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$307+ 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 1/13. Fares are subject to change and may not be available on all flights or dates of travel.
MAF — CHI
ene. 17 — ene. 241
sáb. 1/17
sáb. 1/24
1 adult, Economy
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Cheap 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 diciembre 18, 2025.

This American Airlines deal was found by Cheapflights users on 12/16. 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.
mié. 12/3112:39 pmMAF - ORD
1 stop6h 58mAmerican Airlines
dom. 1/48:58 pmORD - MAF
1 stop11h 43mAmerican Airlines
Deal found 12/16$685
This American Airlines deal was found by Cheapflights users on 12/17. 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.
mar. 12/234:29 pmMAF - ORD
1 stop4h 50mAmerican Airlines
jue. 1/12:50 pmORD - MAF
1 stop5h 08mAmerican Airlines
Deal found 12/17$689
This American Airlines deal was found by Cheapflights users on 12/16. 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.
vie. 12/194:29 pmMAF - ORD
1 stop4h 50mAmerican Airlines
vie. 1/26:52 pmORD - MAF
1 stop5h 06mAmerican Airlines
Deal found 12/16$782
This American Airlines deal was found by Cheapflights users on 12/16. 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.
mar. 12/234:29 pmMAF - ORD
1 stop6h 46mAmerican Airlines
sáb. 12/276:52 pmORD - MAF
1 stop5h 06mAmerican Airlines
Deal found 12/16$797
This Southwest deal was found by Cheapflights users on 12/17. 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.
mar. 12/235:35 amMAF - ORD
1 stop7h 25mSouthwest
jue. 1/11:45 pmORD - MAF
2 stops8h 25mSouthwest
Deal found 12/17$807
This United Airlines deal was found by Cheapflights users on 12/16. 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.
mié. 12/315:15 pmMAF - ORD
1 stop6h 44mUnited Airlines
dom. 1/42:00 pmORD - MAF
2 stops9h 25mUnited Airlines
Deal found 12/16$871
This American Airlines deal was found by Cheapflights users on 12/16. 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.
vie. 12/1910:19 amMAF - ORD
1 stop5h 26mAmerican Airlines
dom. 12/285:21 amORD - MAF
1 stop6h 30mAmerican Airlines
Deal found 12/16$894
This Southwest deal was found by Cheapflights users on 12/16. 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.
vie. 12/195:35 amMAF - ORD
1 stop7h 25mSouthwest
vie. 1/23:05 pmORD - MAF
2 stops9h 15mSouthwest
Deal found 12/16$922

Find flight deals from Odessa to Chicago

Keep the following information in mind while searching for Odessa to Chicago flight deals. Data was last updated diciembre 18, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$307
(United Airlines)

Popular in

February

Cheapest in

November

Average price

$637
Provider with most accurate pricing for Midland Intl-Chicago (CHI) flight deals.
Search Deals
Provider most trusted by Cheapflights users for Midland Intl-Chicago (CHI) flights.
Search Deals
From Odessa to Chicago (CHI)
Search Deals
Highest demand for flights based on searches. 29% potential increase in price ($196 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 6% potential price decrease ($29 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in December 2025
Search Deals

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 diciembre 18, 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

mar. 1/13

7:00 am-1:00 pm

1 stop6h 00m

Chicago O'Hare Intl

mar. 1/20

3:53 pm-9:54 pm

1 stop6h 01m

$307

MidlandChicago

MAF - ORD

MAFORD

Midland Intl

mar. 1/13

7:05 am-1:00 pm

2 stops5h 55m

Chicago O'Hare Intl

mar. 1/20

2:15 pm-9:35 pm

1 stop7h 20m

$312

MidlandChicago

MAF - ORD

MAFORD

Midland Intl

lun. 1/26

7:03 pm-12:28 am

1 stop5h 25m

Chicago O'Hare Intl

vie. 1/30

3:59 pm-10:15 pm

1 stop6h 16m

$379

MidlandChicago

MAF - ORD

MAFORD

Midland Intl

mar. 1/13

5:18 pm-11:59 pm

1 stop6h 41m

Chicago O'Hare Intl

sáb. 1/17

8:54 am-4:21 pm

1 stop7h 27m

$387

MidlandChicago

MAF - ORD

MAFORD

Midland Intl

jue. 1/8

5:35 pm-12:28 am

1 stop6h 53m

Chicago O'Hare Intl

dom. 1/11

5:40 am-11:21 am

1 stop5h 41m

$389

MidlandChicago

MAF - ORD

MAFORD

Midland Intl

vie. 1/9

3:00 pm-10:35 pm

1 stop7h 35m

Chicago O'Hare Intl

lun. 1/12

2:15 pm-9:35 pm

1 stop7h 20m

$399

MidlandChicago

MAF - ORD

MAFORD

Midland Intl

jue. 1/8

6:40 am-1:00 pm

1 stop6h 20m

Chicago O'Hare Intl

dom. 1/11

2:15 pm-10:35 pm

2 stops8h 20m

$404

MidlandChicago

MAF - ORD

MAFORD

Midland Intl

vie. 1/30

5:00 am-11:55 am

1 stop6h 55m

Chicago O'Hare Intl

dom. 2/1

8:10 am-4:25 pm

1 stop8h 15m

$407

MidlandChicago

MAF - ORD

MAFORD

Midland Intl

mar. 12/23

3:45 pm-9:26 pm

1 stop5h 41m

$930

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/17

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 $219). Flying from Odessa to Chicago in February is currently the most expensive (average of $901). 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 diciembre 18, 2025.

It’s optimal to fly from Odessa to Chicago in the afternoon. By choosing this option you can save up to 21% on the cost of your flight, compared to a flight in the evening.

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 diciembre 18, 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
7.9
Good
4,250 reviews

Boarding

8.1

Comfort

8.0

Food

7.0

Overall

7.9

Crew

8.6

Entertainment

7.5

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
7.9
Good
4,250 reviews
Southwest
7.9
Good
4,250 reviews

Boarding

8.1

Comfort

8.0

Food

7.0

Overall

7.9

Crew

8.6

Entertainment

7.5

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
11,054 reviews
Southwest
7.9
Good
4,250 reviews

Boarding

8.1

Comfort

8.0

Food

7.0

Overall

7.9

Crew

8.6

Entertainment

7.5

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 5h 55m. Fly via United Airlines or Southwest 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.

  • 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 $219). Flying from Odessa to Chicago in February is currently the most expensive (average of $901). 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
Lansing
Merrillville
Hammond
Porter
Benton Harbor

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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 diciembre 18, 2025.
AirlineCheapestAverageFlexibilityOn-time
SouthwestCheapest$216Average$446FlexibilityNo cancel feeOn-time63%
American AirlinesCheapest$255Average$365FlexibilityNo cancel feeOn-time71%

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