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Cheap flights from Chicago to Midland from $214

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 7/30. 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.
United Airlines Logo
4:11 pm - 9:34 pm
ORD
-
MAF
5h 23m
1 stop
United Airlines Logo
5:00 am - 10:15 am
MAF
-
ORD
5h 15m
1 stop
$351United Airlines
Tue, Aug 25 - Wed, Sep 2
American Airlines Logo
4:45 pm - 11:59 pm
ORD
-
MAF
7h 14m
1 stop
American Airlines Logo
6:46 pm - 12:50 am
MAF
-
ORD
6h 04m
1 stop
$374American Airlines
Wed, Jul 1 - Wed, Jul 15
American Airlines Logo
3:50 pm - 11:59 pm
ORD
-
MAF
8h 09m
1 stop
American Airlines Logo
2:21 pm - 8:31 pm
MAF
-
ORD
6h 10m
1 stop
$389American Airlines
Wed, Jul 1 - Sat, Jul 25
American Airlines Logo
4:45 pm - 11:59 pm
ORD
-
MAF
7h 14m
1 stop
American Airlines Logo
2:21 pm - 10:32 pm
MAF
-
ORD
8h 11m
1 stop
$399American Airlines
Wed, Jul 1 - Sat, Jul 25
American Airlines Logo
7:00 am - 1:49 pm
ORD
-
MAF
6h 49m
1 stop
American Airlines Logo
6:46 pm - 12:50 am
MAF
-
ORD
6h 04m
1 stop
$427American Airlines
Thu, Jul 2 - Sun, Jul 19
United Airlines Logo
5:53 pm - 11:44 pm
ORD
-
MAF
5h 51m
1 stop
United Airlines Logo
5:00 am - 11:20 am
MAF
-
ORD
6h 20m
1 stop
$441United Airlines
Tue, Aug 18 - Wed, Aug 19
United Airlines Logo
5:30 am - 11:12 am
ORD
-
MAF
5h 42m
1 stop
United Airlines Logo
1:40 pm - 7:30 pm
MAF
-
ORD
5h 50m
1 stop
$443United Airlines
Sun, Aug 23 - Thu, Aug 27
United Airlines Logo
6:00 am - 12:59 pm
ORD
-
MAF
6h 59m
1 stop
United Airlines Logo
5:00 am - 10:20 am
MAF
-
ORD
5h 20m
1 stop
$445United Airlines
Wed, Jun 17 - Wed, Jun 24
United Airlines Logo
5:53 pm - 11:44 pm
ORD
-
MAF
5h 51m
1 stop
United Airlines Logo
5:00 am - 11:20 am
MAF
-
ORD
6h 20m
1 stop
$461United Airlines
Tue, Aug 18 - Wed, Aug 19
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
$477United Airlines
Tue, Jun 16 - Fri, Jun 19

American Airlines flights from Chicago to Midland

Our best American Airlines deals on Chicago to Midland flight tickets
American Airlines
Jul 1
ORD4:45 pmChicago O'Hare Intl
7h 14m
1 stop
MAF11:59 pmMidland Intl
Jul 15
MAF6:46 pmMidland Intl
6h 04m
1 stop
ORD12:50 amChicago O'Hare Intl
$374
American Airlines
Jul 1
ORD3:50 pmChicago O'Hare Intl
8h 09m
1 stop
MAF11:59 pmMidland Intl
Jul 25
MAF2:21 pmMidland Intl
6h 10m
1 stop
ORD8:31 pmChicago O'Hare Intl
$389
American Airlines
Jul 1
ORD4:45 pmChicago O'Hare Intl
7h 14m
1 stop
MAF11:59 pmMidland Intl
Jul 25
MAF2:21 pmMidland Intl
8h 11m
1 stop
ORD10:32 pmChicago O'Hare Intl
$399

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
5h 23m
1 stop
MAF9:34 pmMidland Intl
Sep 2
MAF5:00 amMidland Intl
5h 15m
1 stop
ORD10:15 amChicago O'Hare Intl
$351
United Airlines
Aug 18
ORD5:53 pmChicago O'Hare Intl
5h 51m
1 stop
MAF11:44 pmMidland Intl
Aug 19
MAF5:00 amMidland Intl
6h 20m
1 stop
ORD11:20 amChicago O'Hare Intl
$441
United Airlines
Aug 23
ORD5:30 amChicago O'Hare Intl
5h 42m
1 stop
MAF11:12 amMidland Intl
Aug 27
MAF1:40 pmMidland Intl
5h 50m
1 stop
ORD7:30 pmChicago O'Hare Intl
$443

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 May 30, 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

Tue 8/25

4:11 pm-9:34 pm

1 stop5h 23m

Midland Intl

Wed 9/2

5:00 am-10:15 am

1 stop5h 15m

$351

ChicagoMidland

ORD - MAF

ORDMAF

Chicago O'Hare Intl

Wed 7/1

4:45 pm-11:59 pm

1 stop7h 14m

Midland Intl

Wed 7/15

6:46 pm-12:50 am

1 stop6h 04m

$374

ChicagoMidland

ORD - MAF

ORDMAF

Chicago O'Hare Intl

Wed 7/1

3:50 pm-11:59 pm

1 stop8h 09m

Midland Intl

Sat 7/25

2:21 pm-8:31 pm

1 stop6h 10m

$389

ChicagoMidland

ORD - MAF

ORDMAF

Chicago O'Hare Intl

Wed 7/1

4:45 pm-11:59 pm

1 stop7h 14m

Midland Intl

Sat 7/25

2:21 pm-10:32 pm

1 stop8h 11m

$399

ChicagoMidland

ORD - MAF

ORDMAF

Chicago O'Hare Intl

Thu 7/2

7:00 am-1:49 pm

1 stop6h 49m

Midland Intl

Sun 7/19

6:46 pm-12:50 am

1 stop6h 04m

$427

ChicagoMidland

ORD - MAF

ORDMAF

Chicago O'Hare Intl

Tue 8/18

5:53 pm-11:44 pm

1 stop5h 51m

Midland Intl

Wed 8/19

5:00 am-11:20 am

1 stop6h 20m

$441

ChicagoMidland

ORD - MAF

ORDMAF

Chicago O'Hare Intl

Sun 8/23

5:30 am-11:12 am

1 stop5h 42m

Midland Intl

Thu 8/27

1:40 pm-7:30 pm

1 stop5h 50m

$443

ChicagoMidland

ORD - MAF

ORDMAF

Chicago O'Hare Intl

Wed 6/17

6:00 am-12:59 pm

1 stop6h 59m

Midland Intl

Wed 6/24

5:00 am-10:20 am

1 stop5h 20m

$445

ChicagoMidland

ORD - MAF

ORDMAF

Chicago O'Hare Intl

Tue 8/18

5:53 pm-11:44 pm

1 stop5h 51m

Midland Intl

Wed 8/19

5:00 am-11:20 am

1 stop6h 20m

$461

ChicagoMidland

ORD - MAF

ORDMAF

Chicago O'Hare Intl

Tue 6/16

5:00 am-10:57 am

1 stop5h 57m

Midland Intl

Fri 6/19

7:13 pm-12:45 am

1 stop5h 32m

$477

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 19 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 airline that flies from Chicago to Midland Intl?

United Airlines and American Airlines are the most popular carriers operating from Chicago to Midland Intl

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 42m

Direct flights

None
The fastest flight from Chicago to Midland takes 5h 42m
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 42m, 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
11,640 reviews
Search American Airlines flights
United AirlinesPriceFrom $285Free CancellationRating
7.4
9,766 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.
Start using Trips
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