MAF - ORD

$214 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 5/10. 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

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Everything you should know

Cheapest round-trip
$365
Southwest
Wed 4/15Thu 4/16
MAF - ORD • 1 stop
Cheapest one-way
$214
Typical prices: $108-$139
American Airlines
Sun 5/10
MAF - ORD • 1 stop
Top airlines
Cheapest • from $375 (round-trip)
Best reviews • 7.1 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
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, Apr 15 - Thu, Apr 16
Southwest Logo
7:15 am - 3:00 pm
MAF
-
ORD
7h 45m
1 stop
Southwest Logo
3:45 pm - 11:10 pm
ORD
-
MAF
7h 25m
2 stops
$365Southwest
Wed, Apr 15 - Thu, Apr 16
United Airlines Logo
7:00 pm - 12:45 am
MAF
-
ORD
5h 45m
1 stop
United Airlines Logo
5:15 pm - 11:15 pm
ORD
-
MAF
6h 00m
1 stop
$370United Airlines
Sat, Apr 18 - Sat, Apr 25
American Airlines Logo
9:15 am - 3:18 pm
MAF
-
ORD
6h 03m
1 stop
American Airlines Logo
11:43 am - 5:46 pm
ORD
-
MAF
6h 03m
1 stop
$375American Airlines
Sat, Apr 18 - Sat, Apr 25
Southwest Logo
5:30 am - 3:30 pm
MAF
-
ORD
10h 00m
2 stops
Southwest Logo
2:05 pm - 9:00 pm
ORD
-
MAF
6h 55m
1 stop
$382Southwest
Sat, Apr 18 - Sat, Apr 25
Southwest Logo
5:30 am - 3:30 pm
MAF
-
ORD
10h 00m
2 stops
Southwest Logo
2:05 pm - 10:00 pm
ORD
-
MAF
7h 55m
2 stops
$387Southwest
Mon, May 4 - Mon, May 11
Southwest Logo
6:50 am - 3:00 pm
MAF
-
ORD
8h 10m
1 stop
Southwest Logo
4:15 pm - 11:10 pm
ORD
-
MAF
6h 55m
1 stop
$405Southwest
Mon, May 4 - Mon, May 11
Southwest Logo
6:50 am - 3:00 pm
MAF
-
ORD
8h 10m
1 stop
Southwest Logo
2:40 pm - 11:25 pm
ORD
-
MAF
8h 45m
2 stops
$410Southwest
Mon, May 4 - Mon, May 11
Southwest Logo
6:00 am - 3:00 pm
MAF
-
ORD
9h 00m
2 stops
Southwest Logo
2:40 pm - 11:25 pm
ORD
-
MAF
8h 45m
2 stops
$415Southwest
Mon, Jul 27 - Wed, Jul 29
American Airlines Logo
11:39 am - 6:13 pm
MAF
-
ORD
6h 34m
1 stop
American Airlines Logo
8:19 am - 1:49 pm
ORD
-
MAF
5h 30m
1 stop
$427American Airlines
Mon, May 11 - Sun, May 17
American Airlines Logo
6:16 pm - 11:48 pm
MAF
-
ORD
5h 32m
1 stop
American Airlines Logo
6:57 am - 12:16 pm
ORD
-
MAF
5h 19m
1 stop
$435American 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 72 hours.

In the past 3 days, the cheapest round-trip tickets from Midland to Chicago were found on American Airlines ($375) and Southwest ($382).

Good to know

Low seasonAugust
Cheapest flight$214
Best time to beat the crowds with an average 51% 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 $214 for a one-way ticket and $375 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.
7.1
American AirlinesOverall score based on 11467 reviews
6.9Entertainment
7.9Crew
7.5Boarding
6.4Food
7.2Comfort
Airline reviews

There was no inflight service. Once we landed we were delayed to find a gate for an hour and a half which was 1/2 the total time in the air.

2.0 MediocreBrendan, Mar 2026
LGA - ORD
Read more American Airlines reviews

There was no inflight service. Once we landed we were delayed to find a gate for an hour and a half which was 1/2 the total time in the air.

The chicken wrap was tiny ($13 for what looked like a 1/3 of a normal wrap?) and disgusting.

It was good experience this time. The flight was on time.

There was a delay with the plan which cause the flight to leave later and once arrived in Chicago there was another delay and some passengers missed their connecting flights

The gate agent had a really bad attitude and refused to help me get on the standby list. She just handed me a card and said I needed to call a number. I asked her to help with the AA app on my phone and she just shrugged and said she didnt know. After a few phone calls, I eventually just went to a different gate agent on the other side of the terminal and got the help I needed.

Overall, my last three trips on American Airlines have all been either delayed or "rescheduled" due to mechanical issues. At least on delay caused me to miss two possible connecting flights each later than the first. My last option for my last connection required the assistance of the onsite service desk (O'Hare Airport). The wait time for the service desk was such that it jeopardized getting booked on the last connecting flight available for the night. Suffice it to say, my latest experiences with American Airlines have caused me extensive loss of productive business and personal time and can therefore be classified as significantly less than satisfactory.

Waiting for gate in RDU for more than 20mins is crazy.

American Airlines was great and worked very hard to change my ticket so I could get an earlier, direct flight back to Dallas. However, I was informed that Kayak made mistakes with my itinerary and classified my ticket as desiring to be on the earlier flight instead of taking the necessary step of calling AA to get me on the standby list. This ended up keeping me from being added to the standby list and delayed me getting home by 6 hours. I am happy to discuss this further with Kayak so they can correct their procedures so this won't happen again.

Waited for oxygen tanks for 30 minutes after boarding was complete.

We flew in first class. The crew did not offer drinks before the flight took off, but they treated us well during the flight. The food was excellent. There was actually too much food served, but it was nice to have all the options.

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

Information on your arrival and departure airports