$224+ 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 6/26. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — MAF
Jul 8 — Jul 151
Round-trip
1 adult, Economy
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Find cheap flights from Chicago to Odessa 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
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Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.Cheap flight deals from Chicago to Odessa
Cheapest
Best
Last-minute
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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 June 8, 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 June 8, 2026.
This American Airlines deal was found by Cheapflights users on 6/3. 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 7/14:45 pm
ORD
- MAF
1 stop6h 31m
American Airlines
Tue 7/76:42 pm
MAF
- ORD
1 stop6h 08m
American Airlines
Deal found 6/3![American Airlines logo]()
$371
This American Airlines deal was found by Cheapflights users on 6/7. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/13:50 pm
ORD
- MAF
1 stop7h 26m
American Airlines
Sat 7/252:21 pm
MAF
- ORD
1 stop7h 01m
American Airlines
Deal found 6/7![American Airlines logo]()
$399
This American Airlines deal was found by Cheapflights users on 6/7. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/24:51 pm
ORD
- MAF
1 stop5h 02m
American Airlines
Sun 7/196:46 pm
MAF
- ORD
1 stop6h 04m
American Airlines
Deal found 6/7![American Airlines logo]()
$437
This United Airlines deal was found by Cheapflights users on 6/3. 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 6/267:35 am
ORD
- MAF
1 stop5h 59m
United Airlines
Sat 6/275:00 am
MAF
- ORD
1 stop5h 20m
United Airlines
Deal found 6/3![United Airlines logo]()
$447
This United Airlines deal was found by Cheapflights users on 6/4. 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 8/186:29 pm
ORD
- MAF
1 stop5h 15m
United Airlines
Wed 8/195:00 am
MAF
- ORD
1 stop5h 15m
United Airlines
Deal found 6/4![United Airlines logo]()
$461
This American Airlines deal was found by Cheapflights users on 6/7. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/232:59 pm
ORD
- MAF
1 stop4h 51m
American Airlines
Thu 7/302:21 pm
MAF
- ORD
1 stop6h 08m
American Airlines
Deal found 6/7![American Airlines logo]()
$484
This American Airlines deal was found by Cheapflights users on 6/3. 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 6/175:00 am
ORD
- MAF
1 stop6h 09m
American Airlines
Sat 6/205:00 am
MAF
- ORD
1 stop4h 50m
American Airlines
Deal found 6/3![American Airlines logo]()
$507
This American Airlines deal was found by Cheapflights users on 6/7. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/224:51 pm
ORD
- MAF
1 stop6h 02m
American Airlines
Wed 7/292:21 pm
MAF
- ORD
1 stop6h 08m
American Airlines
Deal found 6/7![American Airlines logo]()
$534
This United Airlines deal was found by Cheapflights users on 6/5. 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 6/202:33 pm
ORD
- MAF
1 stop5h 51m
United Airlines
Wed 6/245:00 am
MAF
- ORD
1 stop6h 02m
United Airlines
Deal found 6/5![United Airlines logo]()
$548
This American Airlines deal was found by Cheapflights users on 6/3. 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 7/56:04 am
ORD
- MAF
1 stop7h 45m
American Airlines
Tue 7/146:42 pm
MAF
- ORD
1 stop6h 08m
American Airlines
Deal found 6/3![American Airlines logo]()
$574
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 June 8, 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 June 8, 2026.
This United Airlines deal was found by Cheapflights users on 6/6. 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 8/2910:55 am
ORD
- MAF
1 stop6h 09m
United Airlines
Sat 9/51:40 pm
MAF
- ORD
1 stop5h 50m
United Airlines
Deal found 6/6![United Airlines logo]()
$399
This American Airlines deal was found by Cheapflights users on 6/7. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/24:51 pm
ORD
- MAF
1 stop5h 02m
American Airlines
Sun 7/196:46 pm
MAF
- ORD
1 stop6h 04m
American Airlines
Deal found 6/7![American Airlines logo]()
$437
This United Airlines deal was found by Cheapflights users on 6/4. 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 8/186:29 pm
ORD
- MAF
1 stop5h 15m
United Airlines
Wed 8/195:00 am
MAF
- ORD
1 stop5h 15m
United Airlines
Deal found 6/4![United Airlines logo]()
$461
This American Airlines deal was found by Cheapflights users on 6/3. 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 6/175:00 am
ORD
- MAF
1 stop6h 09m
American Airlines
Sat 6/205:00 am
MAF
- ORD
1 stop4h 50m
American Airlines
Deal found 6/3![American Airlines logo]()
$507
This United Airlines deal was found by Cheapflights users on 6/3. 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 6/202:33 pm
ORD
- MAF
1 stop5h 51m
United Airlines
Mon 6/221:45 pm
MAF
- ORD
1 stop6h 45m
United Airlines
Deal found 6/3![United Airlines logo]()
$507
This American Airlines deal was found by Cheapflights users on 6/7. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/224:51 pm
ORD
- MAF
1 stop6h 02m
American Airlines
Wed 7/292:21 pm
MAF
- ORD
1 stop6h 08m
American Airlines
Deal found 6/7![American Airlines logo]()
$534
This United Airlines deal was found by Cheapflights users on 6/5. 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 6/202:33 pm
ORD
- MAF
1 stop5h 51m
United Airlines
Wed 6/245:00 am
MAF
- ORD
1 stop6h 02m
United Airlines
Deal found 6/5![United Airlines logo]()
$548
This American Airlines deal was found by Cheapflights users on 6/3. 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 7/56:04 am
ORD
- MAF
1 stop7h 45m
American Airlines
Tue 7/146:42 pm
MAF
- ORD
1 stop6h 08m
American Airlines
Deal found 6/3![American Airlines logo]()
$574
This United Airlines deal was found by Cheapflights users on 6/5. 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 7/19:01 am
ORD
- MAF
2 stops12h 47m
United Airlines
Sat 7/255:00 am
MAF
- ORD
1 stop7h 29m
United Airlines
Deal found 6/5![United Airlines logo]()
$595
Last-minute flights from Chicago to OdessaDiscover last-minute flight deals from Chicago to Odessa. Data last updated June 8, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to Odessa. Data last updated June 8, 2026 and is based on user searches.
This American Airlines deal was found by Cheapflights users on 6/3. 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 6/175:00 am
ORD
- MAF
1 stop6h 09m
American Airlines
Sat 6/205:00 am
MAF
- ORD
1 stop4h 50m
American Airlines
Deal found 6/3![American Airlines logo]()
$507
This United Airlines deal was found by Cheapflights users on 6/5. 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 6/202:33 pm
ORD
- MAF
1 stop5h 51m
United Airlines
Wed 6/245:00 am
MAF
- ORD
1 stop6h 02m
United Airlines
Deal found 6/5![United Airlines logo]()
$548
This United Airlines deal was found by Cheapflights users on 6/3. 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 6/267:35 am
ORD
- MAF
1 stop5h 59m
United Airlines
Sat 6/275:00 am
MAF
- ORD
1 stop5h 20m
United Airlines
Deal found 6/3![United Airlines logo]()
$447
This American Airlines deal was found by Cheapflights users on 6/3. 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 7/14:45 pm
ORD
- MAF
1 stop6h 31m
American Airlines
Tue 7/76:42 pm
MAF
- ORD
1 stop6h 08m
American Airlines
Deal found 6/3![American Airlines logo]()
$371
This American Airlines deal was found by Cheapflights users on 6/7. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/13:50 pm
ORD
- MAF
1 stop7h 26m
American Airlines
Sat 7/252:21 pm
MAF
- ORD
1 stop7h 01m
American Airlines
Deal found 6/7![American Airlines logo]()
$399
This United Airlines deal was found by Cheapflights users on 6/5. 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 7/19:01 am
ORD
- MAF
2 stops12h 47m
United Airlines
Sat 7/255:00 am
MAF
- ORD
1 stop7h 29m
United Airlines
Deal found 6/5![United Airlines logo]()
$595
This American Airlines deal was found by Cheapflights users on 6/7. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/24:51 pm
ORD
- MAF
1 stop5h 02m
American Airlines
Sun 7/196:46 pm
MAF
- ORD
1 stop6h 04m
American Airlines
Deal found 6/7![American Airlines logo]()
$437
This American Airlines deal was found by Cheapflights users on 6/3. 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 7/56:04 am
ORD
- MAF
1 stop7h 45m
American Airlines
Tue 7/146:42 pm
MAF
- ORD
1 stop6h 08m
American Airlines
Deal found 6/3![American Airlines logo]()
$574
This American Airlines deal was found by Cheapflights users on 6/7. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/224:51 pm
ORD
- MAF
1 stop6h 02m
American Airlines
Wed 7/292:21 pm
MAF
- ORD
1 stop6h 08m
American Airlines
Deal found 6/7![American Airlines logo]()
$534
This American Airlines deal was found by Cheapflights users on 6/7. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/232:59 pm
ORD
- MAF
1 stop4h 51m
American Airlines
Thu 7/302:21 pm
MAF
- ORD
1 stop6h 08m
American Airlines
Deal found 6/7![American Airlines logo]()
$484
This United Airlines deal was found by Cheapflights users on 6/5. 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 7/258:45 am
ORD
- MAF
2 stops13h 03m
United Airlines
Tue 7/285:00 am
MAF
- ORD
1 stop6h 01m
United Airlines
Deal found 6/5![United Airlines logo]()
$615
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 June 8, 2026.
Search for one-way flight options from Chicago to Odessa. Find affordable one-way fares based on user searches. Data last updated June 8, 2026.
This American Airlines deal was found by Cheapflights users on 6/3. 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 6/266:20 pm
ORD
- MAF
1 stop4h 56m
American Airlines
Deal found 6/3![American Airlines logo]()
$224
This American Airlines deal was found by Cheapflights users on 6/5. 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 6/2010:50 am
ORD
- MAF
1 stop7h 22m
American Airlines
Deal found 6/5![American Airlines logo]()
$254
This United Airlines deal was found by Cheapflights users on 6/3. 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 6/2610:29 am
ORD
- MAF
2 stops7h 46m
United Airlines
Deal found 6/3![United Airlines logo]()
$494
This United Airlines deal was found by Cheapflights users on 6/5. 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 6/2011:55 am
ORD
- MAF
2 stops8h 29m
United Airlines
Deal found 6/5![United Airlines logo]()
$509
This Kiwi.com deal was found by Cheapflights users on 6/3. 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 6/265:30 pm
ORD
- MAF
3 stops47h 23m
Multiple Airlines
Deal found 6/3![Multiple Airlines logo]()
$946
This Kiwi.com deal was found by Cheapflights users on 6/5. 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.
Sat 6/205:30 pm
ORD
- MAF
3 stops39h 21m
Multiple Airlines
Deal found 6/5![Multiple Airlines logo]()
$1,398
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 June 8, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $371 (American Airlines) |
One-way from | $224 (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 2,558,603 searches. Data last updated June 8, 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 - MAF
ORDMAF
Chicago O'Hare Intl
Sat 8/29
10:55 am-5:04 pm
1 stop6h 09m
Midland Intl
Sat 9/5
1:40 pm-7:30 pm
1 stop5h 50m
$399
ChicagoMidland
ORD - MAF
ORDMAF
Chicago O'Hare Intl
Thu 7/2
4:51 pm-9:53 pm
1 stop5h 02m
Midland Intl
Sun 7/19
6:46 pm-12:50 am
1 stop6h 04m
$437
Quickest round-trip
ChicagoMidland
ORD - MAF
ORDMAF
Chicago O'Hare Intl
Tue 8/18
6:29 pm-11:44 pm
1 stop5h 15m
Midland Intl
Wed 8/19
5:00 am-10:15 am
1 stop5h 15m
$461
ChicagoMidland
ORD - MAF
ORDMAF
Chicago O'Hare Intl
Wed 6/17
5:00 am-11:09 am
1 stop6h 09m
Midland Intl
Sat 6/20
5:00 am-9:50 am
1 stop4h 50m
$507
ChicagoMidland
ORD - MAF
ORDMAF
Chicago O'Hare Intl
Sat 6/20
2:33 pm-8:24 pm
1 stop5h 51m
Midland Intl
Mon 6/22
1:45 pm-8:30 pm
1 stop6h 45m
$507
ChicagoMidland
ORD - MAF
ORDMAF
Chicago O'Hare Intl
Wed 7/22
4:51 pm-10:53 pm
1 stop6h 02m
Midland Intl
Wed 7/29
2:21 pm-8:29 pm
1 stop6h 08m
$534
ChicagoMidland
ORD - MAF
ORDMAF
Chicago O'Hare Intl
Sat 6/20
2:33 pm-8:24 pm
1 stop5h 51m
Midland Intl
Wed 6/24
5:00 am-11:02 am
1 stop6h 02m
$548
ChicagoMidland
ORD - MAF
ORDMAF
Chicago O'Hare Intl
Sun 7/5
6:04 am-1:49 pm
1 stop7h 45m
Midland Intl
Tue 7/14
6:42 pm-12:50 am
1 stop6h 08m
$574
ChicagoMidland
ORD - MAF
ORDMAF
Chicago O'Hare Intl
Wed 7/1
9:01 am-9:48 pm
2 stops12h 47m
Midland Intl
Sat 7/25
5:00 am-12:29 pm
1 stop7h 29m
$595
Cheapest one-way
Quickest one-way
ChicagoMidland
ORD - MAF
ORDMAF
Chicago O'Hare Intl
Sat 6/20
10:50 am-6:12 pm
1 stop7h 22m
$254
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 June 8, 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.
Food
7.0
Comfort
8.0
Crew
8.6
Entertainment
7.5
Boarding
8.1
Overall
7.9
Reviews
1 / 20
2.0
MediocreMike,Aug 2025
OKC - AUS
Food
7.0
Comfort
8.0
Crew
8.6
Entertainment
7.5
Boarding
8.1
Overall
7.9
Reviews
1 / 20
2.0
MediocreMike,Aug 2025
OKC - AUS
Food
7.0
Comfort
8.0
Crew
8.6
Entertainment
7.5
Boarding
8.1
Overall
7.9
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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Alternative routes for Chicago to Odessa
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Complete your trip
Complete your trip to Odessa by adding a car rental and/or hotel reservation to your travel itinerary.
Search flights from Chicago to Odessa by cabin class
Find flights from Chicago to Odessa, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Chicago and Odessa flights
Browse other Chicago and Odessa flight options. Last updated on June 8, 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 June 8, 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 June 8, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$216 | Average$379 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$285 | Average$424 | FlexibilityNo cancel fee | On-time69% |