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$192+ Cheap flights from Midland (MAF) to Chicago (CHI)

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 8/12. Fares are subject to change and may not be available on all flights or dates of travel.
MAF — CHI
Jun 5 — Jun 121
Fri 6/5
Fri 6/12
1 adult, Economy
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Cheap flight deals from Midland to Chicago

Cheapest flights from Midland to Chicago
Explore the most affordable flight options available from Midland to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on May 6, 2026.

This United Airlines deal was found by Cheapflights users on 5/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/35:00 am
MAF
-
ORD
1 stop6h 01m
United Airlines
Tue 6/95:45 pm
ORD
-
MAF
1 stop5h 59m
United Airlines
Deal found 5/3$377
This United Airlines deal was found by Cheapflights users on 5/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/25:18 pm
MAF
-
ORD
1 stop5h 31m
United Airlines
Sat 6/68:51 am
ORD
-
MAF
1 stop7h 24m
United Airlines
Deal found 5/3$378
This United Airlines deal was found by Cheapflights users on 5/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/25:00 am
MAF
-
ORD
1 stop6h 01m
United Airlines
Sun 6/75:00 am
ORD
-
MAF
1 stop5h 57m
United Airlines
Deal found 5/3$389
This United Airlines deal was found by Cheapflights users on 5/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/317:13 pm
MAF
-
ORD
1 stop5h 32m
United Airlines
Wed 6/35:45 pm
ORD
-
MAF
1 stop5h 59m
United Airlines
Deal found 5/3$399
This United Airlines deal was found by Cheapflights users on 5/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/35:00 am
MAF
-
ORD
1 stop5h 20m
United Airlines
Sun 6/75:00 am
ORD
-
MAF
1 stop5h 57m
United Airlines
Deal found 5/3$402
This United Airlines deal was found by Cheapflights users on 5/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/15:00 am
MAF
-
ORD
1 stop5h 20m
United Airlines
Sun 6/75:00 am
ORD
-
MAF
1 stop5h 57m
United Airlines
Deal found 5/2$416
This United Airlines deal was found by Cheapflights users on 5/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/317:13 pm
MAF
-
ORD
1 stop5h 32m
United Airlines
Thu 6/45:45 pm
ORD
-
MAF
1 stop5h 59m
United Airlines
Deal found 5/3$426
This American Airlines deal was found by Cheapflights users on 5/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/26:42 pm
MAF
-
ORD
1 stop4h 55m
American Airlines
Tue 6/95:00 am
ORD
-
MAF
1 stop6h 09m
American Airlines
Deal found 5/5$437
This United Airlines deal was found by Cheapflights users on 5/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/25:00 am
MAF
-
ORD
1 stop5h 20m
United Airlines
Wed 6/37:30 am
ORD
-
MAF
1 stop6h 04m
United Airlines
Deal found 5/1$441
This American Airlines deal was found by Cheapflights users on 5/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/55:23 pm
MAF
-
ORD
1 stop7h 16m
American Airlines
Tue 6/95:00 am
ORD
-
MAF
1 stop6h 09m
American Airlines
Deal found 5/5$456
This United Airlines deal was found by Cheapflights users on 5/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/302:15 pm
MAF
-
ORD
1 stop7h 36m
United Airlines
Tue 6/212:56 pm
ORD
-
MAF
1 stop6h 43m
United Airlines
Deal found 5/3$495

Find flight deals from Midland to Chicago

Discover tips and strategies to find the most affordable flight options for your journey from Midland (MAF) to Chicago (CHI). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated May 6, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$377
(United Airlines)

One-way from

$192
(American Airlines)

Popular in

January

Cheapest in

November

Average price

$450
Provider with most accurate pricing for Midland Intl-Chicago (CHI) flight deals.
Search Deals
Provider most trusted by Cheapflights users for Midland Intl-Chicago (CHI) flights.
Search Deals
From Midland Intl to Chicago (CHI)
Search Deals
One-way flight from Midland Intl to Chicago (CHI)
Search Deals
Highest demand for flights based on searches. 42% potential increase in price ($351 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 13% potential price decrease ($56 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in May 2026
Search Deals

Cheapflights 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, Cheapflights users made 2,558,603 searches. Data last updated May 6, 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 6/2

5:00 am-11:01 am

1 stop6h 01m

Chicago O'Hare Intl

Sun 6/7

5:00 am-10:57 am

1 stop5h 57m

$389
Quickest round-trip

MidlandChicago

MAF - ORD

MAFORD

Midland Intl

Tue 6/2

5:00 am-10:20 am

1 stop5h 20m

Chicago O'Hare Intl

Wed 6/3

7:30 am-1:34 pm

1 stop6h 04m

$441

MidlandChicago

MAF - ORD

MAFORD

Midland Intl

Sat 5/30

2:15 pm-9:51 pm

1 stop7h 36m

Chicago O'Hare Intl

Tue 6/2

12:56 pm-7:39 pm

1 stop6h 43m

$495

MidlandChicago

MAF - ORD

MAFORD

Midland Intl

Sun 5/31

5:25 am-1:15 pm

2 stops7h 50m

Chicago O'Hare Intl

Wed 6/3

6:15 am-1:40 pm

1 stop7h 25m

$527

MidlandChicago

MAF - ORD

MAFORD

Midland Intl

Fri 9/4

7:13 pm-12:48 am

1 stop5h 35m

Chicago O'Hare Intl

Tue 9/8

5:45 pm-11:37 pm

1 stop5h 52m

$557

MidlandChicago

MAF - ORD

MAFORD

Midland Intl

Mon 6/1

2:15 pm-6:28 am

2 stops16h 13m

Chicago O'Hare Intl

Sun 6/7

5:00 am-10:57 am

1 stop5h 57m

$557
Cheapest one-way

MidlandChicago

MAF - ORD

MAFORD

Midland Intl

Wed 8/12

5:31 pm-11:58 pm

1 stop6h 27m

$192

MidlandChicago

MAF - ORD

MAFORD

Midland Intl

Sun 5/31

5:25 am-3:00 pm

2 stops9h 35m

$259

MidlandChicago

MAF - ORD

MAFORD

Midland Intl

Wed 8/12

5:00 am-7:01 pm

2 stops14h 01m

$313
Quickest one-way

MidlandChicago

MAF - ORD

MAFORD

Midland Intl

Mon 5/11

6:16 pm-11:48 pm

1 stop5h 32m

$439

Flights are sorted by cheapest round-trip flights first.

Deals found on 5/5

Showing 1-10 of 14 resultsSorted by cheapest first
1
2

Compare providers for flights from Midland to Chicago

Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Midland to Chicago in May.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars

*The Trust Score is based on feedback from users after their booking experience. It measures overall satisfaction, helping us identify issues like hidden fees, problems during the ticketing process, and the quality of customer service. This score is our best indicator of the provider's quality and reliability.

  • Most accurate provider: When it comes to deals on Midland-Chicago flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Midland-Chicago flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Midland-Chicago flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Midland-Chicago flights, Cheapflights users trust FlightHub the most. FlightHub has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Midland-Chicago flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

Best time to book a flight from Midland to Chicago

Have a flexible travel schedule? Discover the best time to fly to Chicago from Midland with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

Everything you need to know about your flight from Midland to Chicago

How much does it cost to fly round-trip from Midland to Chicago?

What’s the top layover airport for flights from Midland to Chicago?

Share of 1-stop round-trip flights from Midland to Chicago chosen by Cheapflights users in the past 12 months, using the same layover each way.

Dallas (DAL) – chosen by Cheapflights users on 43% of 1-stop itineraries from Midland to Chicago on Cheapflights.

What’s the cheapest layover airport for flights from Midland to Chicago?

Average round-trip fare for 1-stop flights from Midland to Chicago, chosen by Cheapflights users in the past 12 months, with the same layover each way.

Houston (IAH) is the most affordable 1-stop option, with an average round-trip price of $426.

What’s the fastest layover option from Midland to Chicago?

Shortest average travel time for 1-stop one-way flights from Midland to Chicago, based on itineraries clicked by Cheapflights users over the past 12 months, grouped by layover airport.

Flights via Dallas (DFW) have the shortest average one-way travel time for 1-stop routes: 4h 58m.

Which airport typically offers the quickest layover for flights from Midland to Chicago?

Average layover duration for 1-stop one-way flights from Midland to Chicago, chosen by Cheapflights users in the last 12 months, grouped by stopover airport.

Flights via Houston (IAH) offer the fastest connection on this route, with an average layover time of 0h 44m.

Reviews of airlines servicing Chicago

Get insights into the airlines that provide service to Chicago. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Chicago. Reviews last updated May 6, 2026.
Read reviews from past customers who have flown Southwest from Midland to Chicago. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
7.9
Good
4,305 reviews

Comfort

8.0

Entertainment

7.5

Food

7.0

Overall

7.9

Boarding

8.1

Crew

8.6

Reviews

1 / 20
6.0
Good

Scott,Feb 2026

HOU - FLL

Delayed by 45 minutes leaving Houston, making a 3.5 hour layover that much longer.
Southwest
7.9
Good
4,305 reviews
Southwest
7.9
Good
4,305 reviews

Comfort

8.0

Entertainment

7.5

Food

7.0

Overall

7.9

Boarding

8.1

Crew

8.6

Reviews

1 / 20
6.0
Good

Scott,Feb 2026

HOU - FLL

Delayed by 45 minutes leaving Houston, making a 3.5 hour layover that much longer.

Related info for your journey

Find useful and relevant information for your journey from Midland to Chicago. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What airport do you fly from for flights from Midland to Chicago?

    Midland Intl (MAF), located 8.2 mi from the city center, is the airport you fly out of when you book flights from Midland to Chicago. 2 airlines have flights from Midland Intl to Chicago on a regular basis. Booking flights from Midland Intl to Chicago should not be difficult; the airport handles an average of 0 outbound flights to Chicago per day.

  • How long is the flight from Midland to Chicago?

    United Airlines can get you from Midland to Chicago in just under 6h 01m. Your travel time can differ by up to . There are 1047 mi between Midland and Chicago.

  • What are the cheapest airlines flying from Midland to Chicago round-trip?

    American Airlines, at $296, was found to be the cheapest airline from Midland to Chicago. An alternate airline flying to your destination would be United Airlines. Users have found that American Airlines is 37% cheaper than the other options available to this destination.

  • Can I find deals for flights from Midland to Chicago that include hotel bookings?

    Yes. In addition to deals on Midland to Chicago flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Midland to Chicago?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Midland to Chicago.

  • Can I find deals for business class flights from Midland to Chicago?

    Yes. Cheapflights offers flight deals from Midland to Chicago by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

See more FAQs

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Benton Harbor
Lansing
Merrillville
Hammond
Porter

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Alternative routes for Midland to Chicago

See prices for flight routes from nearby airports that may be better suited for you.
Dallas/Fort Worth to O'Hare Intl flights
Hobby to O'Hare Intl flights
Dallas/Fort Worth to Midway flights
George Bush Intcntl to O'Hare Intl flights
Hobby to Midway flights
Austin to O'Hare Intl flights
George Bush Intcntl to Midway flights
Love Field to O'Hare Intl flights
San Antonio to O'Hare Intl flights
Austin to Midway flights
Love Field to Midway flights
Dallas/Fort Worth to St. Louis flights
Hobby to St. Louis flights
El Paso to O'Hare Intl flights
George Bush Intcntl to St. Louis flights
San Antonio to Midway flights
Austin to St. Louis flights
Love Field to St. Louis flights
El Paso to Midway flights
San Antonio to St. Louis flights
Dallas/Fort Worth to Peoria flights
Hobby to Moline flights
Dallas/Fort Worth to Bloomington flights
Austin to Peoria flights
Corpus Christi to O'Hare Intl flights
Austin to Rockford flights
Laredo to O'Hare Intl flights
McAllen to O'Hare Intl flights
Hobby to Bloomington flights
Hobby to Peoria flights
George Bush Intcntl to Peoria flights
Lubbock to O'Hare Intl flights
George Bush Intcntl to Moline flights
Austin to Moline flights
Dallas/Fort Worth to Decatur flights
San Antonio to Moline flights
George Bush Intcntl to Bloomington flights
Dallas/Fort Worth to Moline flights
McAllen to Midway flights
San Antonio to Champaign flights
Amarillo to O'Hare Intl flights
Midland to O'Hare Intl flights
Harlingen to O'Hare Intl flights
Dallas/Fort Worth to Champaign flights
Dallas/Fort Worth to Evansville flights
El Paso to St. Louis flights
Hobby to Rockford flights
Lubbock to St. Louis flights

Top 2 airlines flying from Midland to Chicago

Discover the top 2 airlines that operate flights from Midland to Chicago. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated May 6, 2026.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$296Average$539FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$426Average$451FlexibilityNo cancel feeOn-time69%

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