What are the cheapest airlines flying from Houston Hobby Airport to Chicago O'Hare Intl Airport round-trip?

Cheapflights users have booked flights from Houston Hobby Airport to Chicago O'Hare Intl Airport round-trip from $177. Other airlines that can offer you cheap pricing are Delta, from $217, and American Airlines, from $251. These flights start at 18% lower than the current average price 3 months from now.

In terms of precipitation, rainfall in Chicago O'Hare Intl Airport 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 O'Hare Intl Airport when rainfall is around 1.7 in.

If weather is an important factor for your trip to Chicago O'Hare Intl Airport, 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).

What are the most popular airlines that fly from Houston Hobby Airport to Chicago O'Hare Intl Airport?

When booking a flight from Houston Hobby Airport to Chicago O'Hare Intl Airport, you may want to consider flying on American Airlines, Frontier or Spirit Airlines as they are the most popular for this route.

What is the cheapest day to fly round-trip from Houston Hobby Airport to Chicago O'Hare Intl Airport?

Wednesday is generally a great day to depart. Flying on this day could help you save up to 39%.

What is the cheapest month to fly from Houston Hobby Airport to Chicago O'Hare Intl Airport?

Due to multiple factors, expect to potentially pay more when booking in June. For low rates, February can be a great choice for travel to Chicago O'Hare Intl Airport. Flights to Chicago O'Hare Intl Airport from Houston Hobby Airport in February are about $187 on average during February, but can be found for as low as $65.

Can I find deals for flights from Hobby to O'Hare Intl that include hotel bookings?

Yes. In addition to deals on Hobby to O'Hare Intl flights, Cheapflights offers vacation packages that include both flights and hotel.

How can I find direct flights from Hobby to O'Hare Intl?

After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Hobby to O'Hare Intl.

Can I find deals for business class flights from Hobby to O'Hare Intl?

Yes. Cheapflights offers flight deals from Hobby to O'Hare Intl by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

$89+ Flights from Houston Hobby Airport to Chicago O'Hare Intl Airport

Q: How far in advance should I book a flight from Houston Hobby Airport to Chicago O'Hare Intl Airport?

Travelers have found it’s best to book a flight 26 days in advance to save up to 72% compared to booking the same week of travel. As your travel date approaches, the cost of this flight route may potentially increase. While opting to book 26 days out may not be an option for all, there are still additional ways to secure a deal in the near future. You might find a flight from Houston Hobby Airport to Chicago O'Hare Intl Airport 1-2 weeks in advance for as low as $133, or $264 for flights within the next 24 hours.

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Find cheap flights from Hobby to O'Hare Intl with Cheapflights

1. Tell us where you want to go

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2. Select your favorite providers

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Cheapflights Tip: The best prices from Houston Hobby to Chicago O'Hare Intl are usually found in September or October, booked 84 days in advance, depart on a Thursday or Monday and return on a Wednesday

Cheap flight deals from Hobby to O'Hare Intl

Round-trip from	$177 (Southwest)
One-way from	$89 (Southwest)
Popular in	April
Cheapest in	September
Average price	$213

From Houston Hobby to Chicago O'Hare Intl

Search Deals

One-way flight from Houston Hobby to Chicago O'Hare Intl

Search Deals

Highest demand for flights based on searches. 6% potential increase in price ($14 potential increase over avg. RT price).

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Cheapest flight prices on average. 2% potential price decrease ($6 potential savings vs. average RT price).

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Average for round-trip flights in July 2025

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Find flight deals from Hobby to O'Hare Intl

Cheapest flights from Hobby to O'Hare Intl
Explore the most affordable flight options available from Hobby to O'Hare Intl. Find the lowest fares from popular airlines and budget airlines, with prices last updated on July 2, 2025.

Thu 8/212:55 pmHOU - ORD

1 stop8h 10mSouthwest

Mon 8/255:45 pmORD - HOU

1 stop4h 55mSouthwest

Deal found 7/2

$177

Fri 8/226:34 pmHOU - ORD

1 stop5h 22mDelta

Sat 8/239:47 amORD - HOU

1 stop7h 52mDelta

Deal found 6/30

$217

Tue 10/710:17 amHOU - ORD

1 stop4h 49mAmerican Airlines

Tue 10/146:55 amORD - HOU

1 stop6h 59mAmerican Airlines

Deal found 6/30

$251

Best flights from Hobby to O'Hare Intl
Discover carefully curated flight deals from Hobby to O'Hare Intl that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated July 2, 2025.

Thu 8/212:55 pmHOU - ORD

1 stop8h 10mSouthwest

Mon 8/255:45 pmORD - HOU

1 stop4h 55mSouthwest

Deal found 7/2

$177

Fri 8/226:34 pmHOU - ORD

1 stop5h 22mDelta

Sat 8/233:30 pmORD - HOU

1 stop7h 01mDelta

Deal found 7/2

$217

Tue 10/710:17 amHOU - ORD

1 stop4h 49mAmerican Airlines

Tue 10/146:55 amORD - HOU

1 stop6h 59mAmerican Airlines

Deal found 6/30

$251

Last-minute flights from Hobby to O'Hare Intl
Discover last-minute flight deals from Hobby to O'Hare Intl. Data last updated July 2, 2025 and is based on user searches.

Wed 7/95:00 pmHOU - ORD

1 stop7h 09mDelta

Fri 7/113:29 pmORD - HOU

1 stop6h 52mDelta

Deal found 7/1

$377

Thu 7/106:30 pmHOU - ORD

1 stop5h 16mAmerican Airlines

Wed 7/165:00 amORD - HOU

1 stop4h 40mAmerican Airlines

Deal found 6/30

$347

Sat 7/124:00 pmHOU - ORD

1 stop6h 00mSouthwest

Mon 7/216:15 amORD - HOU

1 stop10h 40mSouthwest

Deal found 6/30

$330

Thu 8/75:05 amHOU - ORD

1 stop6h 45mSouthwest

Mon 8/117:00 amORD - HOU

1 stop6h 05mSouthwest

Deal found 6/29

$177

Fri 8/226:34 pmHOU - ORD

1 stop5h 22mDelta

Sat 8/239:47 amORD - HOU

1 stop7h 52mDelta

Deal found 6/30

$217

Wed 8/278:51 amHOU - ORD

1 stop4h 46mAmerican Airlines

Sat 8/301:21 pmORD - HOU

1 stop4h 39mAmerican Airlines

Deal found 6/30

$251

One-way flights from Hobby to O'Hare Intl
Search for one-way flight options from Hobby to O'Hare Intl. Find affordable one-way fares based on user searches. Data last updated July 2, 2025.

Mon 8/42:30 pmHOU - ORD

1 stop7h 00mSouthwest

Deal found 6/29

$89

Tue 9/3010:44 amHOU - ORD

1 stop5h 47mDelta

Deal found 6/30

$109

Wed 8/136:00 amHOU - ORD

1 stop4h 59mAmerican Airlines

Deal found 6/30

$126

Mon 8/410:00 amHOU - ORD

1 stop7h 15mSun Country Air

Deal found 6/30

$133

Fri 8/88:03 pmHOU - ORD

2 stops27h 55mMultiple Airlines

Deal found 7/1

$148

Cheapflights Fare Finder

Use the filters below to find and compare flights from Houston Hobby Airport to Chicago O'Hare Intl Airport that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

HoustonChicago

HOU - ORD

HOUORD

Houston Hobby

Thu 8/21

2:55 pm-11:05 pm

1 stop8h 10m

Chicago O'Hare Intl

Mon 8/25

5:45 pm-10:40 pm

1 stop4h 55m

$177

HoustonChicago

HOU - ORD

HOUORD

Houston Hobby

Fri 8/22

6:34 pm-11:56 pm

1 stop5h 22m

Chicago O'Hare Intl

Sat 8/23

9:47 am-5:39 pm

1 stop7h 52m

$217

HoustonChicago

HOU - ORD

HOUORD

Houston Hobby

Wed 8/27

8:51 am-1:37 pm

1 stop4h 46m

Chicago O'Hare Intl

Sat 8/30

1:21 pm-6:00 pm

1 stop4h 39m

$251

HoustonChicago

HOU - ORD

HOUORD

Houston Hobby

Mon 8/4

8:10 am-12:45 pm

1 stop4h 35m

$89

HoustonChicago

HOU - ORD

HOUORD

Houston Hobby

Tue 9/30

10:44 am-4:31 pm

1 stop5h 47m

$109

HoustonChicago

HOU - ORD

HOUORD

Houston Hobby

Wed 8/13

6:00 am-10:59 am

1 stop4h 59m

$126

HoustonChicago

HOU - ORD

HOUORD

Houston Hobby

Mon 8/4

10:00 am-5:15 pm

1 stop7h 15m

$133

HoustonChicago

HOU - ORD

HOUORD

Houston Hobby

Fri 8/8

8:03 pm-11:58 pm

2 stops27h 55m

$148

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/1

Best time to book a flight from Hobby to O'Hare Intl

Have a flexible travel schedule? Discover the best time to fly to O'Hare Intl from Hobby 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 Houston Hobby Airport to Chicago O'Hare Intl Airport

How far ahead should I book a flight from Houston Hobby Airport to Chicago O'Hare Intl Airport?

To ensure you get the cheapest price possible for a flight from Houston Hobby Airport to Chicago O'Hare Intl Airport, you should look to book at least 84 days in advance of your intended travel date. The price of your flight may increase if you delay and leave booking until a week or so before departure.

What is the cheapest month to book a flight from Houston Hobby Airport to Chicago O'Hare Intl Airport?

Currently, August is the cheapest month in which you can book a flight from Houston Hobby Airport to Chicago O'Hare Intl Airport (average of $245). Flying from Houston Hobby Airport to Chicago O'Hare Intl Airport 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 HOU to ORD?

When flying from Houston Hobby Airport to Chicago O'Hare Intl Airport, the time of day you fly usually plays a role in the price. Save by searching for a flight in the evening, which can drop the price by up to 26% versus a flight in the afternoon.

What is the cheapest day to fly from Houston Hobby Airport to Chicago O'Hare Intl Airport?

Travelers seeking maximum savings on their Houston Hobby Airport to Chicago O'Hare Intl Airport flight should consider departing on Monday evenings when fares are most often at their lowest. Sunday at noon flights should be avoided if possible as fares are typically the most expensive at this time.

Reviews of airlines servicing O'Hare Intl

Read reviews from past customers who have flown Southwest, Delta, and American Airlines from Houston Hobby Airport to Chicago O'Hare Intl Airport. 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

8.0

Very good

4,272 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

8.0

Very good

4,272 reviews

Southwest

8.0

Very good

4,272 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

7,983 reviews

Southwest

8.0

Very good

4,272 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

8.0

Very good

4,272 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.

Sun Country Air

6.9

Okay

340 reviews

Southwest

8.0

Very good

4,272 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

What are the cheapest airlines flying from Houston Hobby Airport to Chicago O'Hare Intl Airport round-trip?
Cheapflights users have booked flights from Houston Hobby Airport to Chicago O'Hare Intl Airport round-trip from $177. Other airlines that can offer you cheap pricing are Delta, from $217, and American Airlines, from $251. These flights start at 18% lower than the current average price 3 months from now.
What are the cheapest airlines to fly from Houston Hobby Airport to Chicago O'Hare Intl Airport one-way?
The cheapest airlines for a one-way flight from Houston Hobby Airport to Chicago O'Hare Intl Airport are Southwest ($89), Delta ($109), and American Airlines ($126).
Can I find deals for flights from Hobby to O'Hare Intl that include hotel bookings?
Yes. In addition to deals on Hobby to O'Hare Intl flights, Cheapflights offers vacation packages that include both flights and hotel.
How can I find direct flights from Hobby to O'Hare Intl?
After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Hobby to O'Hare Intl.
Can I find deals for business class flights from Hobby to O'Hare Intl?
Yes. Cheapflights offers flight deals from Hobby to O'Hare Intl 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 Houston Hobby Airport to Chicago O'Hare Intl Airport?
Currently, August is the cheapest month in which you can book a flight from Houston Hobby Airport to Chicago O'Hare Intl Airport (average of $245). Flying from Houston Hobby Airport to Chicago O'Hare Intl Airport 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.

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Top 4 airlines flying from Hobby to O'Hare Intl

Airline	Cheapest	Average	Flexibility	On-time
Frontier	Cheapest$59	Average$156	FlexibilityNo cancel fee	On-time62%
Spirit Airlines	Cheapest$62	Average$168	FlexibilityNo cancel fee	On-time65%
United Airlines	Cheapest$154	Average$343	FlexibilityNo cancel fee	On-time69%
American Airlines	Cheapest$158	Average$273	FlexibilityNo cancel fee	On-time71%

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$89+ Cheap flights from Hobby (HOU) to O'Hare Intl (ORD)

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 8/4. Fares are subject to change and may not be available on all flights or dates of travel.

Find cheap flights from Hobby to O'Hare Intl with Cheapflights

1. Tell us where you want to go

2. Select your favorite providers

3. Compare prices and book

Cheapflights Tip: The best prices from Houston Hobby to Chicago O'Hare Intl are usually found in September or October, booked 84 days in advance, depart on a Thursday or Monday and return on a Wednesday

Cheap flight deals from Hobby to O'Hare Intl

Round-trip from

One-way from

Popular in

Cheapest in

Average price

Find flight deals from Hobby to O'Hare Intl

Cheapest flights from Hobby to O'Hare IntlExplore the most affordable flight options available from Hobby to O'Hare Intl. Find the lowest fares from popular airlines and budget airlines, with prices last updated on July 2, 2025.

Explore the most affordable flight options available from Hobby to O'Hare Intl. Find the lowest fares from popular airlines and budget airlines, with prices last updated on July 2, 2025.

Cheapflights Fare Finder

Use the filters below to find and compare flights from Houston Hobby Airport to Chicago O'Hare Intl Airport that are best for you.

Best time to book a flight from Hobby to O'Hare Intl

Have a flexible travel schedule? Discover the best time to fly to O'Hare Intl from Hobby with our price prediction graph.

Cheapflights Insights

Everything you need to know about your flight from Houston Hobby Airport to Chicago O'Hare Intl Airport

How far ahead should I book a flight from Houston Hobby Airport to Chicago O'Hare Intl Airport?

Use this chart to determine the optimal time to book a round-trip flight from Hobby to O'Hare Intl. Price data was last updated on June 27, 2025.

What is the cheapest month to book a flight from Houston Hobby Airport to Chicago O'Hare Intl Airport?

What is the cheapest time of day to fly from HOU to ORD?

Find hourly flight availability from Hobby to O'Hare Intl. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated July 2, 2025.

What is the cheapest day to fly from Houston Hobby Airport to Chicago O'Hare Intl Airport?

Use this chart to determine the cheapest time to fly round-trip from Hobby to O'Hare Intl. Price data was last updated on December 16, 2024.

Reviews of airlines servicing O'Hare Intl

Related info for your journey

Find useful and relevant information for your journey from Hobby to O'Hare Intl. 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 flying from Houston Hobby Airport to Chicago O'Hare Intl Airport round-trip?

What are the cheapest airlines to fly from Houston Hobby Airport to Chicago O'Hare Intl Airport one-way?

Can I find deals for flights from Hobby to O'Hare Intl that include hotel bookings?

How can I find direct flights from Hobby to O'Hare Intl?

Can I find deals for business class flights from Hobby to O'Hare Intl?

What is the cheapest month to book a flight from Houston Hobby Airport to Chicago O'Hare Intl Airport?

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Top 4 airlines flying from Hobby to O'Hare Intl

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Cheapest flights from Hobby to O'Hare Intl
Explore the most affordable flight options available from Hobby to O'Hare Intl. Find the lowest fares from popular airlines and budget airlines, with prices last updated on July 2, 2025.