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$307+ 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 5/1. Fares are subject to change and may not be available on all flights or dates of travel.
MAF — CHI
Feb 2 — Feb 91
Sun 2/2
Sun 2/9
1 adult, Economy
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Cheap 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 28, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$307
(Southwest)
Provider with most accurate pricing for Midland Intl-Chicago (CHI) flight deals.
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Provider most trusted by Cheapflights users for Midland Intl-Chicago (CHI) flights.
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From Midland Intl to Chicago (CHI)
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Find 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 28, 2025.

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 5/12:10 pmMAF - ORD
1 stop8h 55mSouthwest
Mon 5/57:00 amORD - MAF
1 stop8h 50mSouthwest
Deal found 1/28$307
This United 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/44:56 pmMAF - ORD
1 stop6h 02mUnited Airlines
Fri 3/74:00 pmORD - MAF
1 stop7h 31mUnited Airlines
Deal found 1/27$352
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/45:25 amMAF - ORD
2 stops8h 24mDelta
Fri 3/711:15 amORD - MAF
2 stops13h 02mDelta
Deal found 1/27$362
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.
Sat 8/3010:18 amMAF - ORD
1 stop7h 06mAmerican Airlines
Thu 9/43:15 pmORD - MAF
1 stop4h 51mAmerican Airlines
Deal found 1/27$387

Find flights from Midland to Chicago within your budget

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 28, 2025.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

MidlandChicago

MAF - ORD

MAFORD

Midland Intl

Thu 5/1

2:10 pm-11:05 pm

1 stop8h 55m

Chicago O'Hare Intl

Mon 5/5

7:00 am-3:50 pm

1 stop8h 50m

$307

MidlandChicago

MAF - ORD

MAFORD

Midland Intl

Tue 3/4

4:56 pm-10:58 pm

1 stop6h 02m

Chicago O'Hare Intl

Fri 3/7

4:00 pm-11:31 pm

1 stop7h 31m

$352

MidlandChicago

MAF - ORD

MAFORD

Midland Intl

Tue 3/4

5:25 am-1:49 pm

2 stops8h 24m

Chicago O'Hare Intl

Fri 3/7

11:15 am-12:17 am

2 stops13h 02m

$362

MidlandChicago

MAF - ORD

MAFORD

Midland Intl

Fri 2/7

7:10 pm-12:15 am

1 stop5h 05m

$374

MidlandChicago

MAF - ORD

MAFORD

Midland Intl

Fri 2/7

1:07 pm-11:49 pm

2 stops10h 42m

$379

MidlandChicago

MAF - ORD

MAFORD

Midland Intl

Fri 2/7

7:21 am-5:05 pm

3 stops33h 44m

$1,045

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/27

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
eDreamsPrice Accuracy3 starsTrust Score*3 stars
PricelinePrice Accuracy1 starTrust 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.

Travel insights for flights from Midland to Chicago

Get recent, data-driven insights about flights from Midland to Chicago including ideal travel times, pricing trends, and more.

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 $245). Flying from Midland to Chicago in March is currently the most expensive (average of $325). 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.

What is the cheapest time of day to fly from MAF to CHI?

Find hourly flight availability from Midland to Chicago. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated January 28, 2025.

It’s typically best to fly out from Midland to Chicago in the afternoon. Doing so could potentially save you 47% on the flight price compared to flying in the morning, which is usually more expensive.

Rainfall in Chicago by month

Plan your trip to Chicago by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Chicago ranges from 1.7 - 4.9 inches per month. August is typically the wettest month, when rainfall can reach 4.9 in. January is typically the driest time to visit Chicago when rainfall is around 1.7 in.

Temperature in Chicago by month

Plan your trip to Chicago by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Chicago, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 73.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 23.0 F).

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 28, 2025.
Read through reviews of airlines operating flights from Midland to Chicago, such as Southwest, Alaska Airlines and Delta. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.1
Very good
4,608 reviews

Overall

8.1

Crew

8.7

Entertainment

7.7

Comfort

8.1

Boarding

8.2

Food

7.1

Reviews

1 / 20

8.0
Excellent

Justin,May 2024

AUS - SAN

Wish the there were an electrical outlet to plug the phone. it died within 10 minutes of being in the air.

Southwest
8.1
Very good
4,608 reviews
Southwest
8.1
Very good
4,608 reviews

Overall

8.1

Crew

8.7

Entertainment

7.7

Comfort

8.1

Boarding

8.2

Food

7.1

Reviews

1 / 20

8.0
Excellent

Justin,May 2024

AUS - SAN

Wish the there were an electrical outlet to plug the phone. it died within 10 minutes of being in the air.

Alaska Airlines
8.0
Very good
9,690 reviews
Southwest
8.1
Very good
4,608 reviews

Overall

8.1

Crew

8.7

Entertainment

7.7

Comfort

8.1

Boarding

8.2

Food

7.1

Reviews

1 / 20

8.0
Excellent

Justin,May 2024

AUS - SAN

Wish the there were an electrical outlet to plug the phone. it died within 10 minutes of being in the air.

Delta
8.0
Very good
8,468 reviews
Southwest
8.1
Very good
4,608 reviews

Overall

8.1

Crew

8.7

Entertainment

7.7

Comfort

8.1

Boarding

8.2

Food

7.1

Reviews

1 / 20

8.0
Excellent

Justin,May 2024

AUS - SAN

Wish the there were an electrical outlet to plug the phone. it died within 10 minutes of being in the air.

United Airlines
7.4
Good
8,934 reviews
Southwest
8.1
Very good
4,608 reviews

Overall

8.1

Crew

8.7

Entertainment

7.7

Comfort

8.1

Boarding

8.2

Food

7.1

Reviews

1 / 20

8.0
Excellent

Justin,May 2024

AUS - SAN

Wish the there were an electrical outlet to plug the phone. it died within 10 minutes of being in the air.

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.

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

    Southwest, at $307, was found to be the cheapest airline from Midland to Chicago.Alternate airlines to your destination round-trip include United Airlines and Delta.

  • What are the cheapest airlines to fly from Midland to Chicago one-way?

    To fly one-way, consider booking your trip with United Airlines, which is currently one of the cheapest options available, starting at $374. Delta flights start at $379 while deals on Alaska Airlines start at $1,045 one-way.

  • 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 $245). Flying from Midland to Chicago in March is currently the most expensive (average of $325). 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 Midland?

Book flights to Midland if you plan to visit one of these locations
Merrillville
New Buffalo
Hammond
Benton Harbor
Porter
Lansing
Valparaiso
Chesterton

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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 28, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$276Average$347FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$381Average$496FlexibilityNo cancel feeOn-time63%
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