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Cheap flights from Chicago to Midland from $347

This is the cheapest round-trip flight price found by a momondo user in the last 72 hours by searching for a flight from Chicago to Midland departing on 1/29. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
1 adult
0 bags

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Find the cheapest flights from Chicago to Midland

Cheap round-trip flights

Enter your travel dates to find the best prices.
Southwest Logo
2:15 pm - 9:35 pm
ORD
-
MAF
7h 20m1 stop
Southwest Logo
3:00 pm - 10:35 pm
MAF
-
ORD
7h 35m1 stop
$347Southwest
Thu, Jan 29 - Tue, Feb 3
Southwest Logo
1:45 pm - 9:35 pm
ORD
-
MAF
7h 50m2 stops
Southwest Logo
6:40 am - 1:00 pm
MAF
-
ORD
6h 20m1 stop
$352Southwest
Thu, Jan 29 - Tue, Feb 3
Southwest Logo
1:45 pm - 9:35 pm
ORD
-
MAF
7h 50m2 stops
Southwest Logo
7:05 am - 1:00 pm
MAF
-
ORD
5h 55m2 stops
$357Southwest
Thu, Jan 29 - Tue, Feb 3
Southwest Logo
2:15 pm - 10:15 pm
ORD
-
MAF
8h 00m1 stop
Southwest Logo
5:30 am - 1:00 pm
MAF
-
ORD
7h 30m1 stop
$359Southwest
Thu, Feb 5 - Mon, Feb 9
United Airlines Logo
7:35 am - 1:39 pm
ORD
-
MAF
6h 04m1 stop
United Airlines Logo
7:20 am - 2:55 pm
MAF
-
ORD
7h 35m1 stop
$361United Airlines
Sat, Jan 17 - Sun, Jan 18
Southwest Logo
1:45 pm - 10:35 pm
ORD
-
MAF
8h 50m2 stops
Southwest Logo
5:30 am - 1:00 pm
MAF
-
ORD
7h 30m1 stop
$364Southwest
Thu, Feb 5 - Mon, Feb 9
American Airlines Logo
10:48 am - 5:44 pm
ORD
-
MAF
6h 56m1 stop
American Airlines Logo
6:39 pm - 11:25 pm
MAF
-
ORD
4h 46m1 stop
$371American Airlines
Thu, Feb 12 - Tue, Feb 17
United Airlines Logo
3:53 pm - 9:54 pm
ORD
-
MAF
6h 01m1 stop
United Airlines Logo
7:03 pm - 12:26 am
MAF
-
ORD
5h 23m1 stop
$383United Airlines
Mon, Feb 2 - Mon, Feb 16
Southwest Logo
2:15 pm - 10:15 pm
ORD
-
MAF
8h 00m1 stop
Southwest Logo
3:00 pm - 10:35 pm
MAF
-
ORD
7h 35m1 stop
$386Southwest
Mon, Jan 19 - Tue, Jan 27
Southwest Logo
2:15 pm - 10:15 pm
ORD
-
MAF
8h 00m1 stop
Southwest Logo
7:05 am - 1:00 pm
MAF
-
ORD
5h 55m2 stops
$392Southwest
Mon, Jan 19 - Tue, Jan 27

American Airlines flights from Chicago to Midland

Our best American Airlines deals on Chicago to Midland flight tickets
American Airlines
Feb 12
ORD10:48 amChicago O'Hare Intl
6h 56m
1 stop
MAF5:44 pmMidland Intl
Feb 17
MAF6:39 pmMidland Intl
4h 46m
1 stop
ORD11:25 pmChicago O'Hare Intl
$371
Find similar
American Airlines
Feb 12
ORD3:15 pmChicago O'Hare Intl
4h 44m
1 stop
MAF7:59 pmMidland Intl
Feb 16
MAF6:00 amMidland Intl
6h 59m
1 stop
ORD12:59 pmChicago O'Hare Intl
$407
Find similar
American Airlines
Jan 10
ORD5:37 pmChicago O'Hare Intl
5h 17m
1 stop
MAF10:54 pmMidland Intl
Jan 14
MAF7:00 amMidland Intl
6h 55m
1 stop
ORD1:55 pmChicago O'Hare Intl
$487
Find similar

Southwest flights from Chicago to Midland

Our best Southwest deals on Chicago to Midland flight tickets
Southwest
Jan 29
ORD2:15 pmChicago O'Hare Intl
7h 20m
1 stop
MAF9:35 pmMidland Intl
Feb 3
MAF3:00 pmMidland Intl
7h 35m
1 stop
ORD10:35 pmChicago O'Hare Intl
$347
Find similar
Southwest
Jan 29
ORD1:45 pmChicago O'Hare Intl
7h 50m
2 stops
MAF9:35 pmMidland Intl
Feb 3
MAF6:40 amMidland Intl
6h 20m
1 stop
ORD1:00 pmChicago O'Hare Intl
$352
Find similar
Southwest
Jan 29
ORD1:45 pmChicago O'Hare Intl
7h 50m
2 stops
MAF9:35 pmMidland Intl
Feb 3
MAF7:05 amMidland Intl
5h 55m
2 stops
ORD1:00 pmChicago O'Hare Intl
$357
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 December 28, 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

Thu 1/29

2:15 pm-9:35 pm

1 stop7h 20m

Midland Intl

Tue 2/3

3:00 pm-10:35 pm

1 stop7h 35m

$347

ChicagoMidland

ORD - MAF

ORDMAF

Chicago O'Hare Intl

Thu 1/29

1:45 pm-9:35 pm

2 stops7h 50m

Midland Intl

Tue 2/3

6:40 am-1:00 pm

1 stop6h 20m

$352

ChicagoMidland

ORD - MAF

ORDMAF

Chicago O'Hare Intl

Thu 1/29

1:45 pm-9:35 pm

2 stops7h 50m

Midland Intl

Tue 2/3

7:05 am-1:00 pm

2 stops5h 55m

$357

ChicagoMidland

ORD - MAF

ORDMAF

Chicago O'Hare Intl

Thu 2/5

2:15 pm-10:15 pm

1 stop8h 00m

Midland Intl

Mon 2/9

5:30 am-1:00 pm

1 stop7h 30m

$359

ChicagoMidland

ORD - MAF

ORDMAF

Chicago O'Hare Intl

Sat 1/17

7:35 am-1:39 pm

1 stop6h 04m

Midland Intl

Sun 1/18

7:20 am-2:55 pm

1 stop7h 35m

$361

ChicagoMidland

ORD - MAF

ORDMAF

Chicago O'Hare Intl

Thu 2/5

1:45 pm-10:35 pm

2 stops8h 50m

Midland Intl

Mon 2/9

5:30 am-1:00 pm

1 stop7h 30m

$364

ChicagoMidland

ORD - MAF

ORDMAF

Chicago O'Hare Intl

Thu 2/12

10:48 am-5:44 pm

1 stop6h 56m

Midland Intl

Tue 2/17

6:39 pm-11:25 pm

1 stop4h 46m

$371

ChicagoMidland

ORD - MAF

ORDMAF

Chicago O'Hare Intl

Mon 2/2

3:53 pm-9:54 pm

1 stop6h 01m

Midland Intl

Mon 2/16

7:03 pm-12:26 am

1 stop5h 23m

$383

ChicagoMidland

ORD - MAF

ORDMAF

Chicago O'Hare Intl

Mon 1/19

2:15 pm-10:15 pm

1 stop8h 00m

Midland Intl

Tue 1/27

3:00 pm-10:35 pm

1 stop7h 35m

$386

ChicagoMidland

ORD - MAF

ORDMAF

Chicago O'Hare Intl

Mon 1/19

2:15 pm-10:15 pm

1 stop8h 00m

Midland Intl

Tue 1/27

7:05 am-1:00 pm

2 stops5h 55m

$392

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 12 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.

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

Fastest flight time

5h 55m

Direct flights

None
The fastest flight from Chicago to Midland takes 5h 55m
There are no direct flights from Chicago to Midland. There are no popular flight routes from Chicago to Midland.
Search flight deals

  • 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 55m, 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
11,073 reviews
Search American Airlines flights
United AirlinesPriceFrom $285Free CancellationRating
7.4
9,113 reviews
Search United Airlines flights

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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