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 8/4. Fares are subject to change and may not be available on all flights or dates of travel.
HOU — ORD
Jul 7 — Jul 141
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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

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 July 2, 2025.

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
One-way flight from Houston Hobby to Chicago O'Hare Intl
Highest demand for flights based on searches. 6% potential increase in price ($14 potential increase over avg. RT price).
Cheapest flight prices on average. 2% potential price decrease ($6 potential savings vs. average RT price).
Average for round-trip flights in July 2025

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.

This Southwest deal was found by Cheapflights users on 7/2. 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 8/212:55 pmHOU - ORD
1 stop8h 10mSouthwest
Mon 8/255:45 pmORD - HOU
1 stop4h 55mSouthwest
Deal found 7/2$177
This Delta deal was found by Cheapflights users on 6/30. 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 8/226:34 pmHOU - ORD
1 stop5h 22mDelta
Sat 8/239:47 amORD - HOU
1 stop7h 52mDelta
Deal found 6/30$217
This American Airlines deal was found by Cheapflights users on 6/30. 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.
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

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 July 2, 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 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?

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.

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?

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.

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 July 2, 2025.
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.

Crew

8.6

Comfort

8.0

Entertainment

7.6

Overall

8.0

Boarding

8.2

Food

7.0

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.

Crew

8.6

Comfort

8.0

Entertainment

7.6

Overall

8.0

Boarding

8.2

Food

7.0

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.
8.0
Very good

Crew

8.6

Comfort

8.0

Entertainment

7.6

Overall

8.0

Boarding

8.2

Food

7.0

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.

Crew

8.6

Comfort

8.0

Entertainment

7.6

Overall

8.0

Boarding

8.2

Food

7.0

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.

Crew

8.6

Comfort

8.0

Entertainment

7.6

Overall

8.0

Boarding

8.2

Food

7.0

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 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?

    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.

See more FAQs

Traveling to a place near Houston Hobby Airport?

Book flights to Houston Hobby Airport if you plan to visit one of these locations
Schaumburg
Hoffman Estates
Rosemont
Beloit
Skokie
Des Plaines
Arlington Heights
Elgin
Naperville
Orland Park
Elk Grove Village
Racine
Rockford
Tinley Park
Merrillville
Bridgeview
Glenview
Lake Geneva
Joliet
Waukegan

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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.

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 July 2, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$59Average$156FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$62Average$168FlexibilityNo cancel feeOn-time65%
United AirlinesCheapest$154Average$343FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$158Average$273FlexibilityNo cancel feeOn-time71%

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