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Odessa

$275+ 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 6/26. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — MAF
Jun 23 — Jun 301
Mon 6/23
Mon 6/30
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 June 18, 2025.

Round-trip from

$282
(American Airlines)

One-way from

$275
(American Airlines)

Popular in

February

Cheapest in

January

Average price

$387
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. 6% potential increase in price ($36 potential increase over avg. RT price).
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Cheapest flight prices on average. 7% potential price decrease ($32 potential savings vs. average RT price).
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Average for round-trip flights in June 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 June 18, 2025.

This American Airlines deal was found by Cheapflights users on 6/18. 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.
Sat 8/28:25 amORD - MAF
1 stop5h 34mAmerican Airlines
Sat 8/912:14 pmMAF - ORD
1 stop4h 56mAmerican Airlines
Deal found 6/18$282
This Delta deal was found by Cheapflights users on 6/18. 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.
Sat 8/27:10 amORD - MAF
2 stops9h 43mDelta
Sat 8/912:37 pmMAF - ORD
2 stops11h 32mDelta
Deal found 6/18$292
This United Airlines deal was found by Cheapflights users on 6/18. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/2012:45 pmORD - MAF
1 stop5h 30mUnited Airlines
Sat 11/295:30 pmMAF - ORD
1 stop6h 45mUnited Airlines
Deal found 6/18$387
This Southwest deal was found by Cheapflights users on 6/18. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/87:30 amORD - MAF
1 stop6h 25mSouthwest
Wed 7/93:50 pmMAF - ORD
1 stop5h 40mSouthwest
Deal found 6/18$423

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 June 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 8/2

8:25 am-1:59 pm

1 stop5h 34m

Midland Intl

Sat 8/9

12:14 pm-5:10 pm

1 stop4h 56m

$282

ChicagoMidland

ORD - MAF

ORDMAF

Chicago O'Hare Intl

Sat 8/2

7:00 am-4:53 pm

2 stops9h 53m

Midland Intl

Sat 8/9

12:37 pm-12:09 am

2 stops11h 32m

$292

ChicagoMidland

ORD - MAF

ORDMAF

Chicago O'Hare Intl

Sat 8/2

8:50 am-9:54 pm

2 stops13h 04m

Midland Intl

Sat 8/9

1:58 pm-8:05 pm

1 stop6h 07m

$402

ChicagoMidland

ORD - MAF

ORDMAF

Chicago O'Hare Intl

Tue 7/8

7:30 am-1:55 pm

1 stop6h 25m

Midland Intl

Wed 7/9

3:50 pm-9:30 pm

1 stop5h 40m

$423

ChicagoMidland

ORD - MAF

ORDMAF

Chicago O'Hare Intl

Thu 6/26

11:55 am-5:47 pm

1 stop5h 52m

$275

ChicagoMidland

ORD - MAF

ORDMAF

Chicago O'Hare Intl

Thu 6/26

6:00 am-4:34 pm

2 stops10h 34m

$286

ChicagoMidland

ORD - MAF

ORDMAF

Chicago O'Hare Intl

Sat 6/21

5:02 am-12:54 pm

1 stop7h 52m

$332

ChicagoMidland

ORD - MAF

ORDMAF

Chicago O'Hare Intl

Sun 6/22

4:00 pm-12:05 am

2 stops8h 05m

$425

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/16

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

Rainfall in Odessa by month

Plan your trip to Odessa by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Odessa ranges from 0.6 - 2.2 inches per month. September is typically the wettest month, when rainfall can reach 2.2 in. January is typically the driest time to visit Odessa when rainfall is around 0.6 in.

Temperature in Odessa by month

Plan your trip to Odessa by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Odessa, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 82.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 44.6 F).

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 June 18, 2025.
Southwest
8.0
Very good
4,280 reviews

Overall

8.0

Entertainment

7.6

Boarding

8.2

Food

7.1

Comfort

8.0

Crew

8.6

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
4,280 reviews
Southwest
8.0
Very good
4,280 reviews

Overall

8.0

Entertainment

7.6

Boarding

8.2

Food

7.1

Comfort

8.0

Crew

8.6

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.
Delta
8.0
Very good
7,964 reviews
Southwest
8.0
Very good
4,280 reviews

Overall

8.0

Entertainment

7.6

Boarding

8.2

Food

7.1

Comfort

8.0

Crew

8.6

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.
United Airlines
7.4
Good
8,810 reviews
Southwest
8.0
Very good
4,280 reviews

Overall

8.0

Entertainment

7.6

Boarding

8.2

Food

7.1

Comfort

8.0

Crew

8.6

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
4,280 reviews

Overall

8.0

Entertainment

7.6

Boarding

8.2

Food

7.1

Comfort

8.0

Crew

8.6

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.

  • What are the cheapest airlines to fly from Chicago to Odessa one-way?

    One-way options have recently been found by users for as low as $275 on American Airlines. Other airlines that offer cheap prices include Delta from $286 and United Airlines from $332 one-way.

  • 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 June is currently the most expensive (average of $393). 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

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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 June 18, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$271Average$416FlexibilityNo cancel feeOn-time71%

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