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Midland

$127+ 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 10/11. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — MAF
Oct 15 — Oct 221
Wed 10/15
Wed 10/22
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 September 15, 2025.

Round-trip from

$217
(American Airlines)

One-way from

$127
(American Airlines)

Popular in

February

Cheapest in

September

Average price

$279
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. 6% potential increase in price ($34 potential increase over avg. RT price).
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Cheapest flight prices on average. 6% potential price decrease ($29 potential savings vs. average RT price).
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Average for round-trip flights in September 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 September 15, 2025.

This American Airlines deal was found by Cheapflights users on 9/13. 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 10/36:30 pmORD - MAF
1 stop4h 34mAmerican Airlines
Sun 10/56:17 pmMAF - ORD
1 stop5h 35mAmerican Airlines
Deal found 9/13$217
This American Airlines deal was found by Cheapflights users on 9/13. 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 10/118:30 amORD - MAF
1 stop10h 40mAmerican Airlines
Sat 10/188:10 amMAF - ORD
1 stop9h 50mAmerican Airlines
Deal found 9/13$243
This American Airlines deal was found by Cheapflights users on 9/13. 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 10/2810:32 amORD - MAF
1 stop8h 38mAmerican Airlines
Tue 11/412:25 pmMAF - ORD
1 stop8h 56mAmerican Airlines
Deal found 9/13$244
This Delta deal was found by Cheapflights users on 9/13. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/311:20 amORD - MAF
2 stops12h 38mDelta
Sun 10/55:30 amMAF - ORD
2 stops8h 50mDelta
Deal found 9/13$278
This Delta deal was found by Cheapflights users on 9/13. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/284:05 pmORD - MAF
2 stops7h 51mDelta
Tue 11/45:30 amMAF - ORD
2 stops11h 11mDelta
Deal found 9/13$307
This Delta deal was found by Cheapflights users on 9/13. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/307:10 amORD - MAF
2 stops9h 21mDelta
Wed 11/512:33 pmMAF - ORD
2 stops11h 25mDelta
Deal found 9/13$322
This American Airlines deal was found by Cheapflights users on 9/14. 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 11/165:18 amORD - MAF
1 stop6h 35mAmerican Airlines
Mon 11/176:05 amMAF - ORD
1 stop11h 12mAmerican Airlines
Deal found 9/14$325
This Delta deal was found by Cheapflights users on 9/13. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/117:10 amORD - MAF
2 stops10h 16mDelta
Sat 10/185:30 amMAF - ORD
2 stops13h 19mDelta
Deal found 9/13$327
This Southwest deal was found by Cheapflights users on 9/13. 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 10/302:50 pmORD - MAF
2 stops9h 00mSouthwest
Wed 11/56:15 amMAF - ORD
1 stop6h 45mSouthwest
Deal found 9/13$357
This American Airlines deal was found by Cheapflights users on 9/13. 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 11/2110:05 pmORD - MAF
1 stop10h 36mAmerican Airlines
Sun 11/2312:25 pmMAF - ORD
1 stop7h 17mAmerican Airlines
Deal found 9/13$385
This United Airlines deal was found by Cheapflights users on 9/13. 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 10/116:00 amORD - MAF
1 stop5h 04mUnited Airlines
Sat 10/185:00 amMAF - ORD
2 stops13h 50mUnited Airlines
Deal found 9/13$410

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 September 15, 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

Fri 10/3

6:30 pm-11:04 pm

1 stop4h 34m

Midland Intl

Sun 10/5

6:17 pm-11:52 pm

1 stop5h 35m

$217

ChicagoMidland

ORD - MAF

ORDMAF

Chicago O'Hare Intl

Sat 10/11

8:30 am-7:10 pm

1 stop10h 40m

Midland Intl

Sat 10/18

8:10 am-6:00 pm

1 stop9h 50m

$243

ChicagoMidland

ORD - MAF

ORDMAF

Chicago O'Hare Intl

Fri 10/3

11:20 am-11:58 pm

2 stops12h 38m

Midland Intl

Sun 10/5

5:30 am-2:20 pm

2 stops8h 50m

$278

ChicagoMidland

ORD - MAF

ORDMAF

Chicago O'Hare Intl

Wed 2/18

12:05 pm-5:51 pm

1 stop5h 46m

Midland Intl

Sat 2/21

5:00 am-9:36 am

1 stop4h 36m

$286

ChicagoMidland

ORD - MAF

ORDMAF

Chicago O'Hare Intl

Tue 10/28

4:05 pm-11:56 pm

2 stops7h 51m

Midland Intl

Tue 11/4

5:30 am-4:41 pm

2 stops11h 11m

$307

ChicagoMidland

ORD - MAF

ORDMAF

Chicago O'Hare Intl

Thu 10/30

7:10 am-4:31 pm

2 stops9h 21m

Midland Intl

Wed 11/5

12:33 pm-11:58 pm

2 stops11h 25m

$322

ChicagoMidland

ORD - MAF

ORDMAF

Chicago O'Hare Intl

Sun 11/16

5:18 am-11:53 am

1 stop6h 35m

Midland Intl

Mon 11/17

6:05 am-5:17 pm

1 stop11h 12m

$325

ChicagoMidland

ORD - MAF

ORDMAF

Chicago O'Hare Intl

Thu 10/30

2:50 pm-11:50 pm

2 stops9h 00m

Midland Intl

Wed 11/5

6:15 am-1:00 pm

1 stop6h 45m

$357

ChicagoMidland

ORD - MAF

ORDMAF

Chicago O'Hare Intl

Fri 11/21

10:05 pm-8:41 am

1 stop10h 36m

Midland Intl

Sun 11/23

12:25 pm-7:42 pm

1 stop7h 17m

$385

ChicagoMidland

ORD - MAF

ORDMAF

Chicago O'Hare Intl

Sat 10/11

6:00 am-11:04 am

1 stop5h 04m

Midland Intl

Sat 10/18

5:00 am-6:50 pm

2 stops13h 50m

$410

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/15

Showing 1-10 of 17 results
1
2

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
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 15, 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
4,242 reviews

Crew

8.6

Overall

8.0

Boarding

8.1

Entertainment

7.5

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
4,242 reviews
Southwest
8.0
Very good
4,242 reviews

Crew

8.6

Overall

8.0

Boarding

8.1

Entertainment

7.5

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
10,000 reviews
Southwest
8.0
Very good
4,242 reviews

Crew

8.6

Overall

8.0

Boarding

8.1

Entertainment

7.5

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 2 different airlines.

  • How long is the flight from Chicago to Midland?

    For as low as $217, American Airlines can have you in Midland from Chicago in 4h 34m. 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 55% 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.

  • What is the cheapest month to book a flight from Chicago to Midland?

    Currently, April is the cheapest month in which you can book a flight from Chicago to Midland (average of $336). Flying from Chicago to Midland in March is currently the most expensive (average of $389). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

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 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 September 15, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$216Average$377FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$285Average$408FlexibilityNo cancel feeOn-time69%

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