ORD - MAF

$127 Find Cheap Flights from Chicago to Midland

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Chicago to Midland departing on 10/11. 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.
1 adult
1 adult, Economy

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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Flight Deals

Cheap Flights from Chicago to Midland (ORD-MAF)

 
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.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Chicago to Midland

Fri, Oct 3 - Sun, Oct 5
American Airlines Logo
6:30 pm - 11:04 pmORD-MAF
4h 34m1 stop
American Airlines Logo
6:17 pm - 11:52 pmMAF-ORD
5h 35m1 stop
$217American Airlines
Find Deal
Sat, Oct 11 - Sat, Oct 18
American Airlines Logo
8:30 am - 7:10 pmORD-MAF
10h 40m1 stop
American Airlines Logo
8:10 am - 6:00 pmMAF-ORD
9h 50m1 stop
$243American Airlines
Find Deal
Tue, Oct 28 - Tue, Nov 4
American Airlines Logo
10:32 am - 7:10 pmORD-MAF
8h 38m1 stop
American Airlines Logo
12:25 pm - 9:21 pmMAF-ORD
8h 56m1 stop
$244American Airlines
Find Deal
Fri, Oct 3 - Sun, Oct 5
Delta Logo
11:20 am - 11:58 pmORD-MAF
12h 38m2 stops
Delta Logo
5:30 am - 2:20 pmMAF-ORD
8h 50m2 stops
$278Delta
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Wed, Feb 18 - Sat, Feb 21
American Airlines Logo
12:05 pm - 5:51 pmORD-MAF
5h 46m1 stop
American Airlines Logo
5:00 am - 9:36 amMAF-ORD
4h 36m1 stop
$286American Airlines
Find Deal
Tue, Oct 28 - Tue, Nov 4
Delta Logo
4:05 pm - 11:56 pmORD-MAF
7h 51m2 stops
Delta Logo
5:30 am - 4:41 pmMAF-ORD
11h 11m2 stops
$307Delta
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Thu, Oct 30 - Wed, Nov 5
Southwest Logo
2:50 pm - 11:50 pmORD-MAF
9h 00m2 stops
Southwest Logo
6:15 am - 1:00 pmMAF-ORD
6h 45m1 stop
$357Southwest
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Sat, Oct 11 - Sat, Oct 18
United Airlines Logo
6:00 am - 11:04 amORD-MAF
5h 04m1 stop
United Airlines Logo
5:00 am - 6:50 pmMAF-ORD
13h 50m2 stops
$410United Airlines
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Sun, Nov 16 - Mon, Nov 17
United Airlines Logo
7:10 am - 12:45 pmORD-MAF
5h 35m1 stop
United Airlines Logo
5:30 pm - 11:48 amMAF-ORD
18h 18m2 stops
$455United Airlines
Find Deal
Fri, Sep 26 - Sun, Sep 28
Southwest Logo
4:20 pm - 9:35 pmORD-MAF
5h 15m1 stop
Southwest Logo
6:10 am - 4:25 pmMAF-ORD
10h 15m2 stops
$560Southwest
Find Deal

Everything you should know

Top airlines
American Airlines
Cheapest • from $217 (round-trip)
United Airlines
Best reviews • 7.4 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
Cheapest round-trip
$217
Typical prices: $332-435
American Airlines
Fri 10/3Sun 10/5
ORD - MAF • 1 stop
Cheapest one-way
$127
Typical prices: $165-204
American Airlines
Sat 10/11
ORD - MAF • 1 stop
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KAYAK searches 100s of sites at once to find you the best travel deals.
We hope you love your trip to Midland!
Booking Insights

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
Cheapest flight$127
Best time to beat the crowds with an average 13% drop in price.
Most popular time to fly and prices are also 0% 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 $127 for a one-way ticket and $217 for a round-trip.

  • 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.

  • 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.

Reviews of the 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 8929 reviews
6.6Food
7.7Boarding
7.3Comfort
8.1Crew
7.1Entertainment
Airline reviews

Once we got in the air the pilot made up some of the time of the delay. So that was really nice.

10.0 ExcellentAnonymous, Aug 2025ORD - MEM
Read more United Airlines reviews

Once we got in the air the pilot made up some of the time of the delay. So that was really nice.

Excellent flight. Boarding was efficient and departure was on time. Smooth flight with on time arrival. Deplaning was also efficient.

It was delayed instead of departing at 9:20pm, we departed at 11pm… putting us in Columbus after 2am! It was awful. Had I known about the delay, I could have spent some time in the United Lounge… I was starving because I started my journey in Budapest… so I was exhausted and hungry. Plus I had to make new arrangements to be picked up at the airport in Columbus, instead of midnight it was 2:30 am after getting luggage and out of airport. Not feasible. I would have just stayed in Chicago for the night and gotten a morning flight.

It was great, I’m very grateful for the pilots and crew flight attendants for everything.

Evidently, my seat had the only broken TV. I couldn’t plug it in, get it to come on, or watch anything, and of course, no one could fix it while we were on the plane. The service was good and the boarding was quick

I was charged for my daughters bag when I am supposed to receive two free checked bags with my United Explorer card.

The schedule to Moline changed 5 times. The gate changed 6 times. That is a pathetic way to run an airline. No wonder that no one in our company flies on United Express to or from Moline. Changes happen most of the time. I learned my lesson on this trip…never again!

Flight was great. Efficient boarding. Short flight. Early arrival. Friendly flight crew. The entertainment system did not work well. Could not access it until the aircraft reached 10K feet or more. Lots of glitches.

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.

3 hour weather delay followed by 1 hour (and counting) maintenance delay. UGH!

After we'd boarded , they canceled the flight. The crew didn't even know , we just all received text messages. Then after they deplaned us , AA was just like "too bad, go F your self, we sure ain't gonna help you"

After a two hour delay, my flight was CANCELLED! No pilot available. Such BS.

Amazing food, great staff, with one noticable detail missing ...but no seat entertainment in any of aircraft ...I am not a fan

I wish American Airlines would change the airline industry by loading the plane back to front instead of front to back. Planes would board so much more smoothly and quickly.

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.

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

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