Latest deals
Insights
When to book
FAQs
Reviews
Price Alerts

Cheap flights from Chicago to Midland from $180

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 3/7. 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

Discover deals from 900+ travel sites with momondo.

Save money when you book flights with momondo

Big names and deals

Big names and deals

Search 100s of travel sites to compare prices.

Filter for what you want

Filter for what you want

Free Wi-Fi? Stopover? Instantly customize your results.

Trusted and free

Trusted and free

We’re completely free to use - no hidden charges or fees.

Price Alerts

Price Alerts

Not ready to book? to track prices.
Search flight deals

Find the cheapest flights from Chicago to Midland

Cheap round-trip flights

Enter your travel dates to find the best prices.
American Airlines Logo
12:30 pm - 12:06 am
ORD
-
MAF
11h 36m
1 stop
American Airlines Logo
12:39 pm - 10:20 pm
MAF
-
ORD
9h 41m
1 stop
$243American Airlines
水, 5月 6 - 火, 5月 12
American Airlines Logo
6:10 am - 5:29 pm
ORD
-
MAF
11h 19m
1 stop
American Airlines Logo
9:18 am - 7:40 pm
MAF
-
ORD
10h 22m
1 stop
$298American Airlines
木, 3月 12 - 火, 3月 17
American Airlines Logo
6:30 am - 5:50 pm
ORD
-
MAF
11h 20m
1 stop
American Airlines Logo
6:42 pm - 11:36 pm
MAF
-
ORD
4h 54m
1 stop
$311American Airlines
土, 2月 28 - 火, 3月 3
Southwest Logo
11:55 am - 10:15 pm
ORD
-
MAF
10h 20m
2 stops
Southwest Logo
6:50 am - 11:10 am
MAF
-
ORD
4h 20m
1 stop
$340Southwest
水, 5月 6 - 火, 5月 12
Southwest Logo
11:55 am - 10:15 pm
ORD
-
MAF
10h 20m
2 stops
Southwest Logo
6:50 am - 3:00 pm
MAF
-
ORD
8h 10m
2 stops
$345Southwest
水, 5月 6 - 火, 5月 12
American Airlines Logo
2:58 pm - 10:49 pm
ORD
-
MAF
7h 51m
1 stop
American Airlines Logo
9:18 am - 5:45 pm
MAF
-
ORD
8h 27m
1 stop
$365American Airlines
木, 2月 26 - 火, 3月 3
American Airlines Logo
5:00 am - 9:42 am
ORD
-
MAF
4h 42m
1 stop
American Airlines Logo
2:15 pm - 7:57 pm
MAF
-
ORD
5h 42m
1 stop
$372American Airlines
日, 4月 26 - 土, 5月 2
American Airlines Logo
9:13 pm - 8:48 am
ORD
-
MAF
11h 35m
1 stop
American Airlines Logo
9:18 am - 5:45 pm
MAF
-
ORD
8h 27m
1 stop
$373American Airlines
火, 3月 10 - 火, 3月 17
Southwest Logo
2:40 pm - 10:55 pm
ORD
-
MAF
8h 15m
2 stops
Southwest Logo
6:55 am - 1:55 pm
MAF
-
ORD
7h 00m
1 stop
$376Southwest
木, 3月 12 - 火, 3月 17
Southwest Logo
2:15 pm - 10:15 pm
ORD
-
MAF
8h 00m
1 stop
Southwest Logo
6:55 am - 1:55 pm
MAF
-
ORD
7h 00m
1 stop
$381Southwest
月, 3月 2 - 火, 3月 10

United Airlines flights from Chicago to Midland

Our best United Airlines deals on Chicago to Midland flight tickets
United Airlines
May 7
ORD10:49 amChicago O'Hare Intl
5h 39m
1 stop
MAF4:28 pmMidland Intl
May 10
MAF7:00 pmMidland Intl
6h 27m
1 stop
ORD1:27 amChicago O'Hare Intl
$383
United Airlines
Mar 28
ORD5:20 pmChicago O'Hare Intl
5h 55m
1 stop
MAF11:15 pmMidland Intl
Apr 4
MAF5:00 amMidland Intl
5h 05m
1 stop
ORD10:05 amChicago O'Hare Intl
$405
United Airlines
Jul 29
ORD5:45 pmChicago O'Hare Intl
5h 50m
1 stop
MAF11:35 pmMidland Intl
Aug 4
MAF6:00 amMidland Intl
5h 23m
1 stop
ORD11:23 amChicago O'Hare Intl
$407

American Airlines flights from Chicago to Midland

Our best American Airlines deals on Chicago to Midland flight tickets
American Airlines
May 6
ORD12:30 pmChicago O'Hare Intl
11h 36m
1 stop
MAF12:06 amMidland Intl
May 12
MAF12:39 pmMidland Intl
9h 41m
1 stop
ORD10:20 pmChicago O'Hare Intl
$243
American Airlines
Mar 12
ORD6:10 amChicago O'Hare Intl
11h 19m
1 stop
MAF5:29 pmMidland Intl
Mar 17
MAF9:18 amMidland Intl
10h 22m
1 stop
ORD7:40 pmChicago O'Hare Intl
$298
American Airlines
Feb 28
ORD6:30 amChicago O'Hare Intl
11h 20m
1 stop
MAF5:50 pmMidland Intl
Mar 3
MAF6:42 pmMidland Intl
4h 54m
1 stop
ORD11:36 pmChicago O'Hare Intl
$311

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 2月 11, 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

ChicagoMidland

ORD - MAF

ORDMAF

Chicago O'Hare Intl

水 5/6

12:30 pm-12:06 am

1 stop11h 36m

Midland Intl

火 5/12

12:39 pm-10:20 pm

1 stop9h 41m

$243

ChicagoMidland

ORD - MAF

ORDMAF

Chicago O'Hare Intl

木 3/12

6:10 am-5:29 pm

1 stop11h 19m

Midland Intl

火 3/17

9:18 am-7:40 pm

1 stop10h 22m

$298

ChicagoMidland

ORD - MAF

ORDMAF

Chicago O'Hare Intl

土 2/28

6:30 am-5:50 pm

1 stop11h 20m

Midland Intl

火 3/3

6:42 pm-11:36 pm

1 stop4h 54m

$311

ChicagoMidland

ORD - MAF

ORDMAF

Chicago O'Hare Intl

水 5/6

11:55 am-10:15 pm

2 stops10h 20m

Midland Intl

火 5/12

6:50 am-11:10 am

1 stop4h 20m

$340

ChicagoMidland

ORD - MAF

ORDMAF

Chicago O'Hare Intl

水 5/6

11:55 am-10:15 pm

2 stops10h 20m

Midland Intl

火 5/12

6:50 am-3:00 pm

2 stops8h 10m

$345

ChicagoMidland

ORD - MAF

ORDMAF

Chicago O'Hare Intl

木 2/26

2:58 pm-10:49 pm

1 stop7h 51m

Midland Intl

火 3/3

9:18 am-5:45 pm

1 stop8h 27m

$365

ChicagoMidland

ORD - MAF

ORDMAF

Chicago O'Hare Intl

日 4/26

5:00 am-9:42 am

1 stop4h 42m

Midland Intl

土 5/2

2:15 pm-7:57 pm

1 stop5h 42m

$372

ChicagoMidland

ORD - MAF

ORDMAF

Chicago O'Hare Intl

火 3/10

9:13 pm-8:48 am

1 stop11h 35m

Midland Intl

火 3/17

9:18 am-5:45 pm

1 stop8h 27m

$373

ChicagoMidland

ORD - MAF

ORDMAF

Chicago O'Hare Intl

木 3/12

2:40 pm-10:55 pm

2 stops8h 15m

Midland Intl

火 3/17

6:55 am-1:55 pm

1 stop7h 00m

$376

ChicagoMidland

ORD - MAF

ORDMAF

Chicago O'Hare Intl

月 3/2

2:15 pm-10:15 pm

1 stop8h 00m

Midland Intl

火 3/10

6:55 am-1:55 pm

1 stop7h 00m

$381

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 14 resultsSorted by cheapest first
1
2

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 44m

Direct flights

None
The fastest flight from Chicago to Midland takes 5h 44m
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 44m, 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
11,262 reviews
Search American Airlines flights
United AirlinesPriceFrom $285Free CancellationRating
7.4
9,269 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

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.
Start using Trips
Find my bookings

Get notified when prices go down

Daily price changes in your inbox - only with Price Alerts.
1 adult
金 3/13
金 3/20
By creating a price alert you accept our terms of use and privacy policy.

Find better results for your trip to the United States