$201+ Cheap flights from Midland (MAF) to Chicago (CHI)
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 10/9. Fares are subject to change and may not be available on all flights or dates of travel.
MAF — CHI
Sep 28 — Oct 51
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 August 29, 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 August 29, 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.
Mon 10/55:00 pm -
1 stop6h 27m
Wed 10/75:53 pm -
1 stop5h 31m
Deal found 8/26![United Airlines logo]()
$339
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 11/255:28 pm -
1 stop5h 40m
Tue 12/13:51 pm -
1 stop8h 13m
Deal found 8/26![American Airlines logo]()
$393
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.
Mon 10/52:27 pm -
1 stop7h 43m
Wed 10/75:00 am -
1 stop5h 01m
Deal found 8/28![American Airlines logo]()
$407
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.
Fri 10/3010:31 am -
1 stop8h 05m
Sun 11/16:59 am -
1 stop6h 39m
Deal found 8/27![American Airlines logo]()
$411
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 9/92:23 pm -
1 stop6h 07m
Sun 9/135:00 am -
1 stop4h 45m
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.
Sat 9/125:00 am -
1 stop5h 15m
Wed 9/165:53 pm -
1 stop5h 51m
Deal found 8/26![United Airlines logo]()
$429
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 9/246:28 pm -
1 stop5h 46m
Mon 9/285:00 am -
1 stop4h 45m
Deal found 8/27![American Airlines logo]()
$434
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.
Thu 9/176:28 pm -
1 stop5h 46m
Sun 9/205:00 am -
1 stop4h 45m
Deal found 8/25![American Airlines logo]()
$446
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 9/177:00 am -
1 stop5h 25m
Sun 9/205:30 am -
1 stop5h 41m
Deal found 8/29![United Airlines logo]()
$487
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.
Sun 9/135:23 pm -
1 stop6h 07m
Tue 9/153:00 pm -
1 stop6h 19m
Deal found 8/27![American Airlines logo]()
$517
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 August 29, 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 August 29, 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.
Mon 10/51:41 pm -
1 stop5h 49m
Tue 10/63:50 pm -
1 stop6h 08m
Deal found 8/26![United Airlines logo]()
$339
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 11/255:28 pm -
1 stop5h 40m
Tue 12/13:51 pm -
1 stop8h 13m
Deal found 8/26![American Airlines logo]()
$393
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.
Mon 10/52:27 pm -
1 stop7h 43m
Wed 10/75:00 am -
1 stop5h 01m
Deal found 8/28![American Airlines logo]()
$407
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.
Sat 9/125:00 am -
1 stop5h 15m
Wed 9/165:53 pm -
1 stop5h 51m
Deal found 8/26![United Airlines logo]()
$429
This American Airlines deal was found by Cheapflights users on 8/24. 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 9/246:28 pm -
1 stop5h 46m
Mon 9/285:00 am -
1 stop4h 45m
Deal found 8/24![American Airlines logo]()
$434
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 9/177:00 am -
1 stop5h 25m
Sun 9/205:30 am -
1 stop5h 41m
Deal found 8/29![United Airlines logo]()
$487
Last-minute flights from Midland to ChicagoDiscover last-minute flight deals from Midland to Chicago. Data last updated August 29, 2026 and is based on user searches.
Discover last-minute flight deals from Midland to Chicago. Data last updated August 29, 2026 and is based on user searches.
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.
Fri 8/285:31 pm -
1 stop5h 59m
Sun 8/305:00 am -
1 stop6h 19m
Deal found 8/28![American Airlines logo]()
$665
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.
Wed 9/95:20 pm -
1 stop6h 39m
Tue 9/156:25 pm -
1 stop5h 19m
Deal found 8/25![United 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 9/92:23 pm -
1 stop6h 07m
Sun 9/135:00 am -
1 stop4h 45m
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.
Wed 9/911:54 am -
2 stops18h 34m
Sun 9/135:30 am -
1 stop5h 41m
Deal found 8/25![United Airlines logo]()
$652
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.
Sat 9/125:00 am -
1 stop5h 15m
Wed 9/165:53 pm -
1 stop5h 51m
Deal found 8/26![United Airlines logo]()
$429
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.
Sun 9/135:23 pm -
1 stop6h 07m
Tue 9/153:00 pm -
1 stop6h 19m
Deal found 8/27![American Airlines logo]()
$517
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.
Thu 9/176:28 pm -
1 stop5h 46m
Sun 9/205:00 am -
1 stop4h 45m
Deal found 8/25![American Airlines logo]()
$446
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 9/177:00 am -
1 stop5h 25m
Sun 9/205:30 am -
1 stop5h 41m
Deal found 8/29![United Airlines logo]()
$487
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 9/246:28 pm -
1 stop5h 46m
Mon 9/285:00 am -
1 stop4h 45m
Deal found 8/27![American Airlines logo]()
$434
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 August 29, 2026.
Search for one-way flight options from Midland to Chicago. Find affordable one-way fares based on user searches. Data last updated August 29, 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 10/97:19 pm -
1 stop5h 04m
Deal found 8/26![United Airlines logo]()
$201
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.
Fri 10/912:51 pm -
3 stops30h 39m
Deal found 8/26![Multiple Airlines logo]()
$1,171
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 August 29, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $339 (United Airlines) |
One-way from | $201 (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 August 29, 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
MidlandChicago
MAF Midland Intl - ORD Chicago O'Hare Intl
MAFORD
Midland Intl
Mon 10/5
1:41 pm-7:30 pm
1 stop5h 49m
Chicago O'Hare Intl
Tue 10/6
3:50 pm-9:58 pm
1 stop6h 08m
$339
MidlandChicago
MAF Midland Intl - ORD Chicago O'Hare Intl
MAFORD
Midland Intl
Wed 11/25
5:28 pm-11:08 pm
1 stop5h 40m
Chicago O'Hare Intl
Tue 12/1
3:51 pm-12:04 am
1 stop8h 13m
$393
MidlandChicago
MAF Midland Intl - ORD Chicago O'Hare Intl
MAFORD
Midland Intl
Mon 10/5
2:27 pm-10:10 pm
1 stop7h 43m
Chicago O'Hare Intl
Wed 10/7
5:00 am-10:01 am
1 stop5h 01m
$407
MidlandChicago
MAF Midland Intl - ORD Chicago O'Hare Intl
MAFORD
Midland Intl
Sat 9/12
5:00 am-10:15 am
1 stop5h 15m
Chicago O'Hare Intl
Wed 9/16
5:53 pm-11:44 pm
1 stop5h 51m
$429
Quickest round-trip
MidlandChicago
MAF Midland Intl - ORD Chicago O'Hare Intl
MAFORD
Midland Intl
Thu 9/24
6:28 pm-12:14 am
1 stop5h 46m
Chicago O'Hare Intl
Mon 9/28
5:00 am-9:45 am
1 stop4h 45m
$434
MidlandChicago
MAF Midland Intl - ORD Chicago O'Hare Intl
MAFORD
Midland Intl
Thu 9/17
7:00 am-12:25 pm
1 stop5h 25m
Chicago O'Hare Intl
Sun 9/20
5:30 am-11:11 am
1 stop5h 41m
$487
Cheapest one-way
Quickest one-way
MidlandChicago
MAF Midland Intl - ORD Chicago O'Hare Intl
MAFORD
Midland Intl
Fri 10/9
7:19 pm-12:23 am
1 stop5h 04m
$201
MidlandChicago
MAF Midland Intl - ORD Chicago O'Hare Intl
MAFORD
Midland Intl
Fri 10/9
12:51 pm-7:30 pm
3 stops30h 39m
$1,171
Sorted 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 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 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 43% 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 0h 44m.
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 August 29, 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.
Overall
8.0
Food
7.0
Boarding
8.1
Comfort
8.0
Crew
8.6
Entertainment
7.5
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Overall
8.0
Food
7.0
Boarding
8.1
Comfort
8.0
Crew
8.6
Entertainment
7.5
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
Lansing
Merrillville
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 August 29, 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 August 29, 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 August 29, 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 August 29, 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% |