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O'Hare Intl

$69+ 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 1/17. Fares are subject to change and may not be available on all flights or dates of travel.
HOU — ORD
Dec 26 — Jan 21
Fri 12/26
Fri 1/2
1 adult, Economy
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Cheapflights Tip: The best prices from Houston Hobby to Chicago O'Hare Intl are usually found in August or December, booked 88 days in advance, depart on a Thursday or Monday and return on a Wednesday

Cheap flight deals from Hobby to O'Hare Intl

Discover tips and strategies to find the most affordable flight options for your journey from Hobby (HOU) to O'Hare Intl (ORD). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated November 26, 2025.

Most accurate provider

CheapOair
3 stars

Most trusted provider

CheapOair
3 stars

Round-trip from

$177
(Southwest)

One-way from

$69
(Southwest)

Popular in

April

Cheapest in

August

Average price

$237
Provider with most accurate pricing for Houston Hobby-Chicago O'Hare Intl flight deals.
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Provider most trusted by Cheapflights users for Houston Hobby-Chicago O'Hare Intl flights.
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From Houston Hobby to Chicago O'Hare Intl
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One-way flight from Houston Hobby to Chicago O'Hare Intl
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Highest demand for flights based on searches. 5% potential increase in price ($12 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 November 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 November 26, 2025.

This Delta deal was found by Cheapflights users on 11/25. 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.
Thu 12/2510:46 amHOU - ORD
1 stop5h 35mDelta
Thu 1/82:50 pmORD - HOU
1 stop7h 43mDelta
Deal found 11/25$197
This Delta deal was found by Cheapflights users on 11/23. 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.
Tue 12/166:00 amHOU - ORD
1 stop6h 10mDelta
Tue 12/164:20 pmORD - HOU
1 stop6h 28mDelta
Deal found 11/23$199
This Delta deal was found by Cheapflights users on 11/25. 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.
Tue 12/910:39 amHOU - ORD
1 stop4h 41mDelta
Tue 12/165:30 amORD - HOU
1 stop7h 58mDelta
Deal found 11/25$234
This Southwest deal was found by Cheapflights users on 11/24. 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.
Tue 12/166:00 amHOU - ORD
1 stop7h 00mSouthwest
Wed 12/171:45 pmORD - HOU
1 stop5h 50mSouthwest
Deal found 11/24$237
This Southwest deal was found by Cheapflights users on 11/24. 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.
Tue 12/97:15 amHOU - ORD
1 stop5h 00mSouthwest
Thu 2/51:45 pmORD - HOU
1 stop6h 40mSouthwest
Deal found 11/24$243
This Southwest deal was found by Cheapflights users on 11/24. 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 12/246:00 amHOU - ORD
1 stop7h 00mSouthwest
Tue 1/61:45 pmORD - HOU
1 stop6h 40mSouthwest
Deal found 11/24$248
This Delta deal was found by Cheapflights users on 11/24. 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.
Fri 12/126:47 pmHOU - ORD
1 stop5h 14mDelta
Tue 12/165:30 amORD - HOU
1 stop7h 58mDelta
Deal found 11/24$258
This Southwest deal was found by Cheapflights users on 11/24. 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.
Sat 12/138:45 amHOU - ORD
2 stops13h 50mSouthwest
Tue 12/161:45 pmORD - HOU
2 stops6h 05mSouthwest
Deal found 11/24$259
This Southwest deal was found by Cheapflights users on 11/24. 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 12/317:15 amHOU - ORD
1 stop5h 00mSouthwest
Tue 1/67:15 amORD - HOU
2 stops10h 40mSouthwest
Deal found 11/24$263
This Southwest deal was found by Cheapflights users on 11/25. 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.
Sun 12/145:45 amHOU - ORD
1 stop7h 45mSouthwest
Tue 12/166:05 amORD - HOU
1 stop8h 30mSouthwest
Deal found 11/25$267

Cheapflights Fare Finder

 
Customize your flight search to find flights from Hobby to O'Hare Intl 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 November 26, 2025.
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

Hobby

Fly to

O'Hare Intl

Route

Depart

Return

Price

HoustonChicago

HOU - ORD

HOUORD

Houston Hobby

Fri 1/23

5:04 pm-11:55 pm

1 stop6h 51m

Chicago O'Hare Intl

Tue 1/27

9:55 am-4:10 pm

1 stop6h 15m

$197

HoustonChicago

HOU - ORD

HOUORD

Houston Hobby

Tue 12/16

10:39 am-4:45 pm

1 stop6h 06m

Chicago O'Hare Intl

Wed 12/17

5:30 am-1:28 pm

1 stop7h 58m

$199

HoustonChicago

HOU - ORD

HOUORD

Houston Hobby

Thu 1/8

6:20 am-3:25 pm

1 stop9h 05m

Chicago O'Hare Intl

Sun 1/11

11:55 am-8:20 pm

1 stop8h 25m

$217

HoustonChicago

HOU - ORD

HOUORD

Houston Hobby

Wed 1/21

2:00 pm-10:35 pm

1 stop8h 35m

Chicago O'Hare Intl

Fri 1/23

11:55 am-7:50 pm

2 stops7h 55m

$222

HoustonChicago

HOU - ORD

HOUORD

Houston Hobby

Thu 2/19

5:55 am-1:30 pm

1 stop7h 35m

Chicago O'Hare Intl

Sun 2/22

3:45 pm-10:30 pm

1 stop6h 45m

$236

HoustonChicago

HOU - ORD

HOUORD

Houston Hobby

Tue 12/16

6:00 am-1:00 pm

1 stop7h 00m

Chicago O'Hare Intl

Wed 12/17

1:45 pm-7:35 pm

1 stop5h 50m

$237

HoustonChicago

HOU - ORD

HOUORD

Houston Hobby

Fri 1/30

6:20 am-3:25 pm

1 stop9h 05m

Chicago O'Hare Intl

Sun 2/1

1:45 pm-8:35 pm

1 stop6h 50m

$243

HoustonChicago

HOU - ORD

HOUORD

Houston Hobby

Wed 12/24

6:00 am-1:00 pm

1 stop7h 00m

Chicago O'Hare Intl

Tue 1/6

1:45 pm-8:25 pm

1 stop6h 40m

$248

HoustonChicago

HOU - ORD

HOUORD

Houston Hobby

Fri 12/12

6:47 pm-12:01 am

1 stop5h 14m

Chicago O'Hare Intl

Tue 12/16

5:30 am-1:28 pm

1 stop7h 58m

$258

HoustonChicago

HOU - ORD

HOUORD

Houston Hobby

Thu 1/15

12:25 pm-10:35 pm

2 stops10h 10m

Chicago O'Hare Intl

Sat 1/17

7:15 am-5:10 pm

2 stops9h 55m

$258

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/24

Showing 1-10 of 21 results
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Compare providers for flights from Hobby to O'Hare Intl

Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Hobby to O'Hare Intl in November.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy2 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*1 star
eDreamsPrice Accuracy3 starsTrust Score*3 stars
CheapflightsfaresPrice Accuracy3 starsTrust Score*2 stars
Kiwi.comPrice Accuracy3 starsTrust Score*3 stars
CheapTicketsDealPrice Accuracy3 starsTrust Score*3 stars
JustAirTicketPrice Accuracy-Trust Score*1 star
CheapOairPrice Accuracy3 starsTrust Score*3 stars
Justfly.comPrice Accuracy3 starsTrust Score*3 stars

*The Trust Score is based on feedback from users after their booking experience. It measures overall satisfaction, helping us identify issues like hidden fees, problems during the ticketing process, and the quality of customer service. This score is our best indicator of the provider's quality and reliability.

  • Most accurate provider: When it comes to deals on Houston Hobby Airport-Chicago O'Hare Intl Airport flights, users find the pricing of CheapOair to be most consistent on Cheapflights vs. CheapOair Users can find the same prices on Houston Hobby Airport-Chicago O'Hare Intl Airport flight deals on Cheapflights vs. CheapOair >95% of the time. Price accuracy is based on data collected from Houston Hobby Airport-Chicago O'Hare Intl Airport flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Houston Hobby Airport-Chicago O'Hare Intl Airport flights, Cheapflights users trust CheapOair the most. CheapOair has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Houston Hobby Airport-Chicago O'Hare Intl Airport flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

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?

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 November 21, 2025.

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 88 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, March is the cheapest month in which you can book a flight from Houston Hobby Airport to Chicago O'Hare Intl Airport (average of $56). Flying from Houston Hobby Airport to Chicago O'Hare Intl Airport in June is currently the most expensive (average of $128). 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?

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 November 26, 2025.

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 25% versus a flight in the afternoon.

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.

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.

How much does it cost to fly round-trip from Houston Hobby Airport to Chicago O'Hare Intl Airport?

Reviews of airlines servicing O'Hare Intl

Get insights into the airlines that provide service to O'Hare Intl. 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 O'Hare Intl. Reviews last updated November 26, 2025.
Read reviews from past customers who have flown United Airlines, American Airlines, and Spirit 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.
United Airlines
7.4
Good
9,046 reviews

Comfort

7.3

Food

6.6

Overall

7.4

Boarding

7.7

Crew

8.1

Entertainment

7.1

Reviews

1 / 20
2.0
Mediocre

Sebrena,Oct 2025

IAH - RSW

The worst that I have ever experienced in my life so bad if it was free I'm not ever going to use your Airline again I dont believe ..... very disappointed 😞 😔0000000000000
United Airlines
7.4
Good
9,046 reviews
United Airlines
7.4
Good
9,046 reviews

Comfort

7.3

Food

6.6

Overall

7.4

Boarding

7.7

Crew

8.1

Entertainment

7.1

Reviews

1 / 20
2.0
Mediocre

Sebrena,Oct 2025

IAH - RSW

The worst that I have ever experienced in my life so bad if it was free I'm not ever going to use your Airline again I dont believe ..... very disappointed 😞 😔0000000000000
American Airlines
7.2
Good
11,038 reviews
United Airlines
7.4
Good
9,046 reviews

Comfort

7.3

Food

6.6

Overall

7.4

Boarding

7.7

Crew

8.1

Entertainment

7.1

Reviews

1 / 20
2.0
Mediocre

Sebrena,Oct 2025

IAH - RSW

The worst that I have ever experienced in my life so bad if it was free I'm not ever going to use your Airline again I dont believe ..... very disappointed 😞 😔0000000000000
Spirit Airlines
6.3
Okay
8,158 reviews
United Airlines
7.4
Good
9,046 reviews

Comfort

7.3

Food

6.6

Overall

7.4

Boarding

7.7

Crew

8.1

Entertainment

7.1

Reviews

1 / 20
2.0
Mediocre

Sebrena,Oct 2025

IAH - RSW

The worst that I have ever experienced in my life so bad if it was free I'm not ever going to use your Airline again I dont believe ..... very disappointed 😞 😔0000000000000
Frontier
5.8
Fair
3,099 reviews
United Airlines
7.4
Good
9,046 reviews

Comfort

7.3

Food

6.6

Overall

7.4

Boarding

7.7

Crew

8.1

Entertainment

7.1

Reviews

1 / 20
2.0
Mediocre

Sebrena,Oct 2025

IAH - RSW

The worst that I have ever experienced in my life so bad if it was free I'm not ever going to use your Airline again I dont believe ..... very disappointed 😞 😔0000000000000

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.

  • How long is the flight from Houston Hobby Airport to Chicago O'Hare Intl Airport?

    A quick flight from Houston Hobby Airport to Chicago O'Hare Intl Airport can take about 6h 51m. Delta provides one of the quickest options available for as low as $197. Houston Hobby Airport and Chicago O'Hare Intl Airport are separated by a distance of 945 mi. Both multi-stop and nonstop flights can be found to your destination and back.

  • 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 $77. Other airlines that can offer you cheap pricing are Frontier, from $77, and United Airlines, from $135. These flights start at 65% lower than the current average price 3 months from now.

  • 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, March is the cheapest month in which you can book a flight from Houston Hobby Airport to Chicago O'Hare Intl Airport (average of $56). Flying from Houston Hobby Airport to Chicago O'Hare Intl Airport in June is currently the most expensive (average of $128). 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 Chicago O'Hare Intl Airport?

Book flights to Chicago O'Hare Intl Airport if you plan to visit one of these locations
Schaumburg
Rosemont
Gurnee
Naperville
Hoffman Estates
Beloit
Elgin
Skokie
Delavan
Oak Brook
Des Plaines
Elk Grove Village
Lake Geneva
Downers Grove
Bridgeview
Warrenville
Waukegan
Aurora
Kenosha
Evanston

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Alternative routes for Hobby to O'Hare Intl

See prices for flight routes from nearby airports that may be better suited for you.
Hobby to Midway flights
George Bush Intcntl to O'Hare Intl flights
George Bush Intcntl to Midway flights

Top 4 airlines flying from Hobby to O'Hare Intl

Discover the top 4 airlines that operate flights from Hobby to O'Hare Intl. 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 November 26, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$77Average$173FlexibilityNo cancel feeOn-time65%
FrontierCheapest$77Average$184FlexibilityNo cancel feeOn-time62%
United AirlinesCheapest$135Average$335FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$177Average$261FlexibilityNo cancel feeOn-time71%

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