MAF - ORD

$309 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 1/10. 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
Travelers love KAYAK
41 299 237 searches in the past 7 days on KAYAK

Save 24% or moreCompare multiple travel sites with one search.

Track pricesNot ready to book? Create a price alert for when prices drop.

Bundle and saveSave money when you bundle your flight + hotel.

Filter your dealsChoose cabin class, free Wi-Fi and more.

Everything you should know

Cheapest round-trip
$309
Overall average: $431
American Airlines
Sat 1/10Sat 1/17
MAF - ORD • 1 stop
Cheapest one-way
$399
Typical prices: $567-$573
American Airlines
Sun 12/21
MAF - ORD • 1 stop
Top airlines
American Airlines
Cheapest • from $309 (round-trip)
American Airlines
Best reviews • 7.2 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
When to travel
August
Cheapest • 50% price drop
July
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

Sat, Jan 10 - Sat, Jan 17
American Airlines Logo
7:00 am - 11:55 am
MAF
-
ORD
4h 55m1 stop
American Airlines Logo
6:54 am - 12:11 pm
ORD
-
MAF
5h 17m1 stop
$309American Airlines
Tue, Jan 13 - Sat, Jan 17
United Airlines Logo
5:18 pm - 11:59 pm
MAF
-
ORD
6h 41m1 stop
United Airlines Logo
8:54 am - 4:21 pm
ORD
-
MAF
7h 27m1 stop
$387United Airlines
Tue, Jan 13 - Sat, Jan 17
United Airlines Logo
9:41 am - 2:40 pm
MAF
-
ORD
4h 59m1 stop
United Airlines Logo
2:17 pm - 9:54 pm
ORD
-
MAF
7h 37m1 stop
$389United Airlines
Fri, Jan 9 - Mon, Jan 12
Southwest Logo
3:00 pm - 10:35 pm
MAF
-
ORD
7h 35m1 stop
Southwest Logo
2:15 pm - 9:35 pm
ORD
-
MAF
7h 20m1 stop
$399Southwest
Thu, Jan 8 - Sun, Jan 11
Southwest Logo
6:40 am - 1:00 pm
MAF
-
ORD
6h 20m1 stop
Southwest Logo
2:15 pm - 10:35 pm
ORD
-
MAF
8h 20m2 stops
$404Southwest
Thu, Jan 8 - Sun, Jan 11
Southwest Logo
7:05 am - 1:00 pm
MAF
-
ORD
5h 55m2 stops
Southwest Logo
2:15 pm - 10:35 pm
ORD
-
MAF
8h 20m2 stops
$409Southwest
Tue, Jan 13 - Sat, Jan 17
United Airlines Logo
2:55 pm - 9:29 am
MAF
-
ORD
18h 34m2 stops
United Airlines Logo
5:37 am - 1:39 pm
ORD
-
MAF
8h 02m1 stop
$436United Airlines
Tue, Jan 13 - Sat, Jan 17
United Airlines Logo
5:18 pm - 11:59 pm
MAF
-
ORD
6h 41m1 stop
United Airlines Logo
9:15 am - 9:54 pm
ORD
-
MAF
12h 39m2 stops
$441United Airlines
Tue, Jan 13 - Sat, Jan 17
United Airlines Logo
7:00 am - 6:53 pm
MAF
-
ORD
11h 53m2 stops
United Airlines Logo
7:35 am - 1:39 pm
ORD
-
MAF
6h 04m1 stop
$450United Airlines
Sat, Jan 10 - Sat, Jan 17
Southwest Logo
6:15 am - 1:00 pm
MAF
-
ORD
6h 45m1 stop
Southwest Logo
6:05 am - 7:55 pm
ORD
-
MAF
13h 50m2 stops
$476Southwest
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.

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.

Find deals

Good to know

Low seasonMarch
Cheapest flight$309
Best time to beat the crowds with an average 8% drop in price.
Most popular time to fly and prices are also 45% 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 $399 for a one-way ticket and $309 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?

    oneworld is the only airline alliance operating flights between Midland and Chicago.

  • 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 airline 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.
7.2
American AirlinesOverall score based on 11049 reviews
7.5Boarding
7.2Comfort
8.0Crew
6.5Food
6.9Entertainment
Airline reviews

Awful. They won’t help me with anything. I booked on American but they abdicated to Iberia. The ticket was overpriced. Everything negative

2.0 MediocreJohn, Dec 2025
GSO - ORD
Read more American Airlines reviews

Awful. They won’t help me with anything. I booked on American but they abdicated to Iberia. The ticket was overpriced. Everything negative

I enjoyed the extra leg room compared to other airlines. The first stewards made my daughter’s birthday special by giving her an extra snack. Then the last one coming home from Chicago to Appleton made our night really enjoyable Thanks for making our trip enjoyable

It was good..clean, comfy seat. Friendly warm welcoming crew. Was able to check my cabin luggage at the gate which I was able to pickup in a decent time from baggage claim. The app gave all updates from delays to baggage claim info. Overall smooth flight.

It was a typical flight. We had a delay which seems to be the normality now. And we had no in flight service due to conditions.

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

Terrible. Flight delayed for more than 8 hours with only a $12 meal voucher provided for the inconvenience. The airplane did not have breaks on arrival yet they still made us go through the motions and board on time knowing we could not take off then sit for 40+ minutes before having to get of the time. A complete waste of my time. I cannot believe they can stay business with these shenanigans. I’ll avoid this company like the plague moving forward as the lack of accountability is disgraceful.

This was the best 2 flights I have had with American out of SGF. Great crew both flights.

Excellent - explanations were clear staff was nice and flight was comfortable

Lost bag and 2 days no word leaving for cruise no clothes or stuff

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.

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

Information on your arrival and departure airports

Midland (MAF)
O'Hare Intl (ORD)