$203+ Cheap flights from Chicago (CHI) to Odessa, TX
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 5/14. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — MAF
May 18 — May 251
Round-trip
1 adult, Economy
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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 April 18, 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 April 18, 2026.
This American Airlines deal was found by Cheapflights users on 4/14. 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 5/76:57 am
ORD
- MAF
1 stop5h 19m
American Airlines
Tue 5/122:15 pm
MAF
- ORD
1 stop7h 30m
American Airlines
Deal found 4/14![American Airlines logo]()
$392
This United Airlines deal was found by Cheapflights users on 4/14. 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 5/234:05 pm
ORD
- MAF
1 stop5h 52m
United Airlines
Sat 5/305:00 am
MAF
- ORD
1 stop5h 20m
United Airlines
Deal found 4/14![United Airlines logo]()
$405
This Southwest deal was found by Cheapflights users on 4/13. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/96:15 am
ORD
- MAF
1 stop8h 50m
Southwest
Sat 5/1610:40 am
MAF
- ORD
1 stop12h 45m
Southwest
Deal found 4/13![Southwest logo]()
$410
This American Airlines deal was found by Cheapflights users on 4/15. 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 5/106:05 am
ORD
- MAF
1 stop6h 11m
American Airlines
Sat 5/166:16 pm
MAF
- ORD
1 stop5h 32m
American Airlines
Deal found 4/15![American Airlines logo]()
$412
This Southwest deal was found by Cheapflights users on 4/14. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/232:05 pm
ORD
- MAF
2 stops7h 55m
Southwest
Sat 5/305:30 am
MAF
- ORD
1 stop6h 00m
Southwest
Deal found 4/14![Southwest logo]()
$431
This Southwest deal was found by Cheapflights users on 4/16. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/44:15 pm
ORD
- MAF
1 stop6h 55m
Southwest
Thu 5/76:50 am
MAF
- ORD
1 stop8h 10m
Southwest
Deal found 4/16![Southwest logo]()
$456
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 April 18, 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 April 18, 2026.
This United Airlines deal was found by Cheapflights users on 4/14. 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 5/234:05 pm
ORD
- MAF
1 stop5h 52m
United Airlines
Sat 5/305:00 am
MAF
- ORD
1 stop5h 20m
United Airlines
Deal found 4/14![United Airlines logo]()
$405
This Southwest deal was found by Cheapflights users on 4/13. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/96:15 am
ORD
- MAF
1 stop8h 50m
Southwest
Sat 5/1610:40 am
MAF
- ORD
1 stop12h 45m
Southwest
Deal found 4/13![Southwest logo]()
$410
This Southwest deal was found by Cheapflights users on 4/16. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/42:40 pm
ORD
- MAF
2 stops8h 30m
Southwest
Thu 5/79:50 am
MAF
- ORD
1 stop5h 40m
Southwest
Deal found 4/16![Southwest logo]()
$461
This United Airlines deal was found by Cheapflights users on 4/17. 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 5/212:40 pm
ORD
- MAF
1 stop5h 32m
United Airlines
Wed 5/67:00 pm
MAF
- ORD
1 stop6h 27m
United Airlines
Deal found 4/17![United Airlines logo]()
$507
This Southwest deal was found by Cheapflights users on 4/14. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/232:05 pm
ORD
- MAF
2 stops7h 55m
Southwest
Sat 5/305:30 am
MAF
- ORD
2 stops10h 00m
Southwest
Deal found 4/14![Southwest logo]()
$467
This United Airlines deal was found by Cheapflights users on 4/13. 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 6/25:30 am
ORD
- MAF
1 stop16h 27m
United Airlines
Wed 6/35:18 pm
MAF
- ORD
1 stop5h 31m
United Airlines
Deal found 4/13![United Airlines logo]()
$513
This Southwest deal was found by Cheapflights users on 4/14. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/2312:15 pm
ORD
- MAF
2 stops8h 45m
Southwest
Fri 5/299:50 am
MAF
- ORD
1 stop5h 40m
Southwest
Deal found 4/14![Southwest logo]()
$482
This Southwest deal was found by Cheapflights users on 4/17. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/22:05 pm
ORD
- MAF
2 stops7h 55m
Southwest
Wed 5/67:15 am
MAF
- ORD
1 stop7h 45m
Southwest
Deal found 4/17![Southwest logo]()
$512
Last-minute flights from Chicago to OdessaDiscover last-minute flight deals from Chicago to Odessa. Data last updated April 18, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to Odessa. Data last updated April 18, 2026 and is based on user searches.
This Southwest deal was found by Cheapflights users on 4/16. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/44:15 pm
ORD
- MAF
1 stop6h 55m
Southwest
Thu 5/76:50 am
MAF
- ORD
1 stop8h 10m
Southwest
Deal found 4/16![Southwest logo]()
$456
This American Airlines deal was found by Cheapflights users on 4/14. 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 5/76:57 am
ORD
- MAF
1 stop5h 19m
American Airlines
Tue 5/122:15 pm
MAF
- ORD
1 stop7h 30m
American Airlines
Deal found 4/14![American Airlines logo]()
$392
This Southwest deal was found by Cheapflights users on 4/13. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/96:15 am
ORD
- MAF
1 stop8h 50m
Southwest
Sat 5/1610:40 am
MAF
- ORD
1 stop12h 45m
Southwest
Deal found 4/13![Southwest logo]()
$410
This American Airlines deal was found by Cheapflights users on 4/15. 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 5/106:05 am
ORD
- MAF
1 stop6h 11m
American Airlines
Sat 5/166:16 pm
MAF
- ORD
1 stop5h 32m
American Airlines
Deal found 4/15![American Airlines logo]()
$412
This United Airlines deal was found by Cheapflights users on 4/14. 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 5/234:05 pm
ORD
- MAF
1 stop5h 52m
United Airlines
Sat 5/305:00 am
MAF
- ORD
1 stop5h 20m
United Airlines
Deal found 4/14![United Airlines logo]()
$405
This Southwest deal was found by Cheapflights users on 4/14. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/232:05 pm
ORD
- MAF
2 stops7h 55m
Southwest
Sat 5/305:30 am
MAF
- ORD
1 stop6h 00m
Southwest
Deal found 4/14![Southwest logo]()
$431
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 April 18, 2026.
Search for one-way flight options from Chicago to Odessa. Find affordable one-way fares based on user searches. Data last updated April 18, 2026.
This American Airlines deal was found by Cheapflights users on 4/14. 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 5/146:05 am
ORD
- MAF
1 stop6h 11m
American Airlines
Deal found 4/14![American Airlines logo]()
$203
This Southwest deal was found by Cheapflights users on 4/14. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/142:40 pm
ORD
- MAF
2 stops8h 45m
Southwest
Deal found 4/14![Southwest logo]()
$208
This American Airlines deal was found by Cheapflights users on 4/14. 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 5/35:00 am
ORD
- MAF
1 stop7h 16m
American Airlines
Deal found 4/14![American Airlines logo]()
$254
This Southwest deal was found by Cheapflights users on 4/14. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/44:15 pm
ORD
- MAF
2 stops7h 10m
Southwest
Deal found 4/14![Southwest logo]()
$259
This Southwest deal was found by Cheapflights users on 4/14. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/34:15 pm
ORD
- MAF
2 stops7h 55m
Southwest
Deal found 4/14![Southwest logo]()
$285
This American Airlines deal was found by Cheapflights users on 4/15. 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 6/145:00 am
ORD
- MAF
1 stop5h 06m
American Airlines
Deal found 4/15![American Airlines logo]()
$327
This American Airlines deal was found by Cheapflights users on 4/17. 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 4/3011:43 am
ORD
- MAF
1 stop8h 13m
American Airlines
Deal found 4/17![American Airlines logo]()
$397
This Southwest deal was found by Cheapflights users on 4/17. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/302:40 pm
ORD
- MAF
2 stops8h 30m
Southwest
Deal found 4/17![Southwest logo]()
$424
This United Airlines deal was found by Cheapflights users on 4/15. 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 6/147:15 am
ORD
- MAF
2 stops14h 42m
United Airlines
Deal found 4/15![United Airlines logo]()
$435
This Kiwi.com deal was found by Cheapflights users on 4/14. 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.
Mon 5/45:30 pm
ORD
- MAF
3 stops39h 15m
Multiple Airlines
Deal found 4/14![Multiple Airlines logo]()
$542
This Kiwi.com deal was found by Cheapflights users on 4/17. 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.
Thu 4/305:30 pm
ORD
- MAF
3 stops39h 15m
Multiple Airlines
Deal found 4/17![Multiple Airlines logo]()
$783
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 April 18, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $392 (American Airlines) |
One-way from | $203 (American Airlines) |
Popular in | April |
Cheapest in | May |
Average price | $666 |
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 2,558,603 searches. Data last updated April 18, 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
Quickest round-trip
ChicagoMidland
ORD - MAF
ORDMAF
Chicago O'Hare Intl
Sat 5/23
4:05 pm-9:57 pm
1 stop5h 52m
Midland Intl
Sat 5/30
5:00 am-10:20 am
1 stop5h 20m
$405
ChicagoMidland
ORD - MAF
ORDMAF
Chicago O'Hare Intl
Sat 5/9
6:15 am-3:05 pm
1 stop8h 50m
Midland Intl
Sat 5/16
10:40 am-11:25 pm
1 stop12h 45m
$410
ChicagoMidland
ORD - MAF
ORDMAF
Chicago O'Hare Intl
Mon 5/4
2:40 pm-11:10 pm
2 stops8h 30m
Midland Intl
Thu 5/7
9:50 am-3:30 pm
1 stop5h 40m
$461
ChicagoMidland
ORD - MAF
ORDMAF
Chicago O'Hare Intl
Sat 5/23
2:05 pm-10:00 pm
2 stops7h 55m
Midland Intl
Sat 5/30
5:30 am-3:30 pm
2 stops10h 00m
$467
ChicagoMidland
ORD - MAF
ORDMAF
Chicago O'Hare Intl
Sat 5/23
12:15 pm-9:00 pm
2 stops8h 45m
Midland Intl
Fri 5/29
9:50 am-3:30 pm
1 stop5h 40m
$482
ChicagoMidland
ORD - MAF
ORDMAF
Chicago O'Hare Intl
Sat 5/2
12:40 pm-6:12 pm
1 stop5h 32m
Midland Intl
Wed 5/6
7:00 pm-1:27 am
1 stop6h 27m
$507
ChicagoMidland
ORD - MAF
ORDMAF
Chicago O'Hare Intl
Sat 5/2
2:05 pm-10:00 pm
2 stops7h 55m
Midland Intl
Wed 5/6
7:15 am-3:00 pm
1 stop7h 45m
$512
ChicagoMidland
ORD - MAF
ORDMAF
Chicago O'Hare Intl
Tue 6/2
5:30 am-9:57 pm
1 stop16h 27m
Midland Intl
Wed 6/3
5:18 pm-10:49 pm
1 stop5h 31m
$513
Cheapest one-way
ChicagoMidland
ORD - MAF
ORDMAF
Chicago O'Hare Intl
Thu 5/14
6:05 am-12:16 pm
1 stop6h 11m
$203
ChicagoMidland
ORD - MAF
ORDMAF
Chicago O'Hare Intl
Thu 5/14
2:40 pm-11:25 pm
2 stops8h 45m
$208
Showing 1-10 of 18 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 April 18, 2026.
See what other customers who have flown with Southwest and American Airlines 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.
Crew
8.6
Comfort
8.0
Food
7.0
Overall
8.0
Boarding
8.1
Entertainment
7.5
Reviews
1 / 20
2.0
MediocreMike,Aug 2025
OKC - AUS
Crew
8.6
Comfort
8.0
Food
7.0
Overall
8.0
Boarding
8.1
Entertainment
7.5
Reviews
1 / 20
2.0
MediocreMike,Aug 2025
OKC - AUS
Crew
8.6
Comfort
8.0
Food
7.0
Overall
8.0
Boarding
8.1
Entertainment
7.5
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 April 18, 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 April 18, 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 2,558,603 searches. Data last updated April 18, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$216 | Average$379 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$331 | Average$396 | FlexibilityNo cancel fee | On-time69% |