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Cheap flights from Midland to Chicago from $192

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 8/12. 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 Midland to Chicago

Cheap round-trip flights

Enter your travel dates to find the best prices.
United Airlines Logo
5:00 am - 11:01 am
MAF
-
ORD
6h 01m
1 stop
United Airlines Logo
5:45 pm - 11:44 pm
ORD
-
MAF
5h 59m
1 stop
$377United Airlines
Wed, Jun 3 - Tue, Jun 9
United Airlines Logo
5:18 pm - 10:49 pm
MAF
-
ORD
5h 31m
1 stop
United Airlines Logo
8:51 am - 4:15 pm
ORD
-
MAF
7h 24m
1 stop
$378United Airlines
Tue, Jun 2 - Sat, Jun 6
United Airlines Logo
5:00 am - 11:01 am
MAF
-
ORD
6h 01m
1 stop
United Airlines Logo
5:00 am - 10:57 am
ORD
-
MAF
5h 57m
1 stop
$389United Airlines
Tue, Jun 2 - Sun, Jun 7
United Airlines Logo
7:13 pm - 12:45 am
MAF
-
ORD
5h 32m
1 stop
United Airlines Logo
5:45 pm - 11:44 pm
ORD
-
MAF
5h 59m
1 stop
$399United Airlines
Sun, May 31 - Wed, Jun 3
United Airlines Logo
5:00 am - 10:20 am
MAF
-
ORD
5h 20m
1 stop
United Airlines Logo
5:00 am - 10:57 am
ORD
-
MAF
5h 57m
1 stop
$402United Airlines
Wed, Jun 3 - Sun, Jun 7
United Airlines Logo
5:00 am - 10:20 am
MAF
-
ORD
5h 20m
1 stop
United Airlines Logo
5:00 am - 10:57 am
ORD
-
MAF
5h 57m
1 stop
$416United Airlines
Mon, Jun 1 - Sun, Jun 7
United Airlines Logo
7:13 pm - 12:45 am
MAF
-
ORD
5h 32m
1 stop
United Airlines Logo
5:45 pm - 11:44 pm
ORD
-
MAF
5h 59m
1 stop
$426United Airlines
Sun, May 31 - Thu, Jun 4
American Airlines Logo
6:42 pm - 11:37 pm
MAF
-
ORD
4h 55m
1 stop
American Airlines Logo
5:00 am - 11:09 am
ORD
-
MAF
6h 09m
1 stop
$437American Airlines
Tue, Jun 2 - Tue, Jun 9
United Airlines Logo
5:00 am - 10:20 am
MAF
-
ORD
5h 20m
1 stop
United Airlines Logo
7:30 am - 1:34 pm
ORD
-
MAF
6h 04m
1 stop
$441United Airlines
Tue, Jun 2 - Wed, Jun 3
American Airlines Logo
5:23 pm - 12:39 am
MAF
-
ORD
7h 16m
1 stop
American Airlines Logo
5:00 am - 11:09 am
ORD
-
MAF
6h 09m
1 stop
$456American Airlines
Fri, Jun 5 - Tue, Jun 9

American Airlines flights from Midland to Chicago

Our best American Airlines deals on Midland to Chicago flight tickets
American Airlines
Jun 2
MAF6:42 pmMidland Intl
4h 55m
1 stop
ORD11:37 pmChicago O'Hare Intl
Jun 9
ORD5:00 amChicago O'Hare Intl
6h 09m
1 stop
MAF11:09 amMidland Intl
$437
American Airlines
Jun 5
MAF5:23 pmMidland Intl
7h 16m
1 stop
ORD12:39 amChicago O'Hare Intl
Jun 9
ORD5:00 amChicago O'Hare Intl
6h 09m
1 stop
MAF11:09 amMidland Intl
$456
American Airlines
Jun 4
MAF6:47 pmMidland Intl
5h 57m
1 stop
ORD12:44 amChicago O'Hare Intl
Jun 7
ORD5:00 amChicago O'Hare Intl
5h 06m
1 stop
MAF10:06 amMidland Intl
$581

United Airlines flights from Midland to Chicago

Our best United Airlines deals on Midland to Chicago flight tickets
United Airlines
Jun 3
MAF5:00 amMidland Intl
6h 01m
1 stop
ORD11:01 amChicago O'Hare Intl
Jun 9
ORD5:45 pmChicago O'Hare Intl
5h 59m
1 stop
MAF11:44 pmMidland Intl
$377
United Airlines
Jun 2
MAF5:18 pmMidland Intl
5h 31m
1 stop
ORD10:49 pmChicago O'Hare Intl
Jun 6
ORD8:51 amChicago O'Hare Intl
7h 24m
1 stop
MAF4:15 pmMidland Intl
$378
United Airlines
Jun 2
MAF5:00 amMidland Intl
6h 01m
1 stop
ORD11:01 amChicago O'Hare Intl
Jun 7
ORD5:00 amChicago O'Hare Intl
5h 57m
1 stop
MAF10:57 amMidland Intl
$389

momondo Fare Finder

 
Customize your flight search to find flights from Midland to Chicago 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 6, 2026.
Use the filters below to find and compare flights from Midland to Chicago that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

MidlandChicago

MAF - ORD

MAFORD

Midland Intl

Wed 6/3

5:00 am-11:01 am

1 stop6h 01m

Chicago O'Hare Intl

Tue 6/9

5:45 pm-11:44 pm

1 stop5h 59m

$377

MidlandChicago

MAF - ORD

MAFORD

Midland Intl

Tue 6/2

5:18 pm-10:49 pm

1 stop5h 31m

Chicago O'Hare Intl

Sat 6/6

8:51 am-4:15 pm

1 stop7h 24m

$378

MidlandChicago

MAF - ORD

MAFORD

Midland Intl

Tue 6/2

5:00 am-11:01 am

1 stop6h 01m

Chicago O'Hare Intl

Sun 6/7

5:00 am-10:57 am

1 stop5h 57m

$389

MidlandChicago

MAF - ORD

MAFORD

Midland Intl

Sun 5/31

7:13 pm-12:45 am

1 stop5h 32m

Chicago O'Hare Intl

Wed 6/3

5:45 pm-11:44 pm

1 stop5h 59m

$399

MidlandChicago

MAF - ORD

MAFORD

Midland Intl

Wed 6/3

5:00 am-10:20 am

1 stop5h 20m

Chicago O'Hare Intl

Sun 6/7

5:00 am-10:57 am

1 stop5h 57m

$402

MidlandChicago

MAF - ORD

MAFORD

Midland Intl

Mon 6/1

5:00 am-10:20 am

1 stop5h 20m

Chicago O'Hare Intl

Sun 6/7

5:00 am-10:57 am

1 stop5h 57m

$416

MidlandChicago

MAF - ORD

MAFORD

Midland Intl

Sun 5/31

7:13 pm-12:45 am

1 stop5h 32m

Chicago O'Hare Intl

Thu 6/4

5:45 pm-11:44 pm

1 stop5h 59m

$426
Quickest round-trip

MidlandChicago

MAF - ORD

MAFORD

Midland Intl

Tue 6/2

6:42 pm-11:37 pm

1 stop4h 55m

Chicago O'Hare Intl

Tue 6/9

5:00 am-11:09 am

1 stop6h 09m

$437

MidlandChicago

MAF - ORD

MAFORD

Midland Intl

Tue 6/2

5:00 am-10:20 am

1 stop5h 20m

Chicago O'Hare Intl

Wed 6/3

7:30 am-1:34 pm

1 stop6h 04m

$441

MidlandChicago

MAF - ORD

MAFORD

Midland Intl

Fri 6/5

5:23 pm-12:39 am

1 stop7h 16m

Chicago O'Hare Intl

Tue 6/9

5:00 am-11:09 am

1 stop6h 09m

$456

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 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

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 Midland and Chicago?

What is the cheapest month to fly to Chicago?

The month of February is, on average, the cheapest month to fly to Chicago from Midland, with most prices found around $0. If you’re not able to fly to Chicago in February, then November is your next best option. Flight prices from Midland to Chicago during November average around $203.

Can stopping save me money on Midland to Chicago flights?

You could potentially save up to 24% on your flight if you consider stops on a Midland to Chicago flight.

When to book flights from Midland to Chicago

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

Cheap Midland to Chicago (MAF to CHI) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Midland to Chicago

Fastest flight time

5h 35m

Direct flights

None
The fastest flight from Midland to Chicago takes 5h 35m
There are no direct flights from Midland to Chicago. There are no popular flight routes from Midland to Chicago.
Search flight deals

Frequently asked questions about flying from Midland to Chicago

  • How far is Midland Intl to Chicago by plane?

    The distance between Midland Intl and Chicago is about 1046.8 mi. In terms of flight time, this usually takes a little over 5h 35m.

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

    Prices for flights from Midland Intl Airport to Chicago refresh daily.

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

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

    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.

  • What documentation or ID do you need to fly to Chicago?

    The travel and health documents you'll need for your trip to Chicago may differ based on your itinerary and personal situation. Typically, you should have several documents on hand, such as a national ID card or driver's license and a passport that is valid for six months after your intended arrival at Chicago. It is always advisable to seek advice from your airline or a trusted third party, such as IATA.

  • What is the most popular airline from Midland to Chicago?

Best airlines flying from Midland to Chicago

Compare and see reviews for airlines that fly from Midland to Chicago with momondo
Airline
Rating
Free Cancellation
Price
American AirlinesPriceFrom $296Free CancellationRating
7.1
11,666 reviews
Search American Airlines flights
United AirlinesPriceFrom $426Free CancellationRating
7.4
9,684 reviews
Search United Airlines flights

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Merrillville
New Buffalo
Hammond
Saint Joseph
Benton Harbor
Portage
Lansing
Valparaiso
Munster
Schererville
Crown Point
Monticello
Chesterton
Porter
Griffith
Saint John

Why use momondo?

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

momondo compares prices from hundreds of airlines and agents so you can find and book the best deal on flights from Midland to Chicago. Millions of users trust and use momondo every year so you are in good hands.

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

All flight searches from Midland to Chicago on momondo can be filtered to show those which offer 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 can track prices for Midland to Chicago flights and alert you when they change. Perform a search to set up the price alert. All that is required is a valid email address.

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Find better results for your trip to the United States

Fly into one of these airports located in Chicago

Airports listed have a maximum distance of 78.5 mi from Chicago
Chicago Midway Airport
Chicago O'Hare Intl Airport
Chicago Greater Rockford Airport