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$124+ 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 8/27. Fares are subject to change and may not be available on all flights or dates of travel.
MAF — CHI
Aug 4 — Aug 111
Mon 8/4
Mon 8/11
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 July 30, 2025.

Round-trip from

$217
(American Airlines)

Popular in

February

Cheapest in

November

Average price

$386
From Midland Intl to Chicago (CHI)
Search Deals
Highest demand for flights based on searches. 33% potential increase in price ($218 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 7% potential price decrease ($31 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in July 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 July 30, 2025.

This American Airlines deal was found by Cheapflights users on 7/30. 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 8/3012:14 pmMAF - ORD
1 stop4h 56mAmerican Airlines
Thu 9/46:30 pmORD - MAF
1 stop4h 34mAmerican Airlines
Deal found 7/30$217
This Delta deal was found by Cheapflights users on 7/30. 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 8/2712:31 pmMAF - ORD
2 stops7h 52mDelta
Wed 9/37:15 amORD - MAF
2 stops9h 22mDelta
Deal found 7/30$227
This United Airlines deal was found by Cheapflights users on 7/29. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/253:45 pmMAF - ORD
1 stop5h 41mUnited Airlines
Wed 12/315:03 pmORD - MAF
1 stop6h 22mUnited Airlines
Deal found 7/29$247
This Southwest deal was found by Cheapflights users on 7/30. 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.
Mon 9/295:35 amMAF - ORD
2 stops7h 30mSouthwest
Thu 10/25:45 pmORD - MAF
1 stop5h 10mSouthwest
Deal found 7/30$324

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 July 30, 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

Sat 8/30

12:14 pm-5:10 pm

1 stop4h 56m

Chicago O'Hare Intl

Thu 9/4

6:30 pm-11:04 pm

1 stop4h 34m

$217

MidlandChicago

MAF - ORD

MAFORD

Midland Intl

Wed 8/27

12:31 pm-8:23 pm

2 stops7h 52m

Chicago O'Hare Intl

Wed 9/3

7:15 am-4:37 pm

2 stops9h 22m

$227

MidlandChicago

MAF - ORD

MAFORD

Midland Intl

Mon 9/29

5:35 am-1:05 pm

2 stops7h 30m

Chicago O'Hare Intl

Thu 10/2

5:45 pm-10:55 pm

1 stop5h 10m

$324

MidlandChicago

MAF - ORD

MAFORD

Midland Intl

Mon 9/22

7:09 pm-12:15 am

1 stop5h 06m

Chicago O'Hare Intl

Sat 9/27

7:10 am-12:57 pm

1 stop5h 47m

$327

MidlandChicago

MAF - ORD

MAFORD

Midland Intl

Wed 8/27

12:31 pm-10:37 pm

2 stops10h 06m

$124

MidlandChicago

MAF - ORD

MAFORD

Midland Intl

Wed 8/27

3:30 pm-11:40 pm

1 stop8h 10m

$149

MidlandChicago

MAF - ORD

MAFORD

Midland Intl

Mon 10/6

6:16 pm-11:13 pm

1 stop4h 57m

$194

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/28

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.

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 July 30, 2025.
Read reviews from past customers who have flown Southwest, Delta, and United 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
4,241 reviews

Crew

8.6

Entertainment

7.5

Boarding

8.1

Food

7.0

Comfort

8.0

Overall

8.0

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
4,241 reviews
Southwest
8.0
Very good
4,241 reviews

Crew

8.6

Entertainment

7.5

Boarding

8.1

Food

7.0

Comfort

8.0

Overall

8.0

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.
Delta
8.0
Very good
7,980 reviews
Southwest
8.0
Very good
4,241 reviews

Crew

8.6

Entertainment

7.5

Boarding

8.1

Food

7.0

Comfort

8.0

Overall

8.0

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.
United Airlines
7.4
Good
8,896 reviews
Southwest
8.0
Very good
4,241 reviews

Crew

8.6

Entertainment

7.5

Boarding

8.1

Food

7.0

Comfort

8.0

Overall

8.0

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
4,241 reviews

Crew

8.6

Entertainment

7.5

Boarding

8.1

Food

7.0

Comfort

8.0

Overall

8.0

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.

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

    American Airlines, at $217, was found to be the cheapest airline from Midland to Chicago.Alternate airlines to your destination round-trip include Delta and United Airlines. Users have found that American Airlines is 50% cheaper than the other options available to this destination.

  • 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
Valparaiso
Chesterton

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Alternative routes for Midland to Chicago

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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 July 30, 2025.
AirlineCheapestAverageFlexibilityOn-time
SouthwestCheapest$216Average$496FlexibilityNo cancel feeOn-time63%
American AirlinesCheapest$255Average$360FlexibilityNo cancel feeOn-time71%

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