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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 12/19. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — MAF
Dec 26 — Jan 21
Fri 12/26
Fri 1/2
1 adult, Economy
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Cheap 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 November 26, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$241
(American Airlines)

One-way from

$214
(United Airlines)

Popular in

February

Cheapest in

September

Average price

$697
Provider with most accurate pricing for Chicago (CHI)-Midland Intl flight deals.
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Provider most trusted by Cheapflights users for Chicago (CHI)-Midland Intl flights.
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From Chicago (CHI) to Midland Intl
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One-way flight from Chicago (CHI) to Midland Intl
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Highest demand for flights based on searches. 7% potential increase in price ($41 potential increase over avg. RT price).
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Cheapest flight prices on average. 6% potential price decrease ($30 potential savings vs. average RT price).
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Average for round-trip flights in November 2025
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Find 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 November 26, 2025.

This American Airlines deal was found by Cheapflights users on 11/26. 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.
Tue 12/308:58 pmORD - MAF
1 stop11h 43mAmerican Airlines
Sat 1/174:55 pmMAF - ORD
1 stop5h 24mAmerican Airlines
Deal found 11/26$254
This Southwest deal was found by Cheapflights users on 11/26. 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.
Tue 12/306:05 amORD - MAF
2 stops11h 35mSouthwest
Sat 1/176:15 amMAF - ORD
1 stop6h 45mSouthwest
Deal found 11/26$357
This American Airlines deal was found by Cheapflights users on 11/23. 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 12/221:15 pmORD - MAF
1 stop6h 43mAmerican Airlines
Sun 12/286:04 pmMAF - ORD
1 stop5h 11mAmerican Airlines
Deal found 11/23$484
This Southwest deal was found by Cheapflights users on 11/25. 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 12/122:15 pmORD - MAF
1 stop4h 45mSouthwest
Sun 12/145:45 amMAF - ORD
1 stop7h 15mSouthwest
Deal found 11/25$487
This Southwest deal was found by Cheapflights users on 11/23. 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 12/221:00 pmORD - MAF
2 stops10h 30mSouthwest
Sun 12/281:40 pmMAF - ORD
1 stop8h 55mSouthwest
Deal found 11/23$522
This Southwest deal was found by Cheapflights users on 11/23. 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 12/223:45 pmORD - MAF
1 stop7h 10mSouthwest
Sun 1/45:35 amMAF - ORD
2 stops6h 40mSouthwest
Deal found 11/23$531
This United Airlines deal was found by Cheapflights users on 11/26. 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.
Tue 12/3010:41 amORD - MAF
2 stops12h 44mUnited Airlines
Sat 1/175:35 pmMAF - ORD
2 stops14h 30mUnited Airlines
Deal found 11/26$585
This Southwest deal was found by Cheapflights users on 11/26. 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 12/82:15 pmORD - MAF
1 stop7h 40mSouthwest
Thu 12/185:45 amMAF - ORD
1 stop7h 15mSouthwest
Deal found 11/26$611

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 November 26, 2025.
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

Thu 1/8

5:05 am-10:07 am

1 stop5h 02m

Midland Intl

Sat 1/17

10:37 am-5:09 pm

1 stop6h 32m

$241

ChicagoMidland

ORD - MAF

ORDMAF

Chicago O'Hare Intl

Wed 1/14

3:23 pm-8:49 pm

1 stop5h 26m

Midland Intl

Sun 1/18

7:00 am-2:10 pm

1 stop7h 10m

$241

ChicagoMidland

ORD - MAF

ORDMAF

Chicago O'Hare Intl

Tue 12/30

8:58 pm-8:41 am

1 stop11h 43m

Midland Intl

Sat 1/17

4:55 pm-10:19 pm

1 stop5h 24m

$254

ChicagoMidland

ORD - MAF

ORDMAF

Chicago O'Hare Intl

Thu 1/8

1:45 pm-9:35 pm

2 stops7h 50m

Midland Intl

Sat 1/17

6:15 am-1:00 pm

1 stop6h 45m

$276

ChicagoMidland

ORD - MAF

ORDMAF

Chicago O'Hare Intl

Sat 2/14

3:10 pm-8:44 pm

1 stop5h 34m

Midland Intl

Wed 2/18

9:11 am-10:23 pm

1 stop13h 12m

$305

ChicagoMidland

ORD - MAF

ORDMAF

Chicago O'Hare Intl

Sat 1/10

10:40 am-4:35 pm

1 stop5h 55m

Midland Intl

Mon 1/12

12:00 pm-5:06 pm

1 stop5h 06m

$329

ChicagoMidland

ORD - MAF

ORDMAF

Chicago O'Hare Intl

Tue 12/30

6:05 am-5:40 pm

2 stops11h 35m

Midland Intl

Sat 1/17

6:15 am-1:00 pm

1 stop6h 45m

$357

ChicagoMidland

ORD - MAF

ORDMAF

Chicago O'Hare Intl

Sat 1/10

3:05 pm-7:55 pm

1 stop4h 50m

Midland Intl

Mon 1/12

7:05 am-1:00 pm

2 stops5h 55m

$377

ChicagoMidland

ORD - MAF

ORDMAF

Chicago O'Hare Intl

Wed 1/14

7:35 am-4:21 pm

1 stop8h 46m

Midland Intl

Sun 1/18

9:41 am-9:47 pm

2 stops12h 06m

$384

ChicagoMidland

ORD - MAF

ORDMAF

Chicago O'Hare Intl

Sat 2/14

9:00 am-9:44 pm

2 stops12h 44m

Midland Intl

Wed 2/18

5:14 pm-10:53 pm

1 stop5h 39m

$401

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/25

Showing 1-10 of 14 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 November.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy2 starsTrust Score*3 stars
eDreamsPrice Accuracy3 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 eDreams to be most consistent on Cheapflights vs. eDreams Users can find the same prices on Chicago-Midland flight deals on Cheapflights vs. eDreams >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 eDreams the most. eDreams 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 November 26, 2025.
Read reviews from past customers who have flown Southwest 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
4,254 reviews

Overall

8.0

Entertainment

7.5

Boarding

8.1

Crew

8.6

Comfort

8.0

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
4,254 reviews
Southwest
8.0
Very good
4,254 reviews

Overall

8.0

Entertainment

7.5

Boarding

8.1

Crew

8.6

Comfort

8.0

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
11,038 reviews
Southwest
8.0
Very good
4,254 reviews

Overall

8.0

Entertainment

7.5

Boarding

8.1

Crew

8.6

Comfort

8.0

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 1 airline.

  • How long is the flight from Chicago to Midland?

    For as low as $241, American Airlines can have you in Midland from Chicago in 5h 02m. There are 1047 mi between Chicago and Midland. Both multi-stop and nonstop flights can be found to your destination and back.

  • What is the cheapest airline to fly from Chicago to Midland round-trip?

    American Airlines, at $216, was found to be the cheapest airline from Chicago to Midland.. American Airlines is 54% 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
Big Spring

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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 airline flying from Chicago to Midland

Discover the top airline 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 November 26, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$216Average$377FlexibilityNo cancel feeOn-time71%

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