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

Houston (IAH) was the most common stop: 50% 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 Houston (IAH) offer the lowest average round-trip price of $331.

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.

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

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

How many flights depart from Chicago to Midland on average per week?

As of July 2025, there are 7 flights per week flying from Chicago to Midland. The most common day of the week flights depart is Mon, with 14% of flights taking off on this day.

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.

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 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.

$124 Cheap Flights from Chicago to Midland in 2025

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Find the cheapest flights from Chicago to Midland

Round-trip

One-way

Last minute

Cheap round-trip flights

6:00 am - 11:42 amORD-MAF

5h 42m1 stop

6:22 pm - 11:59 pmMAF-ORD

5h 37m1 stop

$259American Airlines

Find Deal

Thu, Aug 28 - Mon, Sep 1

2:55 pm - 10:34 pmORD-MAF

7h 39m1 stop

4:12 pm - 11:13 pmMAF-ORD

7h 01m1 stop

$282American Airlines

Find Deal

Sat, Oct 25 - Mon, Oct 27

5:20 am - 5:26 pmORD-MAF

12h 06m2 stops

12:33 pm - 11:57 pmMAF-ORD

11h 24m2 stops

$288Delta

Find Deal

Sat, Oct 25 - Mon, Oct 27

4:00 pm - 11:25 pmORD-MAF

7h 25m1 stop

5:00 am - 10:08 amMAF-ORD

5h 08m1 stop

$293United Airlines

Find Deal

Wed, Dec 31 - Thu, Jan 1

10:10 pm - 8:48 amORD-MAF

10h 38m1 stop

5:00 am - 12:22 pmMAF-ORD

7h 22m1 stop

$309American Airlines

Find Deal

Fri, Aug 29 - Mon, Sep 1

2:55 pm - 7:45 pmORD-MAF

4h 50m1 stop

7:36 am - 12:22 pmMAF-ORD

4h 46m1 stop

$317American Airlines

Find Deal

Tue, Aug 19 - Fri, Aug 22

3:55 pm - 11:58 pmORD-MAF

8h 03m2 stops

12:33 pm - 11:54 pmMAF-ORD

11h 21m2 stops

$337Delta

Find Deal

Fri, Sep 12 - Mon, Sep 15

4:20 pm - 9:35 pmORD-MAF

5h 15m1 stop

5:35 am - 1:05 pmMAF-ORD

7h 30m2 stops

$362Southwest

Find Deal

Fri, Sep 12 - Mon, Sep 15

7:00 am - 2:02 pmORD-MAF

7h 02m1 stop

5:20 pm - 8:05 amMAF-ORD

14h 45m2 stops

$403United Airlines

Find Deal

Thu, Aug 28 - Mon, Sep 1

7:00 am - 6:05 pmORD-MAF

11h 05m2 stops

5:35 am - 10:45 amMAF-ORD

5h 10m1 stop

$417Southwest

Find Deal

Tue, Aug 19 - Fri, Aug 22

American Airlines flights from Chicago to Midland

Our best American Airlines deals on Chicago to Midland flight tickets

American Airlines

Aug 28

ORD6:00 amChicago O'Hare Intl

5h 42m

1 stop

MAF11:42 amMidland Intl

Sep 1

MAF6:22 pmMidland Intl

5h 37m

1 stop

ORD11:59 pmChicago O'Hare Intl

$259

Find similar

American Airlines

Oct 25

ORD2:55 pmChicago O'Hare Intl

7h 39m

1 stop

MAF10:34 pmMidland Intl

Oct 27

MAF4:12 pmMidland Intl

7h 01m

1 stop

ORD11:13 pmChicago O'Hare Intl

$282

Find similar

American Airlines

Aug 29

ORD10:10 pmChicago O'Hare Intl

10h 38m

1 stop

MAF8:48 amMidland Intl

Sep 1

MAF5:00 amMidland Intl

7h 22m

1 stop

ORD12:22 pmChicago O'Hare Intl

$309

Find similar

Delta flights from Chicago to Midland

Our best Delta deals on Chicago to Midland flight tickets

Delta

Oct 25

ORD5:20 amChicago O'Hare Intl

12h 06m

2 stops

MAF5:26 pmMidland Intl

Oct 27

MAF12:33 pmMidland Intl

11h 24m

2 stops

ORD11:57 pmChicago O'Hare Intl

$288

Find similar

Delta

Sep 12

ORD3:55 pmChicago O'Hare Intl

8h 03m

2 stops

MAF11:58 pmMidland Intl

Sep 15

MAF12:33 pmMidland Intl

11h 21m

2 stops

ORD11:54 pmChicago O'Hare Intl

$337

Find similar

Delta

Aug 12

ORD7:15 amChicago O'Hare Intl

9h 22m

2 stops

MAF4:37 pmMidland Intl

Aug 16

MAF12:31 pmMidland Intl

9h 03m

2 stops

ORD9:34 pmChicago O'Hare Intl

$407

Find similar

Fly from

Fly to

Route

Depart

Return

Price

ChicagoMidland

ORD - MAF

ORDMAF

Chicago O'Hare Intl

Thu 8/28

6:00 am-11:42 am

1 stop5h 42m

Midland Intl

Mon 9/1

6:22 pm-11:59 pm

1 stop5h 37m

$259

ChicagoMidland

ORD - MAF

ORDMAF

Chicago O'Hare Intl

Sat 10/25

2:55 pm-10:34 pm

1 stop7h 39m

Midland Intl

Mon 10/27

4:12 pm-11:13 pm

1 stop7h 01m

$282

ChicagoMidland

ORD - MAF

ORDMAF

Chicago O'Hare Intl

Sat 10/25

5:20 am-5:26 pm

2 stops12h 06m

Midland Intl

Mon 10/27

12:33 pm-11:57 pm

2 stops11h 24m

$288

ChicagoMidland

ORD - MAF

ORDMAF

Chicago O'Hare Intl

Wed 12/31

4:00 pm-11:25 pm

1 stop7h 25m

Midland Intl

Thu 1/1

5:00 am-10:08 am

1 stop5h 08m

$293

ChicagoMidland

ORD - MAF

ORDMAF

Chicago O'Hare Intl

Fri 8/29

10:10 pm-8:48 am

1 stop10h 38m

Midland Intl

Mon 9/1

5:00 am-12:22 pm

1 stop7h 22m

$309

ChicagoMidland

ORD - MAF

ORDMAF

Chicago O'Hare Intl

Tue 8/19

2:55 pm-7:45 pm

1 stop4h 50m

Midland Intl

Fri 8/22

7:36 am-12:22 pm

1 stop4h 46m

$317

ChicagoMidland

ORD - MAF

ORDMAF

Chicago O'Hare Intl

Fri 9/12

3:55 pm-11:58 pm

2 stops8h 03m

Midland Intl

Mon 9/15

12:33 pm-11:54 pm

2 stops11h 21m

$337

ChicagoMidland

ORD - MAF

ORDMAF

Chicago O'Hare Intl

Fri 9/12

4:20 pm-9:35 pm

1 stop5h 15m

Midland Intl

Mon 9/15

5:35 am-1:05 pm

2 stops7h 30m

$362

ChicagoMidland

ORD - MAF

ORDMAF

Chicago O'Hare Intl

Thu 8/28

7:00 am-2:02 pm

1 stop7h 02m

Midland Intl

Mon 9/1

5:20 pm-8:05 am

2 stops14h 45m

$403

ChicagoMidland

ORD - MAF

ORDMAF

Chicago O'Hare Intl

Tue 8/19

7:00 am-6:05 pm

2 stops11h 05m

Midland Intl

Fri 8/22

5:35 am-10:45 am

1 stop5h 10m

$417

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 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

Other information

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

Best Price Found	$124
Fastest flight time	4h 20m
Direct flights	None
Airports in Midland	1 airport

The best one-way flight to Midland from Chicago in the past 72 hours is $124. The best round-trip flight deal from Chicago to Midland found on momondo in the last 72 hours is $259.

The fastest flight from Chicago to Midland takes 4h 20m

There are no direct flights from Chicago to Midland. Popular non-direct route for this connection is Chicago O'Hare Intl Airport - Midland Intl Airport.

There is 1 airport near Midland: Midland Intl (MAF)

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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 4h 20m, 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 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 58% of all bookings. The subsequent popular airline is American Airlines at 42%.

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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.