ORD - MAF

$168 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 3/4. 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, 0 bags

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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Everything you should know

Cheapest round-trip
$335
United Airlines
Tue 2/17Tue 2/24
ORD - MAF • 1 stop
Cheapest one-way
$168
United Airlines
Wed 3/4
ORD - MAF • 1 stop
Top airlines
United Airlines
Cheapest • from $335 (round-trip)
United Airlines
Best reviews • 7.4 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
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We hope you love your trip to Midland!
Flight Deals
Booking Insights
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

Tue, Feb 17 - Tue, Feb 24
United Airlines Logo
5:20 pm - 11:15 pm
ORD
-
MAF
5h 55m
1 stop
United Airlines Logo
7:00 am - 2:43 pm
MAF
-
ORD
7h 43m
1 stop
$335United Airlines
Tue, Feb 17 - Tue, Feb 24
Southwest Logo
2:15 pm - 10:35 pm
ORD
-
MAF
8h 20m
2 stops
Southwest Logo
6:40 am - 1:00 pm
MAF
-
ORD
6h 20m
1 stop
$340Southwest
Tue, Feb 17 - Tue, Feb 24
Southwest Logo
2:15 pm - 10:35 pm
ORD
-
MAF
8h 20m
2 stops
Southwest Logo
7:05 am - 1:00 pm
MAF
-
ORD
5h 55m
2 stops
$345Southwest
Thu, Feb 26 - Tue, Mar 3
American Airlines Logo
5:00 am - 11:52 am
ORD
-
MAF
6h 52m
1 stop
American Airlines Logo
5:00 am - 9:45 am
MAF
-
ORD
4h 45m
1 stop
$347American Airlines
Wed, Feb 18 - Mon, Feb 23
United Airlines Logo
10:35 am - 4:19 pm
ORD
-
MAF
5h 44m
1 stop
United Airlines Logo
7:03 pm - 12:26 am
MAF
-
ORD
5h 23m
1 stop
$348United Airlines
Fri, Apr 10 - Tue, Apr 14
United Airlines Logo
2:10 pm - 9:39 pm
ORD
-
MAF
7h 29m
1 stop
United Airlines Logo
5:00 am - 10:05 am
MAF
-
ORD
5h 05m
1 stop
$371United Airlines
Fri, Apr 10 - Tue, Apr 14
Southwest Logo
3:45 pm - 11:10 pm
ORD
-
MAF
7h 25m
2 stops
Southwest Logo
2:20 pm - 10:55 pm
MAF
-
ORD
8h 35m
1 stop
$376Southwest
Thu, Feb 19 - Fri, Feb 27
United Airlines Logo
7:10 am - 12:59 pm
ORD
-
MAF
5h 49m
1 stop
United Airlines Logo
7:03 pm - 12:26 am
MAF
-
ORD
5h 23m
1 stop
$383United Airlines
Sun, Apr 26 - Sat, May 2
Southwest Logo
3:45 pm - 11:30 pm
ORD
-
MAF
7h 45m
2 stops
Southwest Logo
5:30 am - 3:30 pm
MAF
-
ORD
10h 00m
2 stops
$393Southwest
Sun, Apr 26 - Sat, May 2
Southwest Logo
3:45 pm - 11:30 pm
ORD
-
MAF
7h 45m
2 stops
Southwest Logo
10:40 am - 11:25 pm
MAF
-
ORD
12h 45m
1 stop
$394Southwest
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.

Which airlines provide the cheapest flights from Chicago to Midland?

The cheapest round-trip price for the route for each airline clicked by KAYAK users in the last 72 hours.

In the past 3 days, the cheapest round-trip tickets from Chicago to Midland were found on United Airlines ($335) and Southwest ($340).

Good to know

Cheapest flight$168
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 $168 for a one-way ticket and $335 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?

    Star Alliance, and oneworld are the airline alliances operating flights between Chicago and Midland, with Star Alliance 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 $383 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 $377 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.

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 9215 reviews
7.1Entertainment
6.6Food
8.1Crew
7.3Comfort
7.7Boarding
Airline reviews

In overall it was a good experience, the only down point was that the entertainment screen was working properly.

8.0 ExcellentAnonymous, Jan 2026
ORD - TPA
Read more United Airlines reviews

In overall it was a good experience, the only down point was that the entertainment screen was working properly.

They lost my luggage, so, not happy. The crew was nice but my suitcases never made it, still trying to find out what happened!

I understand weather is an issue, but making us chase our plane down at five scheduled gates across three terminals in an airport the size of O'Hare was unfair. They'd have probably been better off to leave gates as TBD until the inbound plane is in final approach instead of running us all over the place. Also, props to the consistently-unprepared ground crew in Richmond for once again leaving my lane parked short of the gate because they couldn't have a crew in place on time with 2 hours notice...

cabin crew was OK, food was OK, the trip from the US to Munich was actually pretty bad comfort wise. Noisy aircraft, lights never dimmed even in Business class (night flight) barely sufficient amenities for the price. I have millions of miles with United but TBH American is gaining ground and Delta has always been marginally better then United although on paper United has more longes and cheaper upgrades.

Essy to get on. The hostess gave very little pop, the plane was late getting in, and we are still waiting for our bags. This sucks. :/

Great flight. On time boarding. Smooth flight and on time arrival at EWR. The flight crew was marvelous and there was a great selection of movies on the entertainment system. Our bags were at the carousel before we got there. Another excellent flight from United.

I liked the snacks and the flight attendants were friendly.

After a delay at the gate, C3, at Ohare on Sunday, I left my Blk ski coat on the bench at the gate, lost! Please review my lob claim, thx.

Very thoughtful flight attendant offered me water immediately since I had run to make my connection.

Always wish for more healthy, gluten free options. We have to bring our own.

The aircraft had several problems - from excess fuel to non operational ac. Two hours of delay in Chicago could have been avoided with proper planning and aircraft maintenance.

Crew in Columbia was not prepared for landing. It was a bit of a disaster and getting bags took forever.

We were upgraded to First Class and it was a great flight

We experienced gate changes and a long delay. My seat was dirty when I boarded and I had to use wipes to clean it myself. There was an unpleasant and overpowering cleaning product scent on the plane as well that lingered through the flight.

My carry on baggage was damaged. Entire trip, I had to carry the baggage. When complained to the boarding crew, they got mad at me and still asked me to valet check in the cabin baggage. Rude boarding crew!!!

Crew were all friendly and helpful. It was a short flight so just a beverage service with a cookie. After we were boarded the plane took about 45 minutes to leave the gate but it was New Year’s Eve so not shocking there was some delay. Overall good experience and very grateful.

The boarding process needs to be fixed. The zone don't work, especially when there is hardly anyone in zones 3, 4,and 5, leaving the majority of the passengers backed up in the aisle, especially because passengers seated near the front are blocking passengers who are seated in the rear of the plane. It would also help if the size of carry on bags was more strictly enforced.

The boarding by groups is pointless. The first two groups worked fine, but almost Noone boarded in goups three thru five leaving the vast majority boarding when group six was called. It defeated the purpose of spreading out the crowd.

We loved the steward on the plane. He made the night enjoyable

The plane was late, when we did board the plane was as cold as a freezer. I was freezing the entire flight, no blankets. Lost miserable flight I’ve ever had.

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

Information on your arrival and departure airports