

Overall

8.0

Entertainment

7.5

Comfort

8.0

Crew

8.6

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
United Airlines
7.4
Good
9,191 reviews
Southwest
8.0
Very good
4,266 reviews

Boarding

8.1

Overall

8.0

Entertainment

7.5

Comfort

8.0

Crew

8.6

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
American Airlines
7.2
Good
11,174 reviews
Southwest
8.0
Very good
4,266 reviews

Boarding

8.1

Overall

8.0

Entertainment

7.5

Comfort

8.0

Crew

8.6

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines

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.

  • What airport do you fly into for flights to Midland from Chicago?

    Located just 8.2 mi from the city center, Midland Intl is the airport most travelers will use when flying to Midland from Chicago. Booking flights from Chicago to Midland Intl (MAF) should be relatively easy as there are 0 daily inbound flights from Chicago from 2 different airlines.

  • How long is the flight from Chicago to Midland?

    For as low as $347, Southwest can have you in Midland from Chicago in 5h 42m. There are 1047 mi between Chicago and Midland. Both multi-stop and nonstop flights can be found to your destination and back.

  • What are the cheapest airlines flying from Chicago to Midland round-trip?

    American Airlines, at $216, was found to be the cheapest airline from Chicago to Midland. An alternate airline flying to your destination would be United Airlines. American Airlines is 51% cheaper than the average price of flights available within the next 90 days to this destination.

  • Can I find deals for flights from Chicago to Midland that include hotel bookings?

    Yes. In addition to deals on Chicago to Midland flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Chicago to Midland?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Chicago to Midland.

  • Can I find deals for business class flights from Chicago to Midland?

    Yes. Cheapflights offers flight deals from Chicago to Midland by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

See more FAQs

Traveling to a place near Midland?

Book flights to Midland if you plan to visit one of these locations
Fort Stockton
Barstow

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Alternative routes for Chicago to Midland

See prices for flight routes from nearby airports that may be better suited for you.
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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 2,558,603 searches. Data last updated January 21, 2026.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$216Average$377FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$285Average$347FlexibilityNo cancel feeOn-time69%

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