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$212+ 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 9/13. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — MAF
Aug 23 — Aug 301
Sat 8/23
Sat 8/30
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 August 18, 2025.

Round-trip from

$212
(United Airlines)

Popular in

February

Cheapest in

September

Average price

$421
From Chicago (CHI) to Midland Intl
Search Deals
Highest demand for flights based on searches. 9% potential increase in price ($49 potential increase over avg. RT price).
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Cheapest flight prices on average. 6% potential price decrease ($31 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in August 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 August 18, 2025.

This United Airlines deal was found by Cheapflights users on 8/16. 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 9/133:58 pmORD - MAF
1 stop5h 57mUnited Airlines
Sat 9/203:20 pmMAF - ORD
1 stop6h 20mUnited Airlines
Deal found 8/16$212
This American Airlines deal was found by Cheapflights users on 8/16. 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 9/135:16 pmORD - MAF
1 stop4h 56mAmerican Airlines
Sat 9/204:12 pmMAF - ORD
1 stop7h 47mAmerican Airlines
Deal found 8/16$217
This Delta deal was found by Cheapflights users on 8/16. 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 9/136:15 amORD - MAF
2 stops11h 01mDelta
Sat 9/205:30 amMAF - ORD
2 stops13h 39mDelta
Deal found 8/16$227
This American Airlines deal was found by Cheapflights users on 8/16. 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 10/38:34 pmORD - MAF
1 stop12h 22mAmerican Airlines
Mon 10/64:12 pmMAF - ORD
1 stop7h 01mAmerican Airlines
Deal found 8/16$300
This American Airlines deal was found by Cheapflights users on 8/17. 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 9/128:34 pmORD - MAF
1 stop12h 22mAmerican Airlines
Mon 9/154:12 pmMAF - ORD
1 stop7h 47mAmerican Airlines
Deal found 8/17$304
This American Airlines deal was found by Cheapflights users on 8/18. 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.
Thu 9/116:00 amORD - MAF
1 stop6h 05mAmerican Airlines
Sun 9/146:17 pmMAF - ORD
1 stop5h 00mAmerican Airlines
Deal found 8/18$312
This Delta deal was found by Cheapflights users on 8/18. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/115:30 amORD - MAF
2 stops11h 10mDelta
Sun 9/1412:33 pmMAF - ORD
2 stops11h 21mDelta
Deal found 8/18$322
This Southwest deal was found by Cheapflights users on 8/17. 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 9/1312:40 pmORD - MAF
2 stops8h 15mSouthwest
Sat 9/205:40 amMAF - ORD
1 stop7h 05mSouthwest
Deal found 8/17$327
This Delta deal was found by Cheapflights users on 8/16. 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 10/36:15 amORD - MAF
2 stops10h 25mDelta
Mon 10/612:33 pmMAF - ORD
2 stops11h 24mDelta
Deal found 8/16$343
This American Airlines deal was found by Cheapflights users on 8/17. 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 stop11h 40mAmerican Airlines
Sun 11/234:31 pmMAF - ORD
1 stop5h 52mAmerican Airlines
Deal found 8/17$349
This Southwest deal was found by Cheapflights users on 8/17. 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 9/127:30 amORD - MAF
1 stop5h 10mSouthwest
Mon 9/155:35 amMAF - ORD
2 stops7h 30mSouthwest
Deal found 8/17$358

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 August 18, 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

Sat 9/13

3:58 pm-9:55 pm

1 stop5h 57m

Midland Intl

Sat 9/20

3:20 pm-9:40 pm

1 stop6h 20m

$212

ChicagoMidland

ORD - MAF

ORDMAF

Chicago O'Hare Intl

Sat 9/13

5:16 pm-10:12 pm

1 stop4h 56m

Midland Intl

Sat 9/20

4:12 pm-11:59 pm

1 stop7h 47m

$217

ChicagoMidland

ORD - MAF

ORDMAF

Chicago O'Hare Intl

Sat 9/13

6:15 am-5:16 pm

2 stops11h 01m

Midland Intl

Sat 9/20

5:30 am-7:09 pm

2 stops13h 39m

$227

ChicagoMidland

ORD - MAF

ORDMAF

Chicago O'Hare Intl

Fri 10/3

8:34 pm-8:56 am

1 stop12h 22m

Midland Intl

Mon 10/6

4:12 pm-11:13 pm

1 stop7h 01m

$300

ChicagoMidland

ORD - MAF

ORDMAF

Chicago O'Hare Intl

Fri 9/12

8:34 pm-8:56 am

1 stop12h 22m

Midland Intl

Mon 9/15

6:39 pm-11:59 pm

1 stop5h 20m

$304

ChicagoMidland

ORD - MAF

ORDMAF

Chicago O'Hare Intl

Thu 9/11

6:00 am-12:05 pm

1 stop6h 05m

Midland Intl

Sun 9/14

6:17 pm-11:52 pm

1 stop5h 35m

$312

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/16

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 August 18, 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
4,246 reviews

Crew

8.6

Food

7.0

Overall

8.0

Boarding

8.1

Comfort

8.0

Entertainment

7.5

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
Southwest
8.0
Very good
4,246 reviews
Southwest
8.0
Very good
4,246 reviews

Crew

8.6

Food

7.0

Overall

8.0

Boarding

8.1

Comfort

8.0

Entertainment

7.5

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
American Airlines
7.2
Good
10,000 reviews
Southwest
8.0
Very good
4,246 reviews

Crew

8.6

Food

7.0

Overall

8.0

Boarding

8.1

Comfort

8.0

Entertainment

7.5

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.

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 $217, United Airlines can have you in Midland from Chicago in 4h 56m. 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 $279, was found to be the cheapest airline from Chicago to Midland.. American Airlines is 40% 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 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 August 18, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$279Average$386FlexibilityNo cancel feeOn-time71%

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