Latest deals
Insights
When to book
FAQs
Reviews
Price Alerts

Cheap flights from Midland to Chicago 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 Midland to Chicago departing on 4/6. 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.

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 Midland to Chicago

Cheap round-trip flights

Enter your travel dates to find the best prices.
United Airlines Logo
7:00 pm - 12:45 am
MAF
-
ORD
5h 45m
1 stop
United Airlines Logo
10:30 am - 6:12 pm
ORD
-
MAF
7h 42m
1 stop
$365United Airlines
Tue, May 12 - Wed, May 13
American Airlines Logo
2:15 pm - 9:14 pm
MAF
-
ORD
6h 59m
1 stop
American Airlines Logo
6:05 am - 12:16 pm
ORD
-
MAF
6h 11m
1 stop
$386American Airlines
Mon, May 11 - Sun, May 17
American Airlines Logo
2:15 pm - 9:14 pm
MAF
-
ORD
6h 59m
1 stop
American Airlines Logo
6:57 am - 12:16 pm
ORD
-
MAF
5h 19m
1 stop
$394American Airlines
Mon, May 11 - Sun, May 17
Southwest Logo
9:50 am - 3:30 pm
MAF
-
ORD
5h 40m
1 stop
Southwest Logo
4:15 pm - 11:10 pm
ORD
-
MAF
6h 55m
1 stop
$405Southwest
Mon, Apr 20 - Mon, Apr 27
Southwest Logo
9:50 am - 3:30 pm
MAF
-
ORD
5h 40m
1 stop
Southwest Logo
3:45 pm - 11:10 pm
ORD
-
MAF
7h 25m
2 stops
$410Southwest
Mon, Apr 20 - Mon, Apr 27
Southwest Logo
6:00 am - 1:15 pm
MAF
-
ORD
7h 15m
2 stops
Southwest Logo
2:40 pm - 11:10 pm
ORD
-
MAF
8h 30m
2 stops
$415Southwest
Mon, Apr 20 - Mon, Apr 27
Southwest Logo
9:50 am - 3:30 pm
MAF
-
ORD
5h 40m
1 stop
Southwest Logo
4:15 pm - 11:10 pm
ORD
-
MAF
6h 55m
1 stop
$416Southwest
Mon, May 11 - Fri, May 15
Southwest Logo
6:00 am - 1:15 pm
MAF
-
ORD
7h 15m
2 stops
Southwest Logo
4:15 pm - 11:10 pm
ORD
-
MAF
6h 55m
1 stop
$421Southwest
Mon, May 11 - Fri, May 15
Southwest Logo
6:00 am - 1:15 pm
MAF
-
ORD
7h 15m
2 stops
Southwest Logo
4:15 pm - 11:25 pm
ORD
-
MAF
7h 10m
2 stops
$426Southwest
Mon, May 11 - Fri, May 15
United Airlines Logo
7:00 pm - 12:45 am
MAF
-
ORD
5h 45m
1 stop
United Airlines Logo
10:35 am - 11:15 pm
ORD
-
MAF
12h 40m
2 stops
$435United Airlines
Tue, May 12 - Wed, May 13

United Airlines flights from Midland to Chicago O'Hare Intl Airport

Our best United Airlines deals on Midland to Chicago O'Hare Intl Airport flight tickets
United Airlines
May 12
MAF7:00 pmMidland Intl
5h 45m
1 stop
ORD12:45 amChicago O'Hare Intl
May 13
ORD10:30 amChicago O'Hare Intl
7h 42m
1 stop
MAF6:12 pmMidland Intl
$365
United Airlines
May 12
MAF7:00 pmMidland Intl
5h 45m
1 stop
ORD12:45 amChicago O'Hare Intl
May 13
ORD10:35 amChicago O'Hare Intl
12h 40m
2 stops
MAF11:15 pmMidland Intl
$435
United Airlines
May 12
MAF5:20 pmMidland Intl
7h 38m
1 stop
ORD12:58 amChicago O'Hare Intl
May 13
ORD10:30 amChicago O'Hare Intl
7h 42m
1 stop
MAF6:12 pmMidland Intl
$441

Southwest flights from Midland to Chicago O'Hare Intl Airport

Our best Southwest deals on Midland to Chicago O'Hare Intl Airport flight tickets
Southwest
Apr 20
MAF9:50 amMidland Intl
5h 40m
1 stop
ORD3:30 pmChicago O'Hare Intl
Apr 27
ORD4:15 pmChicago O'Hare Intl
6h 55m
1 stop
MAF11:10 pmMidland Intl
$405
Southwest
Apr 20
MAF9:50 amMidland Intl
5h 40m
1 stop
ORD3:30 pmChicago O'Hare Intl
Apr 27
ORD3:45 pmChicago O'Hare Intl
7h 25m
2 stops
MAF11:10 pmMidland Intl
$410
Southwest
Apr 20
MAF6:00 amMidland Intl
7h 15m
2 stops
ORD1:15 pmChicago O'Hare Intl
Apr 27
ORD2:40 pmChicago O'Hare Intl
8h 30m
2 stops
MAF11:10 pmMidland Intl
$415

momondo Fare Finder

 
Customize your flight search to find flights from Midland to Chicago O'Hare Intl Airport 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 March 25, 2026.
Use the filters below to find and compare flights from Midland to Chicago O'Hare Intl Airport that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

MidlandChicago

MAF - ORD

MAFORD

Midland Intl

Tue 5/12

7:00 pm-12:45 am

1 stop5h 45m

Chicago O'Hare Intl

Wed 5/13

10:30 am-6:12 pm

1 stop7h 42m

$365

MidlandChicago

MAF - ORD

MAFORD

Midland Intl

Mon 5/11

2:15 pm-9:14 pm

1 stop6h 59m

Chicago O'Hare Intl

Sun 5/17

6:05 am-12:16 pm

1 stop6h 11m

$386
Quickest round-trip

MidlandChicago

MAF - ORD

MAFORD

Midland Intl

Mon 5/11

2:15 pm-9:14 pm

1 stop6h 59m

Chicago O'Hare Intl

Sun 5/17

6:57 am-12:16 pm

1 stop5h 19m

$394

MidlandChicago

MAF - ORD

MAFORD

Midland Intl

Mon 4/20

9:50 am-3:30 pm

1 stop5h 40m

Chicago O'Hare Intl

Mon 4/27

4:15 pm-11:10 pm

1 stop6h 55m

$405

MidlandChicago

MAF - ORD

MAFORD

Midland Intl

Mon 4/20

9:50 am-3:30 pm

1 stop5h 40m

Chicago O'Hare Intl

Mon 4/27

3:45 pm-11:10 pm

2 stops7h 25m

$410

MidlandChicago

MAF - ORD

MAFORD

Midland Intl

Mon 4/20

6:00 am-1:15 pm

2 stops7h 15m

Chicago O'Hare Intl

Mon 4/27

2:40 pm-11:10 pm

2 stops8h 30m

$415

MidlandChicago

MAF - ORD

MAFORD

Midland Intl

Mon 5/11

9:50 am-3:30 pm

1 stop5h 40m

Chicago O'Hare Intl

Fri 5/15

4:15 pm-11:10 pm

1 stop6h 55m

$416

MidlandChicago

MAF - ORD

MAFORD

Midland Intl

Mon 5/11

6:00 am-1:15 pm

2 stops7h 15m

Chicago O'Hare Intl

Fri 5/15

4:15 pm-11:10 pm

1 stop6h 55m

$421

MidlandChicago

MAF - ORD

MAFORD

Midland Intl

Mon 5/11

6:00 am-1:15 pm

2 stops7h 15m

Chicago O'Hare Intl

Fri 5/15

4:15 pm-11:25 pm

2 stops7h 10m

$426

MidlandChicago

MAF - ORD

MAFORD

Midland Intl

Tue 5/12

7:00 pm-12:45 am

1 stop5h 45m

Chicago O'Hare Intl

Wed 5/13

10:35 am-11:15 pm

2 stops12h 40m

$435

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 12 resultsSorted by cheapest first
1
2

See travel insights to Chicago from

How to get the cheapest flight ticket from Midland to Chicago O'Hare Intl Airport

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 Midland Intl to Chicago O'Hare Intl?

United Airlines and Southwest are the most popular carriers operating from Midland Intl to Chicago O'Hare Intl

When to book flights from Midland to Chicago O'Hare Intl Airport

Are you open to changing your travel dates? Check out the ideal times to fly from Midland to Chicago O'Hare Intl Airport according to our flight data. Find out which month and days have the cheapest flights.
Estimated round-trip price

Cheap Midland to Chicago O'Hare Intl Airport (MAF to ORD) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Midland to Chicago O'Hare Intl Airport

Fastest flight time

5h 19m

Direct flights

None
The fastest flight from Midland to Chicago O'Hare Intl Airport takes 5h 19m
There are no direct flights from Midland to Chicago O'Hare Intl Airport. There are no popular flight routes from Midland to Chicago O'Hare Intl Airport.
Search flight deals

  • How far is Midland Intl to Chicago O'Hare Intl by plane?

    Chicago O'Hare Intl is 1039.6 mi away from Midland Intl. In terms of flight time, this usually takes a little over 5h 19m.

  • When did momondo last update prices for flights from Midland Intl Airport to Chicago O'Hare Intl Airport?

    Prices for flights from Midland Intl Airport to Chicago O'Hare Intl Airport are refreshed on a daily basis.

  • How many operators does momondo search for flights from Midland Intl Airport to Chicago O'Hare Intl Airport?

  • How old do you have to be to fly from Midland Intl Airport to Chicago O'Hare Intl Airport?

    Although the minimum age for a child to fly alone is five, airlines that offer an unaccompanied minor (UMNR) service may have their own age limits, which could be impacted by factors such as flight length, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Midland Intl Airport to Chicago O'Hare Intl Airport.

  • What documentation or ID do you need to fly to Chicago O'Hare Intl Airport?

    The required travel and health documents for your Chicago O'Hare 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 Chicago O'Hare 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 Midland to Chicago O'Hare Intl Airport?

Best airlines flying from Midland to Chicago O'Hare Intl Airport

Compare and see reviews for airlines that fly from Midland to Chicago O'Hare Intl Airport with momondo
Airline
Rating
Free Cancellation
Price
American AirlinesPriceFrom $241Free CancellationRating
7.1
11,494 reviews
Search American Airlines flights

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Lake Geneva
Schaumburg
South Haven
Rockford
Merrillville
Gurnee
Rosemont
Naperville
New Buffalo
Orland Park
Kenosha
Oak Brook
Joliet
Janesville
Racine
Hammond
Aurora
Elgin
Tinley Park
South Holland

Why use momondo?

Why should I use momondo to find a flight deal from Midland to Chicago?

It is quick and easy to find Midland to Chicago flights on momondo. We search and return numerous flight options from various airlines and agents. You can then use our filters to narrow your search until you have found the most convenient flight to Chicago that suits you.

Can I find flights from Midland to Chicago with flexible booking policies on momondo?

Yes. momondo allows you to filter the results for Midland to Chicago flights to just show those with flexible booking policies.

How can momondo help me find flights from Midland to Chicago?

momondo offers useful filters to help you find the right flight. Choose specific flight times, airports or even what payment method you prefer. We have numerous options to help you book your ideal flight from Midland to Chicago.

I’m not ready to book a flight from Midland to Chicago right now. Can momondo alert me if prices change?

Yes momondo offers price alerts on flights to Chicago from Midland. After performing a search on this page you should be able to see the price alert set up feature. Simply provide a valid email address and momondo will instantly alert you when prices change.

An easier way to manage your Chicago O'Hare Intl Airport 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
Fri 4/24
Fri 5/1
By creating a price alert you accept our terms of use and privacy policy.

Find better results for your trip to Chicago