MAF - ORD

$193 Find Cheap Flights from Midland to Chicago - Compare and Save

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Midland to Chicago departing on 10/3. 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

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Everything you should know

Cheapest round-trip
$339
American Airlines
Thu 9/10Thu 9/17
MAF - ORD • 1 stop
Cheapest one-way
$193
United Airlines
Sat 10/3
MAF - ORD • 1 stop
Top airlines
Cheapest • from $339 (round-trip)
Best reviews • 7.4 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
Nonstop flights
Not available
There are currently no direct flights between Midland and Chicago. You'll need at least 1 connection.
Insights
Insights
Insights
Insights
Top layover airports
Cheapest • Avg $426 (round-trip)
Shortest trip • 4h 30m (one-way)
Insights
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Booking Insights
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, Sep 10 - Thu, Sep 17
American Airlines Logo
11:50 am - 7:36 pm
MAF
-
ORD
7h 46m
1 stop
American Airlines Logo
5:00 am - 9:45 am
ORD
-
MAF
4h 45m
1 stop
$339American Airlines
Sat, Aug 29 - Sat, Sep 5
American Airlines Logo
5:31 pm - 11:30 pm
MAF
-
ORD
5h 59m
1 stop
American Airlines Logo
4:57 pm - 10:34 pm
ORD
-
MAF
5h 37m
1 stop
$339American Airlines
Thu, Sep 10 - Thu, Sep 17
United Airlines Logo
7:15 pm - 12:59 am
MAF
-
ORD
5h 44m
1 stop
United Airlines Logo
5:30 am - 11:11 am
ORD
-
MAF
5h 41m
1 stop
$364United Airlines
Thu, Sep 10 - Thu, Sep 17
American Airlines Logo
11:50 am - 7:36 pm
MAF
-
ORD
7h 46m
1 stop
American Airlines Logo
5:00 am - 9:45 am
ORD
-
MAF
4h 45m
1 stop
$364American Airlines
Wed, Sep 2 - Tue, Sep 8
United Airlines Logo
11:54 am - 6:30 pm
MAF
-
ORD
6h 36m
1 stop
United Airlines Logo
6:25 pm - 11:44 pm
ORD
-
MAF
5h 19m
1 stop
$401United Airlines
Tue, Sep 1 - Tue, Sep 8
United Airlines Logo
7:15 pm - 12:59 am
MAF
-
ORD
5h 44m
1 stop
United Airlines Logo
6:25 pm - 11:44 pm
ORD
-
MAF
5h 19m
1 stop
$401United Airlines
Fri, Sep 4 - Tue, Sep 8
American Airlines Logo
5:31 pm - 12:18 am
MAF
-
ORD
6h 47m
1 stop
American Airlines Logo
6:00 am - 11:19 am
ORD
-
MAF
5h 19m
1 stop
$403American Airlines
Thu, Dec 10 - Tue, Dec 15
American Airlines Logo
9:13 am - 3:00 pm
MAF
-
ORD
5h 47m
1 stop
American Airlines Logo
6:00 am - 2:02 pm
ORD
-
MAF
8h 02m
1 stop
$409American Airlines
Fri, Sep 4 - Tue, Sep 8
American Airlines Logo
6:26 pm - 12:18 am
MAF
-
ORD
5h 52m
1 stop
American Airlines Logo
5:00 am - 11:19 am
ORD
-
MAF
6h 19m
1 stop
$410American Airlines
Sun, Oct 11 - Tue, Oct 13
United Airlines Logo
5:00 pm - 11:27 pm
MAF
-
ORD
6h 27m
1 stop
United Airlines Logo
5:53 pm - 11:24 pm
ORD
-
MAF
5h 31m
1 stop
$411United Airlines
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.

Which airlines provide the cheapest flights from Midland to Chicago?

The cheapest round-trip price for the route for each airline clicked by KAYAK users in the last 5 days.

In the past 5 days, the cheapest round-trip tickets from Midland to Chicago were found on American Airlines ($339) and United Airlines ($364).

Good to know

Cheapest flight

$193
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 5 days, the lowest price for a flight from Midland to Chicago O'Hare Intl Airport was $193 for a one-way ticket and $339 for a round-trip.

  • 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?

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

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

    The two airlines most popular with KAYAK users for flights from Midland to Chicago are United Airlines and American Airlines. With an average price for the route of $451 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 $586 and an overall rating of 7.1.

  • 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.
7.4
United AirlinesOverall score based on 10061 reviews
7.3Comfort
6.6Food
8.1Crew
7.1Entertainment
7.7Boarding
Airline reviews

The flight crew were very helpful. The seats were very close together. There was barely room to sit without touching the person next to you.

4.0 OkayN, Jul 2026
PHL - ORD
Read more United Airlines reviews

The flight crew were very helpful. The seats were very close together. There was barely room to sit without touching the person next to you.

I’m an EP on AA every year for more than a decade but this was a very pleasant and surprising experience. Clean and sizable plane for HOU to CHI. 5 row first class. And excellent food in first class the steak option was really good. Your flight attendants even better. Seat 5A

Gluten free snack options and meals that offer both gluten free and dairy free.

Awful. Delayed flights, missed connection to Toronto. Hotel vouchers were for already booked hotels x3. Giant waste of my time

Boarded early, left early, arrived 40 mins early! A win win for me!

Great flight. Got to watch a movie. Smooth flight and early arrival at ORD.

Overall it was good. I missed my connection but I was put on another flight.

Smooth flight. Boarding was chaotic. Could not hear the gate agent over the intercom. People were lined up in the wrong lines. Groups one and two were told to board through line one and group 3 through line 2. All very confusing. Once in the air, the flight was smooth. There was no entertainment option on this aircraft, even though it was a larger aircraft.

The delays (5 hrs) were a comedy of errors, and the multiple safety issues encountered were very concerning.

I don't understand why they can't have charging ports on seats in 2023. They only offer it as a 'premium seat' service. It's ridiculous

Nothing, I wont be flying American Airlines again and will not be recommending anyone to fly American Airlines. It was the worst experience flying I've ever had.

Delayed flight more than I hour. When boarding we spent some additional time on the plane before takeoff ....

They lost my baggage and I am still struggling to the information and update

It was good, the staff was great, and the food, was as usual, tea and biscuit. Bathroom was clean, and the plane was clean as well.

As a first class customer, there was no power the entire flight which limited my ability to work. I find this unacceptable. The first 11 rows on the left side of the plan were out. I was only offered the option to charge my phone which was not the issue because my laptop was out of power. I asked if there was anything that can be done for me, and the answer was, "no". I was not offered any type of compensation for this AA problem which caused me unnecessary stress due to inability to address business issues on an already challenging travel day. Flight attendants tried to reset the power once but that was the extent of their support. Very disappointing for the lack of expected services on a flight. Please contact me with customer focused response to this complaint.

Update to handle the delay was very bad, crews no smiles or welcome or thanks. Don’t care attitude

After we landed we sat on the tarmac for 1.5 hours waiting to get to our gate. Ridiculous.

3hour delay In the last 3 months i had 3 flights and 2 of these had a more than 2:40 hrs delayed

We received a flight delay notification over 24 hours before the flight, but it seems American didn't do anything in that timeframe to get the flight back on schedule. Gate agents were still determining when our plane would arrive. Didn't have catering ready to go when our plane did arrive. Flight attendant timeout before we left. There was a flight attendant on board who could work the flight (trained on that aricraft type and was within hours), however American chose to wait for a backup to arrive, which delay the flight further.

When you pay for Premium Economy on an 787 and you’re promised amenities for the extra money, you expect them to work. They didn’t. USB connector wouldn’t charge continuously. 120v outlet wouldn’t hold anything you plugged into it. The adapter would just fall out. The noise canceling headphones stopped noise cancelling in the first 15 minutes for EVERYONE. No one on the plane knew how to fix it so I couldn’t listen to any movies. I just put in my AirPods and went to sleep. Very unhappy with the crappy Panasonic entertainment system. I won’t buy premium again.

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

Information on your arrival and departure airports