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$144+ Cheap flights from Midland (MAF) to Chicago (CHI)

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 10/17. Fares are subject to change and may not be available on all flights or dates of travel.
MAF — CHI
Oct 11 — Oct 181
Sat 10/11
Sat 10/18
1 adult, Economy
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Cheap flight deals from Midland to Chicago

Discover tips and strategies to find the most affordable flight options for your journey from Midland (MAF) to Chicago (CHI). 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 September 11, 2025.

Round-trip from

$293
(American Airlines)

One-way from

$144
(American Airlines)

Popular in

February

Cheapest in

November

Average price

$470
From Midland Intl to Chicago (CHI)
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One-way flight from Midland Intl to Chicago (CHI)
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Highest demand for flights based on searches. 31% potential increase in price ($208 potential increase over avg. RT price).
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Cheapest flight prices on average. 6% potential price decrease ($30 potential savings vs. average RT price).
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Average for round-trip flights in September 2025
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Find flight deals from Midland to Chicago

Cheapest flights from Midland to Chicago
Explore the most affordable flight options available from Midland to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 11, 2025.

This American Airlines deal was found by Cheapflights users on 9/9. 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 10/292:25 pmMAF - ORD
1 stop6h 49mAmerican Airlines
Sun 11/25:18 amORD - MAF
1 stop6h 35mAmerican Airlines
Deal found 9/9$293
This American Airlines deal was found by Cheapflights users on 9/10. 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.
Tue 11/252:24 pmMAF - ORD
1 stop4h 28mAmerican Airlines
Thu 1/12:50 pmORD - MAF
1 stop5h 08mAmerican Airlines
Deal found 9/10$337
This United Airlines deal was found by Cheapflights users on 9/11. 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 9/262:01 pmMAF - ORD
1 stop6h 18mUnited Airlines
Tue 9/305:50 pmORD - MAF
1 stop5h 24mUnited Airlines
Deal found 9/11$343
This Delta deal was found by Cheapflights users on 9/9. 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.
Wed 10/2912:33 pmMAF - ORD
2 stops11h 25mDelta
Sun 11/24:56 pmORD - MAF
2 stops7h 00mDelta
Deal found 9/9$348
This United Airlines deal was found by Cheapflights users on 9/10. 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.
Tue 11/253:05 pmMAF - ORD
1 stop8h 05mUnited Airlines
Thu 1/19:00 amORD - MAF
2 stops14h 25mUnited Airlines
Deal found 9/10$450
This Delta deal was found by Cheapflights users on 9/11. 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.
Fri 9/2612:33 pmMAF - ORD
2 stops11h 21mDelta
Tue 9/3011:20 amORD - MAF
2 stops12h 38mDelta
Deal found 9/11$458
This United Airlines deal was found by Cheapflights users on 9/9. 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 9/238:00 amMAF - ORD
1 stop5h 15mUnited Airlines
Fri 9/264:50 pmORD - MAF
1 stop5h 23mUnited Airlines
Deal found 9/9$467
This Delta deal was found by Cheapflights users on 9/9. 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.
Tue 9/2312:33 pmMAF - ORD
2 stops8h 48mDelta
Fri 9/266:15 amORD - MAF
2 stops10h 25mDelta
Deal found 9/9$477
This Delta deal was found by Cheapflights users on 9/11. 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 9/1812:33 pmMAF - ORD
2 stops8h 52mDelta
Mon 9/227:20 amORD - MAF
2 stops9h 20mDelta
Deal found 9/11$581
This United Airlines deal was found by Cheapflights users on 9/9. 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 10/291:55 pmMAF - ORD
2 stops19h 43mUnited Airlines
Sun 11/27:10 amORD - MAF
1 stop5h 35mUnited Airlines
Deal found 9/9$609

Cheapflights Fare Finder

 
Customize your flight search to find flights from Midland to Chicago 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 September 11, 2025.
Use the filters below to find and compare flights from Midland to Chicago that are best for you.

Fly from

Midland

Fly to

Chicago

Route

Depart

Return

Price

MidlandChicago

MAF - ORD

MAFORD

Midland Intl

Wed 10/29

2:25 pm-9:14 pm

1 stop6h 49m

Chicago O'Hare Intl

Sun 11/2

5:18 am-11:53 am

1 stop6h 35m

$293

MidlandChicago

MAF - ORD

MAFORD

Midland Intl

Tue 11/25

2:24 pm-6:52 pm

1 stop4h 28m

Chicago O'Hare Intl

Thu 1/1

2:50 pm-7:58 pm

1 stop5h 08m

$337

MidlandChicago

MAF - ORD

MAFORD

Midland Intl

Fri 9/26

2:01 pm-8:19 pm

1 stop6h 18m

Chicago O'Hare Intl

Tue 9/30

5:50 pm-11:14 pm

1 stop5h 24m

$343

MidlandChicago

MAF - ORD

MAFORD

Midland Intl

Wed 10/29

12:33 pm-11:58 pm

2 stops11h 25m

Chicago O'Hare Intl

Sun 11/2

4:56 pm-11:56 pm

2 stops7h 00m

$348

MidlandChicago

MAF - ORD

MAFORD

Midland Intl

Tue 11/25

3:05 pm-11:10 pm

1 stop8h 05m

Chicago O'Hare Intl

Thu 1/1

9:00 am-11:25 pm

2 stops14h 25m

$450

MidlandChicago

MAF - ORD

MAFORD

Midland Intl

Fri 9/26

12:33 pm-11:54 pm

2 stops11h 21m

Chicago O'Hare Intl

Tue 9/30

11:20 am-11:58 pm

2 stops12h 38m

$458

MidlandChicago

MAF - ORD

MAFORD

Midland Intl

Tue 11/25

5:35 am-12:15 pm

2 stops6h 40m

Chicago O'Hare Intl

Thu 1/1

1:45 pm-10:10 pm

2 stops8h 25m

$467

MidlandChicago

MAF - ORD

MAFORD

Midland Intl

Tue 9/23

8:00 am-1:15 pm

1 stop5h 15m

Chicago O'Hare Intl

Fri 9/26

4:50 pm-10:13 pm

1 stop5h 23m

$467

MidlandChicago

MAF - ORD

MAFORD

Midland Intl

Tue 9/23

12:33 pm-9:21 pm

2 stops8h 48m

Chicago O'Hare Intl

Fri 9/26

6:15 am-4:40 pm

2 stops10h 25m

$477

MidlandChicago

MAF - ORD

MAFORD

Midland Intl

Wed 10/29

1:55 pm-9:38 am

2 stops19h 43m

Chicago O'Hare Intl

Sun 11/2

7:10 am-12:45 pm

1 stop5h 35m

$609

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/10

Showing 1-10 of 18 results
1
2

Best time to book a flight from Midland to Chicago

Have a flexible travel schedule? Discover the best time to fly to Chicago from Midland 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 Midland to Chicago

What is the cheapest month to book a flight from Midland to Chicago?

Currently, August is the cheapest month in which you can book a flight from Midland to Chicago (average of $245). Flying from Midland to Chicago in March is currently the most expensive (average of $321). 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.

How much does it cost to fly round-trip from Midland to Chicago?

Reviews of airlines servicing Chicago

Get insights into the airlines that provide service to Chicago. 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 Chicago. Reviews last updated September 11, 2025.
Read reviews from past customers who have flown Southwest and American Airlines from Midland to Chicago. 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
4,248 reviews

Entertainment

7.5

Crew

8.6

Boarding

8.1

Comfort

8.0

Overall

8.0

Food

7.0

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
4,248 reviews
Southwest
8.0
Very good
4,248 reviews

Entertainment

7.5

Crew

8.6

Boarding

8.1

Comfort

8.0

Overall

8.0

Food

7.0

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
4,248 reviews

Entertainment

7.5

Crew

8.6

Boarding

8.1

Comfort

8.0

Overall

8.0

Food

7.0

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 Midland to Chicago. 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 from for flights from Midland to Chicago?

    Midland Intl (MAF), located 8.2 mi from the city center, is the airport you fly out of when you book flights from Midland to Chicago. 2 airlines have flights from Midland Intl to Chicago on a regular basis. Booking flights from Midland Intl to Chicago should not be difficult; the airport handles an average of 0 outbound flights to Chicago per day.

  • How long is the flight from Midland to Chicago?

    American Airlines, United Airlines, and Delta can get you from Midland to Chicago in just under 6h 18m. Your travel time can differ by up to 5h 07m. There are 1047 mi between Midland and Chicago. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.

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

    Southwest, at $216, was found to be the cheapest airline from Midland to Chicago. An alternate airline flying to your destination would be American Airlines. Users have found that Southwest is 52% cheaper than the other options available to this destination.

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

    To fly one-way, consider booking your trip with American Airlines, which is currently one of the cheapest options available, starting at $144. Southwest flights start at $218 while deals on Delta start at $291 one-way.

  • Can I find deals for flights from Midland to Chicago that include hotel bookings?

    Yes. In addition to deals on Midland to Chicago flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Midland to Chicago?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Midland to Chicago.

  • Can I find deals for business class flights from Midland to Chicago?

    Yes. Cheapflights offers flight deals from Midland to Chicago 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 Midland to Chicago?

    Currently, August is the cheapest month in which you can book a flight from Midland to Chicago (average of $245). Flying from Midland to Chicago in March is currently the most expensive (average of $321). 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?

Book flights to Chicago if you plan to visit one of these locations
Merrillville
Lansing
Hammond
Benton Harbor
Porter
Chesterton

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Alternative routes for Midland to Chicago

See prices for flight routes from nearby airports that may be better suited for you.
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Top 2 airlines flying from Midland to Chicago

Discover the top 2 airlines that operate flights from Midland to Chicago. 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 September 11, 2025.
AirlineCheapestAverageFlexibilityOn-time
SouthwestCheapest$216Average$496FlexibilityNo cancel feeOn-time63%
American AirlinesCheapest$255Average$372FlexibilityNo cancel feeOn-time71%

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