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Odessa

$257+ 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 4/3. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — MAF
Feb 4 — Feb 111
Tue 2/4
Tue 2/11
1 adult, Economy
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Cheap flight deals from Chicago to Odessa

Discover tips and strategies to find the most affordable flight options for your journey from Chicago (CHI) to Odessa (OD3). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated January 30, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$257
(United Airlines)

Popular in

November

Cheapest in

July

Average price

$316
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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Highest demand for flights based on searches. 9% potential increase in price ($54 potential increase over avg. RT price).
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Cheapest flight prices on average. 4% potential price decrease ($19 potential savings vs. average RT price).
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Average for round-trip flights in January 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 January 30, 2025.

This United Airlines deal was found by Cheapflights users on 1/28. 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 4/32:35 pmORD - MAF
1 stop5h 50mUnited Airlines
Mon 4/77:08 pmMAF - ORD
1 stop5h 07mUnited Airlines
Deal found 1/28$257
This Southwest deal was found by Cheapflights users on 1/30. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 2/185:45 pmORD - MAF
1 stop5h 45mSouthwest
Sat 2/228:45 amMAF - ORD
2 stops8h 00mSouthwest
Deal found 1/30$317
This American Airlines deal was found by Cheapflights users on 1/29. 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 4/1612:09 pmORD - MAF
1 stop7h 38mAmerican Airlines
Sun 4/209:20 amMAF - ORD
1 stop4h 55mAmerican Airlines
Deal found 1/29$352
This Delta deal was found by Cheapflights users on 1/29. 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 3/156:45 amORD - MAF
2 stops11h 11mDelta
Sat 3/221:02 pmMAF - ORD
2 stops10h 54mDelta
Deal found 1/29$452

Find flights from Chicago to Odessa within your budget

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 January 30, 2025.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

ChicagoMidland

ORD - MAF

ORDMAF

Chicago O'Hare Intl

Thu 4/3

2:35 pm-8:25 pm

1 stop5h 50m

Midland Intl

Mon 4/7

7:08 pm-12:15 am

1 stop5h 07m

$257

ChicagoMidland

ORD - MAF

ORDMAF

Chicago O'Hare Intl

Tue 2/18

5:45 pm-11:30 pm

1 stop5h 45m

Midland Intl

Sat 2/22

8:45 am-4:45 pm

2 stops8h 00m

$317

ChicagoMidland

ORD - MAF

ORDMAF

Chicago O'Hare Intl

Wed 4/16

12:09 pm-7:47 pm

1 stop7h 38m

Midland Intl

Sun 4/20

9:20 am-2:15 pm

1 stop4h 55m

$352

ChicagoMidland

ORD - MAF

ORDMAF

Chicago O'Hare Intl

Sat 3/15

6:45 am-5:56 pm

2 stops11h 11m

Midland Intl

Sat 3/22

1:02 pm-11:56 pm

2 stops10h 54m

$452

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/28

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.

Travel insights for flights from Chicago to Odessa

Get recent, data-driven insights about flights from Chicago to Odessa including ideal travel times, pricing trends, and more.

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 January 30, 2025.
Southwest
8.1
Very good
4,585 reviews

Comfort

8.1

Entertainment

7.7

Overall

8.1

Boarding

8.2

Food

7.1

Crew

8.7

Reviews

1 / 20

10.0
Excellent

Sarah,Aug 2024

MDW - AUS

My first time, surprisingly good! It was a good ride overall. Coming from Singapore, this budget flight is better than the budget airline for our national carrier Singapore Airlines.

Southwest
8.1
Very good
4,585 reviews
Southwest
8.1
Very good
4,585 reviews

Comfort

8.1

Entertainment

7.7

Overall

8.1

Boarding

8.2

Food

7.1

Crew

8.7

Reviews

1 / 20

10.0
Excellent

Sarah,Aug 2024

MDW - AUS

My first time, surprisingly good! It was a good ride overall. Coming from Singapore, this budget flight is better than the budget airline for our national carrier Singapore Airlines.

Delta
8.0
Very good
8,450 reviews
Southwest
8.1
Very good
4,585 reviews

Comfort

8.1

Entertainment

7.7

Overall

8.1

Boarding

8.2

Food

7.1

Crew

8.7

Reviews

1 / 20

10.0
Excellent

Sarah,Aug 2024

MDW - AUS

My first time, surprisingly good! It was a good ride overall. Coming from Singapore, this budget flight is better than the budget airline for our national carrier Singapore Airlines.

United Airlines
7.4
Good
8,906 reviews
Southwest
8.1
Very good
4,585 reviews

Comfort

8.1

Entertainment

7.7

Overall

8.1

Boarding

8.2

Food

7.1

Crew

8.7

Reviews

1 / 20

10.0
Excellent

Sarah,Aug 2024

MDW - AUS

My first time, surprisingly good! It was a good ride overall. Coming from Singapore, this budget flight is better than the budget airline for our national carrier Singapore Airlines.

American Airlines
7.2
Good
10,000 reviews
Southwest
8.1
Very good
4,585 reviews

Comfort

8.1

Entertainment

7.7

Overall

8.1

Boarding

8.2

Food

7.1

Crew

8.7

Reviews

1 / 20

10.0
Excellent

Sarah,Aug 2024

MDW - AUS

My first time, surprisingly good! It was a good ride overall. Coming from Singapore, this budget flight is better than the budget airline for our national carrier Singapore 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.

  • 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 $453). 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 January 30, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$298Average$436FlexibilityNo cancel feeOn-time71%
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