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Cheap flights from Midland to Chicago from $208

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 3/4. 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 - 10:05 am
MAF
-
ORD
5h 05m
1 stop
United Airlines Logo
7:30 am - 1:32 pm
ORD
-
MAF
6h 02m
1 stop
$371United Airlines
Mon, Mar 30 - Wed, Apr 1
United Airlines Logo
5:00 pm - 11:59 pm
MAF
-
ORD
6h 59m
1 stop
United Airlines Logo
2:45 pm - 10:15 pm
ORD
-
MAF
7h 30m
1 stop
$372United Airlines
Wed, Mar 4 - Mon, Mar 9
Southwest Logo
6:40 am - 1:00 pm
MAF
-
ORD
6h 20m
1 stop
Southwest Logo
2:40 pm - 10:55 pm
ORD
-
MAF
8h 15m
2 stops
$377Southwest
Wed, Mar 4 - Mon, Mar 9
Southwest Logo
7:05 am - 1:00 pm
MAF
-
ORD
5h 55m
2 stops
Southwest Logo
4:15 pm - 12:20 am
ORD
-
MAF
8h 05m
2 stops
$382Southwest
Wed, Mar 4 - Mon, Mar 9
United Airlines Logo
5:00 am - 10:05 am
MAF
-
ORD
5h 05m
1 stop
United Airlines Logo
4:03 pm - 9:39 pm
ORD
-
MAF
5h 36m
1 stop
$388United Airlines
Sun, Mar 29 - Wed, Apr 1
Southwest Logo
3:45 pm - 10:55 pm
MAF
-
ORD
7h 10m
1 stop
Southwest Logo
6:15 am - 1:40 pm
ORD
-
MAF
7h 25m
1 stop
$407Southwest
Wed, Mar 18 - Wed, Mar 25
Southwest Logo
3:45 pm - 10:55 pm
MAF
-
ORD
7h 10m
1 stop
Southwest Logo
7:00 am - 10:05 pm
ORD
-
MAF
15h 05m
2 stops
$412Southwest
Wed, Mar 18 - Wed, Mar 25
Southwest Logo
5:20 am - 2:20 pm
MAF
-
ORD
9h 00m
2 stops
Southwest Logo
6:15 am - 1:40 pm
ORD
-
MAF
7h 25m
1 stop
$416Southwest
Mon, Mar 30 - Wed, Apr 1
Southwest Logo
5:20 am - 2:20 pm
MAF
-
ORD
9h 00m
2 stops
Southwest Logo
2:40 pm - 10:55 pm
ORD
-
MAF
8h 15m
2 stops
$421Southwest
Mon, Mar 30 - Wed, Apr 1
Southwest Logo
5:30 am - 12:50 pm
MAF
-
ORD
7h 20m
2 stops
Southwest Logo
6:15 am - 1:40 pm
ORD
-
MAF
7h 25m
1 stop
$442Southwest
Sun, Mar 29 - Wed, Apr 1

United Airlines flights from Midland to Chicago

Our best United Airlines deals on Midland to Chicago flight tickets
United Airlines
Mar 30
MAF5:00 amMidland Intl
5h 05m
1 stop
ORD10:05 amChicago O'Hare Intl
Apr 1
ORD7:30 amChicago O'Hare Intl
6h 02m
1 stop
MAF1:32 pmMidland Intl
$371
United Airlines
Mar 4
MAF5:00 pmMidland Intl
6h 59m
1 stop
ORD11:59 pmChicago O'Hare Intl
Mar 9
ORD2:45 pmChicago O'Hare Intl
7h 30m
1 stop
MAF10:15 pmMidland Intl
$372
United Airlines
Mar 29
MAF5:00 amMidland Intl
5h 05m
1 stop
ORD10:05 amChicago O'Hare Intl
Apr 1
ORD4:03 pmChicago O'Hare Intl
5h 36m
1 stop
MAF9:39 pmMidland Intl
$388

Southwest flights from Midland to Chicago

Our best Southwest deals on Midland to Chicago flight tickets
Southwest
Mar 4
MAF6:40 amMidland Intl
6h 20m
1 stop
ORD1:00 pmChicago O'Hare Intl
Mar 9
ORD2:40 pmChicago O'Hare Intl
8h 15m
2 stops
MAF10:55 pmMidland Intl
$377
Southwest
Mar 4
MAF7:05 amMidland Intl
5h 55m
2 stops
ORD1:00 pmChicago O'Hare Intl
Mar 9
ORD4:15 pmChicago O'Hare Intl
8h 05m
2 stops
MAF12:20 amMidland Intl
$382
Southwest
Mar 30
MAF5:20 amMidland Intl
9h 00m
2 stops
ORD2:20 pmChicago O'Hare Intl
Apr 1
ORD6:15 amChicago O'Hare Intl
7h 25m
1 stop
MAF1:40 pmMidland Intl
$416

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 February 5, 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

MidlandChicago

MAF - ORD

MAFORD

Midland Intl

Mon 3/30

5:00 am-10:05 am

1 stop5h 05m

Chicago O'Hare Intl

Wed 4/1

7:30 am-1:32 pm

1 stop6h 02m

$371

MidlandChicago

MAF - ORD

MAFORD

Midland Intl

Wed 3/4

5:00 pm-11:59 pm

1 stop6h 59m

Chicago O'Hare Intl

Mon 3/9

2:45 pm-10:15 pm

1 stop7h 30m

$372

MidlandChicago

MAF - ORD

MAFORD

Midland Intl

Wed 3/4

6:40 am-1:00 pm

1 stop6h 20m

Chicago O'Hare Intl

Mon 3/9

2:40 pm-10:55 pm

2 stops8h 15m

$377

MidlandChicago

MAF - ORD

MAFORD

Midland Intl

Wed 3/4

7:05 am-1:00 pm

2 stops5h 55m

Chicago O'Hare Intl

Mon 3/9

4:15 pm-12:20 am

2 stops8h 05m

$382

MidlandChicago

MAF - ORD

MAFORD

Midland Intl

Sun 3/29

5:00 am-10:05 am

1 stop5h 05m

Chicago O'Hare Intl

Wed 4/1

4:03 pm-9:39 pm

1 stop5h 36m

$388

MidlandChicago

MAF - ORD

MAFORD

Midland Intl

Wed 3/18

3:45 pm-10:55 pm

1 stop7h 10m

Chicago O'Hare Intl

Wed 3/25

6:15 am-1:40 pm

1 stop7h 25m

$407

MidlandChicago

MAF - ORD

MAFORD

Midland Intl

Wed 3/18

3:45 pm-10:55 pm

1 stop7h 10m

Chicago O'Hare Intl

Wed 3/25

7:00 am-10:05 pm

2 stops15h 05m

$412

MidlandChicago

MAF - ORD

MAFORD

Midland Intl

Mon 3/30

5:20 am-2:20 pm

2 stops9h 00m

Chicago O'Hare Intl

Wed 4/1

6:15 am-1:40 pm

1 stop7h 25m

$416

MidlandChicago

MAF - ORD

MAFORD

Midland Intl

Mon 3/30

5:20 am-2:20 pm

2 stops9h 00m

Chicago O'Hare Intl

Wed 4/1

2:40 pm-10:55 pm

2 stops8h 15m

$421

MidlandChicago

MAF - ORD

MAFORD

Midland Intl

Sun 3/29

5:30 am-12:50 pm

2 stops7h 20m

Chicago O'Hare Intl

Wed 4/1

6:15 am-1:40 pm

1 stop7h 25m

$442

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 18 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 cheapest month to fly to Chicago?

The month of November is, on average, the cheapest month to fly to Chicago from Midland, with most prices found around $253. If you’re not able to fly to Chicago in November, then May is your next best option. Flight prices from Midland to Chicago during May average around $288.

Can stopping save me money on Midland to Chicago flights?

You could potentially save up to 33% 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 37m

Direct flights

None
The fastest flight from Midland to Chicago takes 5h 37m
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 37m.

  • 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
4,275 reviews
Search Southwest flights
American AirlinesPriceFrom $255Free CancellationRating
7.2
11,237 reviews
Search American Airlines flights

  • Southwest Flights From Midland to Chicago

    The lowest priced Southwest flight from Midland to Chicago from the last 72 hours was $216. Generally, Southwest has 3 flights on this route every week with an average price of $446. Southwest is rated 8.0/10 by our users.

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
Schererville
Valparaiso
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