$371+ 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 7/8. Fares are subject to change and may not be available on all flights or dates of travel.
MAF — CHI
Jul 4 — Jul 111
Round-trip
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 June 4, 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 June 4, 2026.
This American Airlines deal was found by Cheapflights users on 6/2. 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.
Wed 7/86:46 pm
MAF
- ORD
1 stop6h 04m
American Airlines
Tue 7/214:51 pm
ORD
- MAF
1 stop6h 02m
American Airlines
Deal found 6/2![American Airlines logo]()
$371
This United Airlines deal was found by Cheapflights users on 6/1. 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.
Tue 10/207:15 pm
MAF
- ORD
1 stop5h 08m
United Airlines
Sat 10/246:00 am
ORD
- MAF
1 stop6h 55m
United Airlines
Deal found 6/1![United Airlines logo]()
$392
This American Airlines deal was found by Cheapflights users on 6/1. 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 7/206:46 pm
MAF
- ORD
1 stop6h 04m
American Airlines
Tue 7/213:49 pm
ORD
- MAF
1 stop7h 04m
American Airlines
Deal found 6/1![American Airlines logo]()
$399
This American Airlines deal was found by Cheapflights users on 6/1. 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.
Tue 9/15:31 pm
MAF
- ORD
1 stop6h 47m
American Airlines
Mon 9/75:00 am
ORD
- MAF
1 stop4h 47m
American Airlines
Deal found 6/1![American Airlines logo]()
$407
This United Airlines deal was found by Cheapflights users on 5/31. 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 8/15:13 pm
MAF
- ORD
1 stop6h 02m
United Airlines
Sat 8/84:05 pm
ORD
- MAF
1 stop5h 43m
United Airlines
Deal found 5/31![United Airlines logo]()
$420
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.
Sat 7/411:45 am
MAF
- ORD
1 stop7h 59m
American Airlines
Sat 7/116:04 am
ORD
- MAF
1 stop5h 11m
American Airlines
Deal found 6/3![American Airlines logo]()
$427
This United Airlines deal was found by Cheapflights users on 6/1. 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.
Tue 10/201:40 pm
MAF
- ORD
1 stop8h 12m
United Airlines
Wed 10/216:00 am
ORD
- MAF
1 stop6h 55m
United Airlines
Deal found 6/1![United Airlines logo]()
$461
This American Airlines deal was found by Cheapflights users on 5/30. 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 7/411:45 am
MAF
- ORD
1 stop6h 31m
American Airlines
Tue 7/73:49 pm
ORD
- MAF
1 stop7h 04m
American Airlines
Deal found 5/30![American Airlines logo]()
$471
This United Airlines deal was found by Cheapflights users on 5/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 6/287:13 pm
MAF
- ORD
1 stop5h 32m
United Airlines
Tue 7/75:45 pm
ORD
- MAF
1 stop5h 59m
United Airlines
Deal found 5/31![United Airlines logo]()
$477
This United Airlines deal was found by Cheapflights users on 6/1. 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.
Tue 6/165:18 pm
MAF
- ORD
1 stop5h 31m
United Airlines
Sat 6/202:33 pm
ORD
- MAF
1 stop5h 51m
United Airlines
Deal found 6/1![United Airlines logo]()
$507
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 June 4, 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 June 4, 2026.
This American Airlines deal was found by Cheapflights users on 6/1. 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.
Wed 9/25:00 am
MAF
- ORD
1 stop6h 11m
American Airlines
Mon 9/75:00 am
ORD
- MAF
1 stop4h 47m
American Airlines
Deal found 6/1![American Airlines logo]()
$407
This United Airlines deal was found by Cheapflights users on 5/31. 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 8/15:13 pm
MAF
- ORD
1 stop6h 02m
United Airlines
Sat 8/84:05 pm
ORD
- MAF
1 stop5h 43m
United Airlines
Deal found 5/31![United Airlines logo]()
$420
This United Airlines deal was found by Cheapflights users on 6/2. 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.
Tue 10/201:40 pm
MAF
- ORD
1 stop8h 12m
United Airlines
Wed 10/216:00 am
ORD
- MAF
1 stop6h 55m
United Airlines
Deal found 6/2![United Airlines logo]()
$461
This United Airlines deal was found by Cheapflights users on 5/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 6/287:13 pm
MAF
- ORD
1 stop5h 32m
United Airlines
Tue 7/75:45 pm
ORD
- MAF
1 stop5h 59m
United Airlines
Deal found 5/31![United Airlines logo]()
$477
This United Airlines deal was found by Cheapflights users on 5/29. 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 10/201:40 pm
MAF
- ORD
1 stop6h 42m
United Airlines
Sat 10/245:30 am
ORD
- MAF
1 stop5h 44m
United Airlines
Deal found 5/29![United Airlines logo]()
$482
This American Airlines deal was found by Cheapflights users on 5/29. 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 7/35:23 pm
MAF
- ORD
1 stop7h 27m
American Airlines
Mon 7/61:25 pm
ORD
- MAF
1 stop9h 28m
American Airlines
Deal found 5/29![American Airlines logo]()
$614
This United Airlines deal was found by Cheapflights users on 6/1. 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.
Tue 6/165:18 pm
MAF
- ORD
1 stop5h 31m
United Airlines
Sat 6/202:33 pm
ORD
- MAF
1 stop5h 51m
United Airlines
Deal found 6/1![United Airlines logo]()
$507
This United Airlines deal was found by Cheapflights users on 5/29. 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 7/107:13 pm
MAF
- ORD
1 stop5h 32m
United Airlines
Mon 7/139:40 pm
ORD
- MAF
1 stop26h 04m
United Airlines
Deal found 5/29![United Airlines logo]()
$640
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 7/45:00 am
MAF
- ORD
2 stops7h 26m
United Airlines
Sat 7/112:33 pm
ORD
- MAF
1 stop5h 51m
United Airlines
Deal found 6/3![United Airlines logo]()
$663
Last-minute flights from Odessa to ChicagoDiscover last-minute flight deals from Odessa to Chicago. Data last updated June 4, 2026 and is based on user searches.
Discover last-minute flight deals from Odessa to Chicago. Data last updated June 4, 2026 and is based on user searches.
This United Airlines deal was found by Cheapflights users on 6/1. 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.
Tue 6/165:18 pm
MAF
- ORD
1 stop5h 31m
United Airlines
Sat 6/202:33 pm
ORD
- MAF
1 stop5h 51m
United Airlines
Deal found 6/1![United Airlines logo]()
$507
This American Airlines deal was found by Cheapflights users on 6/2. 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 6/266:47 pm
MAF
- ORD
1 stop5h 52m
American Airlines
Mon 6/295:59 am
ORD
- MAF
1 stop5h 10m
American Airlines
Deal found 6/2![American Airlines logo]()
$612
This American Airlines deal was found by Cheapflights users on 6/1. 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.
Sat 6/276:47 pm
MAF
- ORD
1 stop5h 52m
American Airlines
Sun 7/55:00 am
ORD
- MAF
1 stop8h 49m
American Airlines
Deal found 6/1![American Airlines logo]()
$622
This United Airlines deal was found by Cheapflights users on 5/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 6/287:13 pm
MAF
- ORD
1 stop5h 32m
United Airlines
Tue 7/75:45 pm
ORD
- MAF
1 stop5h 59m
United Airlines
Deal found 5/31![United Airlines logo]()
$477
This American Airlines deal was found by Cheapflights users on 5/29. 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 7/35:23 pm
MAF
- ORD
1 stop7h 27m
American Airlines
Mon 7/61:25 pm
ORD
- MAF
1 stop9h 28m
American Airlines
Deal found 5/29![American Airlines logo]()
$614
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.
Sat 7/411:45 am
MAF
- ORD
1 stop7h 59m
American Airlines
Sat 7/116:04 am
ORD
- MAF
1 stop5h 11m
American Airlines
Deal found 6/3![American Airlines logo]()
$427
This American Airlines deal was found by Cheapflights users on 5/30. 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 7/411:45 am
MAF
- ORD
1 stop6h 31m
American Airlines
Tue 7/73:49 pm
ORD
- MAF
1 stop7h 04m
American Airlines
Deal found 5/30![American Airlines logo]()
$471
This American Airlines deal was found by Cheapflights users on 6/2. 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.
Wed 7/86:46 pm
MAF
- ORD
1 stop6h 04m
American Airlines
Tue 7/214:51 pm
ORD
- MAF
1 stop6h 02m
American Airlines
Deal found 6/2![American Airlines logo]()
$371
This American Airlines deal was found by Cheapflights users on 6/1. 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.
Fri 7/105:23 pm
MAF
- ORD
1 stop7h 27m
American Airlines
Mon 7/132:59 pm
ORD
- MAF
1 stop7h 54m
American Airlines
Deal found 6/1![American Airlines logo]()
$625
This United Airlines deal was found by Cheapflights users on 5/30. 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 7/107:13 pm
MAF
- ORD
1 stop5h 32m
United Airlines
Mon 7/135:45 pm
ORD
- MAF
1 stop5h 59m
United Airlines
Deal found 5/30![United Airlines logo]()
$628
This American Airlines deal was found by Cheapflights users on 6/1. 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 7/206:46 pm
MAF
- ORD
1 stop6h 04m
American Airlines
Tue 7/213:49 pm
ORD
- MAF
1 stop7h 04m
American Airlines
Deal found 6/1![American Airlines logo]()
$399
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 June 4, 2026.
Search for one-way flight options from Odessa to Chicago. Find affordable one-way fares based on user searches. Data last updated June 4, 2026.
This American Airlines deal was found by Cheapflights users on 6/2. 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.
Mon 6/85:00 am
MAF
- ORD
1 stop6h 59m
American Airlines
Deal found 6/2![American Airlines logo]()
$509
This United Airlines deal was found by Cheapflights users on 6/2. 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.
Mon 6/87:00 am
MAF
- ORD
2 stops11h 47m
United Airlines
Deal found 6/2![United Airlines logo]()
$705
This Kiwi.com deal was found by Cheapflights users on 6/2. 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.
Mon 6/82:21 pm
MAF
- ORD
3 stops26h 19m
Multiple Airlines
Deal found 6/2![Multiple Airlines logo]()
$1,336
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 June 4, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $371 (American Airlines) |
Popular in | January |
Cheapest in | November |
Average price | $501 |
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 June 4, 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 - ORD
MAFORD
Midland Intl
Wed 9/2
5:00 am-11:11 am
1 stop6h 11m
Chicago O'Hare Intl
Mon 9/7
5:00 am-9:47 am
1 stop4h 47m
$407
MidlandChicago
MAF - ORD
MAFORD
Midland Intl
Sat 8/1
5:13 pm-11:15 pm
1 stop6h 02m
Chicago O'Hare Intl
Sat 8/8
4:05 pm-9:48 pm
1 stop5h 43m
$420
MidlandChicago
MAF - ORD
MAFORD
Midland Intl
Tue 10/20
1:40 pm-9:52 pm
1 stop8h 12m
Chicago O'Hare Intl
Wed 10/21
6:00 am-12:55 pm
1 stop6h 55m
$461
MidlandChicago
MAF - ORD
MAFORD
Midland Intl
Sun 6/28
7:13 pm-12:45 am
1 stop5h 32m
Chicago O'Hare Intl
Tue 7/7
5:45 pm-11:44 pm
1 stop5h 59m
$477
MidlandChicago
MAF - ORD
MAFORD
Midland Intl
Tue 10/20
1:40 pm-8:22 pm
1 stop6h 42m
Chicago O'Hare Intl
Sat 10/24
5:30 am-11:14 am
1 stop5h 44m
$482
MidlandChicago
MAF - ORD
MAFORD
Midland Intl
Tue 6/16
5:18 pm-10:49 pm
1 stop5h 31m
Chicago O'Hare Intl
Sat 6/20
2:33 pm-8:24 pm
1 stop5h 51m
$507
MidlandChicago
MAF - ORD
MAFORD
Midland Intl
Fri 7/3
5:23 pm-12:50 am
1 stop7h 27m
Chicago O'Hare Intl
Mon 7/6
1:25 pm-10:53 pm
1 stop9h 28m
$614
MidlandChicago
MAF - ORD
MAFORD
Midland Intl
Fri 7/10
7:13 pm-12:45 am
1 stop5h 32m
Chicago O'Hare Intl
Mon 7/13
9:40 pm-11:44 pm
1 stop26h 04m
$640
MidlandChicago
MAF - ORD
MAFORD
Midland Intl
Sat 7/4
5:00 am-12:26 pm
2 stops7h 26m
Chicago O'Hare Intl
Sat 7/11
2:33 pm-8:24 pm
1 stop5h 51m
$663
Cheapest one-way
Quickest one-way
MidlandChicago
MAF - ORD
MAFORD
Midland Intl
Mon 6/8
5:00 am-11:59 am
1 stop6h 59m
$509
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
How much does it cost to fly round-trip from Odessa to Chicago?
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 June 4, 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
Overall
8.0
Entertainment
7.5
Boarding
8.1
Crew
8.6
Reviews
1 / 20
6.0
GoodScott,Feb 2026
HOU - FLL
Comfort
8.0
Food
7.0
Overall
8.0
Entertainment
7.5
Boarding
8.1
Crew
8.6
Reviews
1 / 20
6.0
GoodScott,Feb 2026
HOU - FLL
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 locationsBenton Harbor
Lansing
Merrillville
Hammond
Porter
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Alternative routes for Odessa to 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 June 4, 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 June 4, 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 June 4, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$296 | Average$539 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$398 | Average$451 | FlexibilityNo cancel fee | On-time69% |