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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 6/4. Fares are subject to change and may not be available on all flights or dates of travel.
MAF — CHI
May 17 — May 241
Sat 5/17
Sat 5/24
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 May 12, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

Expedia
3 stars

Round-trip from

$271
(American Airlines)

One-way from

$149
(American Airlines)

Popular in

February

Cheapest in

November

Average price

$288
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. 32% potential increase in price ($213 potential increase over avg. RT price).
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Cheapest flight prices on average. 7% potential price decrease ($30 potential savings vs. average RT price).
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Average for round-trip flights in May 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 May 12, 2025.

This American Airlines deal was found by Cheapflights users on 5/12. 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.
Sun 8/315:00 amMAF - ORD
1 stop4h 59mAmerican Airlines
Thu 9/46:20 pmORD - MAF
1 stop5h 25mAmerican Airlines
Deal found 5/12$271
This Delta deal was found by Cheapflights users on 5/12. 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 8/3012:29 pmMAF - ORD
2 stops9h 25mDelta
Thu 9/48:55 amORD - MAF
2 stops8h 04mDelta
Deal found 5/12$281
This Southwest deal was found by Cheapflights users on 5/12. 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.
Wed 6/43:40 pmMAF - ORD
1 stop5h 50mSouthwest
Tue 6/105:45 pmORD - MAF
1 stop5h 10mSouthwest
Deal found 5/12$319
This United Airlines deal was found by Cheapflights users on 5/12. 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.
Tue 5/275:13 pmMAF - ORD
1 stop5h 28mUnited Airlines
Sat 5/317:10 amORD - MAF
1 stop6h 38mUnited Airlines
Deal found 5/12$372

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 May 12, 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

Sun 8/31

5:00 am-9:59 am

1 stop4h 59m

Chicago O'Hare Intl

Thu 9/4

6:20 pm-11:45 pm

1 stop5h 25m

$271

MidlandChicago

MAF - ORD

MAFORD

Midland Intl

Sat 8/30

12:29 pm-9:54 pm

2 stops9h 25m

Chicago O'Hare Intl

Thu 9/4

8:55 am-4:59 pm

2 stops8h 04m

$281

MidlandChicago

MAF - ORD

MAFORD

Midland Intl

Wed 6/4

3:40 pm-9:30 pm

1 stop5h 50m

Chicago O'Hare Intl

Tue 6/10

5:45 pm-10:55 pm

1 stop5h 10m

$319

MidlandChicago

MAF - ORD

MAFORD

Midland Intl

Tue 5/27

5:13 pm-10:41 pm

1 stop5h 28m

Chicago O'Hare Intl

Sat 5/31

7:10 am-1:48 pm

1 stop6h 38m

$372

MidlandChicago

MAF - ORD

MAFORD

Midland Intl

Wed 6/4

10:20 am-5:12 pm

1 stop6h 52m

$149

MidlandChicago

MAF - ORD

MAFORD

Midland Intl

Wed 6/4

12:39 pm-11:58 pm

2 stops11h 19m

$154

MidlandChicago

MAF - ORD

MAFORD

Midland Intl

Mon 6/30

5:30 pm-11:12 pm

1 stop5h 42m

$234

Flights are sorted by cheapest round-trip flights first.

Deals found on 5/12

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 May 12, 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 May 12, 2025.
Southwest
8.0
Very good
4,290 reviews

Overall

8.0

Boarding

8.2

Entertainment

7.6

Food

7.1

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
4,290 reviews
Southwest
8.0
Very good
4,290 reviews

Overall

8.0

Boarding

8.2

Entertainment

7.6

Food

7.1

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
7,950 reviews
Southwest
8.0
Very good
4,290 reviews

Overall

8.0

Boarding

8.2

Entertainment

7.6

Food

7.1

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
8,724 reviews
Southwest
8.0
Very good
4,290 reviews

Overall

8.0

Boarding

8.2

Entertainment

7.6

Food

7.1

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
4,290 reviews

Overall

8.0

Boarding

8.2

Entertainment

7.6

Food

7.1

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.

  • 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 $234, 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
Hammond
Benton Harbor
Porter
Lansing
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 May 12, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$267Average$347FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$381Average$536FlexibilityNo cancel feeOn-time63%

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