$180+ 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 4/4. Fares are subject to change and may not be available on all flights or dates of travel.
MAF — CHI
Mar 5 — Mar 121
1 adult, Economy
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Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”2. Select your favorite providers
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Cheapest flights from 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 February 3, 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 February 3, 2026.
This United Airlines deal was found by Cheapflights users on 2/3. 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.
Sun 3/295:00 am
MAF
- ORD
1 stop5h 05m
United Airlines
Wed 4/14:03 pm
ORD
- MAF
1 stop5h 36m
United Airlines
Deal found 2/3![United Airlines logo]()
$388
This Southwest deal was found by Cheapflights users on 2/2. 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.
Wed 3/183:45 pm
MAF
- ORD
1 stop7h 10m
Southwest
Wed 3/256:15 am
ORD
- MAF
1 stop7h 25m
Southwest
Deal found 2/2![Southwest logo]()
$407
This Southwest deal was found by Cheapflights users on 2/3. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 3/295:30 am
MAF
- ORD
2 stops7h 20m
Southwest
Wed 4/16:15 am
ORD
- MAF
1 stop7h 25m
Southwest
Deal found 2/3![Southwest logo]()
$442
This American Airlines deal was found by Cheapflights users on 2/1. 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 5/112:15 pm
MAF
- ORD
1 stop7h 35m
American Airlines
Sun 5/176:05 am
ORD
- MAF
1 stop7h 40m
American Airlines
Deal found 2/1![American Airlines logo]()
$443
This Southwest deal was found by Cheapflights users on 2/3. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/195:30 am
MAF
- ORD
1 stop7h 30m
Southwest
Mon 2/232:15 pm
ORD
- MAF
1 stop8h 00m
Southwest
Deal found 2/3![Southwest logo]()
$457
This Southwest deal was found by Cheapflights users on 2/2. 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.
Fri 2/205:30 am
MAF
- ORD
2 stops8h 35m
Southwest
Mon 2/231:45 pm
ORD
- MAF
2 stops8h 50m
Southwest
Deal found 2/2![Southwest logo]()
$467
This Southwest deal was found by Cheapflights users on 2/1. 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 3/195:20 am
MAF
- ORD
1 stop5h 50m
Southwest
Sun 3/223:45 pm
ORD
- MAF
2 stops7h 25m
Southwest
Deal found 2/1![Southwest logo]()
$472
This Southwest deal was found by Cheapflights users on 2/1. 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.
Fri 3/202:25 pm
MAF
- ORD
2 stops9h 30m
Southwest
Sun 3/223:45 pm
ORD
- MAF
2 stops7h 25m
Southwest
Deal found 2/1![Southwest logo]()
$477
This American Airlines deal was found by Cheapflights users on 2/2. 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 3/1710:12 am
MAF
- ORD
1 stop6h 43m
American Airlines
Tue 3/247:30 pm
ORD
- MAF
1 stop14h 12m
American Airlines
Deal found 2/2![American Airlines logo]()
$478
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 February 3, 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 February 3, 2026.
This United Airlines deal was found by Cheapflights users on 2/3. 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.
Sun 3/295:00 am
MAF
- ORD
1 stop5h 05m
United Airlines
Wed 4/14:03 pm
ORD
- MAF
1 stop5h 36m
United Airlines
Deal found 2/3![United Airlines logo]()
$388
This Southwest deal was found by Cheapflights users on 2/2. 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.
Wed 3/183:45 pm
MAF
- ORD
1 stop7h 10m
Southwest
Wed 3/256:15 am
ORD
- MAF
1 stop7h 25m
Southwest
Deal found 2/2![Southwest logo]()
$407
This Southwest deal was found by Cheapflights users on 2/3. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 3/295:30 am
MAF
- ORD
2 stops7h 20m
Southwest
Wed 4/16:15 am
ORD
- MAF
1 stop7h 25m
Southwest
Deal found 2/3![Southwest logo]()
$442
This United Airlines deal was found by Cheapflights users on 2/2. 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 3/205:05 pm
MAF
- ORD
1 stop5h 50m
United Airlines
Tue 3/242:01 pm
ORD
- MAF
1 stop8h 14m
United Airlines
Deal found 2/2![United Airlines logo]()
$483
This Southwest deal was found by Cheapflights users on 2/3. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/195:30 am
MAF
- ORD
1 stop7h 30m
Southwest
Mon 2/232:15 pm
ORD
- MAF
1 stop8h 00m
Southwest
Deal found 2/3![Southwest logo]()
$457
This Southwest deal was found by Cheapflights users on 2/1. 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 3/195:20 am
MAF
- ORD
2 stops9h 00m
Southwest
Sun 3/223:45 pm
ORD
- MAF
2 stops7h 25m
Southwest
Deal found 2/1![Southwest logo]()
$457
This Southwest deal was found by Cheapflights users on 2/2. 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.
Fri 2/205:30 am
MAF
- ORD
1 stop7h 30m
Southwest
Mon 2/232:15 pm
ORD
- MAF
2 stops8h 20m
Southwest
Deal found 2/2![Southwest logo]()
$462
This Southwest deal was found by Cheapflights users on 2/1. 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.
Fri 3/202:25 pm
MAF
- ORD
2 stops9h 30m
Southwest
Sun 3/223:45 pm
ORD
- MAF
2 stops7h 25m
Southwest
Deal found 2/1![Southwest logo]()
$477
Last-minute flights from Odessa to ChicagoDiscover last-minute flight deals from Odessa to Chicago. Data last updated February 3, 2026 and is based on user searches.
Discover last-minute flight deals from Odessa to Chicago. Data last updated February 3, 2026 and is based on user searches.
This Southwest deal was found by Cheapflights users on 2/3. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/195:30 am
MAF
- ORD
1 stop7h 30m
Southwest
Mon 2/232:15 pm
ORD
- MAF
1 stop8h 00m
Southwest
Deal found 2/3![Southwest logo]()
$457
This Southwest deal was found by Cheapflights users on 2/2. 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.
Fri 2/205:30 am
MAF
- ORD
2 stops8h 35m
Southwest
Mon 2/231:45 pm
ORD
- MAF
2 stops8h 50m
Southwest
Deal found 2/2![Southwest logo]()
$467
This American Airlines deal was found by Cheapflights users on 2/2. 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 3/1710:12 am
MAF
- ORD
1 stop6h 43m
American Airlines
Tue 3/247:30 pm
ORD
- MAF
1 stop14h 12m
American Airlines
Deal found 2/2![American Airlines logo]()
$478
This Southwest deal was found by Cheapflights users on 2/2. 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.
Wed 3/183:45 pm
MAF
- ORD
1 stop7h 10m
Southwest
Wed 3/256:15 am
ORD
- MAF
1 stop7h 25m
Southwest
Deal found 2/2![Southwest logo]()
$407
This Southwest deal was found by Cheapflights users on 2/1. 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 3/195:20 am
MAF
- ORD
1 stop5h 50m
Southwest
Sun 3/223:45 pm
ORD
- MAF
2 stops7h 25m
Southwest
Deal found 2/1![Southwest logo]()
$472
This Southwest deal was found by Cheapflights users on 2/1. 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.
Fri 3/202:25 pm
MAF
- ORD
2 stops9h 30m
Southwest
Sun 3/223:45 pm
ORD
- MAF
2 stops7h 25m
Southwest
Deal found 2/1![Southwest logo]()
$477
This United Airlines deal was found by Cheapflights users on 2/3. 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.
Sun 3/295:00 am
MAF
- ORD
1 stop5h 05m
United Airlines
Wed 4/14:03 pm
ORD
- MAF
1 stop5h 36m
United Airlines
Deal found 2/3![United Airlines logo]()
$388
This Southwest deal was found by Cheapflights users on 2/3. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 3/295:30 am
MAF
- ORD
2 stops7h 20m
Southwest
Wed 4/16:15 am
ORD
- MAF
1 stop7h 25m
Southwest
Deal found 2/3![Southwest logo]()
$442
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 February 3, 2026.
Search for one-way flight options from Odessa to Chicago. Find affordable one-way fares based on user searches. Data last updated February 3, 2026.
This American Airlines deal was found by Cheapflights users on 2/2. 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 4/45:00 am
MAF
- ORD
1 stop4h 45m
American Airlines
Deal found 2/2![American Airlines logo]()
$180
This United Airlines deal was found by Cheapflights users on 2/1. 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 5/157:00 pm
MAF
- ORD
1 stop5h 45m
United Airlines
Deal found 2/1![United Airlines logo]()
$204
This Southwest deal was found by Cheapflights users on 2/1. 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 3/55:20 am
MAF
- ORD
1 stop5h 50m
Southwest
Deal found 2/1![Southwest logo]()
$224
This American Airlines deal was found by Cheapflights users on 2/2. 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 5/158:24 pm
MAF
- ORD
1 stop11h 07m
American Airlines
Deal found 2/2![American Airlines logo]()
$244
This Southwest deal was found by Cheapflights users on 2/1. 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.
Fri 5/156:00 am
MAF
- ORD
2 stops7h 15m
Southwest
Deal found 2/1![Southwest logo]()
$249
This Southwest deal was found by Cheapflights users on 2/2. 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 4/45:30 am
MAF
- ORD
2 stops9h 30m
Southwest
Deal found 2/2![Southwest logo]()
$404
This Kiwi.com deal was found by Cheapflights users on 2/2. 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 4/48:29 pm
MAF
- ORD
3 stops41h 06m
Multiple Airlines
Deal found 2/2![Multiple Airlines logo]()
$1,010
This Kiwi.com deal was found by Cheapflights users on 2/1. 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 5/152:15 pm
MAF
- ORD
3 stops27h 55m
Multiple Airlines
Deal found 2/1![Multiple Airlines logo]()
$1,523
This Kiwi.com deal was found by Cheapflights users on 2/1. 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 3/512:22 pm
MAF
- ORD
3 stops47h 38m
Multiple Airlines
Deal found 2/1![Multiple Airlines logo]()
$1,766
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 February 3, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $372 (United Airlines) |
One-way from | $180 (American Airlines) |
Popular in | January |
Cheapest in | November |
Average price | $748 |
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 February 3, 2026.
Use the filters below to find and compare flights from Odessa to Chicago that are best for you.
Fly from
Odessa
Fly to
Chicago
Route
Depart
Return
Price
MidlandChicago
MAF - ORD
MAFORD
Midland Intl
Sun 3/29
5:00 am-10:05 am
1 stop5h 05m
Chicago O'Hare Intl
Wed 4/1
4:03 pm-9:39 pm
1 stop5h 36m
$388
MidlandChicago
MAF - ORD
MAFORD
Midland Intl
Wed 3/18
3:45 pm-10:55 pm
1 stop7h 10m
Chicago O'Hare Intl
Wed 3/25
6:15 am-1:40 pm
1 stop7h 25m
$407
MidlandChicago
MAF - ORD
MAFORD
Midland Intl
Sun 3/29
5:30 am-12:50 pm
2 stops7h 20m
Chicago O'Hare Intl
Wed 4/1
6:15 am-1:40 pm
1 stop7h 25m
$442
MidlandChicago
MAF - ORD
MAFORD
Midland Intl
Thu 2/19
5:30 am-1:00 pm
1 stop7h 30m
Chicago O'Hare Intl
Mon 2/23
2:15 pm-10:15 pm
1 stop8h 00m
$457
MidlandChicago
MAF - ORD
MAFORD
Midland Intl
Thu 3/19
5:20 am-2:20 pm
2 stops9h 00m
Chicago O'Hare Intl
Sun 3/22
3:45 pm-11:10 pm
2 stops7h 25m
$457
MidlandChicago
MAF - ORD
MAFORD
Midland Intl
Fri 2/20
5:30 am-1:00 pm
1 stop7h 30m
Chicago O'Hare Intl
Mon 2/23
2:15 pm-10:35 pm
2 stops8h 20m
$462
MidlandChicago
MAF - ORD
MAFORD
Midland Intl
Fri 3/20
2:25 pm-11:55 pm
2 stops9h 30m
Chicago O'Hare Intl
Sun 3/22
3:45 pm-11:10 pm
2 stops7h 25m
$477
MidlandChicago
MAF - ORD
MAFORD
Midland Intl
Fri 3/20
5:05 pm-10:55 pm
1 stop5h 50m
Chicago O'Hare Intl
Tue 3/24
2:01 pm-10:15 pm
1 stop8h 14m
$483
MidlandChicago
MAF - ORD
MAFORD
Midland Intl
Sat 4/4
5:00 am-9:45 am
1 stop4h 45m
$180
MidlandChicago
MAF - ORD
MAFORD
Midland Intl
Fri 5/15
7:00 pm-12:45 am
1 stop5h 45m
$204
Showing 1-10 of 17 results
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
What is the cheapest month to book a flight from Odessa to Chicago?
Currently, August is the cheapest month in which you can book a flight from Odessa to Chicago (average of $219). Flying from Odessa to Chicago in February is currently the most expensive (average of $901). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.
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 February 3, 2026.
Read reviews from past customers who have flown Southwest and American Airlines 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.
Food
7.0
Comfort
8.0
Overall
8.0
Crew
8.6
Boarding
8.1
Entertainment
7.5
Reviews
1 / 20
8.0
ExcellentIla,Mar 2025
HOU - DAL
Food
7.0
Comfort
8.0
Overall
8.0
Crew
8.6
Boarding
8.1
Entertainment
7.5
Reviews
1 / 20
8.0
ExcellentIla,Mar 2025
HOU - DAL
Food
7.0
Comfort
8.0
Overall
8.0
Crew
8.6
Boarding
8.1
Entertainment
7.5
Reviews
1 / 20
8.0
ExcellentIla,Mar 2025
HOU - DAL
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?
Book flights to Chicago if you plan to visit one of these locationsLansing
Merrillville
Hammond
Porter
Benton Harbor
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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 February 3, 2026.
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Odessa and Chicago flights
Browse other Odessa and Chicago flight options. Last updated on February 3, 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 February 3, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$216 | Average$446 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$255 | Average$365 | FlexibilityNo cancel fee | On-time71% |