$219+ Cheap flights from Chicago (CHI) to Midland (MAF)
This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 9/27. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — MAF
Sep 29 — Oct 61
Round-trip
1 adult, Economy
We work with more than 300 partners to bring you better travel deals
Find cheap flights from Chicago to Midland with Cheapflights
1. Tell us where you want to go
Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”2. Select your favorite providers
We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.3. Compare prices and book
Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.Cheap flight deals from Chicago to Midland
Cheapest
Best
Last-minute
One-way
Cheapest flights from Chicago to MidlandExplore the most affordable flight options available from Chicago to Midland. Find the lowest fares from popular airlines and budget airlines, with prices last updated on August 30, 2026.
Explore the most affordable flight options available from Chicago to Midland. Find the lowest fares from popular airlines and budget airlines, with prices last updated on August 30, 2026.
This American Airlines deal was found by Cheapflights users on 8/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/216:55 am -
1 stop5h 26m
Sat 10/246:00 am -
1 stop6h 08m
Deal found 8/27![American Airlines logo]()
$339
This United Airlines deal was found by Cheapflights users on 8/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/94:20 pm -
1 stop5h 38m
Mon 10/125:00 pm -
1 stop6h 27m
Deal found 8/26![United Airlines logo]()
$362
This United Airlines deal was found by Cheapflights users on 8/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/95:53 pm -
1 stop5h 31m
Fri 10/161:41 pm -
1 stop6h 41m
Deal found 8/26![United Airlines logo]()
$385
This American Airlines deal was found by Cheapflights users on 8/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/312:02 pm -
1 stop5h 17m
Sun 11/86:00 am -
1 stop5h 02m
Deal found 8/25![American Airlines logo]()
$388
This American Airlines deal was found by Cheapflights users on 8/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/113:00 pm -
1 stop6h 19m
Sun 9/202:23 pm -
1 stop6h 06m
Deal found 8/26![American Airlines logo]()
$398
This United Airlines deal was found by Cheapflights users on 8/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/96:25 am -
1 stop7h 07m
Sun 10/117:00 am -
1 stop5h 25m
Deal found 8/26![United Airlines logo]()
$411
This American Airlines deal was found by Cheapflights users on 8/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/175:00 am -
1 stop7h 21m
Sun 10/1812:51 pm -
1 stop5h 45m
Deal found 8/28![American Airlines logo]()
$420
This American Airlines deal was found by Cheapflights users on 8/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/86:00 am -
1 stop6h 21m
Sun 10/115:00 am -
1 stop5h 00m
Deal found 8/28![American Airlines logo]()
$424
This American Airlines deal was found by Cheapflights users on 8/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/93:00 pm -
1 stop4h 41m
Sun 9/135:00 am -
1 stop6h 09m
Deal found 8/25![American Airlines logo]()
$428
This United Airlines deal was found by Cheapflights users on 8/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/127:00 am -
1 stop5h 53m
Tue 9/157:15 pm -
1 stop5h 44m
Deal found 8/25![United Airlines logo]()
$429
This American Airlines deal was found by Cheapflights users on 8/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/912:10 pm -
1 stop6h 01m
Fri 10/166:42 pm -
1 stop5h 17m
Deal found 8/25![American Airlines logo]()
$431
Best flights from Chicago to MidlandDiscover carefully curated flight deals from Chicago to Midland that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated August 30, 2026.
Discover carefully curated flight deals from Chicago to Midland that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated August 30, 2026.
This United Airlines deal was found by Cheapflights users on 8/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/94:20 pm -
1 stop5h 38m
Mon 10/125:00 pm -
1 stop6h 27m
Deal found 8/26![United Airlines logo]()
$362
This American Airlines deal was found by Cheapflights users on 8/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/175:00 am -
1 stop7h 21m
Sun 10/1812:51 pm -
1 stop5h 45m
Deal found 8/28![American Airlines logo]()
$420
This American Airlines deal was found by Cheapflights users on 8/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/912:10 pm -
1 stop6h 01m
Fri 10/166:42 pm -
1 stop5h 17m
Deal found 8/25![American Airlines logo]()
$431
This United Airlines deal was found by Cheapflights users on 8/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/179:15 am -
2 stops12h 14m
Mon 10/191:41 pm -
1 stop8h 11m
Deal found 8/27![United Airlines logo]()
$500
This deal was found by Cheapflights users on 8/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/92:50 pm -
1 stop6h 44m
Sat 10/105:23 pm -
1 stop4h 47m
Deal found 8/28![American Airlines logo]()
$497
This United Airlines deal was found by Cheapflights users on 8/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/79:30 pm -
2 stops16h 02m
Sat 10/1011:56 am -
1 stop8h 09m
Deal found 8/26![United Airlines logo]()
$500
This United Airlines deal was found by Cheapflights users on 8/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/215:53 pm -
1 stop5h 31m
Sat 10/247:30 am -
2 stops11h 35m
Deal found 8/27![United Airlines logo]()
$500
This deal was found by Cheapflights users on 8/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/75:00 am -
1 stop5h 01m
Sun 10/115:00 am -
1 stop5h 00m
Deal found 8/28![American Airlines logo]()
$510
This United Airlines deal was found by Cheapflights users on 8/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/35:30 pm -
1 stop6h 13m
Sun 11/82:20 pm -
2 stops16h 39m
Deal found 8/25![United Airlines logo]()
$518
This United Airlines deal was found by Cheapflights users on 8/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/127:00 am -
1 stop5h 53m
Tue 9/157:15 pm -
1 stop5h 44m
Deal found 8/29![United Airlines logo]()
$518
Last-minute flights from Chicago to MidlandDiscover last-minute flight deals from Chicago to Midland. Data last updated August 30, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to Midland. Data last updated August 30, 2026 and is based on user searches.
This American Airlines deal was found by Cheapflights users on 8/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/281:50 pm -
1 stop5h 47m
Thu 9/36:26 pm -
1 stop5h 52m
Deal found 8/25![American Airlines logo]()
$702
This United Airlines deal was found by Cheapflights users on 8/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/86:25 pm -
1 stop5h 19m
Sun 9/135:20 pm -
1 stop6h 39m
Deal found 8/27![United Airlines logo]()
$596
This American Airlines deal was found by Cheapflights users on 8/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/91:46 pm -
1 stop7h 33m
Sat 9/125:00 am -
1 stop5h 08m
Deal found 8/26![American Airlines logo]()
$339
This American Airlines deal was found by Cheapflights users on 8/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/93:00 pm -
1 stop4h 41m
Sun 9/135:00 am -
1 stop6h 09m
Deal found 8/25![American Airlines logo]()
$428
This United Airlines deal was found by Cheapflights users on 8/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/95:53 pm -
1 stop5h 51m
Sat 9/122:13 pm -
2 stops16h 15m
Deal found 8/26![United Airlines logo]()
$533
This American Airlines deal was found by Cheapflights users on 8/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/105:00 am -
1 stop6h 20m
Thu 9/106:28 pm -
1 stop5h 46m
Deal found 8/27![American Airlines logo]()
$470
This American Airlines deal was found by Cheapflights users on 8/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/113:00 pm -
1 stop6h 19m
Sun 9/202:23 pm -
1 stop6h 06m
Deal found 8/26![American Airlines logo]()
$398
This United Airlines deal was found by Cheapflights users on 8/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/112:15 pm -
2 stops7h 19m
Sun 9/205:00 am -
1 stop5h 15m
Deal found 8/26![United Airlines logo]()
$762
This United Airlines deal was found by Cheapflights users on 8/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/127:00 am -
1 stop5h 53m
Tue 9/157:15 pm -
1 stop5h 44m
Deal found 8/25![United Airlines logo]()
$429
This American Airlines deal was found by Cheapflights users on 8/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/135:00 am -
1 stop4h 45m
Thu 9/176:28 pm -
1 stop5h 46m
Deal found 8/29![American Airlines logo]()
$517
This United Airlines deal was found by Cheapflights users on 8/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/1311:50 am -
2 stops9h 45m
Thu 9/175:00 am -
1 stop5h 15m
Deal found 8/29![United Airlines logo]()
$832
One-way flights from Chicago to MidlandSearch for one-way flight options from Chicago to Midland. Find affordable one-way fares based on user searches. Data last updated August 30, 2026.
Search for one-way flight options from Chicago to Midland. Find affordable one-way fares based on user searches. Data last updated August 30, 2026.
This American Airlines deal was found by Cheapflights users on 8/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/276:00 am -
1 stop5h 20m
Deal found 8/26![American Airlines logo]()
$219
This United Airlines deal was found by Cheapflights users on 8/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/177:40 am -
1 stop8h 27m
Deal found 8/29![United Airlines logo]()
$251
This United Airlines deal was found by Cheapflights users on 8/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/1110:39 am -
2 stops12h 48m
Deal found 8/26![United Airlines logo]()
$464
This United Airlines deal was found by Cheapflights users on 8/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/278:50 am -
2 stops14h 37m
Deal found 8/26![United Airlines logo]()
$604
This Kiwi.com deal was found by Cheapflights users on 8/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/275:30 pm -
3 stops39h 16m
Deal found 8/26![Multiple Airlines logo]()
$1,159
Find flight deals from Chicago to Midland
Discover tips and strategies to find the most affordable flight options for your journey from Chicago (CHI) to Midland (MAF). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated August 30, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $339 (American Airlines) |
One-way from | $219 (American Airlines) |
Cheapflights Fare Finder
Customize your flight search to find flights from Chicago to Midland that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 7,457,451 searches. Data last updated August 30, 2026.
Use the filters below to find and compare flights from Chicago to Midland that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
ChicagoMidland
ORD Chicago O'Hare Intl - MAF Midland Intl
ORDMAF
Chicago O'Hare Intl
Fri 10/9
4:20 pm-9:58 pm
1 stop5h 38m
Midland Intl
Mon 10/12
5:00 pm-11:27 pm
1 stop6h 27m
$362
ChicagoMidland
ORD Chicago O'Hare Intl - MAF Midland Intl
ORDMAF
Chicago O'Hare Intl
Sat 10/17
5:00 am-12:21 pm
1 stop7h 21m
Midland Intl
Sun 10/18
12:51 pm-6:36 pm
1 stop5h 45m
$420
ChicagoMidland
ORD Chicago O'Hare Intl - MAF Midland Intl
ORDMAF
Chicago O'Hare Intl
Fri 10/9
12:10 pm-6:11 pm
1 stop6h 01m
Midland Intl
Fri 10/16
6:42 pm-11:59 pm
1 stop5h 17m
$431
ChicagoMidland
ORD Chicago O'Hare Intl - MAF Midland Intl
ORDMAF
Chicago O'Hare Intl
Fri 10/9
2:50 pm-9:34 pm
1 stop6h 44m
Midland Intl
Sat 10/10
5:23 pm-10:10 pm
1 stop4h 47m
$497
ChicagoMidland
ORD Chicago O'Hare Intl - MAF Midland Intl
ORDMAF
Chicago O'Hare Intl
Sat 10/17
9:15 am-9:29 pm
2 stops12h 14m
Midland Intl
Mon 10/19
1:41 pm-9:52 pm
1 stop8h 11m
$500
ChicagoMidland
ORD Chicago O'Hare Intl - MAF Midland Intl
ORDMAF
Chicago O'Hare Intl
Wed 10/7
9:30 pm-1:32 pm
2 stops16h 02m
Midland Intl
Sat 10/10
11:56 am-8:05 pm
1 stop8h 09m
$500
ChicagoMidland
ORD Chicago O'Hare Intl - MAF Midland Intl
ORDMAF
Chicago O'Hare Intl
Wed 10/21
5:53 pm-11:24 pm
1 stop5h 31m
Midland Intl
Sat 10/24
7:30 am-7:05 pm
2 stops11h 35m
$500
Quickest round-trip
ChicagoMidland
ORD Chicago O'Hare Intl - MAF Midland Intl
ORDMAF
Chicago O'Hare Intl
Wed 10/7
5:00 am-10:01 am
1 stop5h 01m
Midland Intl
Sun 10/11
5:00 am-10:00 am
1 stop5h 00m
$510
ChicagoMidland
ORD Chicago O'Hare Intl - MAF Midland Intl
ORDMAF
Chicago O'Hare Intl
Tue 11/3
5:30 pm-11:43 pm
1 stop6h 13m
Midland Intl
Sun 11/8
2:20 pm-6:59 am
2 stops16h 39m
$518
ChicagoMidland
ORD Chicago O'Hare Intl - MAF Midland Intl
ORDMAF
Chicago O'Hare Intl
Sat 9/12
7:00 am-12:53 pm
1 stop5h 53m
Midland Intl
Tue 9/15
7:15 pm-12:59 am
1 stop5h 44m
$518
Showing 1-10 of 13 resultsSorted by cheapest first
Compare providers for flights from Chicago to Midland
Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Chicago to Midland in August.
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars |
- Most accurate provider: When it comes to deals on Chicago-Midland flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Chicago-Midland flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Chicago-Midland flight searches over the past month and is updated monthly.
- Most trusted provider: When it comes to deals on Chicago-Midland flights, Cheapflights users trust FlightHub the most. FlightHub has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Chicago-Midland flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.
Best time to book a flight from Chicago to Midland
Have a flexible travel schedule? Discover the best time to fly to Midland from Chicago with our price prediction graph.
CHI-MAF
ORD-MAF
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.
Cheapflights Insights
Everything you need to know about your flight from Chicago to Midland
CHI-MAF
ORD-MAF
No data available for this route at this time. Please check back soon.
Reviews of airlines servicing Midland
Get insights into the airlines that provide service to Midland. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Midland. Reviews last updated August 30, 2026.
Read reviews from past customers who have flown Southwest from Chicago to Midland. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
Crew
8.6
Entertainment
7.5
Overall
8.0
Boarding
8.1
Food
7.0
Comfort
8.0
Reviews
1 / 20
2.0
MediocreMike,Aug 2025
OKC - AUS
Crew
8.6
Entertainment
7.5
Overall
8.0
Boarding
8.1
Food
7.0
Comfort
8.0
Reviews
1 / 20
2.0
MediocreMike,Aug 2025
OKC - AUS
Related info for your journey
Find useful and relevant information for your journey from Chicago to Midland. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
Traveling to a place near Midland?
Book flights to Midland if you plan to visit one of these locationsBig Spring
Barstow
Fort Stockton
Browse thousands of different options on Cheapflights for your next trip
Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.
Alternative routes
Complete your trip
Flights by cabin class
Midland flight routes
Other flight options
Other flights from Chicago
Popular flights
Alternative routes for Chicago to Midland
See prices for flight routes from nearby airports that may be better suited for you.
Complete your trip
Complete your trip to Midland by adding a car rental and/or hotel reservation to your travel itinerary.
Search flights from Chicago to Midland by cabin class
Find flights from Chicago to Midland, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Other flights to Midland
Explore flights to Midland departing from other origins. Flights are based on user searches made on Cheapflights and were last updated on August 30, 2026.
Chicago and Midland flights
Browse other Chicago and Midland flight options. Last updated on August 30, 2026.
Other flights from Chicago
Browse through other flights departing from Chicago. Flights are based on user searches made on Cheapflights and were last updated on August 30, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Top 2 airlines flying from Chicago to Midland
Discover the top 2 airlines that operate flights from Chicago to Midland. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 7,457,451 searches. Data last updated August 30, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$216 | Average$426 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$347 | Average$435 | FlexibilityNo cancel fee | On-time69% |