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Odessa

$99+ Cheap flights from Chicago (CHI) to Odessa, TX

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 12/6. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — MAF
Nov 21 — Nov 281
Fri 11/21
Fri 11/28
1 adult, Economy
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Cheap flight deals from Chicago to Odessa

Keep the following information in mind while searching for Chicago to Odessa flight deals. Data was last updated October 22, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$277
(American Airlines)

One-way from

$99
(American Airlines)

Popular in

February

Cheapest in

September

Average price

$466
Provider with most accurate pricing for Chicago (CHI)-Midland Intl flight deals.
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Provider most trusted by Cheapflights users for Chicago (CHI)-Midland Intl flights.
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From Chicago (CHI) to Odessa
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One-way flight from Chicago (CHI) to Odessa
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Highest demand for flights based on searches. 8% potential increase in price ($42 potential increase over avg. RT price).
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Cheapest flight prices on average. 6% potential price decrease ($30 potential savings vs. average RT price).
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Average for round-trip flights in October 2025
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Find flight deals from Chicago to Odessa

Cheapest flights from Chicago to Odessa
Explore the most affordable flight options available from Chicago to Odessa. Find the lowest fares from popular airlines and budget airlines, with prices last updated on October 22, 2025.

This United Airlines deal was found by Cheapflights users on 10/19. 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 11/61:55 pmORD - MAF
1 stop8h 08mUnited Airlines
Sun 11/97:00 amMAF - ORD
1 stop5h 16mUnited Airlines
Deal found 10/19$384
This American Airlines deal was found by Cheapflights users on 10/21. 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.
Fri 11/218:10 amORD - MAF
1 stop5h 44mAmerican Airlines
Sun 11/232:24 pmMAF - ORD
1 stop5h 18mAmerican Airlines
Deal found 10/21$425
This United Airlines deal was found by Cheapflights users on 10/20. 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 11/42:40 pmORD - MAF
1 stop7h 23mUnited Airlines
Sat 11/87:10 pmMAF - ORD
1 stop5h 05mUnited Airlines
Deal found 10/20$427
This Delta deal was found by Cheapflights users on 10/20. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/46:45 amORD - MAF
2 stops9h 46mDelta
Sat 11/85:30 amMAF - ORD
2 stops11h 30mDelta
Deal found 10/20$437
This Southwest deal was found by Cheapflights users on 10/19. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/62:15 pmORD - MAF
2 stops9h 40mSouthwest
Sun 11/95:45 amMAF - ORD
1 stop7h 15mSouthwest
Deal found 10/19$454
This United Airlines deal was found by Cheapflights users on 10/21. 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.
Fri 11/216:00 amORD - MAF
1 stop7h 57mUnited Airlines
Sun 11/235:30 pmMAF - ORD
2 stops14h 29mUnited Airlines
Deal found 10/21$456
This United Airlines deal was found by Cheapflights users on 10/22. 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 12/177:35 amORD - MAF
1 stop6h 22mUnited Airlines
Sat 12/205:00 amMAF - ORD
1 stop28h 17mUnited Airlines
Deal found 10/22$475
This Southwest deal was found by Cheapflights users on 10/21. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/13:05 pmORD - MAF
1 stop8h 00mSouthwest
Thu 1/16:15 amMAF - ORD
1 stop6h 45mSouthwest
Deal found 10/21$488

Cheapflights Fare Finder

 
Customize your flight search to find flights from Chicago to Odessa that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated October 22, 2025.
Use the filters below to find and compare flights from Chicago to Odessa that are best for you.

Fly from

Chicago

Fly to

Odessa

Route

Depart

Return

Price

ChicagoMidland

ORD - MAF

ORDMAF

Chicago O'Hare Intl

Wed 2/18

12:05 pm-5:51 pm

1 stop5h 46m

Midland Intl

Sat 2/21

10:07 am-3:20 pm

1 stop5h 13m

$277

ChicagoMidland

ORD - MAF

ORDMAF

Chicago O'Hare Intl

Thu 11/6

1:55 pm-10:03 pm

1 stop8h 08m

Midland Intl

Sun 11/9

7:00 am-12:16 pm

1 stop5h 16m

$384

ChicagoMidland

ORD - MAF

ORDMAF

Chicago O'Hare Intl

Fri 11/21

8:10 am-1:54 pm

1 stop5h 44m

Midland Intl

Sun 11/23

12:25 pm-7:42 pm

1 stop7h 17m

$425

ChicagoMidland

ORD - MAF

ORDMAF

Chicago O'Hare Intl

Thu 11/6

5:10 pm-11:15 pm

1 stop6h 05m

Midland Intl

Mon 11/10

7:56 am-1:15 pm

1 stop5h 19m

$427

ChicagoMidland

ORD - MAF

ORDMAF

Chicago O'Hare Intl

Tue 11/4

2:40 pm-10:03 pm

1 stop7h 23m

Midland Intl

Sat 11/8

7:10 pm-12:15 am

1 stop5h 05m

$427

ChicagoMidland

ORD - MAF

ORDMAF

Chicago O'Hare Intl

Tue 11/4

6:45 am-4:31 pm

2 stops9h 46m

Midland Intl

Sat 11/8

5:30 am-5:00 pm

2 stops11h 30m

$437

ChicagoMidland

ORD - MAF

ORDMAF

Chicago O'Hare Intl

Thu 11/6

2:15 pm-11:55 pm

2 stops9h 40m

Midland Intl

Sun 11/9

5:45 am-1:00 pm

1 stop7h 15m

$454

ChicagoMidland

ORD - MAF

ORDMAF

Chicago O'Hare Intl

Wed 12/17

7:35 am-1:57 pm

1 stop6h 22m

Midland Intl

Sat 12/20

5:00 am-9:17 am

1 stop28h 17m

$475

ChicagoMidland

ORD - MAF

ORDMAF

Chicago O'Hare Intl

Mon 12/1

3:05 pm-11:05 pm

1 stop8h 00m

Midland Intl

Thu 1/1

6:15 am-1:00 pm

1 stop6h 45m

$488

ChicagoMidland

ORD - MAF

ORDMAF

Chicago O'Hare Intl

Fri 10/31

2:40 pm-10:05 pm

1 stop7h 25m

$169

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/20

Showing 1-10 of 11 results
1
2

Best time to book a flight from Chicago to Odessa

Have a flexible travel schedule? Discover the best time to fly to Odessa from Chicago with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

Everything you need to know about your flight from Chicago to Odessa
No data available for this route at this time. Please check back soon.

Reviews of airlines servicing Odessa

Get insights into the airlines that provide service to Odessa. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Odessa. Reviews last updated October 22, 2025.
See what other customers who have flown with Southwest, United Airlines, and American Airlines from Chicago to Odessa have to say. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,237 reviews

Overall

8.0

Food

7.0

Comfort

8.0

Crew

8.6

Boarding

8.1

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Southwest
8.0
Very good
4,237 reviews
Southwest
8.0
Very good
4,237 reviews

Overall

8.0

Food

7.0

Comfort

8.0

Crew

8.6

Boarding

8.1

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
United Airlines
7.4
Good
8,990 reviews
Southwest
8.0
Very good
4,237 reviews

Overall

8.0

Food

7.0

Comfort

8.0

Crew

8.6

Boarding

8.1

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
American Airlines
7.2
Good
11,028 reviews
Southwest
8.0
Very good
4,237 reviews

Overall

8.0

Food

7.0

Comfort

8.0

Crew

8.6

Boarding

8.1

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines

Related info for your journey

Find useful and relevant information for your journey from Chicago to Odessa. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • How long is the flight from Chicago to Odessa?

    A quick flight from Chicago to Odessa can take about 5h 46m. American Airlines provides one of the quickest options available for as low as $277. There are 1047 mi between Chicago and Odessa. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.

  • Can I find deals for flights from Chicago to Odessa that include hotel bookings?

    Yes. In addition to deals on Chicago to Odessa flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Chicago to Odessa?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Chicago to Odessa.

  • Can I find deals for business class flights from Chicago to Odessa?

    Yes. Cheapflights offers flight deals from Chicago to Odessa by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

See more FAQs

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Alternative routes for Chicago to Odessa

See prices for flight routes from nearby airports that may be better suited for you.
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Top airline flying from Chicago to Odessa

Discover the top airline that operate flights from Chicago to Odessa. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated October 22, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$216Average$377FlexibilityNo cancel feeOn-time71%

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