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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.
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
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

Our best United Airlines deals on Midland to Chicago 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

Our best Southwest deals on Midland to Chicago 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 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 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

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 39% 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 08m

Direct flights

None
The fastest flight from Midland to Chicago takes 5h 08m
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 5h 08m.

  • 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
7.9
4,250 reviews
Search Southwest flights
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
Merrillville
New Buffalo
Hammond
Benton Harbor
Saint Joseph
Portage
Lansing
Valparaiso
Schererville
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