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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 7/25. 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
1 adult, Economy, 0 bags

Discover deals from 900+ travel sites with momondo.

Find the cheapest flights from Chicago to Midland

Cheap round-trip flights

Enter your travel dates to find the best prices.
American Airlines Logo
5:00 am - 9:46 am
ORD
-
MAF
4h 46m
1 stop
American Airlines Logo
11:49 am - 7:42 pm
MAF
-
ORD
7h 53m
1 stop
$333American Airlines
Wed, Aug 5 - Sat, Aug 15
American Airlines Logo
6:00 am - 11:19 am
ORD
-
MAF
5h 19m
1 stop
American Airlines Logo
2:21 pm - 8:29 pm
MAF
-
ORD
6h 08m
1 stop
$334American Airlines
Sat, Aug 29 - Sat, Sep 5
American Airlines Logo
5:00 am - 11:19 am
ORD
-
MAF
6h 19m
1 stop
American Airlines Logo
5:31 pm - 12:18 am
MAF
-
ORD
6h 47m
1 stop
$380American Airlines
Fri, Sep 4 - Mon, Sep 7
United Airlines Logo
4:11 pm - 11:44 pm
ORD
-
MAF
7h 33m
1 stop
United Airlines Logo
5:00 am - 11:20 am
MAF
-
ORD
6h 20m
1 stop
$423United Airlines
Tue, Aug 25 - Wed, Aug 26
United Airlines Logo
10:29 am - 10:09 pm
ORD
-
MAF
11h 40m
2 stops
United Airlines Logo
5:00 am - 11:20 am
MAF
-
ORD
6h 20m
1 stop
$493United Airlines
Tue, Aug 25 - Wed, Aug 26
United Airlines Logo
6:29 pm - 11:44 pm
ORD
-
MAF
5h 15m
1 stop
United Airlines Logo
5:00 am - 9:21 am
MAF
-
ORD
28h 21m
2 stops
$506United Airlines
Tue, Aug 25 - Wed, Aug 26
United Airlines Logo
4:11 pm - 9:34 pm
ORD
-
MAF
5h 23m
1 stop
United Airlines Logo
5:00 am - 4:50 pm
MAF
-
ORD
11h 50m
2 stops
$526United Airlines
Tue, Aug 25 - Wed, Aug 26
United Airlines Logo
5:30 am - 1:32 pm
ORD
-
MAF
8h 02m
1 stop
United Airlines Logo
5:00 am - 7:01 pm
MAF
-
ORD
14h 01m
2 stops
$540United Airlines
Fri, Sep 4 - Mon, Sep 7
American Airlines Logo
12:11 pm - 5:00 pm
ORD
-
MAF
4h 49m
1 stop
American Airlines Logo
5:31 pm - 11:30 pm
MAF
-
ORD
5h 59m
1 stop
$556American Airlines
Thu, Aug 27 - Thu, Sep 3
United Airlines Logo
5:30 am - 11:07 am
ORD
-
MAF
5h 37m
1 stop
United Airlines Logo
7:00 am - 2:26 pm
MAF
-
ORD
7h 26m
2 stops
$739United Airlines
Wed, Aug 5 - Sat, Aug 15

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American Airlines flights from Chicago to Midland

Our best American Airlines deals on Chicago to Midland flight tickets
American Airlines
Aug 5
ORD5:00 amChicago O'Hare Intl
4h 46m
1 stop
MAF9:46 amMidland Intl
Aug 15
MAF11:49 amMidland Intl
7h 53m
1 stop
ORD7:42 pmChicago O'Hare Intl
$333
American Airlines
Aug 29
ORD6:00 amChicago O'Hare Intl
5h 19m
1 stop
MAF11:19 amMidland Intl
Sep 5
MAF2:21 pmMidland Intl
6h 08m
1 stop
ORD8:29 pmChicago O'Hare Intl
$334
American Airlines
Sep 4
ORD5:00 amChicago O'Hare Intl
6h 19m
1 stop
MAF11:19 amMidland Intl
Sep 7
MAF5:31 pmMidland Intl
6h 47m
1 stop
ORD12:18 amChicago O'Hare Intl
$380

United Airlines flights from Chicago to Midland

Our best United Airlines deals on Chicago to Midland flight tickets
United Airlines
Aug 25
ORD4:11 pmChicago O'Hare Intl
7h 33m
1 stop
MAF11:44 pmMidland Intl
Aug 26
MAF5:00 amMidland Intl
6h 20m
1 stop
ORD11:20 amChicago O'Hare Intl
$423
United Airlines
Aug 25
ORD10:29 amChicago O'Hare Intl
11h 40m
2 stops
MAF10:09 pmMidland Intl
Aug 26
MAF5:00 amMidland Intl
6h 20m
1 stop
ORD11:20 amChicago O'Hare Intl
$493
United Airlines
Aug 25
ORD6:29 pmChicago O'Hare Intl
5h 15m
1 stop
MAF11:44 pmMidland Intl
Aug 26
MAF5:00 amMidland Intl
28h 21m
2 stops
ORD9:21 amChicago O'Hare Intl
$506

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 July 16, 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

ChicagoMidland

ORD - MAF

ORDMAF

Chicago O'Hare Intl

Wed 8/5

5:00 am-9:46 am

1 stop4h 46m

Midland Intl

Sat 8/15

11:49 am-7:42 pm

1 stop7h 53m

$333

ChicagoMidland

ORD - MAF

ORDMAF

Chicago O'Hare Intl

Sat 8/29

6:00 am-11:19 am

1 stop5h 19m

Midland Intl

Sat 9/5

2:21 pm-8:29 pm

1 stop6h 08m

$334

ChicagoMidland

ORD - MAF

ORDMAF

Chicago O'Hare Intl

Fri 9/4

5:00 am-11:19 am

1 stop6h 19m

Midland Intl

Mon 9/7

5:31 pm-12:18 am

1 stop6h 47m

$380

ChicagoMidland

ORD - MAF

ORDMAF

Chicago O'Hare Intl

Tue 8/25

4:11 pm-11:44 pm

1 stop7h 33m

Midland Intl

Wed 8/26

5:00 am-11:20 am

1 stop6h 20m

$423

ChicagoMidland

ORD - MAF

ORDMAF

Chicago O'Hare Intl

Tue 8/25

10:29 am-10:09 pm

2 stops11h 40m

Midland Intl

Wed 8/26

5:00 am-11:20 am

1 stop6h 20m

$493

ChicagoMidland

ORD - MAF

ORDMAF

Chicago O'Hare Intl

Tue 8/25

6:29 pm-11:44 pm

1 stop5h 15m

Midland Intl

Wed 8/26

5:00 am-9:21 am

2 stops28h 21m

$506

ChicagoMidland

ORD - MAF

ORDMAF

Chicago O'Hare Intl

Tue 8/25

4:11 pm-9:34 pm

1 stop5h 23m

Midland Intl

Wed 8/26

5:00 am-4:50 pm

2 stops11h 50m

$526

ChicagoMidland

ORD - MAF

ORDMAF

Chicago O'Hare Intl

Fri 9/4

5:30 am-1:32 pm

1 stop8h 02m

Midland Intl

Mon 9/7

5:00 am-7:01 pm

2 stops14h 01m

$540
Quickest round-trip

ChicagoMidland

ORD - MAF

ORDMAF

Chicago O'Hare Intl

Thu 8/27

12:11 pm-5:00 pm

1 stop4h 49m

Midland Intl

Thu 9/3

5:31 pm-11:30 pm

1 stop5h 59m

$556

ChicagoMidland

ORD - MAF

ORDMAF

Chicago O'Hare Intl

Wed 8/5

5:30 am-11:07 am

1 stop5h 37m

Midland Intl

Sat 8/15

7:00 am-2:26 pm

2 stops7h 26m

$739

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 13 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, March 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 $0. If you don’t want to visit Midland in March, then you should wait until January to fly from Chicago, when ticket prices are also cheap, with an average price of $0.

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 59m

Direct flights

None
The fastest flight from Chicago to Midland takes 5h 59m
There are no direct flights from Chicago to Midland. There are no popular flight routes from Chicago to Midland.
Search flight deals

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 59m, 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
11,815 reviews
Search American Airlines flights
United AirlinesPriceFrom $347Free CancellationRating
7.4
9,990 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

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