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$79+ 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 8/7. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — HOU
Jul 7 — Jul 141
Mon 7/7
Mon 7/14
1 adult, Economy
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Cheapflights Tip: The best prices from Chicago to Houston Hobby are usually found in August or October, booked 73 days in advance, depart on a Wednesday or Friday 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 July 2, 2025.

Round-trip from

$157
(Southwest)

One-way from

$79
(Southwest)

Popular in

March

Cheapest in

August

Average price

$187

Good round-trip deal

$257 or less

Good one-way deal

$188 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. 10% potential increase in price ($24 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 July 2025
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Price to beat on a round-trip flight from Chicago (CHI) to Houston Hobby.
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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 July 2, 2025.

This Southwest deal was found by Cheapflights users on 7/1. 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 8/198:25 pmMDW - HOU
Nonstop2h 30mSouthwest
Sat 8/238:20 pmHOU - MDW
Nonstop2h 25mSouthwest
Deal found 7/1$157
This Southwest 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/53:10 pmORD - HOU
1 stop4h 35mSouthwest
Wed 8/612:40 pmHOU - ORD
1 stop9h 40mSouthwest
Deal found 6/30$177
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/169:47 amORD - HOU
1 stop7h 52mDelta
Sat 8/236:00 amHOU - ORD
1 stop6h 17mDelta
Deal found 7/2$217
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/166:04 amMDW - HOU
1 stop6h 06mDelta
Sat 8/2310:22 amHOU - MDW
1 stop5h 06mDelta
Deal found 7/2$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.
Thu 8/211:21 pmORD - HOU
1 stop4h 39mAmerican Airlines
Mon 8/254:20 pmHOU - ORD
1 stop4h 37mAmerican Airlines
Deal found 6/30$251

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 July 2, 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

MDW - HOU

MDWHOU

Chicago Midway

Tue 8/19

8:25 pm-10:55 pm

Nonstop2h 30m

Houston Hobby

Sat 8/23

8:20 pm-10:45 pm

Nonstop2h 25m

$157

ChicagoHouston

ORD - HOU

ORDHOU

Chicago O'Hare Intl

Tue 8/5

3:10 pm-7:45 pm

1 stop4h 35m

Houston Hobby

Wed 8/6

12:40 pm-10:20 pm

1 stop9h 40m

$177

ChicagoHouston

ORD - HOU

ORDHOU

Chicago O'Hare Intl

Sat 8/16

9:47 am-5:39 pm

1 stop7h 52m

Houston Hobby

Sat 8/23

6:00 am-12:17 pm

1 stop6h 17m

$217

ChicagoHouston

MDW - HOU

MDWHOU

Chicago Midway

Sat 8/16

4:25 pm-10:31 pm

1 stop6h 06m

Houston Hobby

Sat 8/23

10:22 am-3:28 pm

1 stop5h 06m

$217

ChicagoHouston

ORD - HOU

ORDHOU

Chicago O'Hare Intl

Thu 8/21

1:21 pm-6:00 pm

1 stop4h 39m

Houston Hobby

Mon 8/25

4:20 pm-8:57 pm

1 stop4h 37m

$251

ChicagoHouston

MDW - HOU

MDWHOU

Chicago Midway

Thu 8/7

1:40 pm-4:15 pm

Nonstop2h 35m

$79

ChicagoHouston

ORD - HOU

ORDHOU

Chicago O'Hare Intl

Wed 8/6

7:00 am-2:00 pm

1 stop7h 00m

$89

ChicagoHouston

MDW - HOU

MDWHOU

Chicago Midway

Fri 8/1

1:11 pm-7:13 pm

1 stop6h 02m

$101

ChicagoHouston

ORD - HOU

ORDHOU

Chicago O'Hare Intl

Thu 8/14

5:45 am-12:10 pm

1 stop6h 25m

$109

ChicagoHouston

MDW - HOU

MDWHOU

Chicago Midway

Sat 8/16

6:04 am-12:10 pm

1 stop6h 06m

$109

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/1

Showing 1-10 of 13 results
1
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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 June 27, 2025.

Booking 73 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 $332). 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 July 2, 2025.

Unlike in the morning, when flights are generally more expensive, you can save up to 47% 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 June 29, 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 July 2, 2025.
Read through reviews of airlines operating flights from Chicago to Houston Hobby Airport, such as Southwest, Delta, 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
4,272 reviews

Entertainment

7.6

Food

7.0

Boarding

8.2

Overall

8.0

Crew

8.6

Comfort

8.0

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.
Southwest
8.0
Very good
4,272 reviews
Southwest
8.0
Very good
4,272 reviews

Entertainment

7.6

Food

7.0

Boarding

8.2

Overall

8.0

Crew

8.6

Comfort

8.0

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.
Delta
8.0
Very good
7,983 reviews
Southwest
8.0
Very good
4,272 reviews

Entertainment

7.6

Food

7.0

Boarding

8.2

Overall

8.0

Crew

8.6

Comfort

8.0

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.
American Airlines
7.2
Good
10,000 reviews
Southwest
8.0
Very good
4,272 reviews

Entertainment

7.6

Food

7.0

Boarding

8.2

Overall

8.0

Crew

8.6

Comfort

8.0

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.
Allegiant Air
7.2
Good
709 reviews
Southwest
8.0
Very good
4,272 reviews

Entertainment

7.6

Food

7.0

Boarding

8.2

Overall

8.0

Crew

8.6

Comfort

8.0

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.
Sun Country Air
6.9
Okay
340 reviews
Southwest
8.0
Very good
4,272 reviews

Entertainment

7.6

Food

7.0

Boarding

8.2

Overall

8.0

Crew

8.6

Comfort

8.0

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 Chicago to Hobby. 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 Chicago to Houston Hobby Airport round-trip?

    Southwest, at $157, was found to be the cheapest airline from Chicago to Houston Hobby Airport.Alternate airlines to your destination round-trip include Delta and American Airlines. Southwest is priced at 25% lower than the current average price of a flight leaving 3 months from now.

  • What are the cheapest airlines to fly from Chicago to Houston Hobby Airport one-way?

    $79 is the cheapest one-way deal found within the past few days, from Southwest. You may also be able to find cheap deals on Allegiant Air and Delta, with prices starting from $101 and $109, respectively.

  • 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 $332). 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?

Book flights to Chicago if you plan to visit one of these locations
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Top 6 airlines flying from Chicago to Hobby

Discover the top 6 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 July 2, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$67Average$164FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$68Average$160FlexibilityNo cancel feeOn-time65%
DeltaCheapest$144Average$383FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$157Average$268FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$165Average$389FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$180Average$342FlexibilityNo cancel feeOn-time63%

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