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Cheap flights from Midland to Chicago from $167

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 7/18. 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.
American Airlines Logo
6:46 pm - 12:50 am
MAF
-
ORD
6h 04m
1 stop
American Airlines Logo
10:45 am - 5:56 pm
ORD
-
MAF
7h 11m
1 stop
$401American Airlines
Fri, Jul 31 - Sat, Aug 8
United Airlines Logo
7:30 am - 2:34 pm
MAF
-
ORD
7h 04m
1 stop
United Airlines Logo
2:22 pm - 9:34 pm
ORD
-
MAF
7h 12m
1 stop
$423United Airlines
Tue, Nov 17 - Wed, Nov 18
American Airlines Logo
6:46 pm - 12:50 am
MAF
-
ORD
6h 04m
1 stop
American Airlines Logo
7:00 am - 1:49 pm
ORD
-
MAF
6h 49m
1 stop
$437American Airlines
Fri, Jul 17 - Fri, Jul 24
United Airlines Logo
7:00 am - 12:29 pm
MAF
-
ORD
5h 29m
1 stop
United Airlines Logo
5:45 pm - 11:44 pm
ORD
-
MAF
5h 59m
1 stop
$445United Airlines
Wed, Jul 8 - Tue, Jul 21
United Airlines Logo
5:00 am - 10:15 am
MAF
-
ORD
5h 15m
1 stop
United Airlines Logo
6:25 pm - 11:44 pm
ORD
-
MAF
5h 19m
1 stop
$461United Airlines
Fri, Sep 18 - Mon, Sep 21
United Airlines Logo
5:00 am - 10:20 am
MAF
-
ORD
5h 20m
1 stop
United Airlines Logo
5:45 pm - 11:44 pm
ORD
-
MAF
5h 59m
1 stop
$467United Airlines
Wed, Jul 8 - Tue, Jul 21
American Airlines Logo
6:26 pm - 12:18 am
MAF
-
ORD
5h 52m
1 stop
American Airlines Logo
9:05 pm - 8:46 am
ORD
-
MAF
11h 41m
1 stop
$477American Airlines
Fri, Sep 4 - Tue, Sep 8
American Airlines Logo
6:26 pm - 12:18 am
MAF
-
ORD
5h 52m
1 stop
American Airlines Logo
9:05 pm - 8:46 am
ORD
-
MAF
11h 41m
1 stop
$496American Airlines
Fri, Sep 4 - Tue, Sep 8
American Airlines Logo
6:26 pm - 12:18 am
MAF
-
ORD
5h 52m
1 stop
American Airlines Logo
9:05 pm - 8:46 am
ORD
-
MAF
11h 41m
1 stop
$500American Airlines
Fri, Sep 4 - Tue, Sep 8
American Airlines Logo
6:26 pm - 12:18 am
MAF
-
ORD
5h 52m
1 stop
American Airlines Logo
6:00 am - 11:19 am
ORD
-
MAF
5h 19m
1 stop
$503American Airlines
Fri, Sep 4 - Tue, Sep 8

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United Airlines flights from Midland to Chicago

Our best United Airlines deals on Midland to Chicago flight tickets
United Airlines
Nov 17
MAF11:58 amMidland Intl
5h 07m
1 stop
ORD5:05 pmChicago O'Hare Intl
Nov 18
ORD4:00 pmChicago O'Hare Intl
5h 34m
1 stop
MAF9:34 pmMidland Intl
$423
United Airlines
Jul 8
MAF7:00 amMidland Intl
5h 29m
1 stop
ORD12:29 pmChicago O'Hare Intl
Jul 21
ORD5:45 pmChicago O'Hare Intl
5h 59m
1 stop
MAF11:44 pmMidland Intl
$445
United Airlines
Sep 18
MAF5:00 amMidland Intl
5h 15m
1 stop
ORD10:15 amChicago O'Hare Intl
Sep 21
ORD6:25 pmChicago O'Hare Intl
5h 19m
1 stop
MAF11:44 pmMidland Intl
$461

American Airlines flights from Midland to Chicago

Our best American Airlines deals on Midland to Chicago flight tickets
American Airlines
Jul 31
MAF6:46 pmMidland Intl
6h 04m
1 stop
ORD12:50 amChicago O'Hare Intl
Aug 8
ORD10:45 amChicago O'Hare Intl
7h 11m
1 stop
MAF5:56 pmMidland Intl
$401
American Airlines
Jul 17
MAF6:46 pmMidland Intl
6h 04m
1 stop
ORD12:50 amChicago O'Hare Intl
Jul 24
ORD7:00 amChicago O'Hare Intl
6h 49m
1 stop
MAF1:49 pmMidland Intl
$437
American Airlines
Sep 4
MAF6:26 pmMidland Intl
5h 52m
1 stop
ORD12:18 amChicago O'Hare Intl
Sep 8
ORD9:05 pmChicago O'Hare Intl
11h 41m
1 stop
MAF8:46 amMidland Intl
$477

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 June 22, 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

Fri 7/31

6:46 pm-12:50 am

1 stop6h 04m

Chicago O'Hare Intl

Sat 8/8

10:45 am-5:56 pm

1 stop7h 11m

$401

MidlandChicago

MAF - ORD

MAFORD

Midland Intl

Tue 11/17

7:30 am-2:34 pm

1 stop7h 04m

Chicago O'Hare Intl

Wed 11/18

2:22 pm-9:34 pm

1 stop7h 12m

$423

MidlandChicago

MAF - ORD

MAFORD

Midland Intl

Fri 7/17

6:46 pm-12:50 am

1 stop6h 04m

Chicago O'Hare Intl

Fri 7/24

7:00 am-1:49 pm

1 stop6h 49m

$437

MidlandChicago

MAF - ORD

MAFORD

Midland Intl

Wed 7/8

7:00 am-12:29 pm

1 stop5h 29m

Chicago O'Hare Intl

Tue 7/21

5:45 pm-11:44 pm

1 stop5h 59m

$445
Quickest round-trip

MidlandChicago

MAF - ORD

MAFORD

Midland Intl

Fri 9/18

5:00 am-10:15 am

1 stop5h 15m

Chicago O'Hare Intl

Mon 9/21

6:25 pm-11:44 pm

1 stop5h 19m

$461

MidlandChicago

MAF - ORD

MAFORD

Midland Intl

Wed 7/8

5:00 am-10:20 am

1 stop5h 20m

Chicago O'Hare Intl

Tue 7/21

5:45 pm-11:44 pm

1 stop5h 59m

$467

MidlandChicago

MAF - ORD

MAFORD

Midland Intl

Fri 9/4

6:26 pm-12:18 am

1 stop5h 52m

Chicago O'Hare Intl

Tue 9/8

9:05 pm-8:46 am

1 stop11h 41m

$477

MidlandChicago

MAF - ORD

MAFORD

Midland Intl

Fri 9/4

6:26 pm-12:18 am

1 stop5h 52m

Chicago O'Hare Intl

Tue 9/8

9:05 pm-8:46 am

1 stop11h 41m

$496

MidlandChicago

MAF - ORD

MAFORD

Midland Intl

Fri 9/4

6:26 pm-12:18 am

1 stop5h 52m

Chicago O'Hare Intl

Tue 9/8

9:05 pm-8:46 am

1 stop11h 41m

$500

MidlandChicago

MAF - ORD

MAFORD

Midland Intl

Fri 9/4

6:26 pm-12:18 am

1 stop5h 52m

Chicago O'Hare Intl

Tue 9/8

6:00 am-11:19 am

1 stop5h 19m

$503

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 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 airline that flies from Midland Intl to Chicago?

United Airlines and American 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 15m

Direct flights

None
The fastest flight from Midland to Chicago takes 5h 15m
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 15m.

  • 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
American AirlinesPriceFrom $296Free CancellationRating
7.1
11,739 reviews
Search American Airlines flights
United AirlinesPriceFrom $398Free CancellationRating
7.4
9,875 reviews
Search United 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
Portage
Saint Joseph
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