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$108+ 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 5/25. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — MAF
Apr 16 — Apr 231
Wed 4/16
Wed 4/23
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 April 11, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$257
(American Airlines)

One-way from

$108
(American Airlines)

Popular in

February

Cheapest in

July

Average price

$461
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. 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 April 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 April 11, 2025.

This American Airlines deal was found by Cheapflights users on 4/10. 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 7/55:00 amORD - MAF
1 stop4h 32mAmerican Airlines
Sat 7/125:00 amMAF - ORD
1 stop5h 04mAmerican Airlines
Deal found 4/10$257
This Delta deal was found by Cheapflights users on 4/10. 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.
Sun 5/1111:05 amORD - MAF
2 stops12h 57mDelta
Tue 5/1312:39 pmMAF - ORD
2 stops8h 51mDelta
Deal found 4/10$261
This United Airlines deal was found by Cheapflights users on 4/10. 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.
Thu 5/13:45 pmORD - MAF
1 stop7h 33mUnited Airlines
Sat 5/33:30 pmMAF - ORD
1 stop6h 00mUnited Airlines
Deal found 4/10$308
This Southwest deal was found by Cheapflights users on 4/10. 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 5/17:00 amORD - MAF
1 stop8h 50mSouthwest
Sat 5/35:45 amMAF - ORD
2 stops9h 15mSouthwest
Deal found 4/10$347

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 April 11, 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 7/5

5:00 am-9:32 am

1 stop4h 32m

Midland Intl

Sat 7/12

5:00 am-10:04 am

1 stop5h 04m

$257

ChicagoMidland

ORD - MAF

ORDMAF

Chicago O'Hare Intl

Sun 5/11

11:05 am-12:02 am

2 stops12h 57m

Midland Intl

Tue 5/13

12:39 pm-9:30 pm

2 stops8h 51m

$261

ChicagoMidland

ORD - MAF

ORDMAF

Chicago O'Hare Intl

Thu 5/1

3:45 pm-11:18 pm

1 stop7h 33m

Midland Intl

Sat 5/3

3:30 pm-9:30 pm

1 stop6h 00m

$308

ChicagoMidland

ORD - MAF

ORDMAF

Chicago O'Hare Intl

Thu 5/1

7:00 am-3:50 pm

1 stop8h 50m

Midland Intl

Sat 5/3

5:45 am-3:00 pm

2 stops9h 15m

$347

ChicagoMidland

ORD - MAF

ORDMAF

Chicago O'Hare Intl

Sun 5/25

6:00 am-11:49 am

1 stop5h 49m

$108

ChicagoMidland

ORD - MAF

ORDMAF

Chicago O'Hare Intl

Sun 5/25

5:30 am-4:54 pm

2 stops11h 24m

$114

ChicagoMidland

ORD - MAF

ORDMAF

Chicago O'Hare Intl

Thu 4/17

7:56 pm-11:17 am

2 stops15h 21m

$319

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/10

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 April.
ProviderPrice AccuracyTrust Score*
eDreamsPrice Accuracy3 starsTrust Score*3 stars
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars

*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 FlightHub the most. FlightHub 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

Rainfall in Midland by month

Plan your trip to Midland by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Midland ranges from 0.6 - 2.2 inches per month. September is typically the wettest month, when rainfall can reach 2.2 in. January is typically the driest time to visit Midland when rainfall is around 0.6 in.

Temperature in Midland by month

Plan your trip to Midland by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Midland, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 82.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 44.6 F).

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 April 11, 2025.
Southwest
8.0
Very good
4,279 reviews

Overall

8.0

Comfort

8.0

Crew

8.6

Food

7.1

Entertainment

7.6

Boarding

8.2

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
4,279 reviews
Southwest
8.0
Very good
4,279 reviews

Overall

8.0

Comfort

8.0

Crew

8.6

Food

7.1

Entertainment

7.6

Boarding

8.2

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
7,911 reviews
Southwest
8.0
Very good
4,279 reviews

Overall

8.0

Comfort

8.0

Crew

8.6

Food

7.1

Entertainment

7.6

Boarding

8.2

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
8,636 reviews
Southwest
8.0
Very good
4,279 reviews

Overall

8.0

Comfort

8.0

Crew

8.6

Food

7.1

Entertainment

7.6

Boarding

8.2

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
4,279 reviews

Overall

8.0

Comfort

8.0

Crew

8.6

Food

7.1

Entertainment

7.6

Boarding

8.2

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 $257, was found to be the cheapest airline from Chicago to Midland.Alternate airlines to your destination round-trip include Delta and United Airlines. American Airlines is 47% 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?

    $108 is the cheapest one-way deal found within the past few days, from American Airlines. You may also be able to find cheap deals on Delta and United Airlines, with prices starting from $114 and $319, 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 June is currently the most expensive (average of $399). 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 Chicago?

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Fort Stockton
Big Spring

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Alternative routes for Chicago to Midland

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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 April 11, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$271Average$416FlexibilityNo cancel feeOn-time71%

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