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Odessa

$167+ 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 9/16. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — MAF
Aug 26 — Sep 21
Wed 8/26
Wed 9/2
1 adult, Economy
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Cheap 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 July 27, 2026.

This American 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/2212:10 pm
ORD
-
MAF
1 stop4h 50m
American Airlines
Sat 8/295:31 pm
MAF
-
ORD
1 stop5h 59m
American Airlines
Deal found 7/23$333
This American Airlines deal was found by Cheapflights users on 7/26. 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 9/912:09 pm
ORD
-
MAF
1 stop5h 41m
American Airlines
Wed 9/166:25 pm
MAF
-
ORD
1 stop5h 05m
American Airlines
Deal found 7/26$339
This United Airlines deal was found by Cheapflights users on 7/25. 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 9/85:53 pm
ORD
-
MAF
1 stop5h 51m
United Airlines
Tue 9/157:15 pm
MAF
-
ORD
1 stop5h 44m
United Airlines
Deal found 7/25$360
This American Airlines deal was found by Cheapflights users on 7/24. 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 9/86:00 am
ORD
-
MAF
1 stop5h 19m
American Airlines
Tue 9/152:23 pm
MAF
-
ORD
1 stop5h 13m
American Airlines
Deal found 7/24$419
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 8/95:00 am
ORD
-
MAF
1 stop6h 19m
American Airlines
Wed 8/125:31 pm
MAF
-
ORD
1 stop6h 47m
American Airlines
Deal found 7/22$425
This United Airlines deal was found by Cheapflights users on 7/25. 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 11/105:15 pm
ORD
-
MAF
1 stop6h 28m
United Airlines
Wed 11/115:00 am
MAF
-
ORD
1 stop5h 11m
United Airlines
Deal found 7/25$429
This United Airlines deal was found by Cheapflights users on 7/26. 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 9/55:53 pm
ORD
-
MAF
1 stop5h 51m
United Airlines
Wed 9/97:40 am
MAF
-
ORD
2 stops25h 54m
United Airlines
Deal found 7/26$500
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.
Thu 8/68:20 am
ORD
-
MAF
1 stop5h 31m
American Airlines
Mon 8/102:21 pm
MAF
-
ORD
1 stop7h 52m
American Airlines
Deal found 7/22$507

Find flight deals from Chicago to Odessa

Keep the following information in mind while searching for Chicago to Odessa flight deals. Data was last updated July 27, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$333
(American Airlines)

One-way from

$167
(United Airlines)
Provider with most accurate pricing for Chicago (CHI)-Midland Intl flight deals.
Search Deals
Provider most trusted by Cheapflights users for Chicago (CHI)-Midland Intl flights.
Search Deals
From Chicago (CHI) to Odessa
Search Deals
One-way flight from Chicago (CHI) to Odessa
Search Deals

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 July 27, 2026.
Use the filters below to find and compare flights from Chicago to Odessa that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip
Quickest round-trip

ChicagoMidland

ORD - MAF

ORDMAF

Chicago O'Hare Intl

Wed 9/9

12:09 pm-5:50 pm

1 stop5h 41m

Midland Intl

Wed 9/16

6:25 pm-11:30 pm

1 stop5h 05m

$339

ChicagoMidland

ORD - MAF

ORDMAF

Chicago O'Hare Intl

Tue 9/8

5:53 pm-11:44 pm

1 stop5h 51m

Midland Intl

Tue 9/15

7:15 pm-12:59 am

1 stop5h 44m

$360

ChicagoMidland

ORD - MAF

ORDMAF

Chicago O'Hare Intl

Tue 9/8

6:00 am-11:19 am

1 stop5h 19m

Midland Intl

Tue 9/15

6:25 pm-12:14 am

1 stop5h 49m

$420

ChicagoMidland

ORD - MAF

ORDMAF

Chicago O'Hare Intl

Tue 11/10

5:15 pm-11:43 pm

1 stop6h 28m

Midland Intl

Wed 11/11

5:00 am-10:11 am

1 stop5h 11m

$429

ChicagoMidland

ORD - MAF

ORDMAF

Chicago O'Hare Intl

Sat 9/5

5:53 pm-11:44 pm

1 stop5h 51m

Midland Intl

Wed 9/9

7:40 am-9:34 am

2 stops25h 54m

$500

ChicagoMidland

ORD - MAF

ORDMAF

Chicago O'Hare Intl

Fri 8/7

8:20 am-1:51 pm

1 stop5h 31m

Midland Intl

Sun 8/9

2:21 pm-8:30 pm

1 stop6h 09m

$507

ChicagoMidland

ORD - MAF

ORDMAF

Chicago O'Hare Intl

Wed 9/9

10:25 am-10:09 pm

2 stops11h 44m

Midland Intl

Wed 9/16

5:00 am-10:55 am

1 stop5h 55m

$512

ChicagoMidland

ORD - MAF

ORDMAF

Chicago O'Hare Intl

Sat 8/8

12:10 pm-5:56 pm

1 stop5h 46m

Midland Intl

Wed 8/12

2:21 pm-10:13 pm

1 stop7h 52m

$517
Cheapest one-way

ChicagoMidland

ORD - MAF

ORDMAF

Chicago O'Hare Intl

Wed 9/16

5:53 pm-11:44 pm

1 stop5h 51m

$167
Quickest one-way

ChicagoMidland

ORD - MAF

ORDMAF

Chicago O'Hare Intl

Mon 10/5

5:53 pm-11:24 pm

1 stop5h 31m

$167

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/23

Showing 1-10 of 13 resultsSorted by cheapest first
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 July 27, 2026.
See what other customers who have flown with Southwest 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
4,228 reviews

Entertainment

7.5

Food

7.0

Crew

8.6

Boarding

8.1

Comfort

8.0

Overall

8.0

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
4,228 reviews
Southwest
8.0
Very good
4,228 reviews

Entertainment

7.5

Food

7.0

Crew

8.6

Boarding

8.1

Comfort

8.0

Overall

8.0

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 41m. American Airlines provides one of the quickest options available for as low as $339. 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 2 airlines flying from Chicago to Odessa

Discover the top 2 airlines 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 July 27, 2026.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$216Average$419FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$347Average$435FlexibilityNo cancel feeOn-time69%

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