What is the cheapest airline that flies from Chicago to Midland Intl?

American Airlines, Southwest, and United Airlines are the most popular carriers operating from Chicago to Midland Intl

Which airport is the most popular layover for flights between Chicago and Midland?

Dallas (DFW) was the most common stop: 80% of momondo users choosing 1-stop flights on this route connected there.

Which layover airport offers the lowest fares from Chicago to Midland?

Flights via Dallas (DAL) offer the lowest average round-trip price of $281.

Which layover airport has the shortest travel time from Chicago to Midland?

Flights connecting via Dallas (DFW) have the shortest average one-way travel time: 4h 33m.

Which layover airport has the shortest connection time from Chicago to Midland?

Dallas (DFW) has the shortest average layover time for this route: 0h 54m.

When did momondo last update prices for flights from Chicago to Midland Intl Airport?

Prices for flights from Chicago to Midland Intl Airport refresh daily.

How many operators does momondo search for flights from Chicago to Midland Intl Airport?

The number of operators available for flights from Chicago to Midland Intl Airport is 2 as of October 2026.

How old do you have to be to fly from Chicago to Midland Intl Airport?

The minimum age for a child to fly alone is five, but airlines that offer an unaccompanied minor (UNMR) service may have their own age limitations. Flight duration, scheduling, and layovers are among the considerations that may influence age limits. We recommend that you double-check with the airline you are booking with for travel from Chicago to Midland Intl Airport.

What documentation or ID do you need to fly to Midland Intl Airport?

The required travel and health documents for your Midland Intl Airport trip may vary depending on your itinerary and personal circumstances. As a general rule, you should carry multiple documents, including a national ID card or driver's license and a passport valid for six months after your intended arrival at Midland Intl Airport. We recommend that you seek guidance from your airline or a reliable third party such as IATA.

$229 Cheap Flights from Chicago to Midland in 2026/27

Discover deals from 900+ travel sites with momondo.

Find the cheapest flights from Chicago to Midland

Round-trip

One-way

Last minute

Cheap round-trip flights

Enter your travel dates to find the best prices.

6:40 am - 2:00 pmMDW Chicago Midway-MAF Midland Intl

7h 20m1 stop Houston Hobby

11:00 am - 5:10 pmMAF Midland Intl-MDW Chicago Midway

6h 10m1 stop Dallas Love Field

$293Southwest

Tue, Dec 8 - Tue, Dec 15

6:30 am - 11:30 amMDW Chicago Midway-MAF Midland Intl

5h 00m1 stop Austin Bergstrom

6:00 pm - 1:00 amMAF Midland Intl-MDW Chicago Midway

7h 00m1 stop Houston Hobby

$293Southwest

Tue, Dec 22 - Wed, Dec 23

9:55 am - 5:40 pmMDW Chicago Midway-MAF Midland Intl

7h 45m2 stops Nashville Intl Houston Hobby

5:50 am - 11:00 amMAF Midland Intl-MDW Chicago Midway

5h 10m1 stop Dallas Love Field

$298Southwest

Tue, Dec 8 - Tue, Dec 15

8:00 am - 3:35 pmMDW Chicago Midway-MAF Midland Intl

7h 35m2 stops Nashville Intl Dallas Love Field

4:05 pm - 10:45 pmMAF Midland Intl-MDW Chicago Midway

6h 40m2 stops Dallas Love Field Nashville Intl

$303Southwest

Tue, Dec 8 - Tue, Dec 15

12:02 pm - 7:12 pmORD Chicago O'Hare Intl-MAF Midland Intl

7h 10m1 stop Dallas/Fort Worth

6:41 pm - 12:20 amMAF Midland Intl-ORD Chicago O'Hare Intl

5h 39m1 stop Dallas/Fort Worth

$364American Airlines

Tue, Nov 17 - Thu, Nov 19

5:52 pm - 11:44 pmORD Chicago O'Hare Intl-MAF Midland Intl

5h 52m1 stop Houston George Bush Intcntl

11:50 am - 6:19 pmMAF Midland Intl-ORD Chicago O'Hare Intl

6h 29m1 stop Houston George Bush Intcntl

$379United Airlines

Tue, Dec 8 - Tue, Dec 15

4:07 pm - 9:58 pmORD Chicago O'Hare Intl-MAF Midland Intl

5h 51m1 stop Houston George Bush Intcntl

8:30 am - 2:51 pmMAF Midland Intl-ORD Chicago O'Hare Intl

6h 21m1 stop Houston George Bush Intcntl

$425United Airlines

Fri, Nov 6 - Tue, Nov 10

10:55 am - 4:30 pmORD Chicago O'Hare Intl-MAF Midland Intl

5h 35m1 stop Denver Intl

9:41 am - 4:29 pmMAF Midland Intl-ORD Chicago O'Hare Intl

6h 48m1 stop Houston George Bush Intcntl

$425United Airlines

Fri, Nov 6 - Tue, Nov 10

5:59 pm - 10:55 pmORD Chicago O'Hare Intl-MAF Midland Intl

4h 56m1 stop Dallas/Fort Worth

12:39 pm - 7:59 pmMAF Midland Intl-ORD Chicago O'Hare Intl

7h 20m1 stop Dallas/Fort Worth

$430American Airlines

Tue, Dec 15 - Sun, Dec 20

10:34 am - 5:14 pmORD Chicago O'Hare Intl-MAF Midland Intl

6h 40m1 stop Dallas/Fort Worth

7:10 am - 12:24 pmMAF Midland Intl-ORD Chicago O'Hare Intl

5h 14m1 stop Dallas/Fort Worth

$457American Airlines

Sat, Dec 5 - Wed, Dec 9

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United Airlines flights from Chicago to Midland

Our best United Airlines deals on Chicago to Midland flight tickets

United Airlines

Dec 8

ORD5:52 pmChicago O'Hare Intl

5h 52m

1 stop

MAF11:44 pmMidland Intl

Dec 15

MAF11:50 amMidland Intl

6h 29m

1 stop

ORD6:19 pmChicago O'Hare Intl

$379

United Airlines

Nov 6

ORD10:55 amChicago O'Hare Intl

5h 35m

1 stop

MAF4:30 pmMidland Intl

Nov 10

MAF9:41 amMidland Intl

6h 48m

1 stop

ORD4:29 pmChicago O'Hare Intl

$425

United Airlines

Nov 17

ORD5:30 pmChicago O'Hare Intl

6h 13m

1 stop

MAF11:43 pmMidland Intl

Nov 18

MAF1:21 pmMidland Intl

8h 09m

1 stop

ORD9:30 pmChicago O'Hare Intl

$443

American Airlines flights from Chicago to Midland

Our best American Airlines deals on Chicago to Midland flight tickets

American Airlines

Nov 17

ORD12:02 pmChicago O'Hare Intl

7h 10m

1 stop

MAF7:12 pmMidland Intl

Nov 19

MAF6:41 pmMidland Intl

5h 39m

1 stop

ORD12:20 amChicago O'Hare Intl

$364

American Airlines

Dec 15

ORD5:59 pmChicago O'Hare Intl

4h 56m

1 stop

MAF10:55 pmMidland Intl

Dec 20

MAF12:39 pmMidland Intl

7h 20m

1 stop

ORD7:59 pmChicago O'Hare Intl

$430

American Airlines

Oct 28

ORD6:00 amChicago O'Hare Intl

7h 57m

1 stop

MAF1:57 pmMidland Intl

Nov 21

MAF6:41 pmMidland Intl

5h 39m

1 stop

ORD12:20 amChicago O'Hare Intl

$450

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

ChicagoMidland

MDW Chicago Midway - MAF Midland Intl

MDWMAF

Chicago Midway

Tue 12/8

6:40 am-2:00 pm

1 stop7h 20m

Midland Intl

Tue 12/15

11:00 am-5:10 pm

1 stop6h 10m

$293

ChicagoMidland

MDW Chicago Midway - MAF Midland Intl

MDWMAF

Chicago Midway

Tue 12/22

6:30 am-11:30 am

1 stop5h 00m

Midland Intl

Wed 12/23

6:00 pm-1:00 am

1 stop7h 00m

$293

ChicagoMidland

MDW Chicago Midway - MAF Midland Intl

MDWMAF

Chicago Midway

Tue 12/8

9:55 am-5:40 pm

2 stops7h 45m

Midland Intl

Tue 12/15

5:50 am-11:00 am

1 stop5h 10m

$298

ChicagoMidland

MDW Chicago Midway - MAF Midland Intl

MDWMAF

Chicago Midway

Tue 12/8

8:00 am-3:35 pm

2 stops7h 35m

Midland Intl

Tue 12/15

4:05 pm-10:45 pm

2 stops6h 40m

$303

ChicagoMidland

ORD Chicago O'Hare Intl - MAF Midland Intl

ORDMAF

Chicago O'Hare Intl

Tue 11/17

12:02 pm-7:12 pm

1 stop7h 10m

Midland Intl

Thu 11/19

6:41 pm-12:20 am

1 stop5h 39m

$364

ChicagoMidland

ORD Chicago O'Hare Intl - MAF Midland Intl

ORDMAF

Chicago O'Hare Intl

Tue 12/8

5:52 pm-11:44 pm

1 stop5h 52m

Midland Intl

Tue 12/15

11:50 am-6:19 pm

1 stop6h 29m

$379

ChicagoMidland

ORD Chicago O'Hare Intl - MAF Midland Intl

ORDMAF

Chicago O'Hare Intl

Fri 11/6

4:07 pm-9:58 pm

1 stop5h 51m

Midland Intl

Tue 11/10

8:30 am-2:51 pm

1 stop6h 21m

$425

ChicagoMidland

ORD Chicago O'Hare Intl - MAF Midland Intl

ORDMAF

Chicago O'Hare Intl

Fri 11/6

10:55 am-4:30 pm

1 stop5h 35m

Midland Intl

Tue 11/10

9:41 am-4:29 pm

1 stop6h 48m

$425

ChicagoMidland

ORD Chicago O'Hare Intl - MAF Midland Intl

ORDMAF

Chicago O'Hare Intl

Tue 12/15

5:59 pm-10:55 pm

1 stop4h 56m

Midland Intl

Sun 12/20

12:39 pm-7:59 pm

1 stop7h 20m

$430

Quickest round-trip

ChicagoMidland

ORD Chicago O'Hare Intl - MAF Midland Intl

ORDMAF

Chicago O'Hare Intl

Sat 12/5

10:34 am-5:14 pm

1 stop6h 40m

Midland Intl

Wed 12/9

7:10 am-12:24 pm

1 stop5h 14m

$457

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 19 resultsSorted by cheapest first

How to get the cheapest flight ticket from Chicago to Midland

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

Prices

Airlines

Layovers

What is the cheapest month to fly to Midland?

In general, June is the cheapest month to fly from Chicago to Midland. Due to it being the ‘off-season’ during this time, you can expect flight prices to be around $0. If you don’t want to visit Midland in June, then you should wait until April to fly from Chicago, when ticket prices are also cheap, with an average price of $0.

When to book flights from Chicago to Midland

Are you open to changing your travel dates? Check out the ideal times to fly from Chicago to Midland according to our flight data. Find out which month and days have the cheapest flights.

Estimated round-trip price

Cheap Chicago to Midland (CHI to MAF) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Chicago to Midland

Best Price Found	$229
Fastest flight time	5h 47m
Direct flights	None

The best one-way flight to Midland from Chicago in the past 72 hours is $229. The best round-trip flight deal from Chicago to Midland found on momondo in the last 72 hours is $293.

The fastest flight from Chicago to Midland takes 5h 47m

There are no direct flights from Chicago to Midland. There are no popular flight routes from Chicago to Midland.

Search flight deals

Frequently asked questions about flying from Chicago to Midland

How far is Chicago to Midland Intl by plane?
The straight-line distance from Chicago to Midland Intl is 1046.8 mi. Flights usually cover this in 5h 47m, depending on flying conditions and air traffic around both airports.
When did momondo last update prices for flights from Chicago to Midland Intl Airport?
Prices for flights from Chicago to Midland Intl Airport refresh daily.
How many operators does momondo search for flights from Chicago to Midland Intl Airport?
The number of operators available for flights from Chicago to Midland Intl Airport is 2 as of October 2026.
How old do you have to be to fly from Chicago to Midland Intl Airport?
The minimum age for a child to fly alone is five, but airlines that offer an unaccompanied minor (UNMR) service may have their own age limitations. Flight duration, scheduling, and layovers are among the considerations that may influence age limits. We recommend that you double-check with the airline you are booking with for travel from Chicago to Midland Intl Airport.
What documentation or ID do you need to fly to Midland Intl Airport?
The required travel and health documents for your Midland Intl Airport trip may vary depending on your itinerary and personal circumstances. As a general rule, you should carry multiple documents, including a national ID card or driver's license and a passport valid for six months after your intended arrival at Midland Intl Airport. We recommend that you seek guidance from your airline or a reliable third party such as IATA.
What is the most popular airline from Chicago to Midland?
momondo data reveals that the most frequently booked airline on the route from Chicago to Midland is Southwest, representing 43% of all bookings. The subsequent popular airlines are United Airlines at 35% and American Airlines at 22%.

Best airlines flying from Chicago to Midland

Compare and see reviews for airlines that fly from Chicago to Midland with momondo

Airline	Rating	Free Cancellation	Price
United Airlines	PriceFrom $347	Free Cancellation	Rating 7.3 10,404 reviews		Search United Airlines flights
American Airlines	PriceFrom $379	Free Cancellation	Rating 7.0 12,186 reviews		Search American Airlines flights

Odessa

Big Spring

Fort Stockton

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Why should I use momondo to find a flight deal from Chicago to Midland?

To find the flight that best suits your needs, momondo gathers a range of flights from a large pool of different airlines and agents; you can then use our insights and filters to find and book the right flight to Midland from Chicago.

Can I find flights from Chicago to Midland with flexible booking policies on momondo?

All flight searches from Chicago to Midland on momondo can be filtered to show those which offer flexible booking policies.

How can momondo help me find flights from Chicago to Midland?

momondo helps you find the best flight between Chicago and Midland by providing filters to narrow your choice of flights to those matching your criteria. You can select flights based on numerous factors such as price, departure and landing times, airport and airline.

I’m not ready to book a flight from Chicago to Midland right now. Can momondo alert me if prices change?

If you are simply researching potential flights to Midland, momondo offers a useful price alert feature which will track prices for flights to Midland from Chicago and alert you when they change.

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Cheap flights from Chicago to Midland from $229

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Chicago to Midland departing on 11/19. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.

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United Airlines flights from Chicago to Midland

Our best United Airlines deals on Chicago to Midland flight tickets

American Airlines flights from Chicago to Midland

Our best American Airlines deals on Chicago to Midland flight tickets

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How to get the cheapest flight ticket from Chicago to Midland

What is the cheapest month to fly to Midland?

What is the cheapest airline that flies from Chicago to Midland Intl?

Which airport is the most popular layover for flights between Chicago and Midland?

Which layover airport offers the lowest fares from Chicago to Midland?

Which layover airport has the shortest travel time from Chicago to Midland?

Which layover airport has the shortest connection time from Chicago to Midland?

When to book flights from Chicago to Midland

Cheap Chicago to Midland (CHI to MAF) flight deals and tips

Best Price Found

Fastest flight time

Direct flights

Frequently asked questions about flying from Chicago to Midland

Best airlines flying from Chicago to Midland

Compare and see reviews for airlines that fly from Chicago to Midland with momondo

Traveling to a place near Midland?

Why use momondo?

An easier way to manage your Midland trip

We make it super easy to schedule, organize and travel with friends or family. Trips is free — and available to use no matter where you book.

Get notified when prices go down

Daily price changes in your inbox - only with Price Alerts.

Find better results for your trip to the United States

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List of cabin classes available on flights landing in Midland. Availability may vary depending on flight origin and airline.

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