HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Chicago

$148+ 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 4 — May 111
Sun 5/4
Sun 5/11
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Odessa to Chicago with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

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 April 29, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$268
(American Airlines)

One-way from

$148
(Delta)

Popular in

February

Cheapest in

November

Average price

$457
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
One-way flight from Odessa to Chicago (CHI)
Search Deals
Highest demand for flights based on searches. 31% potential increase in price ($210 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 April 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 April 29, 2025.

This American Airlines deal was found by Cheapflights users on 4/29. 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 8/306:22 pmMAF - ORD
1 stop5h 21mAmerican Airlines
Thu 9/45:06 pmORD - MAF
1 stop6h 39mAmerican Airlines
Deal found 4/29$268
This Delta deal was found by Cheapflights users on 4/29. 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 stops11h 26mDelta
Thu 9/47:00 amORD - MAF
2 stops9h 59mDelta
Deal found 4/29$278
This United Airlines deal was found by Cheapflights users on 4/28. 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 6/37:00 amMAF - ORD
1 stop5h 26mUnited Airlines
Sat 6/72:33 pmORD - MAF
1 stop6h 17mUnited Airlines
Deal found 4/28$291
This Southwest deal was found by Cheapflights users on 4/27. 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.
Thu 6/55:20 amMAF - ORD
2 stops7h 25mSouthwest
Sat 6/712:40 pmORD - MAF
2 stops8h 35mSouthwest
Deal found 4/27$413

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 April 29, 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

6:22 pm-11:43 pm

1 stop5h 21m

Chicago O'Hare Intl

Thu 9/4

5:06 pm-11:45 pm

1 stop6h 39m

$268

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

11:19 am-11:52 pm

2 stops12h 33m

$278

MidlandChicago

MAF - ORD

MAFORD

Midland Intl

Tue 6/3

7:00 am-12:26 pm

1 stop5h 26m

Chicago O'Hare Intl

Sat 6/7

2:33 pm-8:50 pm

1 stop6h 17m

$291

MidlandChicago

MAF - ORD

MAFORD

Midland Intl

Thu 6/5

5:20 am-12:45 pm

2 stops7h 25m

Chicago O'Hare Intl

Sat 6/7

12:40 pm-9:15 pm

2 stops8h 35m

$413

MidlandChicago

MAF - ORD

MAFORD

Midland Intl

Wed 6/4

5:29 am-2:47 pm

2 stops9h 18m

$148

MidlandChicago

MAF - ORD

MAFORD

Midland Intl

Wed 6/4

3:40 pm-9:30 pm

1 stop5h 50m

$160

MidlandChicago

MAF - ORD

MAFORD

Midland Intl

Mon 6/23

6:17 pm-12:59 am

1 stop6h 42m

$185

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/28

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 April 29, 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 April 29, 2025.
Southwest
8.0
Very good
4,295 reviews

Boarding

8.2

Crew

8.6

Comfort

8.0

Food

7.1

Overall

8.0

Entertainment

7.6

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
4,295 reviews
Southwest
8.0
Very good
4,295 reviews

Boarding

8.2

Crew

8.6

Comfort

8.0

Food

7.1

Overall

8.0

Entertainment

7.6

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
7,929 reviews
Southwest
8.0
Very good
4,295 reviews

Boarding

8.2

Crew

8.6

Comfort

8.0

Food

7.1

Overall

8.0

Entertainment

7.6

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
8,696 reviews
Southwest
8.0
Very good
4,295 reviews

Boarding

8.2

Crew

8.6

Comfort

8.0

Food

7.1

Overall

8.0

Entertainment

7.6

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
4,295 reviews

Boarding

8.2

Crew

8.6

Comfort

8.0

Food

7.1

Overall

8.0

Entertainment

7.6

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?

    $148 is the cheapest one-way deal found within the past few days, from Delta. You may also be able to find cheap deals on Southwest and American Airlines, with prices starting from $160 and $185, 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

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for Odessa to Chicago

See prices for flight routes from nearby airports that may be better suited for you.
Dallas/Fort Worth to O'Hare Intl flights
Dallas/Fort Worth to Midway flights
Hobby to O'Hare Intl flights
George Bush Intcntl to O'Hare Intl flights
Austin to O'Hare Intl flights
Hobby to Midway flights
Love Field to O'Hare Intl flights
Love Field to Midway flights
San Antonio to O'Hare Intl flights
Dallas/Fort Worth to St. Louis flights
Austin to Midway flights
Hobby to St. Louis flights
George Bush Intcntl to St. Louis flights
George Bush Intcntl to Midway flights
El Paso to O'Hare Intl flights
San Antonio to Midway flights
El Paso to Midway flights
Austin to St. Louis flights
Love Field to St. Louis flights
Dallas/Fort Worth to Peoria flights
Dallas/Fort Worth to Moline flights
McAllen to O'Hare Intl flights
Dallas/Fort Worth to Evansville flights
McAllen to Midway flights
San Antonio to St. Louis flights
Brownsville to O'Hare Intl flights
Dallas/Fort Worth to Decatur flights
Dallas/Fort Worth to Bloomington flights
Midland to O'Hare Intl flights
El Paso to St. Louis flights
Austin to Moline flights
Lubbock to O'Hare Intl flights
Amarillo to O'Hare Intl flights
Harlingen to O'Hare Intl flights
Corpus Christi to O'Hare Intl flights
Hobby to Moline flights
Love Field to Moline flights
George Bush Intcntl to Moline flights
Austin to Rockford flights
San Antonio to Moline flights
San Antonio to Peoria flights
Dallas/Fort Worth to Champaign flights
George Bush Intcntl to Decatur flights
Austin to Peoria flights
Hobby to Champaign flights
Hobby to Springfield flights
Laredo to O'Hare Intl flights
Hobby to Bloomington flights
George Bush Intcntl to Champaign flights

Top 3 airlines flying from Odessa to Chicago

Discover the top 3 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 April 29, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$267Average$347FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$381Average$536FlexibilityNo cancel feeOn-time63%
United AirlinesCheapest$386Average$753FlexibilityNo cancel feeOn-time69%

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.