What is the cheapest airline to fly from Midland to Chicago Midway Airport round-trip?

Flying on Southwest is currently your cheapest option to Chicago Midway Airport, with prices starting at $216.

In terms of precipitation, rainfall in Chicago Midway Airport 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 Midway Airport when rainfall is around 1.7 in.

If weather is an important factor for your trip to Chicago Midway Airport, 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).

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

Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Midland to Chicago Midway Airport as you normally would.

Most accurate provider : When it comes to deals on Midland-Chicago Midway Airport flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Midland-Chicago Midway Airport flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Midland-Chicago Midway Airport flight searches over the past month and is updated monthly.

Most trusted provider : When it comes to deals on Midland-Chicago Midway Airport 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 Midway Airport flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

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

For a flight from Midland to Chicago Midway, you will be flying from Midland Intl. Midland Intl (MAF) is just 8.2 mi from the center of the city. Midland Intl is the only Midland airport and it handles 0 outbound flights to Chicago Midway per day. 1 airline has flights to Chicago Midway from Midland Intl on a regular basis.

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

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

How can I find direct flights from Midland to Midway?

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

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

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

Find Flights from Midland to Chicago Midway Airport

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Find flight deals from Midland to Midway

Most accurate provider	FlightHub 3 stars
Most trusted provider	FlightHub 3 stars
Popular in	January
Cheapest in	November
Average price	$472

Provider with most accurate pricing for Midland Intl-Chicago Midway flight deals.

Search Deals

Provider most trusted by Cheapflights users for Midland Intl-Chicago Midway flights.

Search Deals

Highest demand for flights based on searches. 38% potential increase in price ($308 potential increase over avg. RT price).

Search Deals

Cheapest flight prices on average. 9% potential price decrease ($45 potential savings vs. average RT price).

Search Deals

Average for round-trip flights in March 2026

Search Deals

Compare providers for flights from Midland to Midway

Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Midland to Midway in March.

Provider	Price Accuracy	Trust Score*
FlightHub	Price Accuracy3 stars	Trust Score*3 stars
Expedia	Price Accuracy1 star	Trust 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 Midway Airport flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Midland-Chicago Midway Airport flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Midland-Chicago Midway Airport flight searches over the past month and is updated monthly.
Most trusted provider: When it comes to deals on Midland-Chicago Midway Airport 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 Midway Airport 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 Midway

Have a flexible travel schedule? Discover the best time to fly to Midway from Midland with our price prediction graph.

MAF-MDW

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.

Reviews of airlines servicing Midway

Read reviews from past customers who have flown Southwest from Midland to Chicago Midway Airport. 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

4,306 reviews

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

4,306 reviews

Southwest

8.0

Very good

4,306 reviews

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

What airport do you fly from for flights from Midland to Chicago Midway?
For a flight from Midland to Chicago Midway, you will be flying from Midland Intl. Midland Intl (MAF) is just 8.2 mi from the center of the city. Midland Intl is the only Midland airport and it handles 0 outbound flights to Chicago Midway per day. 1 airline has flights to Chicago Midway from Midland Intl on a regular basis.
What is the cheapest airline to fly from Midland to Chicago Midway Airport round-trip?
Flying on Southwest is currently your cheapest option to Chicago Midway Airport, with prices starting at $216.
Can I find deals for flights from Midland to Midway that include hotel bookings?
Yes. In addition to deals on Midland to Midway flights, Cheapflights offers vacation packages that include both flights and hotel.
How can I find direct flights from Midland to Midway?
After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Midland to Midway.
Can I find deals for business class flights from Midland to Midway?
Yes. Cheapflights offers flight deals from Midland to Midway by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

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Top airline flying from Midland to Midway

Airline	Cheapest	Average	Flexibility	On-time
Southwest	Cheapest$216	Average$446	FlexibilityNo cancel fee	On-time63%

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Cheap flights from Midland (MAF) to Midway (MDW)

Find cheap flights from Midland to Midway with Cheapflights

1. Tell us where you want to go

2. Select your favorite providers

3. Compare prices and book

Find flight deals from Midland to Midway

Most accurate provider

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Popular in

Cheapest in

Average price

Compare providers for flights from Midland to Midway

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 Midway in March.

Best time to book a flight from Midland to Midway

Have a flexible travel schedule? Discover the best time to fly to Midway from Midland with our price prediction graph.

Reviews of airlines servicing Midway

Get insights into the airlines that provide service to Midway. 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 Midway. Reviews last updated March 2, 2026.

Read reviews from past customers who have flown Southwest from Midland to Chicago Midway Airport. 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.

Related info for your journey

Find useful and relevant information for your journey from Midland to Midway. 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 Midway?

What is the cheapest airline to fly from Midland to Chicago Midway Airport round-trip?

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

How can I find direct flights from Midland to Midway?

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

Traveling to a place near Chicago Midway Airport?

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Alternative routes for Midland to Midway

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Complete your trip

Complete your trip to Midway by adding a car rental and/or hotel reservation to your travel itinerary.

Search flights from Midland to Midway by cabin class

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Other flights to Midway

Explore flights to Midway departing from other origins. Flights are based on user searches made on Cheapflights and were last updated on March 2, 2026.

Midland and Midway flights

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Top airline flying from Midland to Midway

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