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$209+ 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 7/24. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — MAF
Jul 8 — Jul 151
Tue 7/8
Tue 7/15
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 July 3, 2025.

Round-trip from

$217
(American Airlines)

One-way from

$209
(Delta)

Popular in

February

Cheapest in

January

Average price

$521
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. 5% potential increase in price ($26 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).
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Average for round-trip flights in July 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 July 3, 2025.

This American Airlines deal was found by Cheapflights users on 7/1. 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 8/146:00 amORD - MAF
1 stop5h 42mAmerican Airlines
Thu 8/215:00 amMAF - ORD
1 stop4h 59mAmerican Airlines
Deal found 7/1$217
This Delta deal was found by Cheapflights users on 7/1. 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 8/142:00 pmORD - MAF
2 stops9h 58mDelta
Thu 8/2112:31 pmMAF - ORD
2 stops7h 52mDelta
Deal found 7/1$227
This Southwest deal was found by Cheapflights users on 7/3. 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 9/181:30 pmORD - MAF
2 stops9h 00mSouthwest
Sun 9/2110:45 amMAF - ORD
1 stop4h 35mSouthwest
Deal found 7/3$337
This United Airlines deal was found by Cheapflights users on 7/2. 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 8/168:45 amORD - MAF
1 stop7h 55mUnited Airlines
Sat 8/235:00 amMAF - ORD
2 stops13h 55mUnited Airlines
Deal found 7/2$392

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 July 3, 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 8/14

6:00 am-11:42 am

1 stop5h 42m

Midland Intl

Thu 8/21

5:00 am-9:59 am

1 stop4h 59m

$217

ChicagoMidland

ORD - MAF

ORDMAF

Chicago O'Hare Intl

Thu 8/14

2:00 pm-11:58 pm

2 stops9h 58m

Midland Intl

Thu 8/21

12:31 pm-8:23 pm

2 stops7h 52m

$227

ChicagoMidland

ORD - MAF

ORDMAF

Chicago O'Hare Intl

Thu 9/18

1:30 pm-10:30 pm

2 stops9h 00m

Midland Intl

Sun 9/21

10:45 am-3:20 pm

1 stop4h 35m

$337

ChicagoMidland

ORD - MAF

ORDMAF

Chicago O'Hare Intl

Sat 8/16

8:45 am-4:40 pm

1 stop7h 55m

Midland Intl

Sat 8/23

5:00 am-6:55 pm

2 stops13h 55m

$392

ChicagoMidland

ORD - MAF

ORDMAF

Chicago O'Hare Intl

Thu 7/24

7:00 am-4:32 pm

2 stops9h 32m

$209

ChicagoMidland

ORD - MAF

ORDMAF

Chicago O'Hare Intl

Thu 7/24

7:30 am-12:20 pm

1 stop4h 50m

$214

ChicagoMidland

ORD - MAF

ORDMAF

Chicago O'Hare Intl

Tue 7/15

7:10 am-2:01 pm

1 stop6h 51m

$332

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/1

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 July 3, 2025.
Read reviews from past customers who have flown Southwest, Delta, and United 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

Overall

8.0

Comfort

8.0

Food

7.0

Crew

8.6

Boarding

8.2

Entertainment

7.6

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
4,266 reviews
Southwest
8.0
Very good
4,266 reviews

Overall

8.0

Comfort

8.0

Food

7.0

Crew

8.6

Boarding

8.2

Entertainment

7.6

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.
Delta
8.0
Very good
7,982 reviews
Southwest
8.0
Very good
4,266 reviews

Overall

8.0

Comfort

8.0

Food

7.0

Crew

8.6

Boarding

8.2

Entertainment

7.6

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.
United Airlines
7.4
Good
8,861 reviews
Southwest
8.0
Very good
4,266 reviews

Overall

8.0

Comfort

8.0

Food

7.0

Crew

8.6

Boarding

8.2

Entertainment

7.6

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
4,266 reviews

Overall

8.0

Comfort

8.0

Food

7.0

Crew

8.6

Boarding

8.2

Entertainment

7.6

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.

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

    American Airlines, at $217, was found to be the cheapest airline from Chicago to Midland.Alternate airlines to your destination round-trip include Delta and Southwest. American Airlines is 55% cheaper than the average price of flights available within the next 90 days to this destination.

  • What are the cheapest airlines to fly from Chicago to Midland one-way?

    $209 is the cheapest one-way deal found within the past few days, from Delta. You may also be able to find cheap deals on Southwest and United Airlines, with prices starting from $214 and $332, respectively.

  • 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

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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 July 3, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$271Average$406FlexibilityNo cancel feeOn-time71%

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