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Cheap flights from Midland to Chicago from $254

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 4/6. 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 pm - 12:45 am
MAF
-
ORD
5h 45m
1 stop
United Airlines Logo
10:30 am - 6:12 pm
ORD
-
MAF
7h 42m
1 stop
$365United Airlines
Tue, May 12 - Wed, May 13
American Airlines Logo
2:15 pm - 9:14 pm
MAF
-
ORD
6h 59m
1 stop
American Airlines Logo
6:05 am - 12:16 pm
ORD
-
MAF
6h 11m
1 stop
$386American Airlines
Mon, May 11 - Sun, May 17
Southwest Logo
9:50 am - 3:30 pm
MAF
-
ORD
5h 40m
1 stop
Southwest Logo
4:15 pm - 11:10 pm
ORD
-
MAF
6h 55m
1 stop
$405Southwest
Mon, Apr 20 - Mon, Apr 27
Southwest Logo
9:50 am - 3:30 pm
MAF
-
ORD
5h 40m
1 stop
Southwest Logo
3:45 pm - 11:10 pm
ORD
-
MAF
7h 25m
2 stops
$410Southwest
Mon, Apr 20 - Mon, Apr 27
Southwest Logo
6:00 am - 1:15 pm
MAF
-
ORD
7h 15m
2 stops
Southwest Logo
2:40 pm - 11:10 pm
ORD
-
MAF
8h 30m
2 stops
$415Southwest
Mon, Apr 20 - Mon, Apr 27
Southwest Logo
9:50 am - 3:30 pm
MAF
-
ORD
5h 40m
1 stop
Southwest Logo
4:15 pm - 11:10 pm
ORD
-
MAF
6h 55m
1 stop
$416Southwest
Mon, May 11 - Fri, May 15
Southwest Logo
6:00 am - 1:15 pm
MAF
-
ORD
7h 15m
2 stops
Southwest Logo
4:15 pm - 11:10 pm
ORD
-
MAF
6h 55m
1 stop
$421Southwest
Mon, May 11 - Fri, May 15
Southwest Logo
6:00 am - 1:15 pm
MAF
-
ORD
7h 15m
2 stops
Southwest Logo
4:15 pm - 11:25 pm
ORD
-
MAF
7h 10m
2 stops
$426Southwest
Mon, May 11 - Fri, May 15
American Airlines Logo
2:15 pm - 9:45 pm
MAF
-
ORD
7h 30m
1 stop
American Airlines Logo
6:05 am - 12:16 pm
ORD
-
MAF
6h 11m
1 stop
$435American Airlines
Mon, May 11 - Sun, May 17
United Airlines Logo
7:00 pm - 12:45 am
MAF
-
ORD
5h 45m
1 stop
United Airlines Logo
5:15 pm - 11:15 pm
ORD
-
MAF
6h 00m
1 stop
$437United Airlines
Fri, Apr 17 - Fri, Apr 24

United Airlines flights from Midland to Chicago

Our best United Airlines deals on Midland to Chicago flight tickets
United Airlines
May 12
MAF7:00 pmMidland Intl
5h 45m
1 stop
ORD12:45 amChicago O'Hare Intl
May 13
ORD10:30 amChicago O'Hare Intl
7h 42m
1 stop
MAF6:12 pmMidland Intl
$365
United Airlines
Apr 17
MAF7:00 pmMidland Intl
5h 45m
1 stop
ORD12:45 amChicago O'Hare Intl
Apr 24
ORD5:15 pmChicago O'Hare Intl
6h 00m
1 stop
MAF11:15 pmMidland Intl
$437
United Airlines
May 12
MAF2:13 pmMidland Intl
7h 38m
1 stop
ORD9:51 pmChicago O'Hare Intl
May 13
ORD2:10 pmChicago O'Hare Intl
7h 36m
1 stop
MAF9:46 pmMidland Intl
$441

Southwest flights from Midland to Chicago

Our best Southwest deals on Midland to Chicago flight tickets
Southwest
Apr 20
MAF9:50 amMidland Intl
5h 40m
1 stop
ORD3:30 pmChicago O'Hare Intl
Apr 27
ORD4:15 pmChicago O'Hare Intl
6h 55m
1 stop
MAF11:10 pmMidland Intl
$405
Southwest
Apr 20
MAF9:50 amMidland Intl
5h 40m
1 stop
ORD3:30 pmChicago O'Hare Intl
Apr 27
ORD3:45 pmChicago O'Hare Intl
7h 25m
2 stops
MAF11:10 pmMidland Intl
$410
Southwest
Apr 20
MAF6:00 amMidland Intl
7h 15m
2 stops
ORD1:15 pmChicago O'Hare Intl
Apr 27
ORD2:40 pmChicago O'Hare Intl
8h 30m
2 stops
MAF11:10 pmMidland Intl
$415

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 March 24, 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

Tue 5/12

7:00 pm-12:45 am

1 stop5h 45m

Chicago O'Hare Intl

Wed 5/13

10:30 am-6:12 pm

1 stop7h 42m

$365

MidlandChicago

MAF - ORD

MAFORD

Midland Intl

Mon 5/11

2:15 pm-9:14 pm

1 stop6h 59m

Chicago O'Hare Intl

Sun 5/17

6:05 am-12:16 pm

1 stop6h 11m

$386

MidlandChicago

MAF - ORD

MAFORD

Midland Intl

Mon 4/20

9:50 am-3:30 pm

1 stop5h 40m

Chicago O'Hare Intl

Mon 4/27

4:15 pm-11:10 pm

1 stop6h 55m

$405

MidlandChicago

MAF - ORD

MAFORD

Midland Intl

Mon 4/20

9:50 am-3:30 pm

1 stop5h 40m

Chicago O'Hare Intl

Mon 4/27

3:45 pm-11:10 pm

2 stops7h 25m

$410

MidlandChicago

MAF - ORD

MAFORD

Midland Intl

Mon 4/20

6:00 am-1:15 pm

2 stops7h 15m

Chicago O'Hare Intl

Mon 4/27

2:40 pm-11:10 pm

2 stops8h 30m

$415

MidlandChicago

MAF - ORD

MAFORD

Midland Intl

Mon 5/11

9:50 am-3:30 pm

1 stop5h 40m

Chicago O'Hare Intl

Fri 5/15

4:15 pm-11:10 pm

1 stop6h 55m

$416

MidlandChicago

MAF - ORD

MAFORD

Midland Intl

Mon 5/11

6:00 am-1:15 pm

2 stops7h 15m

Chicago O'Hare Intl

Fri 5/15

4:15 pm-11:10 pm

1 stop6h 55m

$421

MidlandChicago

MAF - ORD

MAFORD

Midland Intl

Mon 5/11

6:00 am-1:15 pm

2 stops7h 15m

Chicago O'Hare Intl

Fri 5/15

4:15 pm-11:25 pm

2 stops7h 10m

$426

MidlandChicago

MAF - ORD

MAFORD

Midland Intl

Mon 5/11

2:15 pm-9:45 pm

1 stop7h 30m

Chicago O'Hare Intl

Sun 5/17

6:05 am-12:16 pm

1 stop6h 11m

$435
Quickest round-trip

MidlandChicago

MAF - ORD

MAFORD

Midland Intl

Fri 4/17

7:00 pm-12:45 am

1 stop5h 45m

Chicago O'Hare Intl

Fri 4/24

5:15 pm-11:15 pm

1 stop6h 00m

$437

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 12 resultsSorted by cheapest first
1
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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

Can stopping save me money on Midland to Chicago flights?

You could potentially save up to 15% 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 19m

Direct flights

None
The fastest flight from Midland to Chicago takes 5h 19m
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 19m.

  • 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
4,331 reviews
Search Southwest flights
American AirlinesPriceFrom $241Free CancellationRating
7.1
11,491 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
Saint Joseph
Benton Harbor
Portage
Lansing
Valparaiso
Schererville
Munster
Crown Point
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