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$77+ Cheap flights from Chicago (CHI) to Hobby (HOU)

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 10/14. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — HOU
Oct 15 — Oct 221
Wed 10/15
Wed 10/22
1 adult, Economy
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Cheapflights Tip: The best prices from Chicago to Houston Hobby are usually found in October or September, booked 71 days in advance, depart on a Wednesday or Thursday and return on a Wednesday

Cheap flight deals from Chicago to Hobby

Discover tips and strategies to find the most affordable flight options for your journey from Chicago (CHI) to Hobby (HOU). 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 15, 2025.

Round-trip from

$133
(Southwest)

One-way from

$77
(Southwest)

Popular in

March

Cheapest in

October

Average price

$177

Good round-trip deal

$267 or less

Good one-way deal

$195 or less
From Chicago (CHI) to Houston Hobby
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One-way flight from Chicago (CHI) to Houston Hobby
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Highest demand for flights based on searches. 7% potential increase in price ($16 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% 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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Price to beat on a round-trip flight from Chicago (CHI) to Houston Hobby.
Search Deals
Price to beat on a one-way flight from Chicago (CHI) to Houston Hobby.
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Find flight deals from Chicago to Hobby

Cheapest flights from Chicago to Hobby
Explore the most affordable flight options available from Chicago to Hobby. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 15, 2025.

This Southwest deal was found by Cheapflights users on 9/12. 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 11/118:35 pmMDW - HOU
Nonstop2h 45mSouthwest
Sat 11/156:10 pmHOU - MDW
Nonstop2h 25mSouthwest
Deal found 9/12$133
This Southwest deal was found by Cheapflights users on 9/12. 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 10/412:15 pmMDW - HOU
Nonstop2h 40mSouthwest
Sun 10/56:45 amHOU - MDW
Nonstop2h 25mSouthwest
Deal found 9/12$149
This Southwest deal was found by Cheapflights users on 9/12. 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 10/155:45 pmORD - HOU
1 stop4h 25mSouthwest
Sat 10/185:55 amHOU - ORD
1 stop6h 50mSouthwest
Deal found 9/12$153
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.
Sat 10/117:45 pmMDW - HOU
Nonstop2h 35mSouthwest
Sat 10/188:05 pmHOU - MDW
Nonstop2h 20mSouthwest
Deal found 9/15$157
This Southwest deal was found by Cheapflights users on 9/12. 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 11/111:45 pmORD - HOU
2 stops6h 05mSouthwest
Sat 11/156:00 amHOU - ORD
1 stop7h 30mSouthwest
Deal found 9/12$158
This Southwest deal was found by Cheapflights users on 9/13. 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 11/165:10 amMDW - HOU
Nonstop2h 45mSouthwest
Sat 11/228:05 pmHOU - MDW
Nonstop2h 25mSouthwest
Deal found 9/13$161
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.
Sat 10/258:25 amMDW - HOU
1 stop4h 05mSouthwest
Sat 11/18:10 pmHOU - MDW
Nonstop2h 20mSouthwest
Deal found 9/14$163
This Southwest deal was found by Cheapflights users on 9/12. 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 10/39:30 pmMDW - HOU
Nonstop2h 35mSouthwest
Mon 10/610:25 pmHOU - MDW
Nonstop2h 20mSouthwest
Deal found 9/12$165
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.
Sat 10/258:25 amMDW - HOU
1 stop4h 05mSouthwest
Mon 10/278:00 pmHOU - MDW
1 stop4h 05mSouthwest
Deal found 9/14$172
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 10/81:50 pmORD - HOU
1 stop9h 00mSouthwest
Wed 10/1510:30 amHOU - ORD
1 stop4h 50mSouthwest
Deal found 9/14$177
This Southwest deal was found by Cheapflights users on 9/12. 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 10/245:45 pmORD - HOU
1 stop4h 50mSouthwest
Sun 10/266:55 amHOU - ORD
1 stop5h 50mSouthwest
Deal found 9/12$185
This Southwest deal was found by Cheapflights users on 9/13. 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 10/117:30 amORD - HOU
2 stops9h 40mSouthwest
Sat 10/185:55 amHOU - ORD
2 stops8h 30mSouthwest
Deal found 9/13$187

Cheapflights Fare Finder

 
Customize your flight search to find flights from Chicago to Hobby 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 15, 2025.
Use the filters below to find and compare flights from Chicago to Houston Hobby Airport that are best for you.

Fly from

Chicago

Fly to

Hobby

Route

Depart

Return

Price

ChicagoHouston

ORD - HOU

ORDHOU

Chicago O'Hare Intl

Wed 10/15

5:45 pm-10:10 pm

1 stop4h 25m

Houston Hobby

Sat 10/18

5:55 am-12:45 pm

1 stop6h 50m

$153

ChicagoHouston

MDW - HOU

MDWHOU

Chicago Midway

Thu 10/23

5:00 pm-9:30 pm

1 stop4h 30m

Houston Hobby

Mon 10/27

10:25 pm-12:45 am

Nonstop2h 20m

$167

ChicagoHouston

MDW - HOU

MDWHOU

Chicago Midway

Sat 10/18

7:45 pm-10:20 pm

Nonstop2h 35m

Houston Hobby

Tue 10/21

7:30 pm-12:05 am

1 stop4h 35m

$167

ChicagoHouston

MDW - HOU

MDWHOU

Chicago Midway

Sat 10/25

8:25 am-12:30 pm

1 stop4h 05m

Houston Hobby

Sat 11/1

4:00 pm-8:20 pm

1 stop4h 20m

$172

ChicagoHouston

ORD - HOU

ORDHOU

Chicago O'Hare Intl

Wed 11/5

6:05 am-2:35 pm

1 stop8h 30m

Houston Hobby

Sat 11/8

7:00 am-2:45 pm

1 stop7h 45m

$177

ChicagoHouston

ORD - HOU

ORDHOU

Chicago O'Hare Intl

Wed 10/8

1:50 pm-10:50 pm

1 stop9h 00m

Houston Hobby

Wed 10/15

10:30 am-3:20 pm

1 stop4h 50m

$177

ChicagoHouston

MDW - HOU

MDWHOU

Chicago Midway

Wed 11/5

7:05 am-12:50 pm

1 stop5h 45m

Houston Hobby

Sat 11/8

12:45 pm-6:35 pm

1 stop5h 50m

$177

ChicagoHouston

ORD - HOU

ORDHOU

Chicago O'Hare Intl

Fri 10/24

5:45 pm-10:35 pm

1 stop4h 50m

Houston Hobby

Sun 10/26

6:55 am-12:45 pm

1 stop5h 50m

$185

ChicagoHouston

ORD - HOU

ORDHOU

Chicago O'Hare Intl

Sat 10/11

7:30 am-5:10 pm

2 stops9h 40m

Houston Hobby

Sat 10/18

5:55 am-2:25 pm

2 stops8h 30m

$187

ChicagoHouston

MDW - HOU

MDWHOU

Chicago Midway

Sat 11/8

4:30 pm-7:15 pm

Nonstop2h 45m

Houston Hobby

Sun 11/9

5:05 am-9:55 am

1 stop4h 50m

$187

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/12

Showing 1-10 of 40 results
1
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The best insider tips for Chicago to Houston Hobby Airport flights

Snippets provided in this section are AI-generated based on a summarization of Cheapflights-commissioned articles. The articles are presented as-is, for general informational purposes only, and may not be up-to-date. The opinions contained in the articles are original to the author and reflect their authentic experience, which may vary significantly from the experience of others.
Cheapflights partnered with top experts to bring you the best recommendations for your Chicago to Houston Hobby Airport trip
Airports
MDW

Use the Orange Line train for a quick, affordable trip to MDW, taking less than 30 minutes to reach the city center.

Read more about MDWby Ramsey Qubein
HOU

For easy navigation, use a map app with real-time traffic info to avoid I-45 congestion when arriving at HOU.

Read more about HOUby Scott Laird
Our travel experts
Ramsey Qubein

Ramsey Qubein

Expert on MDW

Ramsey Qubein

Ramsey Qubein

An avid traveler and aviation expert who has visited 173 countries, all 50 states and seven continents, Ramsey Qubein flies nearly 400,000 miles a year. As a North Carolina-based freelance journalist for publications including Conde Nast Traveler, Forbes, USA Today and Bloomberg among others, he explores the latest trends in aviation, hospitality, cruises and business.

Read more
Scott Laird

Scott Laird

Expert on HOU

Scott Laird

Scott Laird

Originally from Anchorage, Alaska, Scott is a frequent contributor to Fodor’s Travel Guide, Conde Nast Traveler, TravelAge West, and TravelPulse. He holds a Bachelor of Science in Organizational Management from Alaska Pacific University and a Master of Science in Airline Management from Embry-Riddle Aeronautical University, and has worked in the airline and hotel industries and as a travel consultant.

Read more

Best time to book a flight from Chicago to Hobby

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

How far ahead should I book a flight from Chicago to Houston Hobby Airport?

Use this chart to determine the optimal time to book a round-trip flight from Chicago to Hobby. Price data was last updated on September 12, 2025.

Booking 71 days in advance of your planned departure date is, on average, the best time to get cheap flights from Chicago to Houston Hobby Airport. The general trend is that the closer you book to the departure date, the more expensive your flight will be.

What is the cheapest month to book a flight from Chicago to Houston Hobby Airport?

Currently, September is the cheapest month in which you can book a flight from Chicago to Houston Hobby Airport (average of $230). Flying from Chicago to Houston Hobby Airport in March is currently the most expensive (average of $330). 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 CHI to HOU?

Find hourly flight availability from Chicago to Hobby. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated September 15, 2025.

Unlike in the morning, when flights are generally more expensive, you can save up to 42% on flights from Chicago to Houston Hobby Airport by exploring options for tickets in the evening.

What is the cheapest day to fly from Chicago to Houston Hobby Airport?

Use this chart to determine the cheapest time to fly round-trip from Chicago to Hobby. Price data was last updated on September 14, 2025.

Travelers seeking maximum savings on their Chicago to Houston Hobby Airport flight should consider departing on Saturday 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 Chicago to Houston Hobby Airport?

Reviews of airlines servicing Hobby

Get insights into the airlines that provide service to Hobby. 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 Hobby. Reviews last updated September 15, 2025.
Read through reviews of airlines operating flights from Chicago to Houston Hobby Airport, such as Southwest, United Airlines, and American Airlines. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,242 reviews

Comfort

8.0

Food

7.0

Crew

8.6

Entertainment

7.5

Boarding

8.1

Overall

8.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Southwest
8.0
Very good
4,242 reviews
Southwest
8.0
Very good
4,242 reviews

Comfort

8.0

Food

7.0

Crew

8.6

Entertainment

7.5

Boarding

8.1

Overall

8.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
United Airlines
7.4
Good
8,929 reviews
Southwest
8.0
Very good
4,242 reviews

Comfort

8.0

Food

7.0

Crew

8.6

Entertainment

7.5

Boarding

8.1

Overall

8.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
American Airlines
7.2
Good
10,000 reviews
Southwest
8.0
Very good
4,242 reviews

Comfort

8.0

Food

7.0

Crew

8.6

Entertainment

7.5

Boarding

8.1

Overall

8.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Spirit Airlines
6.3
Okay
8,015 reviews
Southwest
8.0
Very good
4,242 reviews

Comfort

8.0

Food

7.0

Crew

8.6

Entertainment

7.5

Boarding

8.1

Overall

8.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Frontier
5.8
Fair
3,172 reviews
Southwest
8.0
Very good
4,242 reviews

Comfort

8.0

Food

7.0

Crew

8.6

Entertainment

7.5

Boarding

8.1

Overall

8.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines

Related info for your journey

Find useful and relevant information for your journey from Chicago to Hobby. 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 Chicago to Houston Hobby Airport?

    A quick flight from Chicago to Houston Hobby Airport can take about 4h 25m. Southwest provides one of the quickest options available for as low as $153. The distance between Chicago and Houston Hobby Airport is about 945 mi.

  • What are the cheapest airlines flying from Chicago to Houston Hobby Airport round-trip?

    Spirit Airlines, at $68, was found to be the cheapest airline from Chicago to Houston Hobby Airport.Alternate airlines to your destination round-trip include Frontier and American Airlines. Spirit Airlines is priced at 68% lower than the current average price of a flight leaving 3 months from now.

  • Can I find deals for flights from Chicago to Hobby that include hotel bookings?

    Yes. In addition to deals on Chicago to Hobby flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Chicago to Hobby?

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

  • Can I find deals for business class flights from Chicago to Hobby?

    Yes. Cheapflights offers flight deals from Chicago to Hobby 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 Chicago to Houston Hobby Airport?

    Currently, September is the cheapest month in which you can book a flight from Chicago to Houston Hobby Airport (average of $230). Flying from Chicago to Houston Hobby Airport in March is currently the most expensive (average of $330). 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
Sugar Land
Stafford
Pasadena
Kemah
Baytown
Freeport
Texas City
Seabrook
Rosenberg
Webster
Lake Jackson
Missouri City
Pearland
League City
West University Place
Nassau Bay

Browse thousands of different options on Cheapflights for your next trip

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Top 5 airlines flying from Chicago to Hobby

Discover the top 5 airlines that operate flights from Chicago to Hobby. 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 15, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$68Average$178FlexibilityNo cancel feeOn-time65%
FrontierCheapest$75Average$176FlexibilityNo cancel feeOn-time62%
American AirlinesCheapest$158Average$272FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$170Average$395FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$182Average$349FlexibilityNo cancel feeOn-time63%

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