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

American Airlines, at $268, was found to be the cheapest airline from Midland to Chicago.Alternate airlines to your destination round-trip include Delta and Southwest. Users have found that American Airlines is 40% cheaper than the other options available to this destination.

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.

What is the cheapest day to fly from Midland to Chicago?

Travelers seeking maximum savings on their Midland to Chicago flight should consider departing on Saturday afternoons when fares are most often at their lowest. Wednesday mornings flights should be avoided if possible as fares are typically the most expensive at this time.

What are the most popular airlines that fly from Midland to Chicago?

The most popular airlines flying from Midland to Chicago are American Airlines, United Airlines and Southwest. Something to consider prior to booking your flight.

What is the cheapest day to fly round-trip from Midland to Chicago?

Flights from Midland to Chicago are found to be more expensive on Tuesday. This shouldn't discourage you from searching as you can still find great deals by being flexible with your options. Use our search form to find deals on tickets to Chicago.

What is the cheapest month to fly from Midland to Chicago?

Flights from Midland to Chicago lean towards being more expensive in February. Prices are generally better when you fly from Midland to Chicago in November, with the cheapest ticket starting at $286.

Most accurate provider : When it comes to deals on Midland-Chicago flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Midland-Chicago flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Midland-Chicago flight searches over the past month and is updated monthly.

Most trusted provider : When it comes to deals on Midland-Chicago 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 Midland-Chicago flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

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. 3 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.

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.

$109+ Flights from Midland to Chicago

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1. Tell us where you want to go

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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 Midland to Chicago

Most accurate provider	FlightHub 3 stars
Most trusted provider	FlightHub 3 stars
Round-trip from	$268 (American Airlines)
One-way from	$109 (American Airlines)
Popular in	February
Cheapest in	November
Average price	$457

Provider with most accurate pricing for Midland Intl-Chicago (CHI) flight deals.

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Provider most trusted by Cheapflights users for Midland Intl-Chicago (CHI) flights.

Search Deals

From Midland Intl to Chicago (CHI)

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One-way flight from Midland Intl to Chicago (CHI)

Search Deals

Highest demand for flights based on searches. 32% potential increase in price ($212 potential increase over avg. RT price).

Search Deals

Cheapest flight prices on average. 7% potential price decrease ($34 potential savings vs. average RT price).

Search Deals

Average for round-trip flights in April 2025

Search Deals

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 April 11, 2025.

Sat 8/305:10 pmMAF - ORD

1 stop6h 36mAmerican Airlines

Thu 9/41:23 pmORD - MAF

1 stop6h 43mAmerican Airlines

Deal found 4/11

$268

Sat 8/3012:29 pmMAF - ORD

2 stops9h 25mDelta

Thu 9/411:19 amORD - MAF

2 stops12h 33mDelta

Deal found 4/11

$278

Wed 5/73:40 pmMAF - ORD

1 stop5h 50mSouthwest

Mon 5/127:30 amORD - MAF

1 stop4h 55mSouthwest

Deal found 4/10

$302

Sat 8/308:00 amMAF - ORD

1 stop5h 15mUnited Airlines

Thu 9/47:45 amORD - MAF

2 stops15h 30mUnited Airlines

Deal found 4/11

$365

Best flights from Midland to Chicago
Discover carefully curated flight deals from Midland to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated April 11, 2025.

Sat 8/302:34 pmMAF - ORD

1 stop6h 28mAmerican Airlines

Thu 9/45:00 amORD - MAF

1 stop4h 36mAmerican Airlines

Deal found 4/10

$268

Sat 8/3012:29 pmMAF - ORD

2 stops11h 26mDelta

Thu 9/41:16 pmORD - MAF

2 stops10h 36mDelta

Deal found 4/10

$278

Wed 5/73:40 pmMAF - ORD

1 stop5h 50mSouthwest

Mon 5/127:30 amORD - MAF

1 stop4h 55mSouthwest

Deal found 4/10

$302

Sat 8/304:55 pmMAF - ORD

1 stop7h 02mUnited Airlines

Thu 9/49:10 pmORD - MAF

2 stops14h 12mUnited Airlines

Deal found 4/10

$370

Last-minute flights from Midland to Chicago
Discover last-minute flight deals from Midland to Chicago. Data last updated April 11, 2025 and is based on user searches.

Fri 4/255:15 pmMAF - ORD

1 stop5h 58mUnited Airlines

Tue 4/291:05 pmORD - MAF

1 stop7h 20mUnited Airlines

Deal found 4/9

$447

Wed 5/73:40 pmMAF - ORD

1 stop5h 50mSouthwest

Mon 5/127:30 amORD - MAF

1 stop4h 55mSouthwest

Deal found 4/10

$302

Wed 5/75:29 amMAF - ORD

2 stops11h 01mDelta

Mon 5/1211:05 amORD - MAF

2 stops12h 57mDelta

Deal found 4/10

$312

One-way flights from Midland to Chicago
Search for one-way flight options from Midland to Chicago. Find affordable one-way fares based on user searches. Data last updated April 11, 2025.

Sat 5/105:00 amMAF - ORD

1 stop6h 08mAmerican Airlines

Deal found 4/10

$109

Sat 5/105:29 amMAF - ORD

2 stops11h 18mDelta

Deal found 4/10

$114

Cheapflights Fare Finder

Use the filters below to find and compare flights from Midland to Chicago that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

MidlandChicago

MAF - ORD

MAFORD

Midland Intl

Sat 8/30

5:10 pm-11:46 pm

1 stop6h 36m

Chicago O'Hare Intl

Thu 9/4

1:23 pm-8:06 pm

1 stop6h 43m

$268

MidlandChicago

MAF - ORD

MAFORD

Midland Intl

Sat 8/30

12:29 pm-9:54 pm

2 stops9h 25m

Chicago O'Hare Intl

Thu 9/4

11:19 am-11:52 pm

2 stops12h 33m

$278

MidlandChicago

MAF - ORD

MAFORD

Midland Intl

Wed 5/7

3:40 pm-9:30 pm

1 stop5h 50m

Chicago O'Hare Intl

Mon 5/12

7:30 am-12:25 pm

1 stop4h 55m

$302

MidlandChicago

MAF - ORD

MAFORD

Midland Intl

Sat 8/30

8:00 am-1:15 pm

1 stop5h 15m

Chicago O'Hare Intl

Thu 9/4

7:45 am-11:15 pm

2 stops15h 30m

$365

MidlandChicago

MAF - ORD

MAFORD

Midland Intl

Sat 5/10

5:00 am-11:08 am

1 stop6h 08m

$109

MidlandChicago

MAF - ORD

MAFORD

Midland Intl

Sat 5/10

5:29 am-4:47 pm

2 stops11h 18m

$114

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/10

Compare providers for flights from Midland to Chicago

Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Midland to Chicago in April.

Provider	Price Accuracy	Trust Score*
Expedia	Price Accuracy1 star	Trust Score*3 stars
FlightHub	Price Accuracy3 stars	Trust Score*3 stars
eDreams	Price Accuracy3 stars	Trust 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 Midland-Chicago flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Midland-Chicago flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Midland-Chicago flight searches over the past month and is updated monthly.
Most trusted provider: When it comes to deals on Midland-Chicago 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 Midland-Chicago 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 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 time of day to fly from MAF to CHI?

It’s typically best to fly out from Midland to Chicago in the afternoon. Doing so could potentially save you 47% on the flight price compared to flying in the morning, which is usually more expensive.

Rainfall in Chicago by month

In terms of precipitation, rainfall in Chicago ranges from 1.7 - 4.9 inches per month. August is typically the wettest month, when rainfall can reach 4.9 in. January is typically the driest time to visit Chicago when rainfall is around 1.7 in.

Temperature in Chicago by month

If weather is an important factor for your trip to Chicago, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 73.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 23.0 F).

Reviews of airlines servicing Chicago

Southwest

8.0

Very good

4,279 reviews

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

4,279 reviews

Southwest

8.0

Very good

4,279 reviews

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

7,910 reviews

Southwest

8.0

Very good

4,279 reviews

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

8,636 reviews

Southwest

8.0

Very good

4,279 reviews

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

4,279 reviews

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

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. 3 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 $268, was found to be the cheapest airline from Midland to Chicago.Alternate airlines to your destination round-trip include Delta and Southwest. Users have found that American Airlines is 40% 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

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Top 3 airlines flying from Midland to Chicago

Airline	Cheapest	Average	Flexibility	On-time
American Airlines	Cheapest$267	Average$347	FlexibilityNo cancel fee	On-time71%
United Airlines	Cheapest$335	Average$426	FlexibilityNo cancel fee	On-time69%
Southwest	Cheapest$381	Average$536	FlexibilityNo cancel fee	On-time63%

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$109+ 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 5/10. Fares are subject to change and may not be available on all flights or dates of travel.

Find cheap flights from Midland to Chicago with Cheapflights

1. Tell us where you want to go

2. Select your favorite providers

3. Compare prices and book

Cheap flight deals from Midland to Chicago

Most accurate provider

Most trusted provider

Round-trip from

One-way from

Popular in

Cheapest in

Average price

Find flight deals from Midland to Chicago

Cheapest flights from Midland to ChicagoExplore 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 April 11, 2025.

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 April 11, 2025.

Cheapflights Fare Finder

Use the filters below to find and compare flights from Midland to Chicago that are best for you.

Compare providers for flights from Midland to Chicago

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 Midland to Chicago in April.

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.

Cheapflights Insights

Everything you need to know about your flight from Midland to Chicago

What is the cheapest time of day to fly from MAF to CHI?

Find hourly flight availability from Midland to Chicago. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated April 11, 2025.

Rainfall in Chicago by month

Plan your trip to Chicago by taking into account the average rainfall totals by month.

Temperature in Chicago by month

Plan your trip to Chicago by taking into account the average temperature totals by month.

Reviews of airlines servicing Chicago

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?

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

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

How can I find direct flights from Midland to Chicago?

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

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

Traveling to a place near Midland?

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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.

Top 3 airlines flying from Midland to Chicago

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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 April 11, 2025.