ORD - MAF

$297 Find Cheap Flights from Chicago to Midland

This is the cheapest round-trip flight price found by a KAYAK user in the last 72 hours by searching for a flight from Chicago to Midland departing on 6/14. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
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KAYAK searches hundreds of travel sites at once for deals on flights to Midland

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to Midland, as well as popular online travel agencies
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to Midland, as well as popular online travel agencies
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Cheap Flights from Chicago to Midland

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Chicago to Midland that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.

Recent round-trip flight deals from Chicago to Midland

KAYAK's recommended round-trip deals from the most popular airlines that fly from Chicago to Midland.
Discover the best prices for you by selecting your travel dates on KAYAK.
American Airlines Logo
2:40 pm - 7:57 pmORD-MAF
5h 17m1 stop
American Airlines Logo
6:00 am - 10:55 amMAF-ORD
4h 55m1 stop
$297American Airlines
Find Deal
Sat, Jun 14 - Sat, Jun 21
American Airlines Logo
6:30 pm - 11:59 pmORD-MAF
5h 29m1 stop
American Airlines Logo
8:28 pm - 12:59 amMAF-ORD
4h 31m1 stop
$298American Airlines
Find Deal
Sat, Jun 14 - Sat, Jun 21
American Airlines Logo
5:00 am - 9:57 amORD-MAF
4h 57m1 stop
American Airlines Logo
10:27 am - 5:11 pmMAF-ORD
6h 44m1 stop
$301American Airlines
Find Deal
Sat, Jun 14 - Sat, Jun 21
Delta Logo
6:00 am - 4:55 pmORD-MAF
10h 55m2 stops
Delta Logo
5:30 am - 2:35 pmMAF-ORD
9h 05m2 stops
$307Delta
Find Deal
Sat, Jun 14 - Sat, Jun 21
American Airlines Logo
3:52 pm - 10:18 pmORD-MAF
6h 26m1 stop
American Airlines Logo
7:36 am - 1:20 pmMAF-ORD
5h 44m1 stop
$333American Airlines
Find Deal
Fri, Jun 20 - Sat, Jun 21
Delta Logo
5:35 am - 4:34 pmORD-MAF
10h 59m2 stops
Delta Logo
5:30 am - 2:35 pmMAF-ORD
9h 05m2 stops
$343Delta
Find Deal
Fri, Jun 20 - Sat, Jun 21
Delta Logo
3:57 pm - 12:02 amORD-MAF
8h 05m2 stops
Delta Logo
5:29 am - 4:45 pmMAF-ORD
11h 16m2 stops
$354Delta
Find Deal
Fri, May 23 - Mon, May 26
United Airlines Logo
2:26 pm - 9:54 pmORD-MAF
7h 28m1 stop
United Airlines Logo
7:12 pm - 12:13 amMAF-ORD
5h 01m1 stop
$358United Airlines
Find Deal
Fri, May 23 - Mon, May 26
United Airlines Logo
7:50 pm - 8:51 amORD-MAF
13h 01m2 stops
United Airlines Logo
9:00 am - 3:05 pmMAF-ORD
6h 05m1 stop
$417United Airlines
Find Deal
Sat, Jun 14 - Sat, Jun 21
Southwest Logo
5:45 pm - 11:15 pmORD-MAF
5h 30m1 stop
Southwest Logo
9:55 am - 4:25 pmMAF-ORD
6h 30m2 stops
$473Southwest
Find Deal
Fri, May 23 - Mon, May 26
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KAYAK's insights & trends for Chicago to Midland flights

Get data-powered insights and trends into flights from Chicago to Midland to help you find the cheapest flights, the best time to fly and much more.

What’s the cheapest day of the week to fly from Chicago to Midland?

The average price of all round-trip flights from Chicago O'Hare Intl Airport to Midland clicked on KAYAK for each day over the last 12 months.

For Chicago to Midland, Wednesday is the cheapest day to fly on average and Sunday is the most expensive. Flying from Midland back to Chicago, the best deals are generally found on Tuesday, with Saturday being the most expensive.

Good to know

Low seasonMay
High seasonJuly
Cheapest flight$297
Best time to beat the crowds with an average 21% drop in price.
Most popular time to fly and prices are also 14% lower on average.
Flight from Chicago to Midland

When to book flights from Chicago to Midland

Are your dates flexible? Find out the best times to travel from Chicago to Midland based on our flight data from the last year. Discover the cheapest month and even day to fly.
Estimated round-trip price
KAYAK looks at all historical flight data for each date to provide a predicted price for one-way trips or round-trips with a duration up to 40 days. While we try to provide actual minimum prices for each date, some prices are predictions and actual prices may differ.

FAQs for booking Chicago to Midland flights

  • What is the cheapest flight from Chicago O'Hare Intl Airport to Midland?

    In the last 3 days, the lowest price for a flight from Chicago O'Hare Intl Airport to Midland was $297 for a round-trip ticket.

  • Do I need a passport to fly between Chicago and Midland?

    A passport is not required to fly from Chicago to Midland.

  • Which aircraft models fly most regularly from Chicago to Midland?

    We unfortunately don’t have that data for this specific route.

  • Which airline alliances offer flights from Chicago to Midland?

    oneworld, SkyTeam, and Star Alliance are the airline alliances operating flights between Chicago and Midland, with SkyTeam being the most commonly used for this route.

  • Which is the best airline for flights from Chicago to Midland, United Airlines or American Airlines?

    The two airlines most popular with KAYAK users for flights from Chicago to Midland are United Airlines and American Airlines. With an average price for the route of $410 and an overall rating of 7.4, United Airlines is the most popular choice. American Airlines is also a great choice for the route, with an average price of $416 and an overall rating of 7.2.

  • How does KAYAK find such low prices on flights from Chicago to Midland?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Chicago to Midland.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Chicago to Midland?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Midland from Chicago is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights from Chicago to Midland?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly to Midland with an airline and back to Chicago with another airline. Booking your flights between Chicago and MAF can sometimes prove cheaper using this method.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Chicago to Midland?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying to Midland from Chicago up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

Top airlines flying from Chicago to Midland

 
See real verified KAYAK customer reviews for airlines flying from Chicago to Midland. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
Need help choosing which airline to fly with from Chicago to Midland? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
7.4
United AirlinesOverall score based on 8696 reviews
7.3Comfort
6.6Food
8.1Crew
7.1Entertainment
7.7Boarding
Airline reviews

A bit rush for transit. Food and entertainment are not available

8.0 ExcellentAnonymous, Apr 2025ORD - SFO
Read more United Airlines reviews

A bit rush for transit. Food and entertainment are not available

Smooth boarding process. Early departure, smooth flight, early arrival. The entertainment package has very good recent movie options. The flight crew were friendly and professional.

My flight was scheduled for about 6:05 departure. There were 11 gate changes from 4-7pm and the flight was 3 hours delayed due to operational issues. The plane taxied around the airport for about half an hour before stopping to be de-iced. It would have been nice if we were alerted of the plan to de-ice prior to the 30 minute drive around the airport. The flight attendant was friendly, which was the only redeeming thing about this flight. As a former flight attendant for United, I was extremely disappointed.

Delays took 2hours and thirty minutes making me miss my connecting flight and make me sit in the Chicago airport for 9 hours

Had a short delay once we boarded the aircraft in Chicago, but it was fixed in no time flat then we were on our way. The pilot was able to make up the time lost and we landed 5 minute later then schedualed . Great service

Our seats were all the way in back of the plane,

The seats on this flight were almost roomy enough to be the basic amount needed for human existence. I think my favorite part of this flight was it landed at an A gate, which was the most palatial part of Sea-Tac I've ever seen - a massive improvement from the S gates.

The seats on this flight were almost roomy enough to be the basic amount needed for human existence.

The flight attendants in First Class were mediocre at best. They did not take our tray away until we were about to land and only did so when I press the call button. The United person at the United Club was asked to get us our boarding pass since we missed the flight due in Chicago. She argued that we did not have seats on the flight given to us in Moline. Furthermore, she was adamant that we did not have a First Class ticket. After I spent much time with her trying to show we were correct, she reluctantly agreed. She was probably the most incompetent ticketing person I have ever met and I have traveled 3 million miles on United plus many additional miles with other carriers. United has definitely deteriorated in more than on way.

Short flight - no food understandable. Flight was delayed for over an hour. Overall, it was good.

I have long legs, my foot was out in the aisle and when a flight attendant came walking by and I didn't notice, instead of saying "excuse me" or anything like that, she kicked my foot. Extremely rude

Excellent! The gate agents were kind enough to rebook me on an earlier flight saving me from a 6 hour layover. Even my luggage made it despite the fact that the connection was technically too narrow. The flight itself was very comfortable, roomy, and clean. Plenty of space for my carryon items with plugs to charge my phone. After a long international flight of 14 hours, this was an excellent way to end my travels!

Great experience. Flight boarded easily. Departed early. Smooth flight. Great arrival in DC--almost no taxing! Almost direct to gate from runway. Crew was terrific. Same cookies and beverages in main cabin. I did not use the entertainment system on this flight.

Most of the delay was due to weather which is not what was at issue here. One delay was due to a missing flashlight and in the end the flashlight was actually found on the plane. The entertainment system is very limited. Live TV options offer only a few channels that are not very appealing. Boarding and deplaning are always difficult. It just takes too much time to get on and off the plane. On the plus side, I missed my connecting flight, but was easily able to book a later flight from the app while enroute.

You were more on time than United. I'm so over united delays.

The meals were mediocre and the alcohol selection was poor. I enjoyed the selection of movies and other entertainment.

I chatted with the captain before the flight, and similarly during the welcome announcement, he warned of a turbulent flight that may impact the in-flight service. However, once at altitude, he announced that the weather changed and he immediately turned off the seatbelt sign. But it appeared the cabin crew had already decided to take off this flight. They remained seated and then just chatted in the galley. The flight was fully catered, but only first class received service.

My flight attendant was attentive! The elderly person next to me was flatulent and the flight attendant could see that I was in distress and brought me some face masks

My boarding pass wouldn't pull up in the app very easily and had to really dig through my email. That caused a delay in TSA..

I had a TERRIBLE experience with the AA crew. I believe it was disability-related. It’s unlikely I will fly AA again.

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

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