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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 12/16. Fares are subject to change and may not be available on all flights or dates of travel.
HOU — ORD
Nov 22 — Nov 291
Sat 11/22
Sat 11/29
1 adult, Economy
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1. Tell us where you want to go

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Cheapflights Tip: The best prices from Houston Hobby to Chicago O'Hare Intl are usually found in August or September, 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 October 23, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$178
(Southwest)

One-way from

$89
(Southwest)

Popular in

April

Cheapest in

August

Average price

$203
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. 3% potential increase in price ($7 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 October 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 October 23, 2025.

This Southwest deal was found by Cheapflights users on 10/21. 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 12/116:00 amHOU - ORD
1 stop7h 00mSouthwest
Mon 12/156:05 amORD - HOU
1 stop6h 30mSouthwest
Deal found 10/21$178
This Delta deal was found by Cheapflights users on 10/23. 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.
Fri 12/510:39 amHOU - ORD
1 stop6h 06mDelta
Mon 12/89:49 amORD - HOU
1 stop8h 03mDelta
Deal found 10/23$197
This Delta deal was found by Cheapflights users on 10/21. 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 11/1110:40 amHOU - ORD
1 stop6h 06mDelta
Tue 11/185:23 amORD - HOU
1 stop8h 05mDelta
Deal found 10/21$199
This Delta deal was found by Cheapflights users on 10/21. 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.
Wed 12/36:00 amHOU - ORD
1 stop6h 03mDelta
Sun 12/146:45 amORD - HOU
1 stop6h 43mDelta
Deal found 10/21$205
This Southwest deal was found by Cheapflights users on 10/21. 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 12/137:00 amHOU - ORD
1 stop7h 45mSouthwest
Tue 12/161:45 pmORD - HOU
2 stops6h 05mSouthwest
Deal found 10/21$214
This Southwest deal was found by Cheapflights users on 10/21. 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 12/116:00 amHOU - ORD
1 stop7h 00mSouthwest
Sat 12/132:15 pmORD - HOU
1 stop6h 20mSouthwest
Deal found 10/21$217
This Southwest deal was found by Cheapflights users on 10/20. 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 12/46:00 amHOU - ORD
1 stop7h 00mSouthwest
Sun 12/72:15 pmORD - HOU
1 stop4h 55mSouthwest
Deal found 10/20$218
This Delta deal was found by Cheapflights users on 10/22. 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.
Sat 11/810:13 amHOU - ORD
1 stop4h 45mDelta
Wed 11/125:23 amORD - HOU
1 stop8h 05mDelta
Deal found 10/22$224
This Southwest deal was found by Cheapflights users on 10/22. 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 12/57:30 amHOU - ORD
1 stop5h 30mSouthwest
Sat 12/61:45 pmORD - HOU
2 stops6h 50mSouthwest
Deal found 10/22$225
This Southwest deal was found by Cheapflights users on 10/21. 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 12/56:00 amHOU - ORD
1 stop7h 00mSouthwest
Sun 12/72:15 pmORD - HOU
1 stop5h 55mSouthwest
Deal found 10/21$227
This Delta deal was found by Cheapflights users on 10/23. 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.
Sat 11/1510:40 amHOU - ORD
1 stop4h 46mDelta
Mon 11/175:56 pmORD - HOU
1 stop5h 11mDelta
Deal found 10/23$228

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 October 23, 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 12/12

2:32 pm-9:56 pm

1 stop7h 24m

Chicago O'Hare Intl

Tue 12/16

4:20 pm-10:48 pm

1 stop6h 28m

$197

HoustonChicago

HOU - ORD

HOUORD

Houston Hobby

Thu 12/11

6:00 am-12:10 pm

1 stop6h 10m

Chicago O'Hare Intl

Tue 12/16

5:30 am-1:28 pm

1 stop7h 58m

$197

HoustonChicago

HOU - ORD

HOUORD

Houston Hobby

Sat 11/15

10:40 am-5:17 pm

1 stop6h 37m

Chicago O'Hare Intl

Tue 11/18

6:45 am-1:28 pm

1 stop6h 43m

$199

HoustonChicago

HOU - ORD

HOUORD

Houston Hobby

Fri 12/5

7:30 am-1:00 pm

1 stop5h 30m

Chicago O'Hare Intl

Sat 12/6

1:45 pm-8:35 pm

2 stops6h 50m

$225

HoustonChicago

HOU - ORD

HOUORD

Houston Hobby

Fri 12/12

5:55 am-1:30 pm

1 stop7h 35m

Chicago O'Hare Intl

Mon 12/15

6:05 am-12:35 pm

1 stop6h 30m

$227

HoustonChicago

HOU - ORD

HOUORD

Houston Hobby

Fri 11/14

6:48 pm-12:01 am

1 stop5h 13m

Chicago O'Hare Intl

Sat 11/15

9:51 am-5:33 pm

1 stop7h 42m

$228

HoustonChicago

HOU - ORD

HOUORD

Houston Hobby

Wed 12/3

5:55 am-3:25 pm

1 stop9h 30m

Chicago O'Hare Intl

Mon 12/8

6:05 am-12:45 pm

1 stop6h 40m

$238

HoustonChicago

HOU - ORD

HOUORD

Houston Hobby

Fri 12/12

2:32 pm-9:56 pm

1 stop7h 24m

Chicago O'Hare Intl

Sun 12/14

6:45 am-1:28 pm

1 stop6h 43m

$252

HoustonChicago

HOU - ORD

HOUORD

Houston Hobby

Tue 10/28

6:44 pm-11:58 pm

1 stop5h 14m

Chicago O'Hare Intl

Fri 10/31

5:51 pm-11:00 pm

1 stop5h 09m

$257

HoustonChicago

HOU - ORD

HOUORD

Houston Hobby

Sat 12/20

6:00 am-11:29 am

1 stop5h 29m

Chicago O'Hare Intl

Mon 1/5

9:30 am-3:02 pm

1 stop5h 32m

$267

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/21

Showing 1-10 of 20 results
1
2

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 October.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy2 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars
eDreamsPrice Accuracy3 starsTrust Score*3 stars
CheapflightsfaresPrice Accuracy2 starsTrust Score*1 star
Kiwi.comPrice Accuracy3 starsTrust Score*3 stars
CheapTicketsDealPrice Accuracy3 starsTrust Score*3 stars
JustAirTicketPrice Accuracy-Trust Score*3 stars
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 FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Houston Hobby Airport-Chicago O'Hare Intl Airport flight deals on Cheapflights vs. FlightHub >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 FlightHub the most. FlightHub 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 October 17, 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 $52). 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 October 23, 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.

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 October 23, 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
8,991 reviews

Comfort

7.3

Food

6.6

Boarding

7.7

Crew

8.1

Entertainment

7.1

Overall

7.4

Reviews

1 / 20
8.0
Excellent

Anonymous,Oct 2025

YUL - ORD

Crew and customer service are 5 stars. I had a lot of luggage for a very long trip and they were nothing but helpful and found solutions to every problem. It was my first time flying with United, and they really are the friendly skies. Leg room however, on 2/3 flights was terrible. Same for entertainment: There was only a seat-mounted screen on 1/3 flights. It would have been nice to have on the longest leg of the journey.
United Airlines
7.4
Good
8,991 reviews
United Airlines
7.4
Good
8,991 reviews

Comfort

7.3

Food

6.6

Boarding

7.7

Crew

8.1

Entertainment

7.1

Overall

7.4

Reviews

1 / 20
8.0
Excellent

Anonymous,Oct 2025

YUL - ORD

Crew and customer service are 5 stars. I had a lot of luggage for a very long trip and they were nothing but helpful and found solutions to every problem. It was my first time flying with United, and they really are the friendly skies. Leg room however, on 2/3 flights was terrible. Same for entertainment: There was only a seat-mounted screen on 1/3 flights. It would have been nice to have on the longest leg of the journey.
American Airlines
7.2
Good
11,028 reviews
United Airlines
7.4
Good
8,991 reviews

Comfort

7.3

Food

6.6

Boarding

7.7

Crew

8.1

Entertainment

7.1

Overall

7.4

Reviews

1 / 20
8.0
Excellent

Anonymous,Oct 2025

YUL - ORD

Crew and customer service are 5 stars. I had a lot of luggage for a very long trip and they were nothing but helpful and found solutions to every problem. It was my first time flying with United, and they really are the friendly skies. Leg room however, on 2/3 flights was terrible. Same for entertainment: There was only a seat-mounted screen on 1/3 flights. It would have been nice to have on the longest leg of the journey.
Spirit Airlines
6.3
Okay
8,098 reviews
United Airlines
7.4
Good
8,991 reviews

Comfort

7.3

Food

6.6

Boarding

7.7

Crew

8.1

Entertainment

7.1

Overall

7.4

Reviews

1 / 20
8.0
Excellent

Anonymous,Oct 2025

YUL - ORD

Crew and customer service are 5 stars. I had a lot of luggage for a very long trip and they were nothing but helpful and found solutions to every problem. It was my first time flying with United, and they really are the friendly skies. Leg room however, on 2/3 flights was terrible. Same for entertainment: There was only a seat-mounted screen on 1/3 flights. It would have been nice to have on the longest leg of the journey.
Frontier
5.8
Fair
3,128 reviews
United Airlines
7.4
Good
8,991 reviews

Comfort

7.3

Food

6.6

Boarding

7.7

Crew

8.1

Entertainment

7.1

Overall

7.4

Reviews

1 / 20
8.0
Excellent

Anonymous,Oct 2025

YUL - ORD

Crew and customer service are 5 stars. I had a lot of luggage for a very long trip and they were nothing but helpful and found solutions to every problem. It was my first time flying with United, and they really are the friendly skies. Leg room however, on 2/3 flights was terrible. Same for entertainment: There was only a seat-mounted screen on 1/3 flights. It would have been nice to have on the longest leg of the journey.

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 30m. Delta provides one of the quickest options available for as low as $225. 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 $78, and United Airlines, from $177. 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 $52). 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
Skokie
Des Plaines
Gurnee
Hoffman Estates
Elgin
Oak Brook
Elk Grove Village
Beloit
Rockford
Naperville
Racine
Downers Grove
Orland Park
Merrillville
Bridgeview
Warrenville
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.
George Bush Intcntl to O'Hare Intl flights
Hobby to Midway 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 October 23, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$77Average$176FlexibilityNo cancel feeOn-time65%
FrontierCheapest$78Average$187FlexibilityNo cancel feeOn-time62%
United AirlinesCheapest$177Average$354FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$177Average$266FlexibilityNo cancel feeOn-time71%

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