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Odessa

$274+ 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 2/16. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — MAF
Mrz 5 — Mrz 121
Do 3/5
Do 3/12
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 Februar 3, 2026.

This American Airlines deal was found by Cheapflights users on 1/31. 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.
So 4/266:05 am
ORD
-
MAF
1 stop7h 40m
American Airlines
Sa 5/29:15 am
MAF
-
ORD
1 stop10h 40m
American Airlines
Deal found 1/31$384
This American Airlines deal was found by Cheapflights users on 2/1. 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.
Do 2/2611:45 am
ORD
-
MAF
1 stop5h 36m
American Airlines
Di 3/35:00 am
MAF
-
ORD
1 stop4h 45m
American Airlines
Deal found 2/1$421
This United Airlines deal was found by Cheapflights users on 1/31. 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.
So 4/265:48 am
ORD
-
MAF
1 stop7h 44m
United Airlines
Sa 5/27:00 am
MAF
-
ORD
2 stops15h 08m
United Airlines
Deal found 1/31$434
This United Airlines deal was found by Cheapflights users on 2/1. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
So 3/15:45 am
ORD
-
MAF
1 stop5h 40m
United Airlines
So 3/87:03 pm
MAF
-
ORD
1 stop4h 56m
United Airlines
Deal found 2/1$444
This United Airlines deal was found by Cheapflights users on 1/31. 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.
Mi 2/184:00 pm
ORD
-
MAF
1 stop7h 15m
United Airlines
Sa 2/215:00 am
MAF
-
ORD
2 stops10h 36m
United Airlines
Deal found 1/31$474
This Southwest deal was found by Cheapflights users on 2/2. 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.
Di 2/172:15 pm
ORD
-
MAF
1 stop8h 00m
Southwest
Sa 2/216:20 am
MAF
-
ORD
1 stop7h 45m
Southwest
Deal found 2/2$487
This United Airlines deal was found by Cheapflights users on 2/1. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Do 2/265:20 pm
ORD
-
MAF
1 stop5h 55m
United Airlines
Di 3/37:00 am
MAF
-
ORD
2 stops13h 22m
United Airlines
Deal found 2/1$488
This American Airlines deal was found by Cheapflights users on 2/1. 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.
Do 3/55:00 am
ORD
-
MAF
1 stop6h 52m
American Airlines
So 3/85:00 am
MAF
-
ORD
1 stop4h 45m
American Airlines
Deal found 2/1$500
This American Airlines deal was found by Cheapflights users on 2/1. 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.
So 3/15:00 am
ORD
-
MAF
1 stop4h 42m
American Airlines
So 3/86:07 pm
MAF
-
ORD
1 stop5h 29m
American Airlines
Deal found 2/1$511

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 Februar 3, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$384
(American Airlines)

One-way from

$274
(United Airlines)

Popular in

August

Cheapest in

September

Average price

$582
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
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. 3% potential price decrease ($15 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in February 2026
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 Februar 3, 2026.
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

Do 2/26

11:45 am-5:21 pm

1 stop5h 36m

Midland Intl

Di 3/3

5:00 am-9:45 am

1 stop4h 45m

$421

ChicagoMidland

ORD - MAF

ORDMAF

Chicago O'Hare Intl

So 4/26

5:48 am-1:32 pm

1 stop7h 44m

Midland Intl

Sa 5/2

7:00 am-10:08 pm

2 stops15h 08m

$434

ChicagoMidland

ORD - MAF

ORDMAF

Chicago O'Hare Intl

So 3/1

5:45 am-11:25 am

1 stop5h 40m

Midland Intl

So 3/8

7:03 pm-11:59 pm

1 stop4h 56m

$444

ChicagoMidland

ORD - MAF

ORDMAF

Chicago O'Hare Intl

Mi 2/18

4:00 pm-11:15 pm

1 stop7h 15m

Midland Intl

Sa 2/21

5:00 am-3:36 pm

2 stops10h 36m

$474

ChicagoMidland

ORD - MAF

ORDMAF

Chicago O'Hare Intl

Di 2/17

2:15 pm-10:15 pm

1 stop8h 00m

Midland Intl

Sa 2/21

6:20 am-2:05 pm

1 stop7h 45m

$487

ChicagoMidland

ORD - MAF

ORDMAF

Chicago O'Hare Intl

Di 2/17

4:00 pm-9:44 pm

1 stop5h 44m

Midland Intl

Sa 2/21

7:00 am-12:37 pm

1 stop5h 37m

$487

ChicagoMidland

ORD - MAF

ORDMAF

Chicago O'Hare Intl

Do 2/26

5:20 pm-11:15 pm

1 stop5h 55m

Midland Intl

Di 3/3

7:00 am-8:22 pm

2 stops13h 22m

$488

ChicagoMidland

ORD - MAF

ORDMAF

Chicago O'Hare Intl

Mo 2/16

4:00 pm-9:44 pm

1 stop5h 44m

$274

ChicagoMidland

ORD - MAF

ORDMAF

Chicago O'Hare Intl

Mo 2/16

3:05 pm-11:50 pm

2 stops8h 45m

$302

ChicagoMidland

ORD - MAF

ORDMAF

Chicago O'Hare Intl

Fr 2/13

2:58 pm-10:49 pm

1 stop7h 51m

$395

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/2

Showing 1-10 of 11 results
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 Februar 3, 2026.
See what other customers who have flown with Southwest, United Airlines, 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
4,272 reviews

Food

7.0

Comfort

8.0

Crew

8.6

Boarding

8.1

Entertainment

7.5

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
4,272 reviews
Southwest
8.0
Very good
4,272 reviews

Food

7.0

Comfort

8.0

Crew

8.6

Boarding

8.1

Entertainment

7.5

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
United Airlines
7.4
Good
9,236 reviews
Southwest
8.0
Very good
4,272 reviews

Food

7.0

Comfort

8.0

Crew

8.6

Boarding

8.1

Entertainment

7.5

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
American Airlines
7.2
Good
11,217 reviews
Southwest
8.0
Very good
4,272 reviews

Food

7.0

Comfort

8.0

Crew

8.6

Boarding

8.1

Entertainment

7.5

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 36m. American Airlines provides one of the quickest options available for as low as $421. 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 Februar 3, 2026.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$216Average$377FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$285Average$372FlexibilityNo cancel feeOn-time69%

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