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$149+ 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 7/4. Fares are subject to change and may not be available on all flights or dates of travel.
MAF — CHI
Jun 21 — Jun 281
Sat 6/21
Sat 6/28
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 June 16, 2025.

Round-trip from

$242
(American Airlines)

One-way from

$149
(American Airlines)

Popular in

February

Cheapest in

November

Average price

$428
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. 33% potential increase in price ($220 potential increase over avg. RT price).
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Cheapest flight prices on average. 7% potential price decrease ($31 potential savings vs. average RT price).
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Average for round-trip flights in June 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 June 16, 2025.

This American Airlines deal was found by Cheapflights users on 6/14. 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 8/302:32 pmMAF - ORD
1 stop6h 25mAmerican Airlines
Thu 9/45:00 pmORD - MAF
1 stop5h 56mAmerican Airlines
Deal found 6/14$242
This Delta deal was found by Cheapflights users on 6/15. 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 9/41:30 pmORD - MAF
2 stops10h 28mDelta
Deal found 6/15$252
This Southwest deal was found by Cheapflights users on 6/15. 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 8/229:50 amMAF - ORD
1 stop5h 30mSouthwest
Sun 8/245:45 pmORD - MAF
1 stop6h 10mSouthwest
Deal found 6/15$350
This United Airlines deal was found by Cheapflights users on 6/14. 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.
Sat 8/305:00 amMAF - ORD
2 stops11h 56mUnited Airlines
Thu 9/42:53 pmORD - MAF
1 stop5h 24mUnited Airlines
Deal found 6/14$367

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 June 16, 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

2:32 pm-8:57 pm

1 stop6h 25m

Chicago O'Hare Intl

Thu 9/4

5:00 pm-10:56 pm

1 stop5h 56m

$242

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

1:30 pm-11:58 pm

2 stops10h 28m

$252

MidlandChicago

MAF - ORD

MAFORD

Midland Intl

Fri 8/22

9:50 am-3:20 pm

1 stop5h 30m

Chicago O'Hare Intl

Sun 8/24

5:45 pm-11:55 pm

1 stop6h 10m

$350

MidlandChicago

MAF - ORD

MAFORD

Midland Intl

Sat 8/30

5:00 am-4:56 pm

2 stops11h 56m

Chicago O'Hare Intl

Thu 9/4

2:53 pm-8:17 pm

1 stop5h 24m

$367

MidlandChicago

MAF - ORD

MAFORD

Midland Intl

Fri 7/4

4:15 pm-9:52 pm

1 stop5h 37m

$149

MidlandChicago

MAF - ORD

MAFORD

Midland Intl

Fri 7/4

12:34 pm-8:27 pm

2 stops7h 53m

$154

MidlandChicago

MAF - ORD

MAFORD

Midland Intl

Fri 6/20

5:30 pm-12:13 am

1 stop6h 43m

$420

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/14

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 June 16, 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.

Rainfall in Chicago by month

Plan your trip to Chicago by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Chicago ranges from 1.7 - 4.9 inches per month. August is typically the wettest month, when rainfall can reach 4.9 in. January is typically the driest time to visit Chicago when rainfall is around 1.7 in.

Temperature in Chicago by month

Plan your trip to Chicago by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Chicago, 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 73.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 23.0 F).

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 June 16, 2025.
Southwest
8.0
Very good
4,285 reviews

Comfort

8.0

Entertainment

7.6

Boarding

8.2

Food

7.1

Overall

8.0

Crew

8.6

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
4,285 reviews
Southwest
8.0
Very good
4,285 reviews

Comfort

8.0

Entertainment

7.6

Boarding

8.2

Food

7.1

Overall

8.0

Crew

8.6

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
7,963 reviews
Southwest
8.0
Very good
4,285 reviews

Comfort

8.0

Entertainment

7.6

Boarding

8.2

Food

7.1

Overall

8.0

Crew

8.6

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
8,798 reviews
Southwest
8.0
Very good
4,285 reviews

Comfort

8.0

Entertainment

7.6

Boarding

8.2

Food

7.1

Overall

8.0

Crew

8.6

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
4,285 reviews

Comfort

8.0

Entertainment

7.6

Boarding

8.2

Food

7.1

Overall

8.0

Crew

8.6

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 Odessa to Chicago. 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 Odessa to Chicago one-way?

    $149 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 $154 and $420, 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 Odessa?

Book flights to Odessa if you plan to visit one of these locations
Merrillville
Lansing
Benton Harbor
Porter
Hammond
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 June 16, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$267Average$360FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$381Average$536FlexibilityNo cancel feeOn-time63%

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