HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Odessa

$212+ Cheap flights from Chicago (CHI) to Odessa, TX

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 9/13. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — MAF
Aug 23 — Aug 301
Sat 8/23
Sat 8/30
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Chicago to Odessa 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

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

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 August 18, 2025.

Round-trip from

$212
(United Airlines)

Popular in

February

Cheapest in

September

Average price

$421
From Chicago (CHI) to Odessa
Search Deals
Highest demand for flights based on searches. 9% potential increase in price ($49 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 6% potential price decrease ($31 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in August 2025
Search Deals

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 August 18, 2025.

This United Airlines deal was found by Cheapflights users on 8/16. 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 9/133:58 pmORD - MAF
1 stop5h 57mUnited Airlines
Sat 9/203:20 pmMAF - ORD
1 stop6h 20mUnited Airlines
Deal found 8/16$212
This American Airlines deal was found by Cheapflights users on 8/16. 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 9/135:16 pmORD - MAF
1 stop4h 56mAmerican Airlines
Sat 9/204:12 pmMAF - ORD
1 stop7h 47mAmerican Airlines
Deal found 8/16$217
This Delta deal was found by Cheapflights users on 8/16. 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.
Sat 9/136:15 amORD - MAF
2 stops11h 01mDelta
Sat 9/205:30 amMAF - ORD
2 stops13h 39mDelta
Deal found 8/16$227
This American Airlines deal was found by Cheapflights users on 8/16. 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 10/38:34 pmORD - MAF
1 stop12h 22mAmerican Airlines
Mon 10/64:12 pmMAF - ORD
1 stop7h 01mAmerican Airlines
Deal found 8/16$300
This American Airlines deal was found by Cheapflights users on 8/17. 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 9/128:34 pmORD - MAF
1 stop12h 22mAmerican Airlines
Mon 9/154:12 pmMAF - ORD
1 stop7h 47mAmerican Airlines
Deal found 8/17$304
This American Airlines deal was found by Cheapflights users on 8/18. 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 9/116:00 amORD - MAF
1 stop6h 05mAmerican Airlines
Sun 9/146:17 pmMAF - ORD
1 stop5h 00mAmerican Airlines
Deal found 8/18$312
This Delta deal was found by Cheapflights users on 8/18. 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.
Thu 9/115:30 amORD - MAF
2 stops11h 10mDelta
Sun 9/1412:33 pmMAF - ORD
2 stops11h 21mDelta
Deal found 8/18$322
This Southwest deal was found by Cheapflights users on 8/17. 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 9/1312:40 pmORD - MAF
2 stops8h 15mSouthwest
Sat 9/205:40 amMAF - ORD
1 stop7h 05mSouthwest
Deal found 8/17$327
This Delta deal was found by Cheapflights users on 8/16. 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.
Fri 10/36:15 amORD - MAF
2 stops10h 25mDelta
Mon 10/612:33 pmMAF - ORD
2 stops11h 24mDelta
Deal found 8/16$343
This American Airlines deal was found by Cheapflights users on 8/17. 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 11/2110:05 pmORD - MAF
1 stop11h 40mAmerican Airlines
Sun 11/234:31 pmMAF - ORD
1 stop5h 52mAmerican Airlines
Deal found 8/17$349
This Southwest deal was found by Cheapflights users on 8/17. 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 9/127:30 amORD - MAF
1 stop5h 10mSouthwest
Mon 9/155:35 amMAF - ORD
2 stops7h 30mSouthwest
Deal found 8/17$358

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 August 18, 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

Sat 9/13

3:58 pm-9:55 pm

1 stop5h 57m

Midland Intl

Sat 9/20

3:20 pm-9:40 pm

1 stop6h 20m

$212

ChicagoMidland

ORD - MAF

ORDMAF

Chicago O'Hare Intl

Sat 9/13

5:16 pm-10:12 pm

1 stop4h 56m

Midland Intl

Sat 9/20

4:12 pm-11:59 pm

1 stop7h 47m

$217

ChicagoMidland

ORD - MAF

ORDMAF

Chicago O'Hare Intl

Sat 9/13

6:15 am-5:16 pm

2 stops11h 01m

Midland Intl

Sat 9/20

5:30 am-7:09 pm

2 stops13h 39m

$227

ChicagoMidland

ORD - MAF

ORDMAF

Chicago O'Hare Intl

Fri 10/3

8:34 pm-8:56 am

1 stop12h 22m

Midland Intl

Mon 10/6

4:12 pm-11:13 pm

1 stop7h 01m

$300

ChicagoMidland

ORD - MAF

ORDMAF

Chicago O'Hare Intl

Fri 9/12

8:34 pm-8:56 am

1 stop12h 22m

Midland Intl

Mon 9/15

6:39 pm-11:59 pm

1 stop5h 20m

$304

ChicagoMidland

ORD - MAF

ORDMAF

Chicago O'Hare Intl

Thu 9/11

6:00 am-12:05 pm

1 stop6h 05m

Midland Intl

Sun 9/14

6:17 pm-11:52 pm

1 stop5h 35m

$312

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/16

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 August 18, 2025.
See what other customers who have flown with Southwest 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
4,246 reviews

Food

7.0

Boarding

8.1

Overall

8.0

Comfort

8.0

Crew

8.6

Entertainment

7.5

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
Southwest
8.0
Very good
4,246 reviews
Southwest
8.0
Very good
4,246 reviews

Food

7.0

Boarding

8.1

Overall

8.0

Comfort

8.0

Crew

8.6

Entertainment

7.5

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
American Airlines
7.2
Good
10,000 reviews
Southwest
8.0
Very good
4,246 reviews

Food

7.0

Boarding

8.1

Overall

8.0

Comfort

8.0

Crew

8.6

Entertainment

7.5

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.

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 4h 56m. United Airlines provides one of the quickest options available for as low as $217. 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.

  • What is the cheapest month to book a flight from Chicago to Odessa?

    Currently, April is the cheapest month in which you can book a flight from Chicago to Odessa (average of $336). Flying from Chicago to Odessa in March is currently the most expensive (average of $389). 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.

See more FAQs

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for Chicago to Odessa

See prices for flight routes from nearby airports that may be better suited for you.
O'Hare Intl to Dallas/Fort Worth flights
Midway to Dallas/Fort Worth flights
O'Hare Intl to Austin flights
O'Hare Intl to Hobby flights
Midway to Hobby flights
O'Hare Intl to George Bush Intcntl flights
O'Hare Intl to San Antonio flights
O'Hare Intl to Love Field flights
St. Louis to Dallas/Fort Worth flights
Midway to George Bush Intcntl flights
Moline to Dallas/Fort Worth flights
St. Louis to Hobby flights
Midway to Love Field flights
St. Louis to George Bush Intcntl flights
Midway to Austin flights
O'Hare Intl to El Paso flights
Midway to San Antonio flights
Peoria to Dallas/Fort Worth flights
St. Louis to Austin flights
St. Louis to San Antonio flights
St. Louis to Love Field flights
O'Hare Intl to Midland flights
O'Hare Intl to McAllen flights
Moline to Hobby flights
Moline to George Bush Intcntl flights
Moline to Austin flights
Peoria to San Antonio flights
Peoria to Hobby flights
Peoria to George Bush Intcntl flights
Evansville to Dallas/Fort Worth flights
O'Hare Intl to Brownsville flights
Bloomington to Hobby flights
Moline to San Antonio flights
O'Hare Intl to Lubbock flights
Evansville to Hobby flights
Moline to Love Field flights
Bloomington to George Bush Intcntl flights
Decatur to Dallas/Fort Worth flights
Bloomington to Dallas/Fort Worth flights
O'Hare Intl to Harlingen flights
Champaign to Dallas/Fort Worth flights
Evansville to George Bush Intcntl flights
Peoria to Austin flights
Bloomington to Austin flights
St. Louis to El Paso flights
Midway to El Paso flights
O'Hare Intl to Laredo flights
Springfield to Dallas/Fort Worth flights
St. Louis to McAllen flights

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 August 18, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$279Average$386FlexibilityNo cancel feeOn-time71%

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.