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$117+ Cheap flights from Odessa, TX to Chicago (CHI)

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 10/14. Fares are subject to change and may not be available on all flights or dates of travel.
MAF — CHI
Oct 23 — Oct 301
Thu 10/23
Thu 10/30
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 September 23, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$330
(American Airlines)

One-way from

$117
(American Airlines)

Popular in

February

Cheapest in

November

Average price

$470
Provider with most accurate pricing for Midland Intl-Chicago (CHI) flight deals.
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Provider most trusted by Cheapflights users for Midland Intl-Chicago (CHI) flights.
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From Odessa to Chicago (CHI)
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One-way flight from Odessa to Chicago (CHI)
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Highest demand for flights based on searches. 30% potential increase in price ($200 potential increase over avg. RT price).
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Cheapest flight prices on average. 6% potential price decrease ($29 potential savings vs. average RT price).
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Average for round-trip flights in September 2025
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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 September 23, 2025.

This American Airlines deal was found by Cheapflights users on 9/23. 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 11/129:13 amMAF - ORD
1 stop10h 27mAmerican Airlines
Tue 11/187:25 amORD - MAF
1 stop11h 02mAmerican Airlines
Deal found 9/23$223
This American Airlines deal was found by Cheapflights users on 9/23. 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.
Tue 10/217:10 amMAF - ORD
1 stop10h 50mAmerican Airlines
Tue 10/289:45 pmORD - MAF
1 stop11h 06mAmerican Airlines
Deal found 9/23$263
This American Airlines deal was found by Cheapflights users on 9/23. 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.
Fri 10/174:12 pmMAF - ORD
1 stop6h 24mAmerican Airlines
Tue 10/219:45 pmORD - MAF
1 stop11h 06mAmerican Airlines
Deal found 9/23$310
This Delta deal was found by Cheapflights users on 9/23. 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.
Tue 10/2112:33 pmMAF - ORD
2 stops7h 50mDelta
Tue 10/286:45 amORD - MAF
2 stops9h 46mDelta
Deal found 9/23$327
This Southwest deal was found by Cheapflights users on 9/23. 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 10/216:00 amMAF - ORD
1 stop4h 45mSouthwest
Tue 10/284:20 pmORD - MAF
2 stops7h 45mSouthwest
Deal found 9/23$329
This American Airlines deal was found by Cheapflights users on 9/22. 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.
Fri 10/174:12 pmMAF - ORD
1 stop6h 24mAmerican Airlines
Wed 10/2210:32 amORD - MAF
1 stop8h 38mAmerican Airlines
Deal found 9/22$330
This American Airlines deal was found by Cheapflights users on 9/23. 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.
Fri 10/104:12 pmMAF - ORD
1 stop7h 01mAmerican Airlines
Wed 10/1510:32 amORD - MAF
1 stop8h 38mAmerican Airlines
Deal found 9/23$345
This American Airlines deal was found by Cheapflights users on 9/23. 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.
Tue 11/115:00 amMAF - ORD
1 stop10h 24mAmerican Airlines
Wed 11/1911:46 amORD - MAF
1 stop11h 07mAmerican Airlines
Deal found 9/23$353
This American Airlines deal was found by Cheapflights users on 9/23. 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.
Mon 11/102:32 pmMAF - ORD
1 stop7h 48mAmerican Airlines
Tue 11/1811:46 amORD - MAF
1 stop8h 40mAmerican Airlines
Deal found 9/23$363
This Delta deal was found by Cheapflights users on 9/23. 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.
Fri 10/175:30 amMAF - ORD
2 stops11h 20mDelta
Tue 10/216:45 amORD - MAF
2 stops9h 46mDelta
Deal found 9/23$367
This American Airlines deal was found by Cheapflights users on 9/23. 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.
Mon 11/102:32 pmMAF - ORD
1 stop7h 48mAmerican Airlines
Thu 11/2011:46 amORD - MAF
1 stop8h 03mAmerican Airlines
Deal found 9/23$373
This American Airlines deal was found by Cheapflights users on 9/22. 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.
Thu 12/119:13 amMAF - ORD
1 stop8h 01mAmerican Airlines
Sun 12/148:11 amORD - MAF
1 stop5h 52mAmerican Airlines
Deal found 9/22$380

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 September 23, 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

Tue 10/21

12:33 pm-8:23 pm

2 stops7h 50m

Chicago O'Hare Intl

Tue 10/28

6:45 am-4:31 pm

2 stops9h 46m

$327

MidlandChicago

MAF - ORD

MAFORD

Midland Intl

Wed 11/12

6:15 am-1:00 pm

1 stop6h 45m

Chicago O'Hare Intl

Tue 11/18

2:15 pm-10:10 pm

2 stops7h 55m

$329

MidlandChicago

MAF - ORD

MAFORD

Midland Intl

Tue 10/21

6:00 am-10:45 am

1 stop4h 45m

Chicago O'Hare Intl

Tue 10/28

4:20 pm-12:05 am

2 stops7h 45m

$329

MidlandChicago

MAF - ORD

MAFORD

Midland Intl

Fri 10/17

4:12 pm-10:36 pm

1 stop6h 24m

Chicago O'Hare Intl

Wed 10/22

10:32 am-7:10 pm

1 stop8h 38m

$330

MidlandChicago

MAF - ORD

MAFORD

Midland Intl

Fri 10/10

4:12 pm-11:13 pm

1 stop7h 01m

Chicago O'Hare Intl

Wed 10/15

10:32 am-7:10 pm

1 stop8h 38m

$345

MidlandChicago

MAF - ORD

MAFORD

Midland Intl

Wed 11/12

9:13 am-5:17 pm

1 stop8h 04m

Chicago O'Hare Intl

Wed 11/19

8:45 pm-8:41 am

1 stop11h 56m

$353

MidlandChicago

MAF - ORD

MAFORD

Midland Intl

Mon 11/10

2:32 pm-10:20 pm

1 stop7h 48m

Chicago O'Hare Intl

Wed 11/19

11:46 am-8:26 pm

1 stop8h 40m

$363

MidlandChicago

MAF - ORD

MAFORD

Midland Intl

Tue 11/11

6:05 am-3:24 pm

1 stop9h 19m

Chicago O'Hare Intl

Mon 11/17

10:05 pm-8:41 am

1 stop10h 36m

$363

MidlandChicago

MAF - ORD

MAFORD

Midland Intl

Fri 10/17

5:30 am-4:50 pm

2 stops11h 20m

Chicago O'Hare Intl

Wed 10/22

1:26 pm-11:56 pm

2 stops10h 30m

$367

MidlandChicago

MAF - ORD

MAFORD

Midland Intl

Thu 10/23

12:33 pm-11:58 pm

2 stops11h 25m

Chicago O'Hare Intl

Sun 10/26

6:45 am-4:31 pm

2 stops9h 46m

$389

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/23

Showing 1-10 of 23 results
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2
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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 September 23, 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.

How much does it cost to fly round-trip from Odessa to Chicago?

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 September 23, 2025.
Read reviews from past customers who have flown Southwest and American 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
4,244 reviews

Comfort

8.0

Food

7.0

Crew

8.6

Entertainment

7.5

Overall

8.0

Boarding

8.1

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
4,244 reviews
Southwest
8.0
Very good
4,244 reviews

Comfort

8.0

Food

7.0

Crew

8.6

Entertainment

7.5

Overall

8.0

Boarding

8.1

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
4,244 reviews

Comfort

8.0

Food

7.0

Crew

8.6

Entertainment

7.5

Overall

8.0

Boarding

8.1

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.

  • How long is the flight from Odessa to Chicago?

    There are many flights that can get you from Odessa to Chicago in 6h 24m. Fly via Delta, Southwest, or American Airlines to get the fastest option. The distance from Odessa to Chicago is about 1047 mi. Both multi-stop and nonstop flights can be found to your destination and back.

  • What are the cheapest airlines to fly from Odessa to Chicago one-way?

    $117 is the cheapest one-way deal found within the past few days, from American Airlines. You may also be able to find cheap deals on Delta and United Airlines, with prices starting from $164 and $166, respectively.

  • 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
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 September 23, 2025.
AirlineCheapestAverageFlexibilityOn-time
SouthwestCheapest$216Average$496FlexibilityNo cancel feeOn-time63%
American AirlinesCheapest$255Average$372FlexibilityNo cancel feeOn-time71%

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