MAF - ORD

$244 Find Cheap Flights from Midland to Chicago

This is the cheapest round-trip flight price found by a KAYAK user in the last 72 hours by searching for a flight from Midland to Chicago departing on 10/30. 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 Chicago O'Hare Intl Airport

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

Cheap Flights from Midland to Chicago (MAF-ORD)

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Midland to Chicago 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 Midland to Chicago

Thu, Oct 30 - Mon, Nov 3
American Airlines Logo
6:00 am - 3:06 pmMAF-ORD
9h 06m1 stop
American Airlines Logo
10:05 pm - 8:41 amORD-MAF
10h 36m1 stop
$244American Airlines
Find Deal
Thu, Oct 30 - Mon, Nov 3
Delta Logo
5:30 am - 4:41 pmMAF-ORD
11h 11m2 stops
Delta Logo
8:55 am - 4:31 pmORD-MAF
7h 36m2 stops
$337Delta
Find Deal
Thu, Oct 30 - Mon, Nov 3
Southwest Logo
4:30 pm - 9:30 pmMAF-ORD
5h 00m1 stop
Southwest Logo
2:15 pm - 10:10 pmORD-MAF
7h 55m2 stops
$402Southwest
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Fri, Oct 17 - Mon, Oct 20
Southwest Logo
4:30 pm - 9:30 pmMAF-ORD
5h 00m1 stop
Southwest Logo
5:45 pm - 10:55 pmORD-MAF
5h 10m1 stop
$427Southwest
Find Deal
Thu, Oct 9 - Wed, Oct 15
American Airlines Logo
5:00 am - 10:06 amMAF-ORD
5h 06m1 stop
American Airlines Logo
12:03 pm - 10:34 pmORD-MAF
10h 31m1 stop
$433American Airlines
Find Deal
Fri, Oct 17 - Mon, Oct 20
Southwest Logo
4:30 pm - 9:30 pmMAF-ORD
5h 00m1 stop
Southwest Logo
2:50 pm - 11:50 pmORD-MAF
9h 00m2 stops
$452Southwest
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Mon, Sep 29 - Fri, Oct 3
American Airlines Logo
6:39 pm - 11:17 pmMAF-ORD
4h 38m1 stop
American Airlines Logo
5:16 pm - 10:12 pmORD-MAF
4h 56m1 stop
$467American Airlines
Find Deal
Mon, Sep 29 - Fri, Oct 3
Delta Logo
5:30 am - 4:20 pmMAF-ORD
10h 50m2 stops
Delta Logo
3:35 pm - 11:58 pmORD-MAF
8h 23m2 stops
$477Delta
Find Deal
Tue, Sep 30 - Sat, Oct 4
United Airlines Logo
5:00 am - 3:43 pmMAF-ORD
10h 43m2 stops
United Airlines Logo
5:01 am - 12:57 pmORD-MAF
7h 56m1 stop
$513United Airlines
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Fri, Sep 26 - Sun, Sep 28
United Airlines Logo
2:01 pm - 7:55 pmMAF-ORD
5h 54m1 stop
United Airlines Logo
7:10 am - 2:02 pmORD-MAF
6h 52m1 stop
$571United Airlines
Find Deal

Everything you should know

Top airlines
American Airlines
Cheapest • from $244 (round-trip)
Southwest
Best reviews • 8.0 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
When to travel
August
Cheapest • 50% price drop
December
Most popular
Good to know
Good to know
+1
+1
Good to know
Good to know
+1
Cheapest round-trip
$244
Typical prices: $397-453
American Airlines
Thu 10/30Mon 11/3
MAF - ORD • 1 stop
Cheapest one-way
Multiple Airlines
Tue 9/16
MAF - ORD • multi-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 Chicago!
Booking Insights

KAYAK's insights & trends for Midland to Chicago flights

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

How much is a round-trip flight from Midland to Chicago O'Hare Intl Airport?

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

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

When flying from Midland to Chicago, you should consider leaving on a Tuesday and avoid Saturdays if you are looking for the best rates. For your return to Midland, you’ll find the best rates on Wednesdays and the most expensive ones on Sundays.

What is the cheapest month to fly from Midland to Chicago O'Hare Intl Airport?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Midland to Chicago O'Hare Intl Airport, removes the top 0.1% to account for outliers, and then takes the median of all values for each month.

The cheapest month for flights from Midland to Chicago O'Hare Intl Airport is August, where tickets cost $290 (return) on average. On the other hand, the most expensive months are February and April, where the average cost of round-trip tickets is $1,514 and $926 respectively.

Good to know

Low seasonMarch
Cheapest flight$244
Best time to beat the crowds with an average 7% drop in price.
Most popular time to fly and prices are also 27% lower on average.
Flight from Midland to Chicago

When to book flights from Midland to Chicago

Are your dates flexible? Find out the best times to travel from Midland to Chicago 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 Midland to Chicago flights

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

    In the last 3 days, the lowest price for a flight from Midland to Chicago O'Hare Intl Airport was $244 for a round-trip ticket.

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

    No, a passport isn't needed to fly from Midland to Chicago. However, local authorities might ask for an official ID.

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

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

  • Which airline alliances offer flights from Midland to Chicago?

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

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

    The two airlines most popular with KAYAK users for flights from Midland to Chicago are Southwest and American Airlines. With an average price for the route of $496 and an overall rating of 8.0, Southwest is the most popular choice. American Airlines is also a great choice for the route, with an average price of $372 and an overall rating of 7.2.

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

    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 Midland to Chicago.

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

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Chicago from Midland 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 Midland to Chicago?

    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 Chicago with an airline and back to Midland with another airline. Booking your flights between Midland and ORD 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 Midland to Chicago?

    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 Chicago from Midland 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 Midland to Chicago

 
See real verified KAYAK customer reviews for airlines flying from Midland to Chicago. 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 Midland to Chicago? 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.
8.0
SouthwestOverall score based on 4242 reviews
8.1Boarding
8.6Crew
7.5Entertainment
7.0Food
8.0Comfort
Airline reviews

AC sub par. WiFi not working correctly. Ac sucked. Seats very narrow.

2.0 MediocreMike, Aug 2025AUS - BWI
Read more Southwest reviews

AC sub par. WiFi not working correctly. Ac sucked. Seats very narrow.

southwest just starting charging for luggage. hadnt realized it until it was too late. now out $70 when i couldve bought a carry on if i wouldve known. free bags was one of the only reasons i chose southwest over another airline (the other being no assigned seats, which is apparently also being changed). stupid business decision. wont be flying southwest anymore.

Worst experience I had on Southwest. Still better than most, but the seating was barely tolerable.

It was okay. The plane was delayed from earlier in the day, but they kept updating the departure time, sometimes later, sometimes earlier. That was stressful. Once we finally got on and took off, it was fine. I was supposed to have a connection in Chicago to Los Angeles, and the time for so late I was rebooked to arrive in LA 3 hours late. The departure time to Chicago later became early enough to have taken my original connection and arrive earlier but that wasn't an option.

Everything was on time. I was disappointed by the front section female, African American flight attendant. I did not see her name tag or would have identified by name not race. As passengers moved to the bathroom early in flight, she would say with a disdainful tone “I have to say the seat belt light is on” then go back to her book. Better trained flight attendants say something like be careful the seat belt light is on.

Flight crew and cabin crew were great. I had to rearrange flights because my original flight was 3hrs delayed for weather, the rub is the flight I moved to boarded on time then we sat at the gate for 2 hours because scheduling stole our first officer for another flight, TWICE. Then our actual FO was an hour delayed. To make it worse my original flight went from a 3 hour delay to departing 15min EARLY. Just poor scheduling operations all around.

Bring back peanuts Take our drink orders when were all seated, especially after you switch to assigned seating.

I’ve always loved Southwest. No issues at all. I was flying standby and the gate agent was extremely friendly and helpful. Boarding was smooth and I was able to get a window seat in the emergency exit row. Crew was fantastic! They were very professional and accommodating. We had to divert from our destination due to weather but the flight crew kept everyone at ease and informed us of all pertinent information. Excellent flight

Plz don't take away free bags and free seating

Plane late from DC to Austin 30 minutes. Crew made up much of the time enroute to San Diego.

Any flight to ORD after about 2pm this summer has been challenging. Flight was delayed getting in (coming from ORD) and that led to it not leaving before a ground stop due to lightening before they could fuel the plane, and so forth. They made up some time but we were still late in arriving at ORD, and that led to missed connections.

Food was ok, but not as good as I have had before on AA.

Pretty good. The food was just mediocre, the boarding and crew were good.

My flight got switched and my prepaid bag didnt transfer over properly so I paid to check ANOTHER BAG. I was placed in a middle seat and it was just miserable. At least it was a bulkhead row so I had legroom. The flight just never seem3d to end

Was not able to watch most shows on the entertainment site. They would not load

On Wednesday, July 30 we were in mid flight from Manchester to Charlotte and we turned around because the right engine was malfunctioning. That was the last flight out of Manchester that night. I was rebooked for Thursday, which became a weather event Friday. There were no seats left on the flight from Manchester to Charlotte. Consequently I didn’t leave Manchester until Saturday morning and we flew to Chicago so to say the least my scheduled flight and return to Iowa was three days off and it messed with my business schedule. Consequently cash flow. I would like some sort of acknowledgment of this event.

Dreadful experience. Our flight was delayed more than 8 hours due to a maintenance issue and the assistance from rebooking was poor. I was travelling with a bad knee and needed assistance waited in one place more than 3 hours before someone came with a wheelchair. The woman next to me was a 91 year old great grandmother who had waited more than 4 hours. There were moments of support from the staff but it appeared as they were going against the direction of management. It was apathy, lack of ownership and dismissive responses with small moments of kindness and understanding typically from grey haired, female, veteran staff..

Couldn’t get the door on the plane to close leading to a nearly 2 hour delay. But, hey at least they didn’t cancel the flight.

The flight was fine and the crew awesome. The problem is ORD and AA. Computers went down, ORD fell apart and a 40 min flight turned into a 3 hour trip. Guess the answer is to not try and fly to ORD after noon. But, as I said, crew was awesome and did everything they could to lesson the flight time.

The flight was fine but the 8 hour delay in Chicago was awful - 5 gate changes and repeated delays without an explanation. No vouchers. Nothing.

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

Information on your arrival and departure airports

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