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Odessa

$251+ 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 5/25. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — MAF
May 6 — May 131
Tue 5/6
Tue 5/13
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 May 1, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$251
(American Airlines)

Popular in

February

Cheapest in

July

Average price

$515
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
Search Deals
Highest demand for flights based on searches. 5% potential increase in price ($26 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 6% potential price decrease ($31 potential savings vs. average RT price).
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Average for round-trip flights in May 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 May 1, 2025.

This American Airlines deal was found by Cheapflights users on 5/1. 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.
Sun 5/2510:15 amORD - MAF
1 stop7h 45mAmerican Airlines
Tue 6/36:30 pmMAF - ORD
1 stop5h 26mAmerican Airlines
Deal found 5/1$251
This Delta deal was found by Cheapflights users on 5/1. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/256:24 amORD - MAF
2 stops10h 30mDelta
Tue 6/35:29 amMAF - ORD
2 stops13h 19mDelta
Deal found 5/1$261
This Southwest deal was found by Cheapflights users on 5/1. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/134:00 pmORD - MAF
2 stops8h 20mSouthwest
Sat 6/145:25 amMAF - ORD
1 stop7h 20mSouthwest
Deal found 5/1$349
This United Airlines deal was found by Cheapflights users on 4/30. 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.
Sat 6/147:50 pmORD - MAF
2 stops13h 01mUnited Airlines
Sat 6/215:00 amMAF - ORD
1 stop5h 56mUnited Airlines
Deal found 4/30$417

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 May 1, 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

Sun 5/25

10:15 am-6:00 pm

1 stop7h 45m

Midland Intl

Tue 6/3

6:30 pm-11:56 pm

1 stop5h 26m

$251

ChicagoMidland

ORD - MAF

ORDMAF

Chicago O'Hare Intl

Sun 5/25

6:24 am-4:54 pm

2 stops10h 30m

Midland Intl

Tue 6/3

5:29 am-6:48 pm

2 stops13h 19m

$261

ChicagoMidland

ORD - MAF

ORDMAF

Chicago O'Hare Intl

Fri 6/13

4:00 pm-12:20 am

2 stops8h 20m

Midland Intl

Sat 6/14

5:25 am-12:45 pm

1 stop7h 20m

$349

ChicagoMidland

ORD - MAF

ORDMAF

Chicago O'Hare Intl

Sat 6/14

7:50 pm-8:51 am

2 stops13h 01m

Midland Intl

Sat 6/21

5:00 am-10:56 am

1 stop5h 56m

$417

ChicagoMidland

ORD - MAF

ORDMAF

Chicago O'Hare Intl

Wed 6/25

7:10 am-4:34 pm

2 stops9h 24m

$368

ChicagoMidland

ORD - MAF

ORDMAF

Chicago O'Hare Intl

Wed 6/25

5:36 pm-10:18 pm

1 stop4h 42m

$383

ChicagoMidland

ORD - MAF

ORDMAF

Chicago O'Hare Intl

Wed 6/25

7:10 am-6:06 pm

3 stops10h 56m

$853

Flights are sorted by cheapest round-trip flights first.

Deals found on 5/1

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 May 1, 2025.
Southwest
8.0
Very good
4,293 reviews

Overall

8.0

Crew

8.6

Comfort

8.0

Food

7.1

Entertainment

7.6

Boarding

8.2

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
4,293 reviews
Southwest
8.0
Very good
4,293 reviews

Overall

8.0

Crew

8.6

Comfort

8.0

Food

7.1

Entertainment

7.6

Boarding

8.2

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
7,934 reviews
Southwest
8.0
Very good
4,293 reviews

Overall

8.0

Crew

8.6

Comfort

8.0

Food

7.1

Entertainment

7.6

Boarding

8.2

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
8,696 reviews
Southwest
8.0
Very good
4,293 reviews

Overall

8.0

Crew

8.6

Comfort

8.0

Food

7.1

Entertainment

7.6

Boarding

8.2

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
4,293 reviews

Overall

8.0

Crew

8.6

Comfort

8.0

Food

7.1

Entertainment

7.6

Boarding

8.2

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 $368 on Delta. Other airlines that offer cheap prices include American Airlines from $383 and United Airlines from $853 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 May is currently the most expensive (average of $394). 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 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 May 1, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$271Average$416FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$330Average$410FlexibilityNo cancel feeOn-time69%

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