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

Houston (IAH) has the shortest average layover time for this route: 0h 53m.

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

Houston (IAH) was the most common stop: 40% of momondo users choosing 1-stop flights on this route connected there.

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 54m.

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

Flights via Houston (IAH) offer the lowest average round-trip price of $331.

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 1 as of November 2025.

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.

$277 Cheap Flights from Chicago to Midland in 2025/26

Q: What is the typical price of a round-trip flight between Chicago and Midland?

Prices are currently low for flights on this route. Typical prices usually range from $643 to $720. The lowest price recently found on this route was $277.

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2:55 pm - 10:49 pmORD-MAF

7h 54m1 stop

9:12 am - 3:09 pmMAF-ORD

5h 57m1 stop

$277American Airlines

Find Deal

Wed, Feb 18 - Sat, Feb 21

6:52 pm - 11:59 pmORD-MAF

5h 07m1 stop

10:20 am - 5:40 pmMAF-ORD

7h 20m1 stop

$310American Airlines

Find Deal

Fri, Feb 20 - Sun, Feb 22

2:15 pm - 10:15 pmORD-MAF

8h 00m1 stop

3:00 pm - 10:35 pmMAF-ORD

7h 35m1 stop

$325Southwest

Find Deal

Mon, Feb 23 - Wed, Feb 25

1:45 pm - 10:35 pmORD-MAF

8h 50m2 stops

3:00 pm - 10:35 pmMAF-ORD

7h 35m1 stop

$330Southwest

Find Deal

Mon, Feb 23 - Wed, Feb 25

2:15 pm - 10:35 pmORD-MAF

8h 20m2 stops

7:05 am - 1:00 pmMAF-ORD

5h 55m2 stops

$335Southwest

Find Deal

Mon, Feb 23 - Wed, Feb 25

11:43 am - 10:49 pmORD-MAF

11h 06m2 stops

5:00 am - 9:48 amMAF-ORD

4h 48m1 stop

$350American Airlines

Find Deal

Wed, Feb 18 - Sat, Feb 21

5:10 pm - 11:15 pmORD-MAF

6h 05m1 stop

5:00 am - 10:02 amMAF-ORD

5h 02m1 stop

$380United Airlines

Find Deal

Fri, Nov 28 - Sat, Dec 6

1:45 pm - 10:10 pmORD-MAF

8h 25m2 stops

6:15 am - 1:00 pmMAF-ORD

6h 45m1 stop

$386Southwest

Find Deal

Mon, Dec 15 - Wed, Dec 17

11:35 am - 4:26 pmORD-MAF

28h 51m2 stops

7:00 am - 12:16 pmMAF-ORD

5h 16m1 stop

$592United Airlines

Find Deal

Fri, Nov 21 - Sun, Nov 23

7:10 am - 9:42 pmORD-MAF

14h 32m2 stops

5:30 pm - 11:10 pmMAF-ORD

5h 40m1 stop

$607United Airlines

Find Deal

Mon, Nov 24 - Fri, Nov 28

American Airlines flights from Chicago to Midland

Our best American Airlines deals on Chicago to Midland flight tickets

American Airlines

Feb 18

ORD2:55 pmChicago O'Hare Intl

7h 54m

1 stop

MAF10:49 pmMidland Intl

Feb 21

MAF9:12 amMidland Intl

5h 57m

1 stop

ORD3:09 pmChicago O'Hare Intl

$277

Find similar

American Airlines

Feb 20

ORD6:52 pmChicago O'Hare Intl

5h 07m

1 stop

MAF11:59 pmMidland Intl

Feb 22

MAF10:20 amMidland Intl

7h 20m

1 stop

ORD5:40 pmChicago O'Hare Intl

$310

Find similar

American Airlines

Feb 18

ORD11:43 amChicago O'Hare Intl

11h 06m

2 stops

MAF10:49 pmMidland Intl

Feb 21

MAF5:00 amMidland Intl

4h 48m

1 stop

ORD9:48 amChicago O'Hare Intl

$350

Find similar

United Airlines flights from Chicago to Midland

Our best United Airlines deals on Chicago to Midland flight tickets

United Airlines

Nov 28

ORD5:10 pmChicago O'Hare Intl

6h 05m

1 stop

MAF11:15 pmMidland Intl

Dec 6

MAF5:00 amMidland Intl

5h 02m

1 stop

ORD10:02 amChicago O'Hare Intl

$380

Find similar

United Airlines

Nov 18

ORD2:21 pmChicago O'Hare Intl

7h 21m

1 stop

MAF9:42 pmMidland Intl

Nov 19

MAF1:55 pmMidland Intl

5h 45m

1 stop

ORD7:40 pmChicago O'Hare Intl

$547

Find similar

United Airlines

Nov 21

ORD11:35 amChicago O'Hare Intl

28h 51m

2 stops

MAF4:26 pmMidland Intl

Nov 23

MAF7:00 amMidland Intl

5h 16m

1 stop

ORD12:16 pmChicago O'Hare Intl

$592

Find similar

Fly from

Fly to

Route

Depart

Return

Price

ChicagoMidland

ORD - MAF

ORDMAF

Chicago O'Hare Intl

Wed 2/18

2:55 pm-10:49 pm

1 stop7h 54m

Midland Intl

Sat 2/21

9:12 am-3:09 pm

1 stop5h 57m

$277

ChicagoMidland

ORD - MAF

ORDMAF

Chicago O'Hare Intl

Fri 2/20

6:52 pm-11:59 pm

1 stop5h 07m

Midland Intl

Sun 2/22

10:20 am-5:40 pm

1 stop7h 20m

$310

ChicagoMidland

ORD - MAF

ORDMAF

Chicago O'Hare Intl

Mon 2/23

2:15 pm-10:15 pm

1 stop8h 00m

Midland Intl

Wed 2/25

3:00 pm-10:35 pm

1 stop7h 35m

$325

ChicagoMidland

ORD - MAF

ORDMAF

Chicago O'Hare Intl

Mon 2/23

1:45 pm-10:35 pm

2 stops8h 50m

Midland Intl

Wed 2/25

3:00 pm-10:35 pm

1 stop7h 35m

$330

ChicagoMidland

ORD - MAF

ORDMAF

Chicago O'Hare Intl

Mon 2/23

2:15 pm-10:35 pm

2 stops8h 20m

Midland Intl

Wed 2/25

7:05 am-1:00 pm

2 stops5h 55m

$335

ChicagoMidland

ORD - MAF

ORDMAF

Chicago O'Hare Intl

Wed 2/18

11:43 am-10:49 pm

2 stops11h 06m

Midland Intl

Sat 2/21

5:00 am-9:48 am

1 stop4h 48m

$350

ChicagoMidland

ORD - MAF

ORDMAF

Chicago O'Hare Intl

Fri 11/28

5:10 pm-11:15 pm

1 stop6h 05m

Midland Intl

Sat 12/6

5:00 am-10:02 am

1 stop5h 02m

$380

ChicagoMidland

ORD - MAF

ORDMAF

Chicago O'Hare Intl

Mon 12/15

1:45 pm-10:10 pm

2 stops8h 25m

Midland Intl

Wed 12/17

6:15 am-1:00 pm

1 stop6h 45m

$386

ChicagoMidland

ORD - MAF

ORDMAF

Chicago O'Hare Intl

Fri 11/21

11:35 am-4:26 pm

2 stops28h 51m

Midland Intl

Sun 11/23

7:00 am-12:16 pm

1 stop5h 16m

$592

ChicagoMidland

ORD - MAF

ORDMAF

Chicago O'Hare Intl

Mon 11/24

7:10 am-9:42 pm

2 stops14h 32m

Midland Intl

Fri 11/28

5:30 pm-11:10 pm

1 stop5h 40m

$607

Flights are sorted by cheapest round-trip flights first.

Sorted 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

Layovers

What is the typical price of a round-trip flight between Chicago and Midland?

What is the cheapest month to fly to Midland?

In general, September 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 $279. If you don’t want to visit Midland in September, then you should wait until January to fly from Chicago, when ticket prices are also cheap, with an average price of $316.

What is the cheapest day to depart on your flight to Midland?

The cheapest day to depart on your flight to Midland is on a Saturday when prices can be found for as low as $346. This is often the case because there is less demand to fly during this day of the week. On the other hand, Sunday is the most expensive day to depart from Chicago because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $778.

What is the cheapest time of day to depart on your flight to Midland?

Our most recent data shows that the best time of day to fly to Midland is in the morning. Flights from Chicago to Midland during this time can be as low as $416. Flights to Midland are more costly in the afternoon, with an average ticket price of $609. Departure times in the afternoon fall within the peak daily travel times, which is why tickets can be more expensive.

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

Direct flights	None

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

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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 07m, 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 1 as of November 2025.
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 53% of all bookings. The subsequent popular airline is American Airlines at 47%.

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
American Airlines	PriceFrom $216	Free Cancellation	Rating 7.2 11,045 reviews		Search American Airlines flights

Odessa

Fort Stockton

Big Spring

Why use momondo?

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.