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Midland

$214+ 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 5/22. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — MAF
May 23 — May 301
Sat 5/23
Sat 5/30
1 adult, Economy
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Find cheap flights from Chicago to Midland with Cheapflights

1. Tell us where you want to go

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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 April 23, 2026.

This United Airlines deal was found by Cheapflights users on 4/22. 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 5/147:30 am
ORD
-
MAF
1 stop6h 02m
United Airlines
Mon 5/187:00 pm
MAF
-
ORD
1 stop5h 45m
United Airlines
Deal found 4/22$347
This United Airlines deal was found by Cheapflights users on 4/22. 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.
Fri 5/1510:30 am
ORD
-
MAF
1 stop5h 47m
United Airlines
Mon 5/187:00 pm
MAF
-
ORD
1 stop6h 27m
United Airlines
Deal found 4/22$377
This United Airlines deal was found by Cheapflights users on 4/21. 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.
Sun 8/166:30 am
ORD
-
MAF
1 stop7h 02m
United Airlines
Sat 8/225:00 am
MAF
-
ORD
1 stop5h 14m
United Airlines
Deal found 4/21$380
This United Airlines deal was found by Cheapflights users on 4/17. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/312:56 pm
ORD
-
MAF
1 stop6h 43m
United Airlines
Fri 6/197:13 pm
MAF
-
ORD
1 stop5h 32m
United Airlines
Deal found 4/17$389
This United Airlines deal was found by Cheapflights users on 4/19. 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 6/64:05 pm
ORD
-
MAF
1 stop5h 52m
United Airlines
Sat 6/135:13 pm
MAF
-
ORD
1 stop6h 01m
United Airlines
Deal found 4/19$427
This American Airlines deal was found by Cheapflights users on 4/20. 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 5/2110:38 am
ORD
-
MAF
1 stop7h 34m
American Airlines
Fri 5/295:23 pm
MAF
-
ORD
1 stop6h 14m
American Airlines
Deal found 4/20$429
This American Airlines deal was found by Cheapflights users on 4/18. 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.
Sun 5/35:00 am
ORD
-
MAF
1 stop4h 42m
American Airlines
Sat 5/92:15 pm
MAF
-
ORD
1 stop5h 42m
American Airlines
Deal found 4/18$442
This American Airlines deal was found by Cheapflights users on 4/22. 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 5/710:41 am
ORD
-
MAF
1 stop7h 05m
American Airlines
Tue 5/122:15 pm
MAF
-
ORD
1 stop7h 30m
American Airlines
Deal found 4/22$444
This United Airlines deal was found by Cheapflights users on 4/22. 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 5/710:30 am
ORD
-
MAF
1 stop5h 47m
United Airlines
Mon 5/115:06 pm
MAF
-
ORD
1 stop6h 09m
United Airlines
Deal found 4/22$450

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 April 23, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$347
(United Airlines)

One-way from

$214
(American Airlines)

Popular in

April

Cheapest in

May

Average price

$666
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
Search Deals
Highest demand for flights based on searches. 1% potential increase in price ($5 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 4% potential price decrease ($20 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in April 2026
Search Deals

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 23, 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

Sat 6/6

4:05 pm-9:57 pm

1 stop5h 52m

Midland Intl

Sat 6/13

5:13 pm-11:14 pm

1 stop6h 01m

$427

ChicagoMidland

ORD - MAF

ORDMAF

Chicago O'Hare Intl

Fri 8/28

10:32 am-4:12 pm

1 stop5h 40m

Midland Intl

Mon 8/31

1:45 pm-8:27 pm

1 stop6h 42m

$427

ChicagoMidland

ORD - MAF

ORDMAF

Chicago O'Hare Intl

Thu 7/16

5:00 am-10:52 am

1 stop5h 52m

Midland Intl

Mon 7/20

2:15 pm-8:05 pm

1 stop5h 50m

$427
Quickest round-trip

ChicagoMidland

ORD - MAF

ORDMAF

Chicago O'Hare Intl

Sun 5/3

5:00 am-9:42 am

1 stop4h 42m

Midland Intl

Sat 5/9

2:15 pm-7:57 pm

1 stop5h 42m

$442

ChicagoMidland

ORD - MAF

ORDMAF

Chicago O'Hare Intl

Fri 5/15

3:45 pm-11:10 pm

2 stops7h 25m

Midland Intl

Mon 5/18

9:50 am-3:30 pm

1 stop5h 40m

$459

ChicagoMidland

ORD - MAF

ORDMAF

Chicago O'Hare Intl

Thu 5/7

2:40 pm-11:10 pm

2 stops8h 30m

Midland Intl

Mon 5/11

6:50 am-3:00 pm

1 stop8h 10m

$465

ChicagoMidland

ORD - MAF

ORDMAF

Chicago O'Hare Intl

Tue 6/2

6:45 am-9:57 pm

2 stops15h 12m

Midland Intl

Wed 6/3

5:00 am-10:20 am

1 stop5h 20m

$469

ChicagoMidland

ORD - MAF

ORDMAF

Chicago O'Hare Intl

Tue 5/5

11:55 am-5:40 pm

1 stop5h 45m

Midland Intl

Sat 5/9

6:50 am-2:20 pm

1 stop7h 30m

$507
Cheapest one-way

ChicagoMidland

ORD - MAF

ORDMAF

Chicago O'Hare Intl

Sat 5/9

6:05 am-1:45 pm

1 stop7h 40m

$254
Quickest one-way

ChicagoMidland

ORD - MAF

ORDMAF

Chicago O'Hare Intl

Fri 5/22

3:45 pm-11:10 pm

2 stops7h 25m

$259

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/19

Showing 1-10 of 11 resultsSorted by cheapest first
1
2

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*
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

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 April 23, 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
8.0
Very good
4,327 reviews

Overall

8.0

Food

7.0

Comfort

8.0

Crew

8.6

Entertainment

7.5

Boarding

8.1

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
4,327 reviews
Southwest
8.0
Very good
4,327 reviews

Overall

8.0

Food

7.0

Comfort

8.0

Crew

8.6

Entertainment

7.5

Boarding

8.1

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
11,659 reviews
Southwest
8.0
Very good
4,327 reviews

Overall

8.0

Food

7.0

Comfort

8.0

Crew

8.6

Entertainment

7.5

Boarding

8.1

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 $442, United Airlines can have you in Midland from Chicago in 4h 42m. 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 53% 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.

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 April 23, 2026.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$216Average$379FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$331Average$396FlexibilityNo cancel feeOn-time69%

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