MAF - ORD

$203 Find Cheap Flights from Midland to Chicago

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 5/23. 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 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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Everything you should know

Cheapest round-trip
$351
Typical prices: $774-$658
Southwest
Wed 5/27Wed 6/3
MAF - ORD • 1 stop
Cheapest one-way
$203
Typical prices: $156-$306
United Airlines
Sat 5/23
MAF - ORD • 1 stop
Top airlines
Cheapest • from $351 (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 $351 (round-trip)
Shortest trip • 4h 38m (one-way)
Insights
Insights
Insights
Insights
When to travel
Cheapest • 100% price drop
Most popular
Good to know
Good to know
+1
+1
Good to know
Good to know
+1
Start a new search
KAYAK searches 100s of sites at once to find you the best travel deals.
We hope you love your trip to Chicago!
Flight Deals
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

Wed, May 27 - Wed, Jun 3
Southwest Logo
6:50 am - 11:10 am
MAF
-
ORD
4h 20m
1 stop
Southwest Logo
6:15 am - 1:40 pm
ORD
-
MAF
7h 25m
1 stop
$351Southwest
Wed, May 27 - Wed, Jun 3
Southwest Logo
7:15 am - 3:00 pm
MAF
-
ORD
7h 45m
1 stop
Southwest Logo
11:55 am - 10:15 pm
ORD
-
MAF
10h 20m
2 stops
$383Southwest
Fri, Jun 5 - Tue, Jun 9
United Airlines Logo
5:18 pm - 11:19 pm
MAF
-
ORD
6h 01m
1 stop
United Airlines Logo
5:45 pm - 11:44 pm
ORD
-
MAF
5h 59m
1 stop
$402United Airlines
Sat, Jun 13 - Sat, Jun 20
American Airlines Logo
6:00 am - 11:13 am
MAF
-
ORD
5h 13m
1 stop
American Airlines Logo
2:59 pm - 7:51 pm
ORD
-
MAF
4h 52m
1 stop
$427American Airlines
Tue, Jun 2 - Wed, Jun 3
United Airlines Logo
1:45 pm - 8:44 pm
MAF
-
ORD
6h 59m
1 stop
United Airlines Logo
4:05 pm - 9:57 pm
ORD
-
MAF
5h 52m
1 stop
$441United Airlines
Fri, Jul 10 - Sun, Jul 12
United Airlines Logo
7:13 pm - 12:45 am
MAF
-
ORD
5h 32m
1 stop
United Airlines Logo
5:30 am - 11:07 am
ORD
-
MAF
5h 37m
1 stop
$452United Airlines
Wed, May 27 - Wed, Jun 3
Southwest Logo
6:50 am - 3:00 pm
MAF
-
ORD
8h 10m
2 stops
Southwest Logo
11:55 am - 10:15 pm
ORD
-
MAF
10h 20m
2 stops
$455Southwest
Tue, May 19 - Sat, May 23
United Airlines Logo
1:45 pm - 9:23 pm
MAF
-
ORD
7h 38m
1 stop
United Airlines Logo
4:05 pm - 9:57 pm
ORD
-
MAF
5h 52m
1 stop
$468United Airlines
Wed, Jul 29 - Tue, Aug 4
United Airlines Logo
7:13 pm - 12:45 am
MAF
-
ORD
5h 32m
1 stop
United Airlines Logo
5:45 pm - 11:44 pm
ORD
-
MAF
5h 59m
1 stop
$472United Airlines
Tue, Jun 2 - Wed, Jun 3
United Airlines Logo
1:45 pm - 8:44 pm
MAF
-
ORD
6h 59m
1 stop
United Airlines Logo
11:47 am - 11:44 pm
ORD
-
MAF
11h 57m
2 stops
$494United 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.

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

This analysis is based on the cheapest round-trip price found on KAYAK in the last 12 months by searching for a flight from Midland to Chicago O'Hare Intl Airport departing in May.

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 January, where tickets cost $0 (return) on average. On the other hand, the most expensive months are March and April, where the average cost of round-trip tickets is $1,105 and $926 respectively.

Good to know

Low seasonOctober
Cheapest flight$203
Best time to beat the crowds with an average 50% drop in price.
Most popular time to fly and prices are also 17% 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 $203 for a one-way ticket and $351 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 $474 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 $456 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 9677 reviews
7.7Boarding
6.6Food
8.1Crew
7.1Entertainment
7.3Comfort
Airline reviews

Standard flight with a drinks and a snack- overall very quick flight. The flight attendants were very strict, bordered on rude.

8.0 ExcellentWendi, Apr 2026
MSP - ORD
Read more United Airlines reviews

Standard flight with a drinks and a snack- overall very quick flight. The flight attendants were very strict, bordered on rude.

Delayed - weather wasn't bad at either end. Also sat on tarmac in ORD.

boarded early to only find out that flight would sit at gate for 45 min to an hour. Landed in chicago and sat on runway for over an hour before got to gate. Total delay was extensive for a 45 min flight door to door.

The flight was significantly delayed. The inbound flight from EWR was delayed departing because of mechanical problems. My original departure from CLT was 5:28 pm but due to the delay of the inbound flight, after arrival, deplaning, cleaning, boarding, we did not push back from the gate until 9:00 pm. Once in the air, the flight was smooth and what was originally supposed to be an arrival in ORD at 7:30 pm local time turned out to be 9:35 pm.

The flight I was supposed to be on was supposed to take off at 1:50 from State College. It was delayed over and over and over again until somehow I had to rebook on a flight that was supposed to have left State College at 8 am that morning but didn't end up taking off until almost 6 pm. Not only was this completely unacceptable, the "token from United" was a 15 dollar meal voucher that has to be used by today. I would personally like some miles added to my account for this inconvenience. I was in transit for 8 hours from the time I arrive at State College Aiport to when I got home. I was supposed to be home at 3 pm and I returned at 8 pm. Unacceptable. I have not been on an on Time united flight in nearly 5 years.

newer aircraft, ability to connect my headset via blue tooth for entertainment.

Very comfortable flight, snacks and drinks were good, good communication from crew. Could have used a little more information on timing of boarding for group 5

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

It was better than excellent. The staff in Mason City were great. The young woman that pushed my wheelchair did more than could be expected of her. She came from India 17 years ago. I don't remember her name.

After arriving in Chicago, we were taxiing for 1.5 hours with infrequent and untruthful updates about the amount of time it would take to arrive at the gate. Minimally, the team could have provided timing expectations that were more truthful, especially one their original expectations were not met.

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.

Very good I can’t complain one bit. Thank you American Airlines for making my flight enjoyable and safe!

The staff and service on American Airlines were truly outstanding. I had requested wheelchair assistance for my mother due to her knee issues, and the team went above and beyond every step of the way—from boarding in Boston to our arrival in Chicago. Their care, professionalism, and attentiveness made the entire experience smooth and stress-free. I’m very grateful for the support they provided.

The new planes (American Eagle) are beautiful and especially comfortable. The flight attendants are consistently professional and courteous. And, while it may seem inconsequential, the new liquid tube of coffee creamer—in contrast to the powdered coffee creamer—makes all the difference in a cup of coffee.

I'm not sure American is capable of on-time arrivals and departures. When you land at ORD, you almost always get held on the tarmac because your gate is still occupied. I may have missed my connection, but that ended up up being significantly delayed as well. Once again, I finally got home well after midnight.

Crew at the gate was very crabby and not at all polite. The plane was very hot the entire flight. And the seat cushion was very worn out.

The staff are very, very professional. It's what flying should feel like.

Flight was delayed half hour before boarding, but when I checked flight aware the plane that would Pick us up had a delay of more than an hour. AA should let us know in advance to avoid waiting several hours in the airport

Delays with no explanation. It could have been handled better.

Jill was the flight attendant in first class she was fabulous!! Best flight attendant I have had in years.!! And I fly every other week. Other can learn from her!!

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

Information on your arrival and departure airports