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$254+ 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 4/3. Fares are subject to change and may not be available on all flights or dates of travel.
MAF — CHI
Apr 23 — Apr 301
Thu 4/23
Thu 4/30
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 March 24, 2026.

This American Airlines deal was found by Cheapflights users on 3/23. 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.
Mon 5/112:15 pm
MAF
-
ORD
1 stop6h 59m
American Airlines
Sun 5/176:05 am
ORD
-
MAF
1 stop6h 11m
American Airlines
Deal found 3/23$386
This Southwest deal was found by Cheapflights users on 3/20. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/209:50 am
MAF
-
ORD
1 stop5h 40m
Southwest
Mon 4/274:15 pm
ORD
-
MAF
1 stop6h 55m
Southwest
Deal found 3/20$405
This Southwest deal was found by Cheapflights users on 3/20. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/119:50 am
MAF
-
ORD
1 stop5h 40m
Southwest
Fri 5/154:15 pm
ORD
-
MAF
1 stop6h 55m
Southwest
Deal found 3/20$416
This United Airlines deal was found by Cheapflights users on 3/20. 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.
Fri 4/177:00 pm
MAF
-
ORD
1 stop5h 45m
United Airlines
Fri 4/245:15 pm
ORD
-
MAF
1 stop6h 00m
United Airlines
Deal found 3/20$437
This United Airlines deal was found by Cheapflights users on 3/19. 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 5/122:13 pm
MAF
-
ORD
1 stop7h 38m
United Airlines
Wed 5/132:10 pm
ORD
-
MAF
1 stop7h 36m
United Airlines
Deal found 3/19$441

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 March 24, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$365
(United Airlines)

One-way from

$254
(United Airlines)

Popular in

January

Cheapest in

November

Average price

$421
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. 43% potential increase in price ($363 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 12% potential price decrease ($52 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in March 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 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

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

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

MidlandChicago

MAF - ORD

MAFORD

Midland Intl

Tue 5/12

2:13 pm-9:51 pm

1 stop7h 38m

Chicago O'Hare Intl

Wed 5/13

2:10 pm-9:46 pm

1 stop7h 36m

$441

MidlandChicago

MAF - ORD

MAFORD

Midland Intl

Fri 4/17

6:50 am-3:00 pm

1 stop8h 10m

Chicago O'Hare Intl

Fri 4/24

2:40 pm-11:10 pm

2 stops8h 30m

$442

MidlandChicago

MAF - ORD

MAFORD

Midland Intl

Sat 6/27

6:47 pm-12:42 am

1 stop5h 55m

Chicago O'Hare Intl

Sun 6/28

6:00 am-1:51 pm

1 stop7h 51m

$456

MidlandChicago

MAF - ORD

MAFORD

Midland Intl

Fri 4/17

6:50 am-3:00 pm

1 stop8h 10m

Chicago O'Hare Intl

Sun 4/19

3:45 pm-11:30 pm

2 stops7h 45m

$462
Quickest round-trip

MidlandChicago

MAF - ORD

MAFORD

Midland Intl

Mon 4/6

5:07 pm-10:54 pm

1 stop5h 47m

Chicago O'Hare Intl

Thu 4/9

10:49 am-4:26 pm

1 stop5h 37m

$507
Cheapest one-way

MidlandChicago

MAF - ORD

MAFORD

Midland Intl

Fri 4/3

1:45 pm-8:14 pm

1 stop6h 29m

$254
Quickest one-way

MidlandChicago

MAF - ORD

MAFORD

Midland Intl

Mon 4/6

7:00 pm-1:26 am

1 stop6h 26m

$254

Flights are sorted by cheapest round-trip flights first.

Deals found on 3/19

Showing 1-10 of 15 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 March.
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
No data available for this route at this time. Please check back soon.

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 March 24, 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
8.0
Very good
4,331 reviews

Food

7.0

Entertainment

7.5

Overall

8.0

Comfort

8.0

Crew

8.6

Boarding

8.1

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
8.0
Very good
4,331 reviews
Southwest
8.0
Very good
4,331 reviews

Food

7.0

Entertainment

7.5

Overall

8.0

Comfort

8.0

Crew

8.6

Boarding

8.1

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?

    Southwest, American Airlines, and United Airlines can get you from Midland to Chicago in just under 7h 15m. Your travel time can differ by up to 23m. There are 1047 mi between Midland and Chicago. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.

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

    Southwest, at $216, was found to be the cheapest airline from Midland to Chicago. An alternate airline flying to your destination would be American Airlines. Users have found that Southwest is 53% 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
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.
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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 March 24, 2026.
AirlineCheapestAverageFlexibilityOn-time
SouthwestCheapest$216Average$446FlexibilityNo cancel feeOn-time63%
American AirlinesCheapest$241Average$365FlexibilityNo cancel feeOn-time71%

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