HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Odessa

$160+ 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 5/22. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — MAF
Apr 6 — Apr 131
Sun 4/6
Sun 4/13
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 April 1, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$302
(United Airlines)

One-way from

$160
(American Airlines)

Popular in

February

Cheapest in

July

Average price

$339
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. 6% potential increase in price ($33 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 6% potential price decrease ($30 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in April 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 April 1, 2025.

This United Airlines deal was found by Cheapflights users on 3/31. 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.
Thu 5/110:40 amORD - MAF
1 stop5h 27mUnited Airlines
Wed 5/76:00 amMAF - ORD
1 stop5h 34mUnited Airlines
Deal found 3/31$302
This Delta deal was found by Cheapflights users on 3/31. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/11:15 pmORD - MAF
2 stops10h 41mDelta
Wed 5/712:39 pmMAF - ORD
2 stops8h 41mDelta
Deal found 3/31$312
This American Airlines deal was found by Cheapflights users on 4/1. 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.
Sat 7/510:37 amORD - MAF
1 stop7h 11mAmerican Airlines
Sat 7/1210:12 amMAF - ORD
1 stop4h 38mAmerican Airlines
Deal found 4/1$317
This Southwest deal was found by Cheapflights users on 4/1. 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 5/912:40 pmORD - MAF
2 stops10h 35mSouthwest
Mon 5/123:05 pmMAF - ORD
1 stop8h 35mSouthwest
Deal found 4/1$398

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 April 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

Thu 5/1

10:40 am-4:07 pm

1 stop5h 27m

Midland Intl

Wed 5/7

6:00 am-11:34 am

1 stop5h 34m

$302

ChicagoMidland

ORD - MAF

ORDMAF

Chicago O'Hare Intl

Thu 5/1

1:15 pm-11:56 pm

2 stops10h 41m

Midland Intl

Wed 5/7

12:39 pm-9:20 pm

2 stops8h 41m

$312

ChicagoMidland

ORD - MAF

ORDMAF

Chicago O'Hare Intl

Sat 7/5

10:37 am-5:48 pm

1 stop7h 11m

Midland Intl

Sat 7/12

10:12 am-2:50 pm

1 stop4h 38m

$317

ChicagoMidland

ORD - MAF

ORDMAF

Chicago O'Hare Intl

Fri 5/9

12:40 pm-11:15 pm

2 stops10h 35m

Midland Intl

Mon 5/12

3:05 pm-11:40 pm

1 stop8h 35m

$398

ChicagoMidland

ORD - MAF

ORDMAF

Chicago O'Hare Intl

Thu 5/22

6:00 am-11:49 am

1 stop5h 49m

$160

ChicagoMidland

ORD - MAF

ORDMAF

Chicago O'Hare Intl

Thu 5/15

11:05 am-12:02 am

2 stops12h 57m

$165

ChicagoMidland

ORD - MAF

ORDMAF

Chicago O'Hare Intl

Tue 4/15

1:30 pm-11:15 pm

2 stops9h 45m

$229

ChicagoMidland

ORD - MAF

ORDMAF

Chicago O'Hare Intl

Thu 5/15

12:45 pm-11:46 pm

3 stops11h 01m

$1,062

Flights are sorted by cheapest round-trip flights first.

Deals found on 3/31

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 April 1, 2025.
To help decide which airline to fly from Chicago to Odessa, see what other customers have to say about Southwest, Delta and United Airlines. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,277 reviews

Crew

8.7

Food

7.1

Overall

8.0

Boarding

8.2

Comfort

8.0

Entertainment

7.6

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
4,277 reviews
Southwest
8.0
Very good
4,277 reviews

Crew

8.7

Food

7.1

Overall

8.0

Boarding

8.2

Comfort

8.0

Entertainment

7.6

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
7,898 reviews
Southwest
8.0
Very good
4,277 reviews

Crew

8.7

Food

7.1

Overall

8.0

Boarding

8.2

Comfort

8.0

Entertainment

7.6

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
8,615 reviews
Southwest
8.0
Very good
4,277 reviews

Crew

8.7

Food

7.1

Overall

8.0

Boarding

8.2

Comfort

8.0

Entertainment

7.6

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
4,277 reviews

Crew

8.7

Food

7.1

Overall

8.0

Boarding

8.2

Comfort

8.0

Entertainment

7.6

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 $160 on American Airlines. Other airlines that offer cheap prices include Delta from $165 and Southwest from $229 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 $399). 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
O'Hare Intl to Hobby flights
O'Hare Intl to Austin flights
O'Hare Intl to San Antonio flights
O'Hare Intl to George Bush Intcntl flights
Midway to Dallas/Fort Worth flights
St. Louis to Dallas/Fort Worth flights
O'Hare Intl to Love Field flights
Midway to Hobby flights
Midway to Love Field flights
St. Louis to Hobby flights
St. Louis to George Bush Intcntl flights
O'Hare Intl to El Paso flights
Midway to Austin flights
Midway to San Antonio flights
St. Louis to Love Field flights
Moline to Dallas/Fort Worth flights
St. Louis to San Antonio flights
Midway to George Bush Intcntl flights
Peoria to Dallas/Fort Worth flights
St. Louis to Austin flights
Midway to El Paso flights
Moline to Hobby flights
O'Hare Intl to Harlingen flights
O'Hare Intl to McAllen flights
Evansville to Dallas/Fort Worth flights
Peoria to Austin flights
O'Hare Intl to Corpus Christi flights
Peoria to San Antonio flights
Bloomington to Dallas/Fort Worth flights
Decatur to Dallas/Fort Worth flights
Moline to San Antonio flights
O'Hare Intl to Lubbock flights
Moline to George Bush Intcntl flights
O'Hare Intl to Brownsville flights
Peoria to Hobby flights
Peoria to George Bush Intcntl flights
Moline to Austin flights
Bloomington to Love Field flights
Moline to Brownsville flights
O'Hare Intl to Midland flights
Moline to Love Field flights
St. Louis to McAllen flights
St. Louis to El Paso flights
Evansville to Hobby flights
Champaign to Dallas/Fort Worth flights
St. Louis to Corpus Christi flights
Springfield to Dallas/Fort Worth flights
Bloomington to Hobby flights
O'Hare Intl to Laredo 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 April 1, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$271Average$431FlexibilityNo 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.