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Cheap flights from Chicago to Midland from $127

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 10/11. 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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0 bags

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Find the cheapest flights from Chicago to Midland

Cheap round-trip flights

American Airlines Logo
2:57 pm - 8:39 pmORD-MAF
5h 42m1 stop
American Airlines Logo
12:22 pm - 9:14 pmMAF-ORD
8h 52m1 stop
$295American Airlines
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Fri, Oct 24 - Mon, Oct 27
Southwest Logo
5:45 pm - 10:55 pmORD-MAF
5h 10m1 stop
Southwest Logo
1:40 pm - 9:30 pmMAF-ORD
7h 50m2 stops
$342Southwest
Find Deal
Fri, Oct 24 - Mon, Oct 27
Delta Logo
4:56 pm - 11:56 pmORD-MAF
7h 00m2 stops
Delta Logo
5:30 am - 3:00 pmMAF-ORD
9h 30m2 stops
$357Delta
Find Deal
Fri, Oct 24 - Mon, Oct 27
American Airlines Logo
10:15 am - 9:22 pmORD-MAF
11h 07m1 stop
American Airlines Logo
12:29 pm - 11:45 pmMAF-ORD
11h 16m1 stop
$373American Airlines
Find Deal
Wed, Feb 18 - Sat, Feb 21
American Airlines Logo
10:05 pm - 8:41 amORD-MAF
10h 36m1 stop
American Airlines Logo
4:31 pm - 11:31 pmMAF-ORD
7h 00m1 stop
$385American Airlines
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Fri, Nov 21 - Sun, Nov 23
American Airlines Logo
4:12 pm - 11:04 pmORD-MAF
6h 52m1 stop
American Airlines Logo
12:35 pm - 5:16 pmMAF-ORD
4h 41m1 stop
$447American Airlines
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Fri, Oct 3 - Sun, Oct 5
Delta Logo
6:45 am - 4:40 pmORD-MAF
9h 55m2 stops
Delta Logo
5:30 am - 2:20 pmMAF-ORD
8h 50m2 stops
$457Delta
Find Deal
Fri, Oct 3 - Sun, Oct 5
United Airlines Logo
5:10 pm - 11:15 pmORD-MAF
6h 05m1 stop
United Airlines Logo
5:30 pm - 7:59 amMAF-ORD
14h 29m2 stops
$497United Airlines
Find Deal
Fri, Nov 21 - Sun, Nov 23
United Airlines Logo
4:50 pm - 10:13 pmORD-MAF
5h 23m1 stop
United Airlines Logo
5:00 am - 6:46 pmMAF-ORD
13h 46m2 stops
$513United Airlines
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Tue, Sep 30 - Sat, Oct 4
Southwest Logo
1:50 pm - 10:30 pmORD-MAF
8h 40m2 stops
Southwest Logo
10:50 am - 3:20 pmMAF-ORD
4h 30m1 stop
$550Southwest
Find Deal
Tue, Sep 30 - Thu, Oct 2

Delta flights from Chicago to Midland

Our best Delta deals on Chicago to Midland flight tickets
Delta
Oct 24
ORD4:56 pmChicago O'Hare Intl
7h 00m
2 stops
MAF11:56 pmMidland Intl
Oct 27
MAF5:30 amMidland Intl
9h 30m
2 stops
ORD3:00 pmChicago O'Hare Intl
$357
Find similar
Delta
Oct 3
ORD6:45 amChicago O'Hare Intl
9h 55m
2 stops
MAF4:40 pmMidland Intl
Oct 5
MAF5:30 amMidland Intl
8h 50m
2 stops
ORD2:20 pmChicago O'Hare Intl
$457
Find similar
Delta
Oct 3
ORD3:35 pmChicago O'Hare Intl
8h 23m
2 stops
MAF11:58 pmMidland Intl
Oct 5
MAF5:30 amMidland Intl
8h 50m
2 stops
ORD2:20 pmChicago O'Hare Intl
$477
Find similar

American Airlines flights from Chicago to Midland

Our best American Airlines deals on Chicago to Midland flight tickets
American Airlines
Oct 24
ORD2:57 pmChicago O'Hare Intl
5h 42m
1 stop
MAF8:39 pmMidland Intl
Oct 27
MAF12:22 pmMidland Intl
8h 52m
1 stop
ORD9:14 pmChicago O'Hare Intl
$295
Find similar
American Airlines
Feb 18
ORD10:15 amChicago O'Hare Intl
11h 07m
1 stop
MAF9:22 pmMidland Intl
Feb 21
MAF12:29 pmMidland Intl
11h 16m
1 stop
ORD11:45 pmChicago O'Hare Intl
$373
Find similar
American Airlines
Nov 21
ORD10:05 pmChicago O'Hare Intl
10h 36m
1 stop
MAF8:41 amMidland Intl
Nov 23
MAF4:31 pmMidland Intl
7h 00m
1 stop
ORD11:31 pmChicago O'Hare Intl
$385
Find similar

momondo Fare Finder

 
Customize your flight search to find flights from Chicago to Midland that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, momondo users made 832,500 searches. Data last updated September 17, 2025.
Use the filters below to find and compare flights from Chicago to Midland that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

ChicagoMidland

ORD - MAF

ORDMAF

Chicago O'Hare Intl

Fri 10/24

2:57 pm-8:39 pm

1 stop5h 42m

Midland Intl

Mon 10/27

12:22 pm-9:14 pm

1 stop8h 52m

$295

ChicagoMidland

ORD - MAF

ORDMAF

Chicago O'Hare Intl

Fri 10/24

5:45 pm-10:55 pm

1 stop5h 10m

Midland Intl

Mon 10/27

1:40 pm-9:30 pm

2 stops7h 50m

$342

ChicagoMidland

ORD - MAF

ORDMAF

Chicago O'Hare Intl

Fri 10/24

4:56 pm-11:56 pm

2 stops7h 00m

Midland Intl

Mon 10/27

5:30 am-3:00 pm

2 stops9h 30m

$357

ChicagoMidland

ORD - MAF

ORDMAF

Chicago O'Hare Intl

Wed 2/18

10:15 am-9:22 pm

1 stop11h 07m

Midland Intl

Sat 2/21

12:29 pm-11:45 pm

1 stop11h 16m

$373

ChicagoMidland

ORD - MAF

ORDMAF

Chicago O'Hare Intl

Fri 11/21

10:05 pm-8:41 am

1 stop10h 36m

Midland Intl

Sun 11/23

4:31 pm-11:31 pm

1 stop7h 00m

$385

ChicagoMidland

ORD - MAF

ORDMAF

Chicago O'Hare Intl

Fri 10/3

4:12 pm-11:04 pm

1 stop6h 52m

Midland Intl

Sun 10/5

12:35 pm-5:16 pm

1 stop4h 41m

$447

ChicagoMidland

ORD - MAF

ORDMAF

Chicago O'Hare Intl

Fri 10/3

6:45 am-4:40 pm

2 stops9h 55m

Midland Intl

Sun 10/5

5:30 am-2:20 pm

2 stops8h 50m

$457

ChicagoMidland

ORD - MAF

ORDMAF

Chicago O'Hare Intl

Fri 11/21

5:10 pm-11:15 pm

1 stop6h 05m

Midland Intl

Sun 11/23

5:30 pm-7:59 am

2 stops14h 29m

$497

ChicagoMidland

ORD - MAF

ORDMAF

Chicago O'Hare Intl

Tue 9/30

4:50 pm-10:13 pm

1 stop5h 23m

Midland Intl

Sat 10/4

5:00 am-6:46 pm

2 stops13h 46m

$513

ChicagoMidland

ORD - MAF

ORDMAF

Chicago O'Hare Intl

Tue 9/30

1:50 pm-10:30 pm

2 stops8h 40m

Midland Intl

Thu 10/2

10:50 am-3:20 pm

1 stop4h 30m

$550

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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See travel insights to Midland from

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

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 4h 48m, 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?

  • 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?

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 AirlinesPriceFrom $216Free CancellationRating
7.2
10,000 reviews
Search American Airlines flights
United AirlinesPriceFrom $285Free CancellationRating
7.4
8,926 reviews
Search United Airlines flights

  • United Airlines Flights From Chicago to Midland

    United Airlines is one of the most popular airlines flying from Chicago to Midland, operating 5 flights/week on average for this route. A good United Airlines flight deal for Chicago to Midland starts from $285 round-trip, up to an average price of $408. Our users have rated United Airlines at 7.4/10.

Traveling to a place near Midland?

Book flights to Midland if you plan to visit one of these locations
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.

An easier way to manage your Midland trip

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