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 $323). 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 day to fly from Odessa to Chicago?

Travelers seeking maximum savings on their Odessa to Chicago flight should consider departing on Saturday afternoons when fares are most often at their lowest. Wednesday mornings flights should be avoided if possible as fares are typically the most expensive at this time.

What are the most popular airlines that fly from Odessa to Chicago?

American Airlines, United Airlines and Southwest are the most popular airlines when flying from Odessa to Chicago.

What is the cheapest month to fly from Odessa to Chicago?

Due to multiple factors, expect to potentially pay more when booking in February. For low rates, November can be a great choice for travel to Chicago. Flights to Chicago from Odessa in November are about $454 on average during November, but can be found for as low as $286.

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.

$175+ Flights from Odessa to Chicago

Home Search by date Vacation packages Hotels Flight deals Car rental Travel tips & news

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

Most accurate provider	FlightHub 3 stars
Most trusted provider	FlightHub 3 stars
Round-trip from	$288 (Delta)
One-way from	$175 (Delta)
Popular in	February
Cheapest in	November
Average price	$672

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. 36% potential increase in price ($256 potential increase over avg. RT price).

Search Deals

Cheapest flight prices on average. 7% potential price decrease ($34 potential savings vs. average RT price).

Search Deals

Average for round-trip flights in March 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 March 28, 2025.

Thu 5/1512:39 pmMAF - ORD

2 stops8h 41mDelta

Mon 5/193:57 pmORD - MAF

2 stops8h 05mDelta

Deal found 3/26

$288

Fri 5/97:08 pmMAF - ORD

1 stop5h 07mUnited Airlines

Sun 5/113:52 pmORD - MAF

1 stop7h 54mUnited Airlines

Deal found 3/27

$312

Sat 8/304:17 pmMAF - ORD

1 stop4h 43mAmerican Airlines

Thu 9/411:55 amORD - MAF

1 stop5h 54mAmerican Airlines

Deal found 3/27

$352

Fri 4/119:55 amMAF - ORD

1 stop5h 05mSouthwest

Mon 4/144:00 pmORD - MAF

2 stops7h 15mSouthwest

Deal found 3/27

$452

Best flights from Odessa to Chicago
Discover carefully curated flight deals from Odessa to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated March 28, 2025.

Thu 5/1512:39 pmMAF - ORD

2 stops8h 41mDelta

Mon 5/193:57 pmORD - MAF

2 stops8h 05mDelta

Deal found 3/26

$288

Fri 5/97:08 pmMAF - ORD

1 stop5h 07mUnited Airlines

Sun 5/113:52 pmORD - MAF

1 stop7h 54mUnited Airlines

Deal found 3/27

$312

Sat 8/304:17 pmMAF - ORD

1 stop4h 43mAmerican Airlines

Thu 9/411:55 amORD - MAF

1 stop5h 54mAmerican Airlines

Deal found 3/27

$352

Thu 6/195:20 amMAF - ORD

2 stops7h 25mSouthwest

Mon 6/235:45 pmORD - MAF

1 stop6h 00mSouthwest

Deal found 3/27

$422

Last-minute flights from Odessa to Chicago
Discover last-minute flight deals from Odessa to Chicago. Data last updated March 28, 2025 and is based on user searches.

Tue 4/16:10 amMAF - ORD

1 stop4h 35mSouthwest

Tue 4/87:30 amORD - MAF

1 stop7h 35mSouthwest

Deal found 3/27

$600

Fri 4/119:55 amMAF - ORD

1 stop5h 05mSouthwest

Mon 4/144:00 pmORD - MAF

2 stops7h 15mSouthwest

Deal found 3/27

$452

Wed 4/164:22 pmMAF - ORD

1 stop7h 27mAmerican Airlines

Sun 4/206:55 amORD - MAF

1 stop5h 04mAmerican Airlines

Deal found 3/27

$427

Wed 4/165:27 amMAF - ORD

2 stops13h 31mDelta

Sun 4/2011:15 amORD - MAF

2 stops12h 41mDelta

Deal found 3/27

$437

Wed 4/164:56 pmMAF - ORD

2 stops18h 14mUnited Airlines

Sun 4/207:45 amORD - MAF

1 stop6h 23mUnited Airlines

Deal found 3/27

$530

One-way flights from Odessa to Chicago
Search for one-way flight options from Odessa to Chicago. Find affordable one-way fares based on user searches. Data last updated March 28, 2025.

Thu 6/125:30 amMAF - ORD

2 stops11h 08mDelta

Deal found 3/26

$175

Thu 6/125:20 amMAF - ORD

1 stop5h 25mSouthwest

Deal found 3/26

$224

Cheapflights Fare Finder

Use the filters below to find and compare flights from Odessa to Chicago that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

MidlandChicago

MAF - ORD

MAFORD

Midland Intl

Thu 5/15

12:39 pm-9:20 pm

2 stops8h 41m

Chicago O'Hare Intl

Mon 5/19

3:57 pm-12:02 am

2 stops8h 05m

$288

MidlandChicago

MAF - ORD

MAFORD

Midland Intl

Fri 5/9

7:08 pm-12:15 am

1 stop5h 07m

Chicago O'Hare Intl

Sun 5/11

3:52 pm-11:46 pm

1 stop7h 54m

$312

MidlandChicago

MAF - ORD

MAFORD

Midland Intl

Sat 8/30

4:17 pm-9:00 pm

1 stop4h 43m

Chicago O'Hare Intl

Thu 9/4

11:55 am-5:49 pm

1 stop5h 54m

$352

MidlandChicago

MAF - ORD

MAFORD

Midland Intl

Thu 6/19

5:20 am-12:45 pm

2 stops7h 25m

Chicago O'Hare Intl

Mon 6/23

5:45 pm-11:45 pm

1 stop6h 00m

$422

MidlandChicago

MAF - ORD

MAFORD

Midland Intl

Thu 6/12

5:30 am-4:38 pm

2 stops11h 08m

$175

MidlandChicago

MAF - ORD

MAFORD

Midland Intl

Thu 6/12

5:20 am-10:45 am

1 stop5h 25m

$224

Flights are sorted by cheapest round-trip flights first.

Deals found on 3/26

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 time of day to fly from OD3 to CHI?

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

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

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

Southwest

8.1

Very good

4,274 reviews

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

8.1

Very good

4,274 reviews

Southwest

8.1

Very good

4,274 reviews

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

7,897 reviews

Southwest

8.1

Very good

4,274 reviews

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

8,603 reviews

Southwest

8.1

Very good

4,274 reviews

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

8.1

Very good

4,274 reviews

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

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 $323). 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

Merrillville

New Buffalo

Hammond

Benton Harbor

Porter

Lansing

Valparaiso

Chesterton

Browse thousands of different options on Cheapflights for your next trip

Top 3 airlines flying from Odessa to Chicago

Airline	Cheapest	Average	Flexibility	On-time
American Airlines	Cheapest$267	Average$347	FlexibilityNo cancel fee	On-time71%
United Airlines	Cheapest$335	Average$426	FlexibilityNo cancel fee	On-time69%
Southwest	Cheapest$381	Average$536	FlexibilityNo cancel fee	On-time63%

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.

$175+ 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 6/12. Fares are subject to change and may not be available on all flights or dates of travel.

Find cheap flights from Odessa to Chicago with Cheapflights

1. Tell us where you want to go

2. Select your favorite providers

3. Compare prices and book

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 March 28, 2025.

Most accurate provider

Most trusted provider

Round-trip from

One-way from

Popular in

Cheapest in

Average price

Find flight deals from Odessa to Chicago

Cheapest flights from Odessa to ChicagoExplore 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 March 28, 2025.

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 March 28, 2025.

Cheapflights Fare Finder

Use the filters below to find and compare flights from Odessa to Chicago that are best for you.

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.

Cheapflights Insights

Everything you need to know about your flight from Odessa to Chicago

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 March 28, 2025.

Rainfall in Chicago by month

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

Temperature in Chicago by month

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

Reviews of airlines servicing Chicago

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.

Can I find deals for flights from Odessa to Chicago that include hotel bookings?

How can I find direct flights from Odessa to Chicago?

Can I find deals for business class flights from Odessa to Chicago?

What is the cheapest month to book a flight from Odessa to Chicago?

Traveling to a place near Odessa?

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.

Top 3 airlines flying from Odessa to Chicago

100% Free

Book with Flexibility

Travel Smart

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 March 28, 2025.