$170+ Cheap flights from Chicago (CHI) to Odessa, TX
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 10/13. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — MAF
Oct 11 — Oct 181
Round-trip
1 adult, Economy
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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
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Cheapest flights from Chicago to OdessaExplore the most affordable flight options available from Chicago to Odessa. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 11, 2026.
Explore the most affordable flight options available from Chicago to Odessa. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 11, 2026.
This United Airlines deal was found by Cheapflights users on 9/10. 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.
Wed 10/217:00 am -
1 stop5h 45m
Sat 10/241:41 pm -
1 stop6h 39m
Deal found 9/10![United Airlines logo]()
$339
This American Airlines deal was found by Cheapflights users on 9/11. 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 10/85:00 am -
1 stop5h 01m
Sun 10/116:42 pm -
1 stop5h 17m
Deal found 9/11![American Airlines logo]()
$388
This United Airlines deal was found by Cheapflights users on 9/9. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/137:29 am -
1 stop6h 09m
Sun 11/155:00 am -
1 stop5h 11m
Deal found 9/9![United Airlines logo]()
$403
This United Airlines deal was found by Cheapflights users on 9/7. 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 11/204:07 pm -
1 stop5h 51m
Fri 11/272:20 pm -
1 stop5h 35m
Deal found 9/7![United Airlines logo]()
$430
This United Airlines deal was found by Cheapflights users on 9/10. 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.
Thu 10/15:53 pm -
1 stop5h 31m
Wed 10/71:41 pm -
1 stop6h 41m
Deal found 9/10![United Airlines logo]()
$431
This American Airlines deal was found by Cheapflights users on 9/10. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/255:00 am -
1 stop5h 01m
Sun 11/15:00 am -
1 stop5h 05m
Deal found 9/10![American Airlines logo]()
$438
This American Airlines deal was found by Cheapflights users on 9/11. 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 10/15:16 pm -
1 stop5h 13m
Wed 10/75:23 pm -
1 stop6h 36m
Deal found 9/11![American Airlines logo]()
$470
This deal was found by Cheapflights users on 9/10. 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 is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/72:10 pm -
1 stop7h 19m
Sat 10/105:00 pm -
1 stop7h 23m
Deal found 9/10![United Airlines logo]()
$474
This American Airlines deal was found by Cheapflights users on 9/6. 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 9/221:46 pm -
1 stop5h 55m
Sat 9/262:23 pm -
1 stop5h 13m
Deal found 9/6![American Airlines logo]()
$517
Best flights from Chicago to OdessaDiscover carefully curated flight deals from Chicago to Odessa that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated September 11, 2026.
Discover carefully curated flight deals from Chicago to Odessa that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated September 11, 2026.
This United Airlines deal was found by Cheapflights users on 9/10. 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.
Wed 10/217:00 am -
1 stop5h 45m
Sat 10/241:41 pm -
1 stop6h 39m
Deal found 9/10![United Airlines logo]()
$339
This American Airlines deal was found by Cheapflights users on 9/9. 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 10/212:50 pm -
1 stop6h 44m
Sat 10/2410:31 am -
1 stop5h 45m
Deal found 9/9![American Airlines logo]()
$339
This United Airlines deal was found by Cheapflights users on 9/9. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/137:29 am -
1 stop6h 09m
Sun 11/155:00 am -
1 stop5h 11m
Deal found 9/9![United Airlines logo]()
$403
This United Airlines deal was found by Cheapflights users on 9/7. 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 11/204:07 pm -
1 stop5h 51m
Fri 11/272:20 pm -
1 stop5h 35m
Deal found 9/7![United Airlines logo]()
$430
This United Airlines deal was found by Cheapflights users on 9/10. 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.
Thu 10/15:53 pm -
1 stop5h 31m
Wed 10/71:41 pm -
1 stop6h 41m
Deal found 9/10![United Airlines logo]()
$431
This United Airlines deal was found by Cheapflights users on 9/8. 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.
Thu 10/155:00 am -
1 stop7h 45m
Sat 10/177:30 am -
2 stops13h 00m
Deal found 9/8![United Airlines logo]()
$500
This United Airlines deal was found by Cheapflights users on 9/10. 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.
Thu 10/86:25 am -
1 stop7h 07m
Sun 10/115:00 pm -
2 stops17h 40m
Deal found 9/10![United Airlines logo]()
$546
Last-minute flights from Chicago to OdessaDiscover last-minute flight deals from Chicago to Odessa. Data last updated September 11, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to Odessa. Data last updated September 11, 2026 and is based on user searches.
This American Airlines deal was found by Cheapflights users on 9/6. 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 9/221:46 pm -
1 stop5h 55m
Sat 9/262:23 pm -
1 stop5h 13m
Deal found 9/6![American Airlines logo]()
$517
This United Airlines deal was found by Cheapflights users on 9/10. 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.
Thu 10/15:53 pm -
1 stop5h 31m
Wed 10/71:41 pm -
1 stop6h 41m
Deal found 9/10![United Airlines logo]()
$431
This American Airlines deal was found by Cheapflights users on 9/11. 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 10/15:16 pm -
1 stop5h 13m
Wed 10/75:23 pm -
1 stop6h 36m
Deal found 9/11![American Airlines logo]()
$470
This deal was found by Cheapflights users on 9/10. 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 is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/72:10 pm -
1 stop7h 19m
Sat 10/105:00 pm -
1 stop7h 23m
Deal found 9/10![United Airlines logo]()
$474
This American Airlines deal was found by Cheapflights users on 9/11. 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 10/85:00 am -
1 stop5h 01m
Sun 10/116:42 pm -
1 stop5h 17m
Deal found 9/11![American Airlines logo]()
$388
This United Airlines deal was found by Cheapflights users on 9/10. 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.
Thu 10/86:25 am -
1 stop7h 07m
Sun 10/115:00 pm -
2 stops17h 40m
Deal found 9/10![United Airlines logo]()
$546
This American Airlines deal was found by Cheapflights users on 9/11. 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.
Fri 10/166:00 am -
1 stop6h 21m
Mon 10/1910:31 am -
1 stop8h 04m
Deal found 9/11![American Airlines logo]()
$403
This United Airlines deal was found by Cheapflights users on 9/10. 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.
Wed 10/217:00 am -
1 stop5h 45m
Sat 10/241:41 pm -
1 stop6h 39m
Deal found 9/10![United Airlines logo]()
$339
This American Airlines deal was found by Cheapflights users on 9/10. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/255:00 am -
1 stop5h 01m
Sun 11/15:00 am -
1 stop5h 05m
Deal found 9/10![American Airlines logo]()
$438
One-way flights from Chicago to OdessaSearch for one-way flight options from Chicago to Odessa. Find affordable one-way fares based on user searches. Data last updated September 11, 2026.
Search for one-way flight options from Chicago to Odessa. Find affordable one-way fares based on user searches. Data last updated September 11, 2026.
This American Airlines deal was found by Cheapflights users on 9/8. 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.
Tue 10/135:16 pm -
1 stop6h 43m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/8![American Airlines logo]()
$170
This United Airlines deal was found by Cheapflights users on 9/6. 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 10/135:53 pm -
1 stop5h 31m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/6![United Airlines logo]()
$202
This American Airlines deal was found by Cheapflights users on 9/8. 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.
Sun 10/45:00 am -
1 stop4h 45m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/8![American Airlines logo]()
$229
This American Airlines deal was found by Cheapflights users on 9/10. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/291:46 pm -
1 stop5h 55m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/10![American Airlines logo]()
$259
This United Airlines deal was found by Cheapflights users on 9/8. 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.
Thu 10/88:57 am -
2 stops13h 01m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/8![United Airlines logo]()
$370
This United Airlines deal was found by Cheapflights users on 9/6. 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 10/109:15 am -
2 stops12h 14m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/6![United Airlines logo]()
$400
This United Airlines deal was found by Cheapflights users on 9/7. 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 10/78:57 am -
2 stops13h 01m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/7![United Airlines logo]()
$402
This United Airlines deal was found by Cheapflights users on 9/11. 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.
Mon 10/125:53 pm -
1 stop5h 31m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/11![United Airlines logo]()
$430
Find flight deals from Chicago to Odessa
Keep the following information in mind while searching for Chicago to Odessa flight deals. Data was last updated September 11, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $339 (United Airlines) |
One-way from | $170 (American Airlines) |
Cheapflights Fare Finder
Customize your flight search to find flights from Chicago to Odessa 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 September 11, 2026.
Use the filters below to find and compare flights from Chicago to Odessa 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
Tue 10/13
5:16 pm-11:59 pm
1 stop6h 43m
Midland Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$170
ChicagoMidland
ORD Chicago O'Hare Intl - MAF Midland Intl
ORDMAF
Chicago O'Hare Intl
Sat 10/10
8:45 am-4:12 pm
1 stop7h 27m
Midland Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$202
ChicagoMidland
ORD Chicago O'Hare Intl - MAF Midland Intl
ORDMAF
Chicago O'Hare Intl
Tue 9/29
1:46 pm-7:41 pm
1 stop5h 55m
Midland Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$259
ChicagoMidland
ORD Chicago O'Hare Intl - MAF Midland Intl
ORDMAF
Chicago O'Hare Intl
Wed 10/21
7:00 am-12:45 pm
1 stop5h 45m
Midland Intl
Sat 10/24
1:41 pm-8:20 pm
1 stop6h 39m
$339
ChicagoMidland
ORD Chicago O'Hare Intl - MAF Midland Intl
ORDMAF
Chicago O'Hare Intl
Wed 10/21
2:50 pm-9:34 pm
1 stop6h 44m
Midland Intl
Sat 10/24
10:31 am-4:16 pm
1 stop5h 45m
$339
ChicagoMidland
ORD Chicago O'Hare Intl - MAF Midland Intl
ORDMAF
Chicago O'Hare Intl
Tue 10/13
8:13 pm-12:45 pm
2 stops16h 32m
Midland Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$344
ChicagoMidland
ORD Chicago O'Hare Intl - MAF Midland Intl
ORDMAF
Chicago O'Hare Intl
Thu 10/8
8:57 am-9:58 pm
2 stops13h 01m
Midland Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$370
ChicagoMidland
ORD Chicago O'Hare Intl - MAF Midland Intl
ORDMAF
Chicago O'Hare Intl
Fri 11/13
7:29 am-1:38 pm
1 stop6h 09m
Midland Intl
Sun 11/15
5:00 am-10:11 am
1 stop5h 11m
$403
Quickest round-trip
ChicagoMidland
ORD Chicago O'Hare Intl - MAF Midland Intl
ORDMAF
Chicago O'Hare Intl
Mon 10/12
5:53 pm-11:24 pm
1 stop5h 31m
Midland Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$430
ChicagoMidland
ORD Chicago O'Hare Intl - MAF Midland Intl
ORDMAF
Chicago O'Hare Intl
Fri 11/20
4:07 pm-9:58 pm
1 stop5h 51m
Midland Intl
Fri 11/27
2:20 pm-7:55 pm
1 stop5h 35m
$430
Showing 1-10 of 14 resultsSorted by cheapest first
Best time to book a flight from Chicago to Odessa
Have a flexible travel schedule? Discover the best time to fly to Odessa from Chicago with our price prediction graph.
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 Odessa
CHI-OD3
ORD-MAF
No data available for this route at this time. Please check back soon.
Reviews of airlines servicing Odessa
Get insights into the airlines that provide service to Odessa. 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 Odessa. Reviews last updated September 11, 2026.
See what other customers who have flown with Southwest from Chicago to Odessa have to say. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
Overall
8.0
Entertainment
7.5
Food
7.0
Crew
8.6
Comfort
8.0
Boarding
8.1
Reviews
1 / 20
2.0
MediocreMike,Aug 2025
OKC - AUS
Overall
8.0
Entertainment
7.5
Food
7.0
Crew
8.6
Comfort
8.0
Boarding
8.1
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 Odessa. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
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Complete your trip
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Chicago and Odessa flights
Browse other Chicago and Odessa flight options. Last updated on September 11, 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 September 11, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Top 2 airlines flying from Chicago to Odessa
Discover the top 2 airlines that operate flights from Chicago to Odessa. 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 September 11, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$347 | Average$473 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$379 | Average$434 | FlexibilityNo cancel fee | On-time71% |