$167+ Cheap flights from Odessa, TX 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 9/9. Fares are subject to change and may not be available on all flights or dates of travel.
MAF — CHI
Aug 22 — Aug 291
Round-trip
1 adult, Economy
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Find cheap flights from Odessa to Chicago with Cheapflights
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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
Best
Last-minute
One-way
Cheapest flights from Odessa to ChicagoExplore the most affordable flight options available from Odessa to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on July 23, 2026.
Explore the most affordable flight options available from Odessa to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on July 23, 2026.
This United Airlines deal was found by Cheapflights users on 7/22. 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 8/1911:54 am
MAF
- ORD
1 stop6h 36m
United Airlines
Wed 8/265:30 am
ORD
- MAF
1 stop5h 41m
United Airlines
Deal found 7/22![United Airlines logo]()
$333
This United Airlines deal was found by Cheapflights users on 7/18. 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 9/95:00 am
MAF
- ORD
1 stop5h 55m
United Airlines
Mon 9/146:25 pm
ORD
- MAF
1 stop5h 19m
United Airlines
Deal found 7/18![United Airlines logo]()
$354
This United Airlines deal was found by Cheapflights users on 7/23. 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 9/25:00 am
MAF
- ORD
1 stop5h 15m
United Airlines
Tue 9/85:53 pm
ORD
- MAF
1 stop5h 51m
United Airlines
Deal found 7/23![United Airlines logo]()
$358
This United Airlines deal was found by Cheapflights users on 7/19. 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 8/187:15 pm
MAF
- ORD
1 stop5h 44m
United Airlines
Mon 8/246:29 pm
ORD
- MAF
1 stop5h 15m
United Airlines
Deal found 7/19![United Airlines logo]()
$375
This American Airlines deal was found by Cheapflights users on 7/21. 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 8/136:26 pm
MAF
- ORD
1 stop5h 52m
American Airlines
Thu 8/205:00 am
ORD
- MAF
1 stop4h 46m
American Airlines
Deal found 7/21![American Airlines logo]()
$379
This United Airlines deal was found by Cheapflights users on 7/21. 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 9/205:00 am
MAF
- ORD
1 stop5h 15m
United Airlines
Sat 9/262:10 pm
ORD
- MAF
1 stop7h 19m
United Airlines
Deal found 7/21![United Airlines logo]()
$380
This United Airlines deal was found by Cheapflights users on 7/21. 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 8/205:00 am
MAF
- ORD
1 stop5h 15m
United Airlines
Sun 8/237:30 am
ORD
- MAF
1 stop6h 02m
United Airlines
Deal found 7/21![United Airlines logo]()
$385
This American Airlines deal was found by Cheapflights users on 7/20. 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 9/207:00 am
MAF
- ORD
1 stop5h 54m
American Airlines
Sat 9/265:00 am
ORD
- MAF
1 stop4h 45m
American Airlines
Deal found 7/20![American Airlines logo]()
$401
This United Airlines deal was found by Cheapflights users on 7/21. 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 8/112:13 pm
MAF
- ORD
1 stop5h 52m
United Airlines
Sat 8/1510:40 am
ORD
- MAF
1 stop5h 25m
United Airlines
Deal found 7/21![United Airlines logo]()
$423
This United Airlines deal was found by Cheapflights users on 7/20. 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 9/205:00 am
MAF
- ORD
1 stop6h 20m
United Airlines
Fri 9/255:53 pm
ORD
- MAF
1 stop5h 31m
United Airlines
Deal found 7/20![United Airlines logo]()
$427
This American Airlines deal was found by Cheapflights users on 7/20. 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 8/145:31 pm
MAF
- ORD
1 stop6h 47m
American Airlines
Sun 8/166:00 am
ORD
- MAF
1 stop5h 19m
American Airlines
Deal found 7/20![American Airlines logo]()
$447
Best flights from Odessa to ChicagoDiscover carefully curated flight deals from Odessa to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated July 23, 2026.
Discover carefully curated flight deals from Odessa to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated July 23, 2026.
This United Airlines deal was found by Cheapflights users on 7/18. 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 9/95:00 am
MAF
- ORD
1 stop5h 55m
United Airlines
Mon 9/146:25 pm
ORD
- MAF
1 stop5h 19m
United Airlines
Deal found 7/18![United Airlines logo]()
$354
This American Airlines deal was found by Cheapflights users on 7/22. 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 9/207:00 am
MAF
- ORD
1 stop5h 54m
American Airlines
Sat 9/265:00 am
ORD
- MAF
1 stop4h 45m
American Airlines
Deal found 7/22![American Airlines logo]()
$380
This United Airlines deal was found by Cheapflights users on 7/23. 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 9/25:00 am
MAF
- ORD
1 stop5h 15m
United Airlines
Tue 9/85:53 pm
ORD
- MAF
1 stop5h 51m
United Airlines
Deal found 7/23![United Airlines logo]()
$358
This United Airlines deal was found by Cheapflights users on 7/22. 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 8/205:00 am
MAF
- ORD
1 stop5h 15m
United Airlines
Sun 8/237:30 am
ORD
- MAF
1 stop6h 02m
United Airlines
Deal found 7/22![United Airlines logo]()
$406
This United Airlines deal was found by Cheapflights users on 7/20. 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 8/112:13 pm
MAF
- ORD
1 stop5h 52m
United Airlines
Sat 8/1510:40 am
ORD
- MAF
1 stop5h 25m
United Airlines
Deal found 7/20![United Airlines logo]()
$423
This United Airlines deal was found by Cheapflights users on 7/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/67:15 pm
MAF
- ORD
1 stop5h 19m
United Airlines
Sun 11/87:40 am
ORD
- MAF
1 stop5h 56m
United Airlines
Deal found 7/19![United Airlines logo]()
$454
This United Airlines deal was found by Cheapflights users on 7/19. 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 9/35:00 am
MAF
- ORD
1 stop19h 59m
United Airlines
Tue 9/85:53 pm
ORD
- MAF
1 stop5h 51m
United Airlines
Deal found 7/19![United Airlines logo]()
$494
This United Airlines deal was found by Cheapflights users on 7/19. 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 8/85:00 am
MAF
- ORD
1 stop5h 20m
United Airlines
Sat 8/84:05 pm
ORD
- MAF
1 stop5h 43m
United Airlines
Deal found 7/19![United Airlines logo]()
$507
This United Airlines deal was found by Cheapflights users on 7/19. 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 9/45:00 am
MAF
- ORD
1 stop5h 15m
United Airlines
Mon 9/75:53 pm
ORD
- MAF
1 stop5h 51m
United Airlines
Deal found 7/19![United Airlines logo]()
$568
Last-minute flights from Odessa to ChicagoDiscover last-minute flight deals from Odessa to Chicago. Data last updated July 23, 2026 and is based on user searches.
Discover last-minute flight deals from Odessa to Chicago. Data last updated July 23, 2026 and is based on user searches.
This American Airlines deal was found by Cheapflights users on 7/19. 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 8/72:21 pm
MAF
- ORD
1 stop5h 21m
American Airlines
Sun 8/95:00 am
ORD
- MAF
1 stop4h 46m
American Airlines
Deal found 7/19![American Airlines logo]()
$477
This American Airlines deal was found by Cheapflights users on 7/19. 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 8/75:31 pm
MAF
- ORD
1 stop6h 47m
American Airlines
Sat 8/89:40 am
ORD
- MAF
1 stop7h 20m
American Airlines
Deal found 7/19![American Airlines logo]()
$507
This United Airlines deal was found by Cheapflights users on 7/21. 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 8/112:13 pm
MAF
- ORD
1 stop5h 52m
United Airlines
Sat 8/1510:40 am
ORD
- MAF
1 stop5h 25m
United Airlines
Deal found 7/21![United Airlines logo]()
$423
This American Airlines deal was found by Cheapflights users on 7/21. 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 8/136:26 pm
MAF
- ORD
1 stop5h 52m
American Airlines
Thu 8/205:00 am
ORD
- MAF
1 stop4h 46m
American Airlines
Deal found 7/21![American Airlines logo]()
$379
This American Airlines deal was found by Cheapflights users on 7/20. 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 8/136:26 pm
MAF
- ORD
1 stop5h 52m
American Airlines
Fri 8/146:00 am
ORD
- MAF
1 stop5h 19m
American Airlines
Deal found 7/20![American Airlines logo]()
$462
This American Airlines deal was found by Cheapflights users on 7/20. 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 8/145:31 pm
MAF
- ORD
1 stop6h 47m
American Airlines
Sun 8/166:00 am
ORD
- MAF
1 stop5h 19m
American Airlines
Deal found 7/20![American Airlines logo]()
$447
This United Airlines deal was found by Cheapflights users on 7/19. 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 8/187:15 pm
MAF
- ORD
1 stop5h 44m
United Airlines
Mon 8/246:29 pm
ORD
- MAF
1 stop5h 15m
United Airlines
Deal found 7/19![United Airlines logo]()
$375
This United Airlines deal was found by Cheapflights users on 7/22. 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 8/1911:54 am
MAF
- ORD
1 stop6h 36m
United Airlines
Wed 8/265:30 am
ORD
- MAF
1 stop5h 41m
United Airlines
Deal found 7/22![United Airlines logo]()
$333
This United Airlines deal was found by Cheapflights users on 7/21. 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 8/205:00 am
MAF
- ORD
1 stop5h 15m
United Airlines
Sun 8/237:30 am
ORD
- MAF
1 stop6h 02m
United Airlines
Deal found 7/21![United Airlines logo]()
$385
One-way flights from Odessa to ChicagoSearch for one-way flight options from Odessa to Chicago. Find affordable one-way fares based on user searches. Data last updated July 23, 2026.
Search for one-way flight options from Odessa to Chicago. Find affordable one-way fares based on user searches. Data last updated July 23, 2026.
This American Airlines deal was found by Cheapflights users on 7/18. 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 9/95:23 pm
MAF
- ORD
1 stop6h 51m
American Airlines
Deal found 7/18![American Airlines logo]()
$167
This American Airlines deal was found by Cheapflights users on 7/22. 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 10/25:23 pm
MAF
- ORD
1 stop6h 51m
American Airlines
Deal found 7/22![American Airlines logo]()
$214
This United Airlines deal was found by Cheapflights users on 7/22. 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 10/21:41 pm
MAF
- ORD
2 stops19h 50m
United Airlines
Deal found 7/22![United Airlines logo]()
$473
This United Airlines deal was found by Cheapflights users on 7/18. 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 9/97:40 am
MAF
- ORD
2 stops9h 25m
United Airlines
Deal found 7/18![United Airlines logo]()
$489
This Kiwi.com deal was found by Cheapflights users on 7/22. 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 10/26:20 pm
MAF
- ORD
3 stops25h 10m
Multiple Airlines
Deal found 7/22![Multiple Airlines logo]()
$1,135
Find flight deals from Odessa to Chicago
Keep the following information in mind while searching for Odessa to Chicago flight deals. Data was last updated July 23, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $333 (United Airlines) |
One-way from | $167 (American Airlines) |
Cheapflights Fare Finder
Customize your flight search to find flights from Odessa 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 2,558,603 searches. Data last updated July 23, 2026.
Use the filters below to find and compare flights from Odessa to Chicago that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
MidlandChicago
MAF - ORD
MAFORD
Midland Intl
Wed 9/9
5:00 am-10:55 am
1 stop5h 55m
Chicago O'Hare Intl
Mon 9/14
6:25 pm-11:44 pm
1 stop5h 19m
$354
MidlandChicago
MAF - ORD
MAFORD
Midland Intl
Wed 9/2
5:00 am-10:15 am
1 stop5h 15m
Chicago O'Hare Intl
Tue 9/8
5:53 pm-11:44 pm
1 stop5h 51m
$358
Quickest round-trip
MidlandChicago
MAF - ORD
MAFORD
Midland Intl
Sun 9/20
7:00 am-12:54 pm
1 stop5h 54m
Chicago O'Hare Intl
Sat 9/26
5:00 am-9:45 am
1 stop4h 45m
$380
MidlandChicago
MAF - ORD
MAFORD
Midland Intl
Thu 8/20
5:00 am-10:15 am
1 stop5h 15m
Chicago O'Hare Intl
Sun 8/23
7:30 am-1:32 pm
1 stop6h 02m
$406
MidlandChicago
MAF - ORD
MAFORD
Midland Intl
Tue 8/11
2:13 pm-8:05 pm
1 stop5h 52m
Chicago O'Hare Intl
Sat 8/15
10:40 am-4:05 pm
1 stop5h 25m
$423
MidlandChicago
MAF - ORD
MAFORD
Midland Intl
Fri 11/6
7:15 pm-12:34 am
1 stop5h 19m
Chicago O'Hare Intl
Sun 11/8
7:40 am-1:36 pm
1 stop5h 56m
$454
MidlandChicago
MAF - ORD
MAFORD
Midland Intl
Thu 9/3
5:00 am-12:59 am
1 stop19h 59m
Chicago O'Hare Intl
Tue 9/8
5:53 pm-11:44 pm
1 stop5h 51m
$494
MidlandChicago
MAF - ORD
MAFORD
Midland Intl
Sat 8/8
5:00 am-10:20 am
1 stop5h 20m
Chicago O'Hare Intl
Sat 8/8
4:05 pm-9:48 pm
1 stop5h 43m
$507
MidlandChicago
MAF - ORD
MAFORD
Midland Intl
Fri 9/4
5:00 am-10:15 am
1 stop5h 15m
Chicago O'Hare Intl
Mon 9/7
5:53 pm-11:44 pm
1 stop5h 51m
$568
Cheapest one-way
Quickest one-way
MidlandChicago
MAF - ORD
MAFORD
Midland Intl
Wed 9/9
5:23 pm-12:14 am
1 stop6h 51m
$167
Showing 1-10 of 13 resultsSorted by cheapest first
Best time to book a flight from Odessa to Chicago
Have a flexible travel schedule? Discover the best time to fly to Chicago from Odessa with our price prediction graph.
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 Odessa to Chicago
OD3-CHI
MAF-ORD
No data available for this route at this time. Please check back soon.
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 July 23, 2026.
Read reviews from past customers who have flown Southwest from Odessa 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.
Boarding
8.1
Crew
8.6
Overall
8.0
Entertainment
7.5
Comfort
8.0
Food
7.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Boarding
8.1
Crew
8.6
Overall
8.0
Entertainment
7.5
Comfort
8.0
Food
7.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Related info for your journey
Find useful and relevant information for your journey from Odessa 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?
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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 July 23, 2026.
Complete your trip
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Odessa and Chicago flights
Browse other Odessa and Chicago flight options. Last updated on July 23, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Top 2 airlines flying from Odessa to Chicago
Discover the top 2 airlines that operate flights from Odessa 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 2,558,603 searches. Data last updated July 23, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$398 | Average$451 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$404 | Average$586 | FlexibilityNo cancel fee | On-time71% |