$170+ Cheap flights from Midland (MAF) to Chicago (CHI)
This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 11/9. Fares are subject to change and may not be available on all flights or dates of travel.
MAF — CHI
Nov 12 — Nov 191
Round-trip
1 adult, Economy
We work with more than 300 partners to bring you better travel deals
Find cheap flights from Midland to Chicago 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 Midland to Chicago
Cheapest
Best
Last-minute
One-way
Cheapest flights from Midland to ChicagoExplore the most affordable flight options available from Midland to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on October 13, 2026.
Explore the most affordable flight options available from Midland to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on October 13, 2026.
This American Airlines deal was found by Cheapflights users on 10/11. 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.
Mon 11/26:43 pm -
1 stop5h 16m
Wed 11/115:59 pm -
1 stop5h 57m
Deal found 10/11![American Airlines logo]()
$339
This United Airlines deal was found by Cheapflights users on 10/12. 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 11/67:15 pm -
1 stop5h 30m
Sun 11/86:55 am -
1 stop6h 43m
Deal found 10/12![United Airlines logo]()
$376
This American Airlines deal was found by Cheapflights users on 10/8. 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 12/412:36 pm -
1 stop5h 54m
Sun 12/66:59 am -
1 stop5h 07m
Deal found 10/8![American Airlines logo]()
$392
This American Airlines deal was found by Cheapflights users on 10/12. 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.
Mon 11/166:43 pm -
1 stop5h 16m
Mon 12/77:01 pm -
1 stop4h 51m
Deal found 10/12![American Airlines logo]()
$402
This American Airlines deal was found by Cheapflights users on 10/9. 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 12/3110:29 am -
1 stop7h 54m
Mon 1/46:20 pm -
1 stop5h 32m
Deal found 10/9![American Airlines logo]()
$455
This American Airlines deal was found by Cheapflights users on 10/11. 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 12/247:03 pm -
1 stop4h 56m
Sat 12/266:59 pm -
1 stop4h 53m
Deal found 10/11![American Airlines logo]()
$467
This American Airlines deal was found by Cheapflights users on 10/9. 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 11/256:41 pm -
1 stop5h 39m
Mon 11/305:05 pm -
1 stop7h 02m
Deal found 10/9![American Airlines logo]()
$486
This United Airlines deal was found by Cheapflights users on 10/8. 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 10/235:00 pm -
1 stop6h 27m
Tue 10/274:07 pm -
1 stop5h 51m
Deal found 10/8![United Airlines logo]()
$537
Best flights from Midland to ChicagoDiscover carefully curated flight deals from Midland to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated October 13, 2026.
Discover carefully curated flight deals from Midland to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated October 13, 2026.
This American Airlines deal was found by Cheapflights users on 10/11. 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.
Mon 11/26:43 pm -
1 stop5h 16m
Wed 11/115:59 pm -
1 stop5h 57m
Deal found 10/11![American Airlines logo]()
$339
This United Airlines deal was found by Cheapflights users on 10/12. 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 11/67:15 pm -
1 stop5h 30m
Sun 11/86:55 am -
1 stop6h 43m
Deal found 10/12![United Airlines logo]()
$376
This American Airlines deal was found by Cheapflights users on 10/8. 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 12/412:36 pm -
1 stop5h 54m
Sun 12/66:59 am -
1 stop5h 07m
Deal found 10/8![American Airlines logo]()
$392
This American Airlines deal was found by Cheapflights users on 10/11. 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 12/247:03 pm -
1 stop4h 56m
Sat 12/266:59 pm -
1 stop4h 53m
Deal found 10/11![American Airlines logo]()
$467
This United Airlines deal was found by Cheapflights users on 10/10. 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 10/255:05 pm -
1 stop6h 21m
Thu 10/295:30 am -
1 stop5h 44m
Deal found 10/10![United Airlines logo]()
$537
This United Airlines deal was found by Cheapflights users on 10/8. 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 10/235:00 pm -
1 stop6h 27m
Tue 10/274:07 pm -
1 stop5h 51m
Deal found 10/8![United Airlines logo]()
$537
This American Airlines deal was found by Cheapflights users on 10/9. 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 10/242:27 pm -
1 stop7h 43m
Wed 10/283:50 pm -
1 stop6h 47m
Deal found 10/9![American Airlines logo]()
$537
This United Airlines deal was found by Cheapflights users on 10/11. 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 10/255:00 am -
1 stop6h 17m
Wed 10/288:40 am -
2 stops13h 18m
Deal found 10/11![United Airlines logo]()
$675
This United Airlines deal was found by Cheapflights users on 10/8. 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 12/45:05 pm -
2 stops16h 08m
Sun 12/65:45 am -
1 stop5h 24m
Deal found 10/8![United Airlines logo]()
$680
This United Airlines deal was found by Cheapflights users on 10/12. 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 10/275:22 pm -
1 stop5h 24m
Sat 10/318:40 am -
2 stops13h 18m
Deal found 10/12![United Airlines logo]()
$713
Last-minute flights from Midland to ChicagoDiscover last-minute flight deals from Midland to Chicago. Data last updated October 13, 2026 and is based on user searches.
Discover last-minute flight deals from Midland to Chicago. Data last updated October 13, 2026 and is based on user searches.
This United Airlines deal was found by Cheapflights users on 10/11. 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 10/205:00 am -
1 stop5h 16m
Wed 10/216:25 am -
1 stop7h 07m
Deal found 10/11![United Airlines logo]()
$697
This United Airlines deal was found by Cheapflights users on 10/8. 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 10/235:00 pm -
1 stop6h 27m
Tue 10/274:07 pm -
1 stop5h 51m
Deal found 10/8![United Airlines logo]()
$537
This United Airlines deal was found by Cheapflights users on 10/11. 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 10/259:41 am -
1 stop6h 48m
Wed 10/283:56 pm -
1 stop6h 19m
Deal found 10/11![United Airlines logo]()
$647
This United Airlines deal was found by Cheapflights users on 10/12. 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 10/275:22 pm -
1 stop5h 24m
Sat 10/318:40 am -
2 stops13h 18m
Deal found 10/12![United Airlines logo]()
$713
This American Airlines deal was found by Cheapflights users on 10/11. 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.
Mon 11/26:43 pm -
1 stop5h 16m
Wed 11/115:59 pm -
1 stop5h 57m
Deal found 10/11![American Airlines logo]()
$339
This United Airlines deal was found by Cheapflights users on 10/12. 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 11/67:15 pm -
1 stop5h 30m
Sun 11/86:55 am -
1 stop6h 43m
Deal found 10/12![United Airlines logo]()
$376
This American Airlines deal was found by Cheapflights users on 10/12. 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.
Mon 11/166:43 pm -
1 stop5h 16m
Mon 12/77:01 pm -
1 stop4h 51m
Deal found 10/12![American Airlines logo]()
$402
This American Airlines deal was found by Cheapflights users on 10/9. 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 11/256:41 pm -
1 stop5h 39m
Mon 11/305:05 pm -
1 stop7h 02m
Deal found 10/9![American Airlines logo]()
$486
One-way flights from Midland to ChicagoSearch for one-way flight options from Midland to Chicago. Find affordable one-way fares based on user searches. Data last updated October 13, 2026.
Search for one-way flight options from Midland to Chicago. Find affordable one-way fares based on user searches. Data last updated October 13, 2026.
This United Airlines deal was found by Cheapflights users on 10/12. 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.
Mon 11/95:22 pm -
1 stop6h 37m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/12![United Airlines logo]()
$170
Find flight deals from Midland to Chicago
Discover tips and strategies to find the most affordable flight options for your journey from Midland (MAF) to Chicago (CHI). 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 October 13, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $339 (American Airlines) |
One-way from | $170 (United Airlines) |
Cheapflights Fare Finder
Customize your flight search to find flights from Midland to Chicago 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 October 13, 2026.
Use the filters below to find and compare flights from Midland to Chicago that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
Quickest round-trip
MidlandChicago
MAF Midland Intl - ORD Chicago O'Hare Intl
MAFORD
Midland Intl
Mon 11/9
5:22 pm-11:59 pm
1 stop6h 37m
Chicago O'Hare Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$170
MidlandChicago
MAF Midland Intl - ORD Chicago O'Hare Intl
MAFORD
Midland Intl
Mon 11/2
6:43 pm-11:59 pm
1 stop5h 16m
Chicago O'Hare Intl
Wed 11/11
5:59 pm-11:56 pm
1 stop5h 57m
$339
MidlandChicago
MAF Midland Intl - ORD Chicago O'Hare Intl
MAFORD
Midland Intl
Fri 11/6
7:15 pm-12:45 am
1 stop5h 30m
Chicago O'Hare Intl
Sun 11/8
6:55 am-1:38 pm
1 stop6h 43m
$376
MidlandChicago
MAF Midland Intl - ORD Chicago O'Hare Intl
MAFORD
Midland Intl
Fri 12/4
12:36 pm-6:30 pm
1 stop5h 54m
Chicago O'Hare Intl
Sun 12/6
6:59 am-12:06 pm
1 stop5h 07m
$392
MidlandChicago
MAF Midland Intl - ORD Chicago O'Hare Intl
MAFORD
Midland Intl
Thu 12/24
7:03 pm-11:59 pm
1 stop4h 56m
Chicago O'Hare Intl
Sat 12/26
6:59 pm-11:52 pm
1 stop4h 53m
$467
MidlandChicago
MAF Midland Intl - ORD Chicago O'Hare Intl
MAFORD
Midland Intl
Sun 10/25
5:05 pm-11:26 pm
1 stop6h 21m
Chicago O'Hare Intl
Thu 10/29
5:30 am-11:14 am
1 stop5h 44m
$537
MidlandChicago
MAF Midland Intl - ORD Chicago O'Hare Intl
MAFORD
Midland Intl
Fri 10/23
5:00 pm-11:27 pm
1 stop6h 27m
Chicago O'Hare Intl
Tue 10/27
4:07 pm-9:58 pm
1 stop5h 51m
$537
MidlandChicago
MAF Midland Intl - ORD Chicago O'Hare Intl
MAFORD
Midland Intl
Sat 10/24
2:27 pm-10:10 pm
1 stop7h 43m
Chicago O'Hare Intl
Wed 10/28
3:50 pm-10:37 pm
1 stop6h 47m
$537
MidlandChicago
MAF Midland Intl - ORD Chicago O'Hare Intl
MAFORD
Midland Intl
Sun 10/25
5:00 am-11:17 am
1 stop6h 17m
Chicago O'Hare Intl
Wed 10/28
8:40 am-9:58 pm
2 stops13h 18m
$675
MidlandChicago
MAF Midland Intl - ORD Chicago O'Hare Intl
MAFORD
Midland Intl
Fri 12/4
5:05 pm-9:13 am
2 stops16h 08m
Chicago O'Hare Intl
Sun 12/6
5:45 am-11:09 am
1 stop5h 24m
$680
Showing 1-10 of 11 resultsSorted by cheapest first
Compare providers for flights from Midland to Chicago
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 Midland to Chicago in October.
| 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 Midland-Chicago flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Midland-Chicago flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Midland-Chicago flight searches over the past month and is updated monthly.
- Most trusted provider: When it comes to deals on Midland-Chicago 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 Midland-Chicago 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 Midland to Chicago
Have a flexible travel schedule? Discover the best time to fly to Chicago from Midland with our price prediction graph.
MAF-CHI
MAF-ORD
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 Midland to Chicago
MAF-CHI
MAF-ORD
What’s the top layover airport for flights from Midland to Chicago?
Share of 1-stop round-trip flights from Midland to Chicago chosen by Cheapflights users in the past 12 months, using the same layover each way.
Dallas (DAL) – chosen by Cheapflights users on 50% of 1-stop itineraries from Midland to Chicago on Cheapflights.
What’s the cheapest layover airport for flights from Midland to Chicago?
Average round-trip fare for 1-stop flights from Midland to Chicago, chosen by Cheapflights users in the past 12 months, with the same layover each way.
Houston (IAH) is the most affordable 1-stop option, with an average round-trip price of $426.
What’s the fastest layover option from Midland to Chicago?
Shortest average travel time for 1-stop one-way flights from Midland to Chicago, based on itineraries clicked by Cheapflights users over the past 12 months, grouped by layover airport.
Flights via Dallas (DFW) have the shortest average one-way travel time for 1-stop routes: 4h 58m.
Which airport typically offers the quickest layover for flights from Midland to Chicago?
Average layover duration for 1-stop one-way flights from Midland to Chicago, chosen by Cheapflights users in the last 12 months, grouped by stopover airport.
Flights via Houston (IAH) offer the fastest connection on this route, with an average layover time of 1h 01m.
Reviews of airlines servicing Chicago
Get insights into the airlines that provide service to Chicago. 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 Chicago. Reviews last updated October 13, 2026.
Read reviews from past customers who have flown Southwest from Midland to Chicago. 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.
Comfort
8.0
Food
7.0
Entertainment
7.5
Boarding
8.1
Overall
7.9
Crew
8.6
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Comfort
8.0
Food
7.0
Entertainment
7.5
Boarding
8.1
Overall
7.9
Crew
8.6
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Related info for your journey
Find useful and relevant information for your journey from Midland to Chicago. 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 Chicago?
Book flights to Chicago if you plan to visit one of these locationsBenton Harbor
Merrillville
Lansing
Valparaiso
Hammond
Saint Joseph
Porter
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
Chicago flight routes
Complete your trip
Flights by cabin class
Other flight options
Other flights from Midland
Popular flights
Alternative routes for Midland to Chicago
See prices for flight routes from nearby airports that may be better suited for you.
Other flights to Chicago
Explore flights to Chicago departing from other origins. Flights are based on user searches made on Cheapflights and were last updated on October 13, 2026.
Complete your trip
Complete your trip to Chicago by adding a car rental and/or hotel reservation to your travel itinerary.
Search flights from Midland to Chicago by cabin class
Find flights from Midland to Chicago, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Midland and Chicago flights
Browse other Midland and Chicago flight options. Last updated on October 13, 2026.
Other flights from Midland
Browse through other flights departing from Midland. Flights are based on user searches made on Cheapflights and were last updated on October 13, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Top 2 airlines flying from Midland to Chicago
Discover the top 2 airlines that operate flights from Midland to Chicago. 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 October 13, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$398 | Average$451 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$426 | Average$619 | FlexibilityNo cancel fee | On-time71% |