HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Midland

$213+ 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 7/9. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — MAF
kesä 29 — heinä 61
ma 6/29
ma 7/6
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Chicago to Midland with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

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 toukokuu 30, 2026.

This United Airlines deal was found by Cheapflights users on 5/25. 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.
ti 8/254:11 pm
ORD
-
MAF
1 stop5h 23m
United Airlines
ke 9/25:00 am
MAF
-
ORD
1 stop5h 15m
United Airlines
Deal found 5/25$351
This American Airlines deal was found by Cheapflights users on 5/26. 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.
ke 7/14:45 pm
ORD
-
MAF
1 stop7h 14m
American Airlines
ke 7/156:46 pm
MAF
-
ORD
1 stop6h 04m
American Airlines
Deal found 5/26$374
This American Airlines deal was found by Cheapflights users on 5/28. 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.
ke 7/13:50 pm
ORD
-
MAF
1 stop8h 09m
American Airlines
la 7/252:21 pm
MAF
-
ORD
1 stop6h 10m
American Airlines
Deal found 5/28$389
This American Airlines deal was found by Cheapflights users on 5/29. 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.
to 7/27:00 am
ORD
-
MAF
1 stop6h 49m
American Airlines
su 7/196:46 pm
MAF
-
ORD
1 stop6h 04m
American Airlines
Deal found 5/29$427
This United Airlines deal was found by Cheapflights users on 5/27. 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.
ti 8/185:53 pm
ORD
-
MAF
1 stop5h 51m
United Airlines
ke 8/195:00 am
MAF
-
ORD
1 stop6h 20m
United Airlines
Deal found 5/27$441
This United Airlines deal was found by Cheapflights users on 5/28. 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.
su 8/235:30 am
ORD
-
MAF
1 stop5h 42m
United Airlines
to 8/271:40 pm
MAF
-
ORD
1 stop5h 50m
United Airlines
Deal found 5/28$443
This United Airlines deal was found by Cheapflights users on 5/27. 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.
ke 6/176:00 am
ORD
-
MAF
1 stop6h 59m
United Airlines
ke 6/245:00 am
MAF
-
ORD
1 stop5h 20m
United Airlines
Deal found 5/27$445
This United Airlines deal was found by Cheapflights users on 5/28. 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.
ti 6/165:00 am
ORD
-
MAF
1 stop5h 57m
United Airlines
pe 6/197:13 pm
MAF
-
ORD
1 stop5h 32m
United Airlines
Deal found 5/28$477

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 toukokuu 30, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$351
(United Airlines)

One-way from

$213
(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
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 toukokuu 30, 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
Quickest round-trip

ChicagoMidland

ORD - MAF

ORDMAF

Chicago O'Hare Intl

ti 8/25

4:11 pm-9:34 pm

1 stop5h 23m

Midland Intl

ke 9/2

5:00 am-10:15 am

1 stop5h 15m

$351

ChicagoMidland

ORD - MAF

ORDMAF

Chicago O'Hare Intl

ke 7/1

3:50 pm-11:59 pm

1 stop8h 09m

Midland Intl

la 7/25

11:45 am-7:44 pm

1 stop7h 59m

$389

ChicagoMidland

ORD - MAF

ORDMAF

Chicago O'Hare Intl

to 7/2

12:05 pm-6:10 pm

1 stop6h 05m

Midland Intl

su 7/19

11:45 am-6:16 pm

1 stop6h 31m

$427

ChicagoMidland

ORD - MAF

ORDMAF

Chicago O'Hare Intl

ti 8/18

5:53 pm-11:44 pm

1 stop5h 51m

Midland Intl

ke 8/19

5:00 am-11:20 am

1 stop6h 20m

$441

ChicagoMidland

ORD - MAF

ORDMAF

Chicago O'Hare Intl

ti 6/16

5:00 am-10:57 am

1 stop5h 57m

Midland Intl

pe 6/19

7:13 pm-12:45 am

1 stop5h 32m

$477

ChicagoMidland

ORD - MAF

ORDMAF

Chicago O'Hare Intl

to 6/11

6:20 pm-11:59 pm

1 stop5h 39m

Midland Intl

pe 6/12

6:47 pm-12:39 am

1 stop5h 52m

$645
Cheapest one-way

ChicagoMidland

ORD - MAF

ORDMAF

Chicago O'Hare Intl

to 7/9

2:59 pm-10:53 pm

1 stop7h 54m

$213

ChicagoMidland

ORD - MAF

ORDMAF

Chicago O'Hare Intl

ke 6/10

5:00 am-11:09 am

1 stop6h 09m

$254

ChicagoMidland

ORD - MAF

ORDMAF

Chicago O'Hare Intl

ma 6/8

5:45 pm-11:44 pm

1 stop5h 59m

$369

ChicagoMidland

ORD - MAF

ORDMAF

Chicago O'Hare Intl

ma 6/15

5:45 pm-11:44 pm

1 stop5h 59m

$398

Flights are sorted by cheapest round-trip flights first.

Deals found on 5/25

Showing 1-10 of 18 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 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 toukokuu 30, 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
4,264 reviews

Entertainment

7.5

Comfort

8.0

Overall

8.0

Crew

8.6

Boarding

8.1

Food

7.0

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
4,264 reviews
Southwest
8.0
Very good
4,264 reviews

Entertainment

7.5

Comfort

8.0

Overall

8.0

Crew

8.6

Boarding

8.1

Food

7.0

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
11,643 reviews
Southwest
8.0
Very good
4,264 reviews

Entertainment

7.5

Comfort

8.0

Overall

8.0

Crew

8.6

Boarding

8.1

Food

7.0

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 $351, United Airlines can have you in Midland from Chicago in 5h 23m. 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

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for Chicago to Midland

See prices for flight routes from nearby airports that may be better suited for you.
O'Hare Intl to Dallas/Fort Worth flights
O'Hare Intl to Hobby flights
O'Hare Intl to George Bush Intcntl flights
Midway to Dallas/Fort Worth flights
Midway to Hobby flights
O'Hare Intl to Austin flights
O'Hare Intl to San Antonio flights
Midway to George Bush Intcntl flights
Midway to Love Field flights
St. Louis to Dallas/Fort Worth flights
St. Louis to Hobby flights
O'Hare Intl to Love Field flights
St. Louis to George Bush Intcntl flights
Midway to Austin flights
St. Louis to Austin flights
Moline to Dallas/Fort Worth flights
Midway to San Antonio flights
St. Louis to San Antonio flights
St. Louis to Love Field flights
O'Hare Intl to El Paso flights
Peoria to Dallas/Fort Worth flights
Bloomington to Dallas/Fort Worth flights
Moline to Hobby flights
Peoria to San Antonio flights
Midway to El Paso flights
Moline to Austin flights
Moline to George Bush Intcntl flights
Springfield to Dallas/Fort Worth flights
Moline to San Antonio flights
O'Hare Intl to McAllen flights
O'Hare Intl to Corpus Christi flights
Peoria to Austin flights
Peoria to Hobby flights
Evansville to Hobby flights
Peoria to George Bush Intcntl flights
St. Louis to El Paso flights
St. Louis to Corpus Christi flights
Bloomington to San Antonio flights
Decatur to Dallas/Fort Worth flights
Evansville to Dallas/Fort Worth flights
Champaign to Dallas/Fort Worth flights
O'Hare Intl to Laredo flights
St. Louis to Lubbock flights
Evansville to George Bush Intcntl flights
O'Hare Intl to Harlingen flights
St. Louis to McAllen flights

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 toukokuu 30, 2026.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$216Average$377FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$285Average$424FlexibilityNo cancel feeOn-time69%

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.