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Cheap flights from Midland to Chicago from $172

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 8/21. 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.

Find the cheapest flights from Midland to Chicago

Cheap round-trip flights

Enter your travel dates to find the best prices.
United Airlines Logo
7:15 pm - 12:59 amMAF  Midland Intl-ORD Chicago O'Hare Intl
5h 44m1 stop Houston George Bush Intcntl
United Airlines Logo
10:40 am - 4:08 pmORD  Chicago O'Hare Intl-MAF Midland Intl
5h 28m1 stop Houston George Bush Intcntl
$343United Airlines
Thu, Sep 10 - Sat, Sep 12
United Airlines Logo
1:40 pm - 7:30 pmMAF  Midland Intl-ORD Chicago O'Hare Intl
5h 50m1 stop Denver Intl
United Airlines Logo
5:55 am - 12:45 pmORD  Chicago O'Hare Intl-MAF Midland Intl
6h 50m1 stop Denver Intl
$362United Airlines
Tue, Sep 1 - Sun, Sep 6
American Airlines Logo
2:21 pm - 10:13 pmMAF  Midland Intl-ORD Chicago O'Hare Intl
7h 52m1 stop Dallas/Fort Worth
American Airlines Logo
8:09 am - 1:51 pmORD  Chicago O'Hare Intl-MAF Midland Intl
5h 42m1 stop Dallas/Fort Worth
$362American Airlines
Mon, Aug 31 - Sun, Sep 6
American Airlines Logo
7:00 am - 12:15 pmMAF  Midland Intl-ORD Chicago O'Hare Intl
5h 15m1 stop Dallas/Fort Worth
American Airlines Logo
8:09 am - 1:51 pmORD  Chicago O'Hare Intl-MAF Midland Intl
5h 42m1 stop Dallas/Fort Worth
$362American Airlines
Tue, Sep 1 - Sun, Sep 6
United Airlines Logo
5:00 am - 10:15 amMAF  Midland Intl-ORD Chicago O'Hare Intl
5h 15m1 stop Houston George Bush Intcntl
United Airlines Logo
6:29 pm - 11:44 pmORD  Chicago O'Hare Intl-MAF Midland Intl
5h 15m1 stop Houston George Bush Intcntl
$362United Airlines
Wed, Sep 2 - Sun, Sep 6
United Airlines Logo
5:00 am - 10:15 amMAF  Midland Intl-ORD Chicago O'Hare Intl
5h 15m1 stop Houston George Bush Intcntl
United Airlines Logo
7:00 am - 12:45 pmORD  Chicago O'Hare Intl-MAF Midland Intl
5h 45m1 stop Denver Intl
$362United Airlines
Tue, Sep 1 - Sun, Sep 6
United Airlines Logo
2:13 pm - 8:05 pmMAF  Midland Intl-ORD Chicago O'Hare Intl
5h 52m1 stop Houston George Bush Intcntl
United Airlines Logo
5:53 pm - 11:44 pmORD  Chicago O'Hare Intl-MAF Midland Intl
5h 51m1 stop Houston George Bush Intcntl
$364United Airlines
Thu, Sep 10 - Thu, Sep 17
United Airlines Logo
7:15 pm - 12:59 amMAF  Midland Intl-ORD Chicago O'Hare Intl
5h 44m1 stop Houston George Bush Intcntl
United Airlines Logo
5:30 am - 11:11 amORD  Chicago O'Hare Intl-MAF Midland Intl
5h 41m1 stop Houston George Bush Intcntl
$364United Airlines
Thu, Sep 10 - Thu, Sep 17
American Airlines Logo
11:50 am - 7:36 pmMAF  Midland Intl-ORD Chicago O'Hare Intl
7h 46m1 stop Dallas/Fort Worth
American Airlines Logo
5:00 am - 9:45 amORD  Chicago O'Hare Intl-MAF Midland Intl
4h 45m1 stop Dallas/Fort Worth
$364American Airlines
Thu, Sep 10 - Thu, Sep 17
American Airlines Logo
5:31 pm - 12:18 amMAF  Midland Intl-ORD Chicago O'Hare Intl
6h 47m1 stop Dallas/Fort Worth
American Airlines Logo
1:46 pm - 7:41 pmORD  Chicago O'Hare Intl-MAF Midland Intl
5h 55m1 stop Dallas/Fort Worth
$364American Airlines
Tue, Sep 8 - Sat, Sep 12

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American Airlines flights from Midland to Chicago

Our best American Airlines deals on Midland to Chicago flight tickets
American Airlines
Sep 2
MAF2:21 pmMidland Intl
5h 21m
1 stop
ORD7:42 pmChicago O'Hare Intl
Sep 6
ORD6:00 amChicago O'Hare Intl
5h 19m
1 stop
MAF11:19 amMidland Intl
$380
American Airlines
Sep 11
MAF5:23 pmMidland Intl
6h 51m
1 stop
ORD12:14 amChicago O'Hare Intl
Sep 13
ORD5:00 amChicago O'Hare Intl
5h 54m
1 stop
MAF10:54 amMidland Intl
$388
American Airlines
Sep 10
MAF11:50 amMidland Intl
7h 46m
1 stop
ORD7:36 pmChicago O'Hare Intl
Sep 13
ORD5:00 amChicago O'Hare Intl
4h 45m
1 stop
MAF9:45 amMidland Intl
$390

United Airlines flights from Midland to Chicago

Our best United Airlines deals on Midland to Chicago flight tickets
United Airlines
Sep 10
MAF7:15 pmMidland Intl
5h 44m
1 stop
ORD12:59 amChicago O'Hare Intl
Sep 12
ORD10:40 amChicago O'Hare Intl
5h 28m
1 stop
MAF4:08 pmMidland Intl
$343
United Airlines
Sep 1
MAF1:40 pmMidland Intl
5h 50m
1 stop
ORD7:30 pmChicago O'Hare Intl
Sep 6
ORD5:55 amChicago O'Hare Intl
6h 50m
1 stop
MAF12:45 pmMidland Intl
$362
United Airlines
Sep 10
MAF2:13 pmMidland Intl
5h 52m
1 stop
ORD8:05 pmChicago O'Hare Intl
Sep 17
ORD5:53 pmChicago O'Hare Intl
5h 51m
1 stop
MAF11:44 pmMidland Intl
$364

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 August 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 Midland Intl - ORD Chicago O'Hare Intl

MAFORD

Midland Intl

Thu 9/10

7:15 pm-12:59 am

1 stop5h 44m

Chicago O'Hare Intl

Sat 9/12

10:40 am-4:08 pm

1 stop5h 28m

$343

MidlandChicago

MAF Midland Intl - ORD Chicago O'Hare Intl

MAFORD

Midland Intl

Tue 9/1

1:40 pm-7:30 pm

1 stop5h 50m

Chicago O'Hare Intl

Sun 9/6

5:55 am-12:45 pm

1 stop6h 50m

$362

MidlandChicago

MAF Midland Intl - ORD Chicago O'Hare Intl

MAFORD

Midland Intl

Mon 8/31

2:21 pm-10:13 pm

1 stop7h 52m

Chicago O'Hare Intl

Sun 9/6

8:09 am-1:51 pm

1 stop5h 42m

$362

MidlandChicago

MAF Midland Intl - ORD Chicago O'Hare Intl

MAFORD

Midland Intl

Tue 9/1

7:00 am-12:15 pm

1 stop5h 15m

Chicago O'Hare Intl

Sun 9/6

8:09 am-1:51 pm

1 stop5h 42m

$362
Quickest round-trip

MidlandChicago

MAF Midland Intl - ORD Chicago O'Hare Intl

MAFORD

Midland Intl

Wed 9/2

5:00 am-10:15 am

1 stop5h 15m

Chicago O'Hare Intl

Sun 9/6

6:29 pm-11:44 pm

1 stop5h 15m

$362

MidlandChicago

MAF Midland Intl - ORD Chicago O'Hare Intl

MAFORD

Midland Intl

Tue 9/1

5:00 am-10:15 am

1 stop5h 15m

Chicago O'Hare Intl

Sun 9/6

7:00 am-12:45 pm

1 stop5h 45m

$362

MidlandChicago

MAF Midland Intl - ORD Chicago O'Hare Intl

MAFORD

Midland Intl

Thu 9/10

2:13 pm-8:05 pm

1 stop5h 52m

Chicago O'Hare Intl

Thu 9/17

5:53 pm-11:44 pm

1 stop5h 51m

$364

MidlandChicago

MAF Midland Intl - ORD Chicago O'Hare Intl

MAFORD

Midland Intl

Thu 9/10

7:15 pm-12:59 am

1 stop5h 44m

Chicago O'Hare Intl

Thu 9/17

5:30 am-11:11 am

1 stop5h 41m

$364

MidlandChicago

MAF Midland Intl - ORD Chicago O'Hare Intl

MAFORD

Midland Intl

Thu 9/10

11:50 am-7:36 pm

1 stop7h 46m

Chicago O'Hare Intl

Thu 9/17

5:00 am-9:45 am

1 stop4h 45m

$364

MidlandChicago

MAF Midland Intl - ORD Chicago O'Hare Intl

MAFORD

Midland Intl

Tue 9/8

5:31 pm-12:18 am

1 stop6h 47m

Chicago O'Hare Intl

Sat 9/12

1:46 pm-7:41 pm

1 stop5h 55m

$364

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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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 cheapest airline that flies from Midland Intl to Chicago?

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

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 04m

Direct flights

None
The fastest flight from Midland to Chicago takes 5h 04m
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 04m.

  • 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
United AirlinesPriceFrom $398Free CancellationRating
7.4
10,072 reviews
Search United Airlines flights
American AirlinesPriceFrom $404Free CancellationRating
7.1
11,864 reviews
Search American 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
Portage
Benton Harbor
Lansing
Saint Joseph
Valparaiso
Schererville
Munster
Chesterton
Monticello
Crown Point
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