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Midland

$288+ 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 6/28. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — MAF
Jun 17 — Jun 241
Wed 6/17
Wed 6/24
1 adult, Economy
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Cheap 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 May 18, 2026.

This American Airlines deal was found by Cheapflights users on 5/13. 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.
Wed 7/13:50 pm
ORD
-
MAF
1 stop6h 08m
American Airlines
Sat 7/252:21 pm
MAF
-
ORD
1 stop7h 01m
American Airlines
Deal found 5/13$399
This American Airlines deal was found by Cheapflights users on 5/17. 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.
Tue 6/233:50 pm
ORD
-
MAF
1 stop7h 26m
American Airlines
Mon 6/292:21 pm
MAF
-
ORD
1 stop6h 39m
American Airlines
Deal found 5/17$403
This American Airlines deal was found by Cheapflights users on 5/13. 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.
Thu 7/26:04 am
ORD
-
MAF
1 stop7h 45m
American Airlines
Sun 7/195:00 am
MAF
-
ORD
1 stop5h 03m
American Airlines
Deal found 5/13$427
This American Airlines deal was found by Cheapflights users on 5/13. 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.
Wed 6/33:50 pm
ORD
-
MAF
1 stop8h 09m
American Airlines
Wed 6/106:47 pm
MAF
-
ORD
1 stop5h 52m
American Airlines
Deal found 5/13$432
This United Airlines deal was found by Cheapflights users on 5/13. 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.
Tue 8/186:29 pm
ORD
-
MAF
1 stop5h 15m
United Airlines
Wed 8/195:00 am
MAF
-
ORD
1 stop6h 20m
United Airlines
Deal found 5/13$461
This American Airlines deal was found by Cheapflights users on 5/14. 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.
Thu 5/287:02 am
ORD
-
MAF
1 stop6h 49m
American Airlines
Sun 5/315:23 pm
MAF
-
ORD
1 stop7h 22m
American Airlines
Deal found 5/14$467
This American Airlines deal was found by Cheapflights users on 5/14. 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.
Wed 6/36:02 pm
ORD
-
MAF
1 stop5h 14m
American Airlines
Fri 6/56:47 pm
MAF
-
ORD
1 stop5h 52m
American Airlines
Deal found 5/14$477
This American Airlines deal was found by Cheapflights users on 5/16. 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 8/214:57 pm
ORD
-
MAF
1 stop5h 37m
American Airlines
Sun 8/235:00 am
MAF
-
ORD
1 stop6h 11m
American Airlines
Deal found 5/16$485
This Southwest deal was found by Cheapflights users on 5/14. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/282:40 pm
ORD
-
MAF
2 stops8h 30m
Southwest
Sun 5/3110:10 am
MAF
-
ORD
1 stop5h 20m
Southwest
Deal found 5/14$502

Find 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 May 18, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$399
(American Airlines)

One-way from

$288
(American Airlines)
Provider with most accurate pricing for Chicago (CHI)-Midland Intl flight deals.
Search Deals
Provider most trusted by Cheapflights users for Chicago (CHI)-Midland Intl flights.
Search Deals
From Chicago (CHI) to Midland Intl
Search Deals
One-way flight from Chicago (CHI) to Midland Intl
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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 May 18, 2026.
Use the filters below to find and compare flights from Chicago to Midland that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

ChicagoMidland

ORD - MAF

ORDMAF

Chicago O'Hare Intl

Thu 7/2

11:00 am-6:10 pm

1 stop7h 10m

Midland Intl

Sun 7/19

11:45 am-7:44 pm

1 stop7h 59m

$427

ChicagoMidland

ORD - MAF

ORDMAF

Chicago O'Hare Intl

Fri 6/26

7:35 am-1:34 pm

1 stop5h 59m

Midland Intl

Sun 6/28

5:13 pm-11:15 pm

1 stop6h 02m

$427

ChicagoMidland

ORD - MAF

ORDMAF

Chicago O'Hare Intl

Fri 9/4

6:59 am-1:51 pm

1 stop6h 52m

Midland Intl

Mon 9/7

5:31 pm-11:58 pm

1 stop6h 27m

$427

ChicagoMidland

ORD - MAF

ORDMAF

Chicago O'Hare Intl

Wed 6/3

3:50 pm-11:59 pm

1 stop8h 09m

Midland Intl

Wed 6/10

6:47 pm-12:39 am

1 stop5h 52m

$432

ChicagoMidland

ORD - MAF

ORDMAF

Chicago O'Hare Intl

Tue 8/18

6:29 pm-11:44 pm

1 stop5h 15m

Midland Intl

Wed 8/19

5:00 am-11:20 am

1 stop6h 20m

$461
Quickest round-trip

ChicagoMidland

ORD - MAF

ORDMAF

Chicago O'Hare Intl

Wed 6/3

6:02 pm-11:16 pm

1 stop5h 14m

Midland Intl

Fri 6/5

6:47 pm-12:39 am

1 stop5h 52m

$477

ChicagoMidland

ORD - MAF

ORDMAF

Chicago O'Hare Intl

Thu 5/28

2:40 pm-11:10 pm

2 stops8h 30m

Midland Intl

Sun 5/31

10:10 am-3:30 pm

1 stop5h 20m

$502

ChicagoMidland

ORD - MAF

ORDMAF

Chicago O'Hare Intl

Fri 8/21

9:40 am-5:00 pm

1 stop7h 20m

Midland Intl

Sun 8/23

6:00 am-11:11 am

1 stop5h 11m

$505
Cheapest one-way
Quickest one-way

ChicagoMidland

ORD - MAF

ORDMAF

Chicago O'Hare Intl

Sun 6/28

5:59 am-11:09 am

1 stop5h 10m

$288

ChicagoMidland

ORD - MAF

ORDMAF

Chicago O'Hare Intl

Sun 6/28

10:25 am-7:39 pm

2 stops9h 14m

$889

Flights are sorted by cheapest round-trip flights first.

Deals found on 5/17

Sorted by cheapest first

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 May.
ProviderPrice AccuracyTrust Score*
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
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 May 18, 2026.
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
7.9
Good
4,287 reviews

Food

7.0

Boarding

8.1

Comfort

8.0

Entertainment

7.5

Overall

7.9

Crew

8.6

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
7.9
Good
4,287 reviews
Southwest
7.9
Good
4,287 reviews

Food

7.0

Boarding

8.1

Comfort

8.0

Entertainment

7.5

Overall

7.9

Crew

8.6

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
7.1
Good
11,648 reviews
Southwest
7.9
Good
4,287 reviews

Food

7.0

Boarding

8.1

Comfort

8.0

Entertainment

7.5

Overall

7.9

Crew

8.6

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 $427, American Airlines can have you in Midland from Chicago in 5h 59m. 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.

  • 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

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Alternative routes for Chicago to Midland

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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 May 18, 2026.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$216Average$377FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$285Average$424FlexibilityNo cancel feeOn-time69%

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