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$347+ Cheap flights from Midland (MAF) to Chicago (CHI)

This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 3/30. Fares are subject to change and may not be available on all flights or dates of travel.
MAF — CHI
Feb 28 — Mar 71
Sat 2/28
Sat 3/7
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 January 29, 2026.

This Southwest deal was found by Cheapflights users on 1/26. 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 3/303:20 pm
MAF
-
ORD
1 stop7h 35m
Southwest
Wed 4/14:15 pm
ORD
-
MAF
1 stop5h 50m
Southwest
Deal found 1/26$347
This United Airlines deal was found by Cheapflights users on 1/26. 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 3/297:00 pm
MAF
-
ORD
1 stop5h 45m
United Airlines
Wed 4/14:03 pm
ORD
-
MAF
1 stop5h 36m
United Airlines
Deal found 1/26$398
This Southwest deal was found by Cheapflights users on 1/28. 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.
Thu 8/205:50 am
MAF
-
ORD
1 stop6h 20m
Southwest
Tue 8/252:55 pm
ORD
-
MAF
1 stop6h 50m
Southwest
Deal found 1/28$407
This American Airlines deal was found by Cheapflights users on 1/27. 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 5/116:16 pm
MAF
-
ORD
1 stop5h 28m
American Airlines
Sun 5/178:09 am
ORD
-
MAF
1 stop5h 36m
American Airlines
Deal found 1/27$443
This Southwest deal was found by Cheapflights users on 1/26. 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.
Sun 3/295:30 am
MAF
-
ORD
2 stops7h 20m
Southwest
Wed 4/16:15 am
ORD
-
MAF
1 stop7h 25m
Southwest
Deal found 1/26$481

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 January 29, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$347
(Southwest)

Popular in

January

Cheapest in

November

Average price

$977
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
Highest demand for flights based on searches. 36% potential increase in price ($292 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 9% potential price decrease ($43 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in January 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 January 29, 2026.
Use the filters below to find and compare flights from Midland to Chicago that are best for you.

Fly from

Midland

Fly to

Chicago

Route

Depart

Return

Price

MidlandChicago

MAF - ORD

MAFORD

Midland Intl

Mon 3/30

3:20 pm-10:55 pm

1 stop7h 35m

Chicago O'Hare Intl

Wed 4/1

6:15 am-1:40 pm

1 stop7h 25m

$347

MidlandChicago

MAF - ORD

MAFORD

Midland Intl

Sun 3/29

7:00 pm-12:45 am

1 stop5h 45m

Chicago O'Hare Intl

Wed 4/1

4:03 pm-9:39 pm

1 stop5h 36m

$398

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

2:40 pm-10:55 pm

2 stops8h 15m

$486

MidlandChicago

MAF - ORD

MAFORD

Midland Intl

Fri 2/13

5:31 pm-12:26 am

1 stop6h 55m

Chicago O'Hare Intl

Tue 2/17

2:00 pm-9:44 pm

1 stop7h 44m

$487

MidlandChicago

MAF - ORD

MAFORD

Midland Intl

Mon 5/11

7:00 pm-9:32 am

2 stops14h 32m

Chicago O'Hare Intl

Sun 5/17

5:30 am-11:21 am

1 stop5h 51m

$492

MidlandChicago

MAF - ORD

MAFORD

Midland Intl

Fri 2/13

5:30 am-1:00 pm

1 stop7h 30m

Chicago O'Hare Intl

Tue 2/17

2:15 pm-10:35 pm

2 stops8h 20m

$502

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/28

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 January.
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

What is the cheapest month to book a flight from Midland to Chicago?

Currently, August is the cheapest month in which you can book a flight from Midland to Chicago (average of $219). Flying from Midland to Chicago in February is currently the most expensive (average of $901). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

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 January 29, 2026.
Read reviews from past customers who have flown Southwest and American Airlines 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
4,267 reviews

Crew

8.6

Food

7.0

Boarding

8.1

Overall

8.0

Comfort

8.0

Entertainment

7.5

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
Southwest
8.0
Very good
4,267 reviews
Southwest
8.0
Very good
4,267 reviews

Crew

8.6

Food

7.0

Boarding

8.1

Overall

8.0

Comfort

8.0

Entertainment

7.5

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
American Airlines
7.2
Good
11,205 reviews
Southwest
8.0
Very good
4,267 reviews

Crew

8.6

Food

7.0

Boarding

8.1

Overall

8.0

Comfort

8.0

Entertainment

7.5

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.

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 and United Airlines can get you from Midland to Chicago in just under 5h 45m. Your travel time can differ by up to 1h 50m. 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 57% 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.

  • What is the cheapest month to book a flight from Midland to Chicago?

    Currently, August is the cheapest month in which you can book a flight from Midland to Chicago (average of $219). Flying from Midland to Chicago in February is currently the most expensive (average of $901). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

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
Benton Harbor

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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 January 29, 2026.
AirlineCheapestAverageFlexibilityOn-time
SouthwestCheapest$216Average$446FlexibilityNo cancel feeOn-time63%
American AirlinesCheapest$255Average$365FlexibilityNo cancel feeOn-time71%

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