MAF - ORD

$180 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 5/11. 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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41.299.237 searches in the past 7 days on KAYAK

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Everything you should know

Cheapest round-trip
$337
Overall average: $1,514
Southwest
Sat 2/21Sat 2/28
MAF - ORD • 1 stop
Cheapest one-way
$180
Typical prices: $118-$223
United Airlines
Mon 5/11
MAF - ORD • 1 stop
Top airlines
Southwest
Cheapest • from $337 (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
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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!
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, Feb 21 - Sat, Feb 28
Southwest Logo
6:20 am - 2:05 pm
MAF
-
ORD
7h 45m
1 stop
Southwest Logo
3:05 pm - 10:05 pm
ORD
-
MAF
7h 00m
1 stop
$337Southwest
Sat, Feb 21 - Sat, Feb 28
Southwest Logo
5:50 am - 1:00 pm
MAF
-
ORD
7h 10m
1 stop
Southwest Logo
3:05 pm - 11:15 pm
ORD
-
MAF
8h 10m
2 stops
$342Southwest
Mon, Mar 30 - Wed, Apr 1
Southwest Logo
3:20 pm - 10:55 pm
MAF
-
ORD
7h 35m
1 stop
Southwest Logo
4:15 pm - 10:05 pm
ORD
-
MAF
5h 50m
1 stop
$347Southwest
Mon, Mar 30 - Wed, Apr 1
Southwest Logo
3:20 pm - 10:55 pm
MAF
-
ORD
7h 35m
1 stop
Southwest Logo
2:40 pm - 10:55 pm
ORD
-
MAF
8h 15m
2 stops
$352Southwest
Mon, Mar 30 - Wed, Apr 1
Southwest Logo
3:20 pm - 10:55 pm
MAF
-
ORD
7h 35m
1 stop
Southwest Logo
4:15 pm - 10:05 pm
ORD
-
MAF
5h 50m
1 stop
$359Southwest
Mon, Mar 30 - Wed, Apr 1
Southwest Logo
3:20 pm - 10:55 pm
MAF
-
ORD
7h 35m
1 stop
Southwest Logo
2:40 pm - 10:55 pm
ORD
-
MAF
8h 15m
2 stops
$364Southwest
Sun, Mar 29 - Wed, Apr 1
United Airlines Logo
7:00 pm - 12:45 am
MAF
-
ORD
5h 45m
1 stop
United Airlines Logo
4:03 pm - 9:39 pm
ORD
-
MAF
5h 36m
1 stop
$398United Airlines
Mon, Mar 30 - Wed, Apr 1
Southwest Logo
10:45 am - 9:55 pm
MAF
-
ORD
11h 10m
2 stops
Southwest Logo
2:40 pm - 10:55 pm
ORD
-
MAF
8h 15m
2 stops
$421Southwest
Mon, Mar 30 - Wed, Apr 1
Southwest Logo
10:45 am - 9:55 pm
MAF
-
ORD
11h 10m
2 stops
Southwest Logo
2:40 pm - 10:55 pm
ORD
-
MAF
8h 15m
2 stops
$433Southwest
Mon, May 11 - Sun, May 17
American Airlines Logo
6:16 pm - 11:44 pm
MAF
-
ORD
5h 28m
1 stop
American Airlines Logo
8:09 am - 1:45 pm
ORD
-
MAF
5h 36m
1 stop
$443American 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.

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 seasonJanuary
Cheapest flight$180
Best time to beat the crowds with an average 38% drop in price.
Most popular time to fly and prices are also 44% 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 $180 for a one-way ticket and $337 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 11197 reviews
7.5Boarding
6.9Entertainment
6.4Food
8.0Crew
7.2Comfort
Airline reviews

Pilot navigated severe weather/snow storm with skill. Described his intentions clearly

10.0 Excellentaras, Jan 2026
PIT - ORD
Read more American Airlines reviews

Pilot navigated severe weather/snow storm with skill. Described his intentions clearly

Little warm on the plane and delayed for an hour

So excited very proud first of all I wanna thank kayak all updates very professional and fast alart And amazing cabin crew so nice to me they deserve big salute

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.

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.

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)