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Cheap flights from Midland to Chicago from $307

This is the cheapest round-trip flight price found by a momondo user in the last 72 hours by searching for a flight from Midland to Chicago departing on 1/13. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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0 bags

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Cheap round-trip flights

Enter your travel dates to find the best prices.
United Airlines Logo
7:00 am - 1:00 pm
MAF
-
ORD
6h 00m1 stop
United Airlines Logo
3:53 pm - 9:54 pm
ORD
-
MAF
6h 01m1 stop
$307United Airlines
Tue, Jan 13 - Tue, Jan 20
Southwest Logo
7:05 am - 1:00 pm
MAF
-
ORD
5h 55m2 stops
Southwest Logo
2:15 pm - 9:35 pm
ORD
-
MAF
7h 20m1 stop
$312Southwest
Tue, Jan 13 - Tue, Jan 20
Southwest Logo
7:05 am - 1:00 pm
MAF
-
ORD
5h 55m2 stops
Southwest Logo
2:15 pm - 10:15 pm
ORD
-
MAF
8h 00m2 stops
$343Southwest
Tue, Jan 13 - Tue, Jan 20
United Airlines Logo
7:03 pm - 12:28 am
MAF
-
ORD
5h 25m1 stop
United Airlines Logo
3:59 pm - 10:15 pm
ORD
-
MAF
6h 16m1 stop
$379United Airlines
Mon, Jan 26 - Fri, Jan 30
Southwest Logo
6:40 am - 1:00 pm
MAF
-
ORD
6h 20m1 stop
Southwest Logo
2:15 pm - 10:15 pm
ORD
-
MAF
8h 00m2 stops
$384Southwest
Mon, Jan 26 - Fri, Jan 30
United Airlines Logo
5:18 pm - 11:59 pm
MAF
-
ORD
6h 41m1 stop
United Airlines Logo
8:54 am - 4:21 pm
ORD
-
MAF
7h 27m1 stop
$387United Airlines
Tue, Jan 13 - Sat, Jan 17
United Airlines Logo
5:35 pm - 12:28 am
MAF
-
ORD
6h 53m1 stop
United Airlines Logo
5:40 am - 11:21 am
ORD
-
MAF
5h 41m1 stop
$389United Airlines
Thu, Jan 8 - Sun, Jan 11
Southwest Logo
3:00 pm - 10:35 pm
MAF
-
ORD
7h 35m1 stop
Southwest Logo
2:15 pm - 9:35 pm
ORD
-
MAF
7h 20m1 stop
$399Southwest
Fri, Jan 9 - Mon, Jan 12
Southwest Logo
6:40 am - 1:00 pm
MAF
-
ORD
6h 20m1 stop
Southwest Logo
2:15 pm - 10:35 pm
ORD
-
MAF
8h 20m2 stops
$404Southwest
Thu, Jan 8 - Sun, Jan 11
American Airlines Logo
5:00 am - 11:55 am
MAF
-
ORD
6h 55m1 stop
American Airlines Logo
8:10 am - 4:25 pm
ORD
-
MAF
8h 15m1 stop
$407American Airlines
Fri, Jan 30 - Sun, Feb 1

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
Jan 13
MAF7:00 amMidland Intl
6h 00m
1 stop
ORD1:00 pmChicago O'Hare Intl
Jan 20
ORD3:53 pmChicago O'Hare Intl
6h 01m
1 stop
MAF9:54 pmMidland Intl
$307
Find similar
United Airlines
Jan 26
MAF7:03 pmMidland Intl
5h 25m
1 stop
ORD12:28 amChicago O'Hare Intl
Jan 30
ORD3:59 pmChicago O'Hare Intl
6h 16m
1 stop
MAF10:15 pmMidland Intl
$379
Find similar
United Airlines
Jan 13
MAF7:20 amMidland Intl
7h 35m
1 stop
ORD2:55 pmChicago O'Hare Intl
Jan 17
ORD5:37 amChicago O'Hare Intl
8h 02m
1 stop
MAF1:39 pmMidland Intl
$387
Find similar

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
Jan 13
MAF7:05 amMidland Intl
5h 55m
2 stops
ORD1:00 pmChicago O'Hare Intl
Jan 20
ORD2:15 pmChicago O'Hare Intl
7h 20m
1 stop
MAF9:35 pmMidland Intl
$312
Find similar
Southwest
Jan 13
MAF7:05 amMidland Intl
5h 55m
2 stops
ORD1:00 pmChicago O'Hare Intl
Jan 20
ORD2:15 pmChicago O'Hare Intl
8h 00m
2 stops
MAF10:15 pmMidland Intl
$343
Find similar
Southwest
Jan 26
MAF6:40 amMidland Intl
6h 20m
1 stop
ORD1:00 pmChicago O'Hare Intl
Jan 30
ORD2:15 pmChicago O'Hare Intl
8h 00m
2 stops
MAF10:15 pmMidland Intl
$384
Find similar

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 December 18, 2025.
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

MidlandChicago

MAF - ORD

MAFORD

Midland Intl

Tue 1/13

7:00 am-1:00 pm

1 stop6h 00m

Chicago O'Hare Intl

Tue 1/20

3:53 pm-9:54 pm

1 stop6h 01m

$307

MidlandChicago

MAF - ORD

MAFORD

Midland Intl

Tue 1/13

7:05 am-1:00 pm

2 stops5h 55m

Chicago O'Hare Intl

Tue 1/20

2:15 pm-9:35 pm

1 stop7h 20m

$312

MidlandChicago

MAF - ORD

MAFORD

Midland Intl

Tue 1/13

7:05 am-1:00 pm

2 stops5h 55m

Chicago O'Hare Intl

Tue 1/20

2:15 pm-10:15 pm

2 stops8h 00m

$343

MidlandChicago

MAF - ORD

MAFORD

Midland Intl

Mon 1/26

7:03 pm-12:28 am

1 stop5h 25m

Chicago O'Hare Intl

Fri 1/30

3:59 pm-10:15 pm

1 stop6h 16m

$379

MidlandChicago

MAF - ORD

MAFORD

Midland Intl

Mon 1/26

6:40 am-1:00 pm

1 stop6h 20m

Chicago O'Hare Intl

Fri 1/30

2:15 pm-10:15 pm

2 stops8h 00m

$384

MidlandChicago

MAF - ORD

MAFORD

Midland Intl

Tue 1/13

5:18 pm-11:59 pm

1 stop6h 41m

Chicago O'Hare Intl

Sat 1/17

8:54 am-4:21 pm

1 stop7h 27m

$387

MidlandChicago

MAF - ORD

MAFORD

Midland Intl

Thu 1/8

5:35 pm-12:28 am

1 stop6h 53m

Chicago O'Hare Intl

Sun 1/11

5:40 am-11:21 am

1 stop5h 41m

$389

MidlandChicago

MAF - ORD

MAFORD

Midland Intl

Fri 1/9

3:00 pm-10:35 pm

1 stop7h 35m

Chicago O'Hare Intl

Mon 1/12

2:15 pm-9:35 pm

1 stop7h 20m

$399

MidlandChicago

MAF - ORD

MAFORD

Midland Intl

Thu 1/8

6:40 am-1:00 pm

1 stop6h 20m

Chicago O'Hare Intl

Sun 1/11

2:15 pm-10:35 pm

2 stops8h 20m

$404

MidlandChicago

MAF - ORD

MAFORD

Midland Intl

Fri 1/30

5:00 am-11:55 am

1 stop6h 55m

Chicago O'Hare Intl

Sun 2/1

8:10 am-4:25 pm

1 stop8h 15m

$407

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 11 resultsSorted by cheapest first
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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 month to fly to Chicago O'Hare Intl Airport?

The month of October is another great option to travel to Chicago O'Hare Intl Airport, with average flight prices from Midland averaging around $311.

What is the cheapest day to depart on your flight to Chicago O'Hare Intl Airport?

The cheapest day to depart on your flight to Chicago O'Hare Intl Airport is on a Tuesday when prices can be found for as low as $347. This is often the case because there is less demand to fly during this day of the week. On the other hand, Saturday is the most expensive day to depart from Midland because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $516.

What is the cheapest time of day to depart on your flight to Chicago O'Hare Intl Airport?

Flying to Chicago O'Hare Intl Airport from Midland in the morning is the least expensive time of day to depart. momondo users have found prices as low as $415 when looking at flights departing in the morning. Try not to purchase tickets in the afternoon because they tend to be around $426. Of course, these prices can vary depending on the time of year and what airport you fly to.

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 25m

Direct flights

None
The fastest flight from Midland to Chicago O'Hare Intl Airport takes 5h 25m
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 25m.

  • 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 $255Free CancellationRating
7.2
11,054 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
Naperville
Rosemont
Kenosha
New Buffalo
Joliet
Oak Brook
Orland Park
Racine
Hammond
Janesville
Tinley Park
Aurora
Elgin
Benton Harbor

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.

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