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Cheap flights from Chicago to Midland from $254

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 4/19. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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.
American Airlines Logo
6:05 am - 12:16 pm
ORD
-
MAF
6h 11m
1 stop
American Airlines Logo
12:39 pm - 5:44 pm
MAF
-
ORD
5h 05m
1 stop
$378American Airlines
Thu, May 7 - Tue, May 12
American Airlines Logo
6:05 am - 1:45 pm
ORD
-
MAF
7h 40m
1 stop
American Airlines Logo
12:39 pm - 7:57 pm
MAF
-
ORD
7h 18m
1 stop
$391American Airlines
Thu, May 7 - Tue, May 12
American Airlines Logo
6:57 am - 1:45 pm
ORD
-
MAF
6h 48m
1 stop
American Airlines Logo
12:39 pm - 7:57 pm
MAF
-
ORD
7h 18m
1 stop
$401American Airlines
Thu, May 7 - Tue, May 12
American Airlines Logo
6:05 am - 12:16 pm
ORD
-
MAF
6h 11m
1 stop
American Airlines Logo
10:12 am - 3:18 pm
MAF
-
ORD
5h 06m
1 stop
$402American Airlines
Sun, May 10 - Sat, May 16
United Airlines Logo
4:03 pm - 9:39 pm
ORD
-
MAF
5h 36m
1 stop
United Airlines Logo
7:00 pm - 12:45 am
MAF
-
ORD
5h 45m
1 stop
$405United Airlines
Thu, Apr 23 - Mon, Apr 27
Southwest Logo
2:40 pm - 11:10 pm
ORD
-
MAF
8h 30m
2 stops
Southwest Logo
6:50 am - 3:00 pm
MAF
-
ORD
8h 10m
1 stop
$410Southwest
Thu, Apr 23 - Mon, Apr 27
Southwest Logo
2:40 pm - 11:10 pm
ORD
-
MAF
8h 30m
2 stops
Southwest Logo
6:00 am - 3:00 pm
MAF
-
ORD
9h 00m
2 stops
$415Southwest
Thu, Apr 23 - Mon, Apr 27
United Airlines Logo
5:00 am - 10:57 am
ORD
-
MAF
5h 57m
1 stop
United Airlines Logo
7:13 pm - 12:45 am
MAF
-
ORD
5h 32m
1 stop
$416United Airlines
Fri, Jun 5 - Mon, Jun 8
United Airlines Logo
5:45 pm - 11:44 pm
ORD
-
MAF
5h 59m
1 stop
United Airlines Logo
5:13 pm - 11:15 pm
MAF
-
ORD
6h 02m
1 stop
$427United Airlines
Tue, Jun 30 - Tue, Jul 7
Southwest Logo
2:40 pm - 10:15 pm
ORD
-
MAF
7h 35m
2 stops
Southwest Logo
6:50 am - 2:20 pm
MAF
-
ORD
7h 30m
1 stop
$441Southwest
Tue, May 26 - Sat, May 30

American Airlines flights from Chicago to Midland

Our best American Airlines deals on Chicago to Midland flight tickets
American Airlines
May 7
ORD6:05 amChicago O'Hare Intl
6h 11m
1 stop
MAF12:16 pmMidland Intl
May 12
MAF12:39 pmMidland Intl
5h 05m
1 stop
ORD5:44 pmChicago O'Hare Intl
$378
American Airlines
May 7
ORD6:05 amChicago O'Hare Intl
7h 40m
1 stop
MAF1:45 pmMidland Intl
May 12
MAF12:39 pmMidland Intl
7h 18m
1 stop
ORD7:57 pmChicago O'Hare Intl
$391
American Airlines
May 10
ORD6:05 amChicago O'Hare Intl
6h 11m
1 stop
MAF12:16 pmMidland Intl
May 16
MAF10:12 amMidland Intl
5h 06m
1 stop
ORD3:18 pmChicago O'Hare Intl
$402

United Airlines flights from Chicago to Midland

Our best United Airlines deals on Chicago to Midland flight tickets
United Airlines
Apr 23
ORD4:03 pmChicago O'Hare Intl
5h 36m
1 stop
MAF9:39 pmMidland Intl
Apr 27
MAF7:00 pmMidland Intl
5h 45m
1 stop
ORD12:45 amChicago O'Hare Intl
$405
United Airlines
Jun 5
ORD5:00 amChicago O'Hare Intl
5h 57m
1 stop
MAF10:57 amMidland Intl
Jun 8
MAF7:13 pmMidland Intl
5h 32m
1 stop
ORD12:45 amChicago O'Hare Intl
$416
United Airlines
Jun 30
ORD5:45 pmChicago O'Hare Intl
5h 59m
1 stop
MAF11:44 pmMidland Intl
Jul 7
MAF5:13 pmMidland Intl
6h 02m
1 stop
ORD11:15 pmChicago O'Hare Intl
$427

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 April 3, 2026.
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

Cheapest round-trip
Quickest round-trip

ChicagoMidland

ORD - MAF

ORDMAF

Chicago O'Hare Intl

Thu 5/7

6:05 am-12:16 pm

1 stop6h 11m

Midland Intl

Tue 5/12

12:39 pm-5:44 pm

1 stop5h 05m

$378

ChicagoMidland

ORD - MAF

ORDMAF

Chicago O'Hare Intl

Thu 5/7

6:05 am-1:45 pm

1 stop7h 40m

Midland Intl

Tue 5/12

12:39 pm-7:57 pm

1 stop7h 18m

$391

ChicagoMidland

ORD - MAF

ORDMAF

Chicago O'Hare Intl

Thu 5/7

6:57 am-1:45 pm

1 stop6h 48m

Midland Intl

Tue 5/12

12:39 pm-7:57 pm

1 stop7h 18m

$401

ChicagoMidland

ORD - MAF

ORDMAF

Chicago O'Hare Intl

Sun 5/10

6:05 am-12:16 pm

1 stop6h 11m

Midland Intl

Sat 5/16

10:12 am-3:18 pm

1 stop5h 06m

$402

ChicagoMidland

ORD - MAF

ORDMAF

Chicago O'Hare Intl

Thu 4/23

4:03 pm-9:39 pm

1 stop5h 36m

Midland Intl

Mon 4/27

7:00 pm-12:45 am

1 stop5h 45m

$405

ChicagoMidland

ORD - MAF

ORDMAF

Chicago O'Hare Intl

Thu 4/23

2:40 pm-11:10 pm

2 stops8h 30m

Midland Intl

Mon 4/27

6:50 am-3:00 pm

1 stop8h 10m

$410

ChicagoMidland

ORD - MAF

ORDMAF

Chicago O'Hare Intl

Thu 4/23

2:40 pm-11:10 pm

2 stops8h 30m

Midland Intl

Mon 4/27

6:00 am-3:00 pm

2 stops9h 00m

$415

ChicagoMidland

ORD - MAF

ORDMAF

Chicago O'Hare Intl

Fri 6/5

5:00 am-10:57 am

1 stop5h 57m

Midland Intl

Mon 6/8

7:13 pm-12:45 am

1 stop5h 32m

$416

ChicagoMidland

ORD - MAF

ORDMAF

Chicago O'Hare Intl

Tue 6/30

5:45 pm-11:44 pm

1 stop5h 59m

Midland Intl

Tue 7/7

5:13 pm-11:15 pm

1 stop6h 02m

$427

ChicagoMidland

ORD - MAF

ORDMAF

Chicago O'Hare Intl

Tue 5/26

2:40 pm-10:15 pm

2 stops7h 35m

Midland Intl

Sat 5/30

6:50 am-2:20 pm

1 stop7h 30m

$441

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 18 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 typical price of a round-trip flight between Chicago and Midland?

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 37m

Direct flights

None
The fastest flight from Chicago to Midland takes 5h 37m
There are no direct flights from Chicago to Midland. There are no popular flight routes from Chicago to Midland.
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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 37m, 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
7.1
11,550 reviews
Search American Airlines flights
United AirlinesPriceFrom $331Free CancellationRating
7.4
9,538 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
Big Spring
Fort Stockton

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

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.
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