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O'Hare Intl

$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 11/15. Fares are subject to change and may not be available on all flights or dates of travel.
HOU — ORD
Oct 16 — Oct 231
Thu 10/16
Thu 10/23
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 October, 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 September 16, 2025.

Round-trip from

$177
(Southwest)

One-way from

$89
(Southwest)

Popular in

April

Cheapest in

August

Average price

$194
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. 3% potential increase in price ($8 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($5 potential savings vs. average RT price).
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Average for round-trip flights in September 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 September 16, 2025.

This Southwest deal was found by Cheapflights users on 9/15. 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 10/228:45 amHOU - ORD
1 stop7h 40mSouthwest
Sat 10/251:50 pmORD - HOU
1 stop6h 05mSouthwest
Deal found 9/15$177
This Southwest deal was found by Cheapflights users on 9/15. 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 10/144:30 pmHOU - ORD
1 stop5h 00mSouthwest
Wed 10/153:10 pmORD - HOU
1 stop7h 50mSouthwest
Deal found 9/15$182
This Southwest deal was found by Cheapflights users on 9/16. 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.
Fri 11/145:40 amHOU - ORD
1 stop9h 45mSouthwest
Mon 11/172:15 pmORD - HOU
1 stop5h 55mSouthwest
Deal found 9/16$197
This Southwest deal was found by Cheapflights users on 9/16. 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 10/196:00 amHOU - ORD
1 stop5h 50mSouthwest
Wed 10/226:15 amORD - HOU
2 stops8h 55mSouthwest
Deal found 9/16$202
This Southwest deal was found by Cheapflights users on 9/14. 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 10/16:00 amHOU - ORD
1 stop4h 45mSouthwest
Wed 10/81:30 pmORD - HOU
1 stop5h 15mSouthwest
Deal found 9/14$213
This Southwest deal was found by Cheapflights users on 9/15. 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 10/235:15 pmHOU - ORD
1 stop5h 50mSouthwest
Mon 10/273:10 pmORD - HOU
1 stop7h 15mSouthwest
Deal found 9/15$217
This Southwest deal was found by Cheapflights users on 9/16. 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.
Mon 11/245:00 amHOU - ORD
1 stop6h 10mSouthwest
Fri 11/284:25 pmORD - HOU
1 stop7h 45mSouthwest
Deal found 9/16$224

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 September 16, 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

Thu 10/30

5:35 am-2:00 pm

1 stop8h 25m

Chicago O'Hare Intl

Mon 11/3

11:55 am-7:50 pm

1 stop7h 55m

$177

HoustonChicago

HOU - ORD

HOUORD

Houston Hobby

Fri 11/14

5:55 am-1:30 pm

1 stop7h 35m

Chicago O'Hare Intl

Sat 11/22

5:15 pm-1:05 am

1 stop7h 50m

$197

HoustonChicago

HOU - ORD

HOUORD

Houston Hobby

Sun 12/7

7:00 am-1:00 pm

1 stop6h 00m

Chicago O'Hare Intl

Sat 12/13

1:45 pm-8:35 pm

2 stops6h 50m

$202

HoustonChicago

HOU - ORD

HOUORD

Houston Hobby

Tue 10/14

6:44 pm-11:58 pm

1 stop5h 14m

Chicago O'Hare Intl

Tue 10/21

11:23 am-5:48 pm

1 stop6h 25m

$217

HoustonChicago

HOU - ORD

HOUORD

Houston Hobby

Mon 10/20

6:44 pm-11:58 pm

1 stop5h 14m

Chicago O'Hare Intl

Tue 10/28

5:51 pm-11:00 pm

1 stop5h 09m

$217

HoustonChicago

HOU - ORD

HOUORD

Houston Hobby

Thu 10/23

6:44 pm-11:58 pm

1 stop5h 14m

Chicago O'Hare Intl

Sat 10/25

6:45 am-1:27 pm

1 stop6h 42m

$217

HoustonChicago

HOU - ORD

HOUORD

Houston Hobby

Sat 11/15

6:00 am-12:06 pm

1 stop6h 06m

Chicago O'Hare Intl

Sat 11/15

4:21 pm-10:33 pm

1 stop6h 12m

$217

HoustonChicago

HOU - ORD

HOUORD

Houston Hobby

Thu 10/23

5:15 pm-11:05 pm

1 stop5h 50m

Chicago O'Hare Intl

Mon 10/27

3:10 pm-10:25 pm

1 stop7h 15m

$217

HoustonChicago

HOU - ORD

HOUORD

Houston Hobby

Sat 10/18

6:44 pm-11:58 pm

1 stop5h 14m

Chicago O'Hare Intl

Tue 10/21

9:42 am-5:48 pm

1 stop8h 06m

$217

HoustonChicago

HOU - ORD

HOUORD

Houston Hobby

Fri 10/31

6:05 am-1:05 pm

2 stops7h 00m

Chicago O'Hare Intl

Sun 11/2

3:45 pm-10:30 pm

1 stop6h 45m

$222

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/14

Showing 1-10 of 19 results
1
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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 September 12, 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, 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?

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 September 16, 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 26% 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.

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 September 16, 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
8,924 reviews

Entertainment

7.1

Overall

7.4

Food

6.6

Crew

8.1

Comfort

7.3

Boarding

7.7

Reviews

1 / 20
2.0
Mediocre

Deb,Jan 2025

MKE - ORD

It was terrible! So much to say, but in a nutshell we used vouchers from United because our last trip with them was awful with many mishaps and errors made. Unfortunately, this trip was even worse!
United Airlines
7.4
Good
8,924 reviews
United Airlines
7.4
Good
8,924 reviews

Entertainment

7.1

Overall

7.4

Food

6.6

Crew

8.1

Comfort

7.3

Boarding

7.7

Reviews

1 / 20
2.0
Mediocre

Deb,Jan 2025

MKE - ORD

It was terrible! So much to say, but in a nutshell we used vouchers from United because our last trip with them was awful with many mishaps and errors made. Unfortunately, this trip was even worse!
American Airlines
7.2
Good
10,000 reviews
United Airlines
7.4
Good
8,924 reviews

Entertainment

7.1

Overall

7.4

Food

6.6

Crew

8.1

Comfort

7.3

Boarding

7.7

Reviews

1 / 20
2.0
Mediocre

Deb,Jan 2025

MKE - ORD

It was terrible! So much to say, but in a nutshell we used vouchers from United because our last trip with them was awful with many mishaps and errors made. Unfortunately, this trip was even worse!
Spirit Airlines
6.3
Okay
8,019 reviews
United Airlines
7.4
Good
8,924 reviews

Entertainment

7.1

Overall

7.4

Food

6.6

Crew

8.1

Comfort

7.3

Boarding

7.7

Reviews

1 / 20
2.0
Mediocre

Deb,Jan 2025

MKE - ORD

It was terrible! So much to say, but in a nutshell we used vouchers from United because our last trip with them was awful with many mishaps and errors made. Unfortunately, this trip was even worse!
Frontier
5.8
Fair
3,174 reviews
United Airlines
7.4
Good
8,924 reviews

Entertainment

7.1

Overall

7.4

Food

6.6

Crew

8.1

Comfort

7.3

Boarding

7.7

Reviews

1 / 20
2.0
Mediocre

Deb,Jan 2025

MKE - ORD

It was terrible! So much to say, but in a nutshell we used vouchers from United because our last trip with them was awful with many mishaps and errors made. Unfortunately, this trip was even worse!

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 5h 14m. Southwest provides one of the quickest options available for as low as $217. 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 $71. Other airlines that can offer you cheap pricing are Frontier, from $76, and United Airlines, from $177. These flights start at 68% 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, 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.

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
Skokie
Gurnee
Hoffman Estates
Des Plaines
Elgin
Arlington Heights
Orland Park
Beloit
Racine
Rockford
Oak Brook
Elk Grove Village
Downers Grove
Naperville
Evanston
Merrillville
Bridgeview
Warrenville

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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 September 16, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$71Average$172FlexibilityNo cancel feeOn-time65%
FrontierCheapest$76Average$182FlexibilityNo cancel feeOn-time62%
United AirlinesCheapest$177Average$352FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$177Average$267FlexibilityNo cancel feeOn-time71%

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