How long is the flight from Midland to Chicago?

American Airlines and United Airlines can get you from Midland to Chicago in just under 4h 55m. Your travel time can differ by up to 1h 46m. 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 53% cheaper than the other options available to this destination.

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.

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).

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

When flying from Midland to Chicago, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

Most accurate provider : When it comes to deals on Midland-Chicago flights, users find the pricing of eDreams to be most consistent on Cheapflights vs. eDreams Users can find the same prices on Midland-Chicago flight deals on Cheapflights vs. eDreams >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 eDreams the most. eDreams 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. 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.

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.

$309+ Flights from Midland to Chicago

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

Airfare is below average for this route at the moment. Midland to Chicago flights typically cost between $605 and $669 in January. The cheapest round-trip price found within the last 3 days was $309 on American Airlines (Jan 10-Jan 17).

Home Search by date Vacation packages Hotels Flight deals Car rental Travel tips & news

Find cheap flights from Midland to Chicago 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 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 December 16, 2025.

Mon 12/299:18 amMAF - ORD

1 stop7h 59mAmerican Airlines

Fri 1/26:52 pmORD - MAF

1 stop5h 06mAmerican Airlines

Deal found 12/14

$487

Tue 12/309:18 amMAF - ORD

1 stop7h 59mAmerican Airlines

Sat 1/36:52 pmORD - MAF

1 stop5h 06mAmerican Airlines

Deal found 12/15

$637

Tue 12/301:06 pmMAF - ORD

2 stops20h 21mUnited Airlines

Sat 1/34:00 pmORD - MAF

1 stop7h 25mUnited Airlines

Deal found 12/15

$660

Wed 12/3112:39 pmMAF - ORD

1 stop6h 58mAmerican Airlines

Sun 1/48:58 pmORD - MAF

1 stop11h 43mAmerican Airlines

Deal found 12/16

$685

Mon 12/291:06 pmMAF - ORD

2 stops18h 55mUnited Airlines

Fri 1/27:35 amORD - MAF

1 stop7h 29mUnited Airlines

Deal found 12/14

$746

Tue 12/234:29 pmMAF - ORD

1 stop6h 46mAmerican Airlines

Sat 12/272:50 pmORD - MAF

1 stop7h 47mAmerican Airlines

Deal found 12/15

$797

Wed 12/315:15 pmMAF - ORD

1 stop6h 44mUnited Airlines

Sun 1/42:00 pmORD - MAF

2 stops9h 25mUnited Airlines

Deal found 12/16

$871

Tue 12/235:15 pmMAF - ORD

2 stops16h 40mUnited Airlines

Sat 12/275:03 pmORD - MAF

1 stop6h 22mUnited Airlines

Deal found 12/15

$885

Fri 12/1910:19 amMAF - ORD

1 stop5h 26mAmerican Airlines

Sun 12/285:21 amORD - MAF

1 stop6h 30mAmerican Airlines

Deal found 12/16

$894

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 December 16, 2025.

Sat 1/107:00 amMAF - ORD

1 stop4h 55mAmerican Airlines

Sat 1/176:54 amORD - MAF

1 stop5h 17mAmerican Airlines

Deal found 12/14

$309

Tue 1/135:18 pmMAF - ORD

1 stop6h 41mUnited Airlines

Sat 1/178:54 amORD - MAF

1 stop7h 27mUnited Airlines

Deal found 12/15

$387

Fri 1/93:00 pmMAF - ORD

1 stop7h 35mSouthwest

Mon 1/122:15 pmORD - MAF

1 stop7h 20mSouthwest

Deal found 12/16

$399

Thu 1/85:35 pmMAF - ORD

1 stop6h 53mUnited Airlines

Sun 1/115:40 amORD - MAF

1 stop5h 41mUnited Airlines

Deal found 12/16

$389

Thu 1/86:40 amMAF - ORD

1 stop6h 20mSouthwest

Sun 1/112:15 pmORD - MAF

2 stops8h 20mSouthwest

Deal found 12/16

$404

Last-minute flights from Midland to Chicago
Discover last-minute flight deals from Midland to Chicago. Data last updated December 16, 2025 and is based on user searches.

Mon 12/299:18 amMAF - ORD

1 stop7h 59mAmerican Airlines

Fri 1/26:52 pmORD - MAF

1 stop5h 06mAmerican Airlines

Deal found 12/14

$487

Tue 12/309:18 amMAF - ORD

1 stop7h 59mAmerican Airlines

Sat 1/36:52 pmORD - MAF

1 stop5h 06mAmerican Airlines

Deal found 12/15

$637

Thu 1/86:40 amMAF - ORD

1 stop6h 20mSouthwest

Sun 1/112:15 pmORD - MAF

2 stops8h 20mSouthwest

Deal found 12/16

$404

Fri 1/93:00 pmMAF - ORD

1 stop7h 35mSouthwest

Mon 1/122:15 pmORD - MAF

1 stop7h 20mSouthwest

Deal found 12/16

$399

Sat 1/107:00 amMAF - ORD

1 stop4h 55mAmerican Airlines

Sat 1/176:54 amORD - MAF

1 stop5h 17mAmerican Airlines

Deal found 12/14

$309

Sat 1/106:15 amMAF - ORD

1 stop6h 45mSouthwest

Sat 1/176:05 amORD - MAF

2 stops13h 50mSouthwest

Deal found 12/14

$476

Tue 1/135:18 pmMAF - ORD

1 stop6h 41mUnited Airlines

Sat 1/178:54 amORD - MAF

1 stop7h 27mUnited Airlines

Deal found 12/15

$387

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 December 16, 2025.

Sun 12/219:18 amMAF - ORD

1 stop6h 27mAmerican Airlines

Deal found 12/14

$399

Sun 12/215:35 amMAF - ORD

2 stops8h 30mSouthwest

Deal found 12/14

$404

Sun 12/214:29 pmMAF - ORD

3 stops46h 24mMultiple Airlines

Deal found 12/14

$1,032

Find flight deals from Midland to Chicago

Most accurate provider	eDreams 3 stars
Most trusted provider	eDreams 3 stars
Round-trip from	$309 (American Airlines)
Popular in	February
Cheapest in	November
Average price	$637

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

Search Deals

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

Search Deals

From Midland Intl to Chicago (CHI)

Search Deals

Highest demand for flights based on searches. 29% potential increase in price ($196 potential increase over avg. RT price).

Search Deals

Cheapest flight prices on average. 6% potential price decrease ($29 potential savings vs. average RT price).

Search Deals

Average for round-trip flights in December 2025

Search Deals

Fly from

Fly to

Route

Depart

Return

Price

MidlandChicago

MAF - ORD

MAFORD

Midland Intl

Sat 1/10

7:00 am-11:55 am

1 stop4h 55m

Chicago O'Hare Intl

Sat 1/17

6:54 am-12:11 pm

1 stop5h 17m

$309

MidlandChicago

MAF - ORD

MAFORD

Midland Intl

Tue 1/13

5:18 pm-11:59 pm

1 stop6h 41m

Chicago O'Hare Intl

Sat 1/17

8:54 am-4:21 pm

1 stop7h 27m

$387

MidlandChicago

MAF - ORD

MAFORD

Midland Intl

Thu 1/8

5:35 pm-12:28 am

1 stop6h 53m

Chicago O'Hare Intl

Sun 1/11

5:40 am-11:21 am

1 stop5h 41m

$389

MidlandChicago

MAF - ORD

MAFORD

Midland Intl

Fri 1/9

3:00 pm-10:35 pm

1 stop7h 35m

Chicago O'Hare Intl

Mon 1/12

2:15 pm-9:35 pm

1 stop7h 20m

$399

MidlandChicago

MAF - ORD

MAFORD

Midland Intl

Thu 1/8

6:40 am-1:00 pm

1 stop6h 20m

Chicago O'Hare Intl

Sun 1/11

2:15 pm-10:35 pm

2 stops8h 20m

$404

MidlandChicago

MAF - ORD

MAFORD

Midland Intl

Sun 12/21

9:18 am-3:45 pm

1 stop6h 27m

$399

MidlandChicago

MAF - ORD

MAFORD

Midland Intl

Sun 12/21

5:35 am-2:05 pm

2 stops8h 30m

$404

MidlandChicago

MAF - ORD

MAFORD

Midland Intl

Sun 12/21

4:29 pm-2:53 pm

3 stops46h 24m

$1,032

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/14

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 December.

Provider	Price Accuracy	Trust Score*
Expedia	Price Accuracy2 stars	Trust Score*3 stars
FlightHub	Price Accuracy3 stars	Trust Score*1 star
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 eDreams to be most consistent on Cheapflights vs. eDreams Users can find the same prices on Midland-Chicago flight deals on Cheapflights vs. eDreams >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 eDreams the most. eDreams 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 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 $219). Flying from Midland to Chicago in February is currently the most expensive (average of $901). 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

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

7.9

Good

4,250 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

7.9

Good

4,250 reviews

Southwest

7.9

Good

4,250 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

11,049 reviews

Southwest

7.9

Good

4,250 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. 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 and United Airlines can get you from Midland to Chicago in just under 4h 55m. Your travel time can differ by up to 1h 46m. 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 53% 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 $219). Flying from Midland to Chicago in February is currently the most expensive (average of $901). 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

Lansing

Merrillville

Hammond

Porter

Benton Harbor

Browse thousands of different options on Cheapflights for your next trip

Top 2 airlines flying from Midland to Chicago

Airline	Cheapest	Average	Flexibility	On-time
Southwest	Cheapest$216	Average$446	FlexibilityNo cancel fee	On-time63%
American Airlines	Cheapest$255	Average$365	FlexibilityNo cancel fee	On-time71%

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.

$309+ Cheap flights from Midland (MAF) to Chicago (CHI)

This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 1/10. 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

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 December 16, 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 December 16, 2025.

Find flight deals from Midland to Chicago

Most accurate provider

Most trusted provider

Round-trip from

Popular in

Cheapest in

Average price

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 December.

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 month to book a flight from Midland to Chicago?

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

Reviews of airlines servicing Chicago

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.

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?

How long is the flight 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 Chicago?

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 Midland to Chicago

See prices for flight routes from nearby airports that may be better suited for you.

Top 2 airlines flying from Midland to Chicago

100% Free

Book with Flexibility

Travel Smart

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 December 16, 2025.