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Cheap flights from Midland to Chicago from $139

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 10/24. 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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Find the cheapest flights from Midland to Chicago

Cheap round-trip flights

United Airlines Logo
5:00 pm - 10:42 pmMAF-ORD
5h 42m1 stop
United Airlines Logo
3:58 pm - 9:55 pmORD-MAF
5h 57m1 stop
$212United Airlines
Find Deal
Mon, Sep 15 - Tue, Sep 23
American Airlines Logo
11:17 am - 5:18 pmMAF-ORD
6h 01m1 stop
American Airlines Logo
6:00 am - 10:47 amORD-MAF
4h 47m1 stop
$217American Airlines
Find Deal
Sat, Sep 13 - Wed, Sep 17
Delta Logo
5:30 am - 1:01 pmMAF-ORD
7h 31m2 stops
Delta Logo
11:20 am - 11:58 pmORD-MAF
12h 38m2 stops
$227Delta
Find Deal
Sat, Sep 13 - Wed, Sep 17
United Airlines Logo
2:01 pm - 7:55 pmMAF-ORD
5h 54m1 stop
United Airlines Logo
6:00 am - 11:04 amORD-MAF
5h 04m1 stop
$242United Airlines
Find Deal
Tue, Sep 30 - Fri, Oct 3
Delta Logo
5:30 am - 4:47 pmMAF-ORD
11h 17m2 stops
Delta Logo
5:30 am - 4:40 pmORD-MAF
11h 10m2 stops
$252Delta
Find Deal
Tue, Sep 30 - Fri, Oct 3
Southwest Logo
6:05 am - 1:05 pmMAF-ORD
7h 00m1 stop
Southwest Logo
7:30 am - 4:25 pmORD-MAF
8h 55m2 stops
$292Southwest
Find Deal
Sat, Sep 13 - Wed, Sep 17
American Airlines Logo
6:01 am - 12:23 pmMAF-ORD
6h 22m1 stop
American Airlines Logo
6:30 pm - 11:04 pmORD-MAF
4h 34m1 stop
$297American Airlines
Find Deal
Sun, Aug 31 - Thu, Sep 4
Delta Logo
12:31 pm - 8:23 pmMAF-ORD
7h 52m2 stops
Delta Logo
1:30 pm - 11:58 pmORD-MAF
10h 28m2 stops
$307Delta
Find Deal
Sun, Aug 31 - Thu, Sep 4
Southwest Logo
2:45 pm - 9:30 pmMAF-ORD
6h 45m1 stop
Southwest Logo
7:30 am - 4:25 pmORD-MAF
8h 55m2 stops
$322Southwest
Find Deal
Wed, Sep 17 - Wed, Sep 24
Southwest Logo
3:30 pm - 11:40 pmMAF-ORD
8h 10m1 stop
Southwest Logo
4:20 pm - 9:35 pmORD-MAF
5h 15m1 stop
$332Southwest
Find Deal
Tue, Sep 9 - Mon, Sep 15

United Airlines flights from Midland to Chicago

Our best United Airlines deals on Midland to Chicago flight tickets
United Airlines
Sep 15
MAF5:00 pmMidland Intl
5h 42m
1 stop
ORD10:42 pmChicago O'Hare Intl
Sep 23
ORD3:58 pmChicago O'Hare Intl
5h 57m
1 stop
MAF9:55 pmMidland Intl
$212
Find similar
United Airlines
Sep 30
MAF2:01 pmMidland Intl
5h 54m
1 stop
ORD7:55 pmChicago O'Hare Intl
Oct 3
ORD6:00 amChicago O'Hare Intl
5h 04m
1 stop
MAF11:04 amMidland Intl
$242
Find similar
United Airlines
Sep 15
MAF3:20 pmMidland Intl
6h 20m
1 stop
ORD9:40 pmChicago O'Hare Intl
Sep 23
ORD7:17 amChicago O'Hare Intl
14h 38m
2 stops
MAF9:55 pmMidland Intl
$342
Find similar

American Airlines flights from Midland to Chicago

Our best American Airlines deals on Midland to Chicago flight tickets
American Airlines
Sep 13
MAF11:17 amMidland Intl
6h 01m
1 stop
ORD5:18 pmChicago O'Hare Intl
Sep 17
ORD6:00 amChicago O'Hare Intl
4h 47m
1 stop
MAF10:47 amMidland Intl
$217
Find similar
American Airlines
Aug 31
MAF6:01 amMidland Intl
6h 22m
1 stop
ORD12:23 pmChicago O'Hare Intl
Sep 4
ORD6:30 pmChicago O'Hare Intl
4h 34m
1 stop
MAF11:04 pmMidland Intl
$297
Find similar
American Airlines
Aug 31
MAF6:22 pmMidland Intl
5h 37m
1 stop
ORD11:59 pmChicago O'Hare Intl
Sep 4
ORD6:30 pmChicago O'Hare Intl
4h 34m
1 stop
MAF11:04 pmMidland Intl
$372
Find similar

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 21, 2025.
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

MidlandChicago

MAF - ORD

MAFORD

Midland Intl

Mon 9/15

5:00 pm-10:42 pm

1 stop5h 42m

Chicago O'Hare Intl

Tue 9/23

3:58 pm-9:55 pm

1 stop5h 57m

$212

MidlandChicago

MAF - ORD

MAFORD

Midland Intl

Sat 9/13

11:17 am-5:18 pm

1 stop6h 01m

Chicago O'Hare Intl

Wed 9/17

6:00 am-10:47 am

1 stop4h 47m

$217

MidlandChicago

MAF - ORD

MAFORD

Midland Intl

Sat 9/13

5:30 am-1:01 pm

2 stops7h 31m

Chicago O'Hare Intl

Wed 9/17

11:20 am-11:58 pm

2 stops12h 38m

$227

MidlandChicago

MAF - ORD

MAFORD

Midland Intl

Tue 9/30

2:01 pm-7:55 pm

1 stop5h 54m

Chicago O'Hare Intl

Fri 10/3

6:00 am-11:04 am

1 stop5h 04m

$242

MidlandChicago

MAF - ORD

MAFORD

Midland Intl

Tue 9/30

5:30 am-4:47 pm

2 stops11h 17m

Chicago O'Hare Intl

Fri 10/3

5:30 am-4:40 pm

2 stops11h 10m

$252

MidlandChicago

MAF - ORD

MAFORD

Midland Intl

Sat 9/13

6:05 am-1:05 pm

1 stop7h 00m

Chicago O'Hare Intl

Wed 9/17

7:30 am-4:25 pm

2 stops8h 55m

$292

MidlandChicago

MAF - ORD

MAFORD

Midland Intl

Sun 8/31

6:01 am-12:23 pm

1 stop6h 22m

Chicago O'Hare Intl

Thu 9/4

6:30 pm-11:04 pm

1 stop4h 34m

$297

MidlandChicago

MAF - ORD

MAFORD

Midland Intl

Sun 8/31

12:31 pm-8:23 pm

2 stops7h 52m

Chicago O'Hare Intl

Thu 9/4

1:30 pm-11:58 pm

2 stops10h 28m

$307

MidlandChicago

MAF - ORD

MAFORD

Midland Intl

Wed 9/17

2:45 pm-9:30 pm

1 stop6h 45m

Chicago O'Hare Intl

Wed 9/24

7:30 am-4:25 pm

2 stops8h 55m

$322

MidlandChicago

MAF - ORD

MAFORD

Midland Intl

Tue 9/9

3:30 pm-11:40 pm

1 stop8h 10m

Chicago O'Hare Intl

Mon 9/15

4:20 pm-9:35 pm

1 stop5h 15m

$332

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 14 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 day to depart on your flight to Chicago?

The cheapest day to depart on your flight to Chicago is on a Saturday when prices can be found for as low as $335. This is often the case because there is less demand to fly during this day of the week. When flying out on a Wednesday, the most expensive travel day of the week, you can expect to see flight prices from Midland to Chicago for around $703.

What is the cheapest time of day to depart on your flight to Chicago?

Our most recent data shows that the best time of day to fly to Chicago is in the evening. Flights from Midland to Chicago during this time can be as low as $286. In contrast, the most expensive time of day to depart to Chicago is in the morning when prices are around $534.

Can stopping save me money on Midland to Chicago flights?

You could potentially save up to 56% 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

Direct flights

None
There are no direct flights from Midland to Chicago. There are no popular flight routes from Midland to Chicago.
Search flight deals

  • 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 4h 55m.

  • 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
SouthwestPriceFrom $216Free CancellationRating
8.0
4,245 reviews
Search Southwest flights
American AirlinesPriceFrom $255Free CancellationRating
7.2
10,000 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
Benton Harbor
Saint Joseph
Lansing
Portage
Schererville
Valparaiso
Crown Point
Munster
Chesterton
Monticello
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