$219+ Cheap flights from Odessa, TX to Chicago (CHI)
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 10/16. Fares are subject to change and may not be available on all flights or dates of travel.
MAF — CHI
Oct 14 — Oct 211
Round-trip
1 adult, Economy
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Find cheap flights from Odessa to Chicago with Cheapflights
1. Tell us where you want to go
Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”2. Select your favorite providers
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Best
Last-minute
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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 September 14, 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 September 14, 2026.
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.
Sat 10/36:20 pm -
1 stop5h 54m
Sat 10/105:00 am -
1 stop5h 01m
Deal found 9/10![American Airlines logo]()
$340
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.
Tue 10/205:23 pm -
1 stop6h 36m
Fri 10/236:00 am -
1 stop6h 21m
Deal found 9/9![American Airlines logo]()
$354
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.
Wed 11/1812:38 pm -
1 stop5h 52m
Wed 11/256:05 am -
1 stop6h 16m
Deal found 9/10![American Airlines logo]()
$396
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.
Sun 10/45:00 am -
1 stop5h 16m
Thu 10/86:25 am -
1 stop7h 07m
Deal found 9/9![United Airlines logo]()
$398
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.
Fri 12/46:43 pm -
1 stop5h 16m
Sun 12/65:00 am -
1 stop7h 08m
Deal found 9/10![American Airlines logo]()
$403
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 10/26:20 pm -
1 stop5h 54m
Mon 10/55:16 pm -
1 stop5h 21m
Deal found 9/11![American Airlines logo]()
$457
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 10/25:23 pm -
1 stop6h 07m
Tue 10/65:16 pm -
1 stop5h 21m
Deal found 9/11![American Airlines logo]()
$493
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 September 14, 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 September 14, 2026.
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.
Sun 10/45:00 am -
1 stop5h 16m
Thu 10/86:25 am -
1 stop7h 07m
Deal found 9/9![United Airlines logo]()
$398
This American Airlines deal was found by Cheapflights users on 9/13. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/285:23 pm -
1 stop6h 07m
Fri 10/212:09 pm -
1 stop5h 41m
Deal found 9/13![American Airlines logo]()
$537
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 10/51:41 pm -
1 stop8h 11m
Tue 10/62:30 pm -
1 stop7h 28m
Deal found 9/11![United Airlines logo]()
$493
This American Airlines deal was found by Cheapflights users on 9/13. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/297:00 am -
1 stop5h 54m
Sat 10/312:09 pm -
1 stop5h 41m
Deal found 9/13![American Airlines logo]()
$537
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.
Sat 10/32:13 pm -
1 stop6h 02m
Sun 10/45:30 am -
1 stop5h 40m
Deal found 9/11![United Airlines logo]()
$520
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.
Sun 10/45:00 am -
1 stop5h 16m
Sun 10/45:53 pm -
1 stop5h 34m
Deal found 9/11![United Airlines logo]()
$613
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 11/181:21 pm -
1 stop7h 08m
Wed 11/258:40 am -
2 stops13h 35m
Deal found 9/10![United Airlines logo]()
$647
This United Airlines deal was found by Cheapflights users on 9/13. 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 9/299:34 am -
1 stop5h 16m
Sat 10/32:15 pm -
2 stops7h 14m
Deal found 9/13![United Airlines logo]()
$761
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.
Fri 12/47:20 pm -
1 stop5h 23m
Sun 12/610:30 am -
2 stops11h 33m
Deal found 9/10![United Airlines logo]()
$771
Last-minute flights from Odessa to ChicagoDiscover last-minute flight deals from Odessa to Chicago. Data last updated September 14, 2026 and is based on user searches.
Discover last-minute flight deals from Odessa to Chicago. Data last updated September 14, 2026 and is based on user searches.
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.
Fri 9/256:20 pm -
1 stop5h 54m
Tue 9/293:00 pm -
1 stop4h 41m
Deal found 9/10![American Airlines logo]()
$517
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 10/26:20 pm -
1 stop5h 54m
Mon 10/55:16 pm -
1 stop5h 21m
Deal found 9/11![American Airlines logo]()
$457
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 10/25:23 pm -
1 stop6h 51m
Sat 10/38:15 am -
1 stop5h 32m
Deal found 9/11![American Airlines logo]()
$493
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 10/26:20 pm -
1 stop5h 54m
Sun 10/45:00 am -
1 stop6h 20m
Deal found 9/11![American Airlines logo]()
$530
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.
Sat 10/36:20 pm -
1 stop5h 54m
Sat 10/105:00 am -
1 stop5h 01m
Deal found 9/10![American Airlines logo]()
$340
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.
Sun 10/45:00 am -
1 stop5h 16m
Thu 10/86:25 am -
1 stop7h 07m
Deal found 9/9![United Airlines logo]()
$398
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.
Sun 10/47:00 am -
1 stop5h 25m
Wed 10/75:53 pm -
1 stop5h 31m
Deal found 9/11![United Airlines logo]()
$520
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.
Sun 10/45:00 am -
1 stop6h 16m
Mon 10/55:53 pm -
1 stop5h 31m
Deal found 9/11![United Airlines logo]()
$547
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.
Tue 10/205:23 pm -
1 stop6h 36m
Fri 10/236:00 am -
1 stop6h 21m
Deal found 9/9![American Airlines logo]()
$354
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 September 14, 2026.
Search for one-way flight options from Odessa to Chicago. Find affordable one-way fares based on user searches. Data last updated September 14, 2026.
This American Airlines deal was found by Cheapflights users on 9/13. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/166:42 pm -
1 stop5h 17m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/13![American Airlines logo]()
$219
This United Airlines deal was found by Cheapflights users on 9/13. 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.
Fri 10/167:00 am -
2 stops13h 30m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/13![United Airlines logo]()
$483
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 September 14, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $340 (American Airlines) |
One-way from | $219 (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 7,457,451 searches. Data last updated September 14, 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
Quickest round-trip
MidlandChicago
MAF Midland Intl - ORD Chicago O'Hare Intl
MAFORD
Midland Intl
Fri 10/16
6:42 pm-11:59 pm
1 stop5h 17m
Chicago O'Hare Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$219
MidlandChicago
MAF Midland Intl - ORD Chicago O'Hare Intl
MAFORD
Midland Intl
Sun 10/4
5:00 am-10:16 am
1 stop5h 16m
Chicago O'Hare Intl
Thu 10/8
6:25 am-1:32 pm
1 stop7h 07m
$398
MidlandChicago
MAF Midland Intl - ORD Chicago O'Hare Intl
MAFORD
Midland Intl
Fri 10/16
7:00 am-8:30 pm
2 stops13h 30m
Chicago O'Hare Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$483
MidlandChicago
MAF Midland Intl - ORD Chicago O'Hare Intl
MAFORD
Midland Intl
Mon 10/5
1:41 pm-9:52 pm
1 stop8h 11m
Chicago O'Hare Intl
Tue 10/6
2:30 pm-9:58 pm
1 stop7h 28m
$493
MidlandChicago
MAF Midland Intl - ORD Chicago O'Hare Intl
MAFORD
Midland Intl
Sat 10/3
2:13 pm-8:15 pm
1 stop6h 02m
Chicago O'Hare Intl
Sun 10/4
5:30 am-11:10 am
1 stop5h 40m
$520
MidlandChicago
MAF Midland Intl - ORD Chicago O'Hare Intl
MAFORD
Midland Intl
Mon 9/28
5:23 pm-11:30 pm
1 stop6h 07m
Chicago O'Hare Intl
Fri 10/2
12:09 pm-5:50 pm
1 stop5h 41m
$537
MidlandChicago
MAF Midland Intl - ORD Chicago O'Hare Intl
MAFORD
Midland Intl
Tue 9/29
7:00 am-12:54 pm
1 stop5h 54m
Chicago O'Hare Intl
Sat 10/3
12:09 pm-5:50 pm
1 stop5h 41m
$537
MidlandChicago
MAF Midland Intl - ORD Chicago O'Hare Intl
MAFORD
Midland Intl
Sun 10/4
5:00 am-10:16 am
1 stop5h 16m
Chicago O'Hare Intl
Sun 10/4
5:53 pm-11:27 pm
1 stop5h 34m
$613
MidlandChicago
MAF Midland Intl - ORD Chicago O'Hare Intl
MAFORD
Midland Intl
Wed 11/18
1:21 pm-8:29 pm
1 stop7h 08m
Chicago O'Hare Intl
Wed 11/25
8:40 am-10:15 pm
2 stops13h 35m
$647
MidlandChicago
MAF Midland Intl - ORD Chicago O'Hare Intl
MAFORD
Midland Intl
Tue 9/29
9:34 am-2:50 pm
1 stop5h 16m
Chicago O'Hare Intl
Sat 10/3
2:15 pm-9:29 pm
2 stops7h 14m
$761
Showing 1-10 of 11 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 September 14, 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.
Comfort
8.0
Food
7.0
Entertainment
7.5
Boarding
8.1
Crew
8.6
Overall
8.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Comfort
8.0
Food
7.0
Entertainment
7.5
Boarding
8.1
Crew
8.6
Overall
8.0
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 September 14, 2026.
Complete your trip
Complete your trip to Chicago by adding a car rental and/or hotel reservation to your travel itinerary.
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Odessa and Chicago flights
Browse other Odessa and Chicago flight options. Last updated on September 14, 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 7,457,451 searches. Data last updated September 14, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$398 | Average$451 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$426 | Average$619 | FlexibilityNo cancel fee | On-time71% |