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$217+ Cheap flights from Odessa, TX to Chicago (CHI)

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 8/30. Fares are subject to change and may not be available on all flights or dates of travel.
MAF — CHI
Aug 5 — Aug 121
Tue 8/5
Tue 8/12
1 adult, Economy
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Cheap flight deals from Odessa to Chicago

Keep the following information in mind while searching for Odessa to Chicago flight deals. Data was last updated July 31, 2025.

Round-trip from

$217
(American Airlines)

Popular in

February

Cheapest in

November

Average price

$386
From Odessa to Chicago (CHI)
Search Deals
Highest demand for flights based on searches. 33% potential increase in price ($218 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 7% potential price decrease ($31 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in July 2025
Search Deals

Find flight deals from Odessa to Chicago

Cheapest flights from Odessa to Chicago
Explore the most affordable flight options available from Odessa to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on July 31, 2025.

This United Airlines deal was found by Cheapflights users on 7/30. 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.
Thu 12/45:00 amMAF - ORD
1 stop5h 02mUnited Airlines
Tue 12/94:45 pmORD - MAF
1 stop6h 28mUnited Airlines
Deal found 7/30$217
This Delta deal was found by Cheapflights users on 7/31. 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.
Sat 8/3012:31 pmMAF - ORD
2 stops7h 52mDelta
Thu 9/45:45 amORD - MAF
2 stops10h 52mDelta
Deal found 7/31$227
This American Airlines deal was found by Cheapflights users on 7/31. 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.
Sat 8/306:33 pmMAF - ORD
1 stop5h 10mAmerican Airlines
Thu 9/41:20 pmORD - MAF
1 stop4h 29mAmerican Airlines
Deal found 7/31$240
This Southwest deal was found by Cheapflights users on 7/30. 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.
Mon 9/295:35 amMAF - ORD
2 stops7h 30mSouthwest
Thu 10/25:45 pmORD - MAF
1 stop5h 10mSouthwest
Deal found 7/30$324

Cheapflights Fare Finder

 
Customize your flight search to find flights from Odessa to Chicago 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 July 31, 2025.
Use the filters below to find and compare flights from Odessa to Chicago that are best for you.

Fly from

Odessa

Fly to

Chicago

Route

Depart

Return

Price

MidlandChicago

MAF - ORD

MAFORD

Midland Intl

Sat 8/30

12:14 pm-5:10 pm

1 stop4h 56m

Chicago O'Hare Intl

Thu 9/4

6:30 pm-11:04 pm

1 stop4h 34m

$217

MidlandChicago

MAF - ORD

MAFORD

Midland Intl

Sat 8/30

12:31 pm-8:23 pm

2 stops7h 52m

Chicago O'Hare Intl

Thu 9/4

5:45 am-4:37 pm

2 stops10h 52m

$227

MidlandChicago

MAF - ORD

MAFORD

Midland Intl

Fri 10/3

7:07 pm-12:14 am

1 stop5h 07m

Chicago O'Hare Intl

Tue 10/7

4:50 pm-11:14 pm

1 stop6h 24m

$237

MidlandChicago

MAF - ORD

MAFORD

Midland Intl

Mon 9/29

5:35 am-1:05 pm

2 stops7h 30m

Chicago O'Hare Intl

Thu 10/2

5:45 pm-10:55 pm

1 stop5h 10m

$324

MidlandChicago

MAF - ORD

MAFORD

Midland Intl

Sun 8/3

4:11 pm-9:15 pm

1 stop5h 04m

$377

MidlandChicago

MAF - ORD

MAFORD

Midland Intl

Sun 8/3

12:37 pm-9:30 pm

2 stops8h 53m

$382

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/29

Best time to book a flight from Odessa to Chicago

Have a flexible travel schedule? Discover the best time to fly to Chicago from Odessa 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 Odessa to Chicago

What is the cheapest month to book a flight from Odessa to Chicago?

Currently, August is the cheapest month in which you can book a flight from Odessa to Chicago (average of $245). Flying from Odessa to Chicago in March is currently the most expensive (average of $321). 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.

What is the cheapest time of day to fly from OD3 to CHI?

Find hourly flight availability from Odessa to Chicago. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated July 31, 2025.

When flying from Odessa to Chicago, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

Reviews of airlines servicing Chicago

Get insights into the airlines that provide service to Chicago. 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 Chicago. Reviews last updated July 31, 2025.
Read reviews from past customers who have flown Southwest, Delta, and United Airlines from Odessa to Chicago. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,246 reviews

Food

7.0

Entertainment

7.5

Boarding

8.1

Overall

8.0

Crew

8.6

Comfort

8.0

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
4,246 reviews
Southwest
8.0
Very good
4,246 reviews

Food

7.0

Entertainment

7.5

Boarding

8.1

Overall

8.0

Crew

8.6

Comfort

8.0

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
7,981 reviews
Southwest
8.0
Very good
4,246 reviews

Food

7.0

Entertainment

7.5

Boarding

8.1

Overall

8.0

Crew

8.6

Comfort

8.0

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
8,900 reviews
Southwest
8.0
Very good
4,246 reviews

Food

7.0

Entertainment

7.5

Boarding

8.1

Overall

8.0

Crew

8.6

Comfort

8.0

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
4,246 reviews

Food

7.0

Entertainment

7.5

Boarding

8.1

Overall

8.0

Crew

8.6

Comfort

8.0

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 Odessa to Chicago. 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 Odessa to Chicago that include hotel bookings?

    Yes. In addition to deals on Odessa to Chicago flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Odessa to Chicago?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Odessa to Chicago.

  • Can I find deals for business class flights from Odessa to Chicago?

    Yes. Cheapflights offers flight deals from Odessa to Chicago 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 Odessa to Chicago?

    Currently, August is the cheapest month in which you can book a flight from Odessa to Chicago (average of $245). Flying from Odessa to Chicago in March is currently the most expensive (average of $321). 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

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Merrillville
Lansing
Hammond
Benton Harbor
Porter
Valparaiso
Chesterton

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Top 2 airlines flying from Odessa to Chicago

Discover the top 2 airlines that operate flights from Odessa to Chicago. 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 July 31, 2025.
AirlineCheapestAverageFlexibilityOn-time
SouthwestCheapest$216Average$496FlexibilityNo cancel feeOn-time63%
American AirlinesCheapest$255Average$360FlexibilityNo cancel feeOn-time71%

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