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$95+ 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 8/6. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — HOU
Aug 11 — Aug 181
Tue 8/11
Tue 8/18
1 adult, Economy
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Find cheap flights from Chicago to Hobby with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

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Cheapflights Tip: The best prices from Chicago to Houston Hobby are usually found in September or January, booked 88 days in advance, depart on a Wednesday or Monday and return on a Saturday

Cheap 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 12, 2026.

This Southwest deal was found by Cheapflights users on 7/8. 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 8/135:25 am
MDW
-
HOU
Nonstop2h 25m
Southwest
Mon 8/177:55 pm
HOU
-
MDW
Nonstop2h 20m
Southwest
Deal found 7/8$179
This Southwest deal was found by Cheapflights users on 7/8. 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 8/65:25 am
MDW
-
HOU
Nonstop2h 25m
Southwest
Thu 8/137:55 pm
HOU
-
MDW
Nonstop2h 20m
Southwest
Deal found 7/8$180
This Southwest deal was found by Cheapflights users on 7/7. 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 8/61:05 pm
MDW
-
HOU
1 stop5h 20m
Southwest
Mon 8/105:45 pm
HOU
-
MDW
Nonstop2h 25m
Southwest
Deal found 7/7$185
This Southwest deal was found by Cheapflights users on 7/10. 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 8/247:25 am
MDW
-
HOU
Nonstop2h 30m
Southwest
Thu 8/2711:30 am
HOU
-
MDW
2 stops5h 25m
Southwest
Deal found 7/10$190
This Southwest deal was found by Cheapflights users on 7/10. 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 8/101:05 pm
MDW
-
HOU
1 stop5h 20m
Southwest
Mon 8/175:00 am
HOU
-
MDW
Nonstop2h 25m
Southwest
Deal found 7/10$191
This Southwest deal was found by Cheapflights users on 7/9. 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 8/61:05 pm
MDW
-
HOU
1 stop5h 20m
Southwest
Tue 8/1112:10 pm
HOU
-
MDW
1 stop4h 50m
Southwest
Deal found 7/9$194
This Southwest deal was found by Cheapflights users on 7/9. 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 8/2010:05 am
MDW
-
HOU
1 stop3h 50m
Southwest
Mon 8/2411:30 am
HOU
-
MDW
2 stops5h 25m
Southwest
Deal found 7/9$196
This Delta deal was found by Cheapflights users on 7/8. 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.
Thu 8/135:30 am
ORD
-
HOU
1 stop6h 46m
Delta
Mon 8/176:00 am
HOU
-
ORD
1 stop8h 09m
Delta
Deal found 7/8$199
This Delta deal was found by Cheapflights users on 7/8. 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 8/510:54 am
MDW
-
HOU
1 stop5h 31m
Delta
Wed 8/126:00 am
HOU
-
MDW
1 stop5h 51m
Delta
Deal found 7/8$199
This Southwest deal was found by Cheapflights users on 7/8. 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 8/226:35 am
MDW
-
HOU
1 stop3h 50m
Southwest
Sat 8/221:20 pm
HOU
-
MDW
1 stop5h 50m
Southwest
Deal found 7/8$200
This Delta deal was found by Cheapflights users on 7/8. 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 8/223:25 pm
ORD
-
HOU
1 stop5h 58m
Delta
Tue 8/256:00 am
HOU
-
ORD
2 stops10h 17m
Delta
Deal found 7/8$204
This Delta deal was found by Cheapflights users on 7/9. 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.
Thu 8/201:44 pm
ORD
-
HOU
2 stops8h 21m
Delta
Mon 8/241:13 pm
HOU
-
ORD
2 stops8h 34m
Delta
Deal found 7/9$210

Find 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 12, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$179
(Southwest)

One-way from

$95
(Southwest)

Popular in

June

Cheapest in

September

Average price

$254

Good round-trip deal

$347 or less

Good one-way deal

$175 or less
Provider with most accurate pricing for Chicago (CHI)-Houston Hobby flight deals.
Search Deals
Provider most trusted by Cheapflights users for Chicago (CHI)-Houston Hobby flights.
Search Deals
From Chicago (CHI) to Houston Hobby
Search Deals
One-way flight from Chicago (CHI) to Houston Hobby
Search Deals
Highest demand for flights based on searches. 17% potential increase in price ($51 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($9 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in July 2026
Search Deals
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.
Search Deals

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 12, 2026.
Use the filters below to find and compare flights from Chicago to Houston Hobby Airport that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

ChicagoHouston

MDW - HOU

MDWHOU

Chicago Midway

Thu 8/6

1:05 pm-6:25 pm

1 stop5h 20m

Houston Hobby

Mon 8/10

5:45 pm-8:10 pm

Nonstop2h 25m

$185

ChicagoHouston

ORD - HOU

ORDHOU

Chicago O'Hare Intl

Wed 8/5

6:40 am-12:16 pm

1 stop5h 36m

Houston Hobby

Mon 8/10

10:50 am-4:51 pm

1 stop6h 01m

$199

ChicagoHouston

ORD - HOU

ORDHOU

Chicago O'Hare Intl

Tue 9/22

5:30 am-1:19 pm

1 stop7h 49m

Houston Hobby

Tue 9/29

5:26 pm-11:59 pm

1 stop6h 33m

$199

ChicagoHouston

ORD - HOU

ORDHOU

Chicago O'Hare Intl

Wed 8/5

6:40 am-12:16 pm

1 stop5h 36m

Houston Hobby

Sat 8/8

10:50 am-4:51 pm

1 stop6h 01m

$199

ChicagoHouston

MDW - HOU

MDWHOU

Chicago Midway

Thu 8/20

7:25 am-9:55 am

Nonstop2h 30m

Houston Hobby

Tue 8/25

9:40 am-12:15 pm

Nonstop2h 35m

$209

ChicagoHouston

MDW - HOU

MDWHOU

Chicago Midway

Thu 10/29

6:05 pm-8:40 pm

Nonstop2h 35m

Houston Hobby

Mon 11/2

12:55 pm-5:00 pm

1 stop4h 05m

$215

ChicagoHouston

MDW - HOU

MDWHOU

Chicago Midway

Fri 8/7

1:05 pm-6:25 pm

1 stop5h 20m

Houston Hobby

Wed 9/9

9:40 am-12:15 pm

Nonstop2h 35m

$218

ChicagoHouston

MDW - HOU

MDWHOU

Chicago Midway

Fri 8/7

1:05 pm-6:25 pm

1 stop5h 20m

Houston Hobby

Mon 8/10

5:45 pm-8:10 pm

Nonstop2h 25m

$218

ChicagoHouston

ORD - HOU

ORDHOU

Chicago O'Hare Intl

Thu 8/6

5:30 am-12:16 pm

1 stop6h 46m

Houston Hobby

Sat 8/8

10:50 am-4:51 pm

1 stop6h 01m

$219

ChicagoHouston

MDW - HOU

MDWHOU

Chicago Midway

Sat 8/15

6:05 pm-8:40 pm

Nonstop2h 35m

Houston Hobby

Mon 8/17

6:05 am-10:05 am

1 stop4h 00m

$219

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/7

Showing 1-10 of 46 resultsSorted by cheapest first
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Compare providers for flights from Chicago to Hobby

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 Chicago to Hobby in July.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars
JustAirTicketPrice Accuracy-Trust Score*1 star
eDreamsPrice Accuracy2 starsTrust Score*3 stars
PricelinePrice Accuracy1 starTrust Score*3 stars
Super.comPrice Accuracy-Trust Score*3 stars
CheapflightsfaresPrice Accuracy2 starsTrust Score*1 star
CheapOairPrice Accuracy3 starsTrust Score*3 stars
MytripPrice Accuracy2 starsTrust Score*3 stars
Kiwi.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 Chicago-Houston Hobby Airport flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Chicago-Houston Hobby Airport flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Chicago-Houston Hobby Airport flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Chicago-Houston Hobby 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 Chicago-Houston Hobby 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 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

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 $45). Flying from Chicago to Houston Hobby Airport in July is currently the most expensive (average of $732). 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 12, 2026.

Unlike in the afternoon, when flights are generally more expensive, you can save up to 18% on flights from Chicago to Houston Hobby Airport by exploring options for tickets in the evening.

How much does it cost to fly round-trip from Chicago to Houston Hobby Airport?

How often are flights from Chicago to Houston delayed?

About 20% of weekly flights between Chicago and Houston have experienced delays in the past year, with the average delay time being 115 minutes.

What is the most punctual flight time for Chicago to Houston flights?

Historically, flights departing in the morning are less likely to be delayed, whereas flights leaving at night tend to experience delays more often.

What day of the week experiences the fewest flight delays on this route?

Wednesday tends to have the lowest number of delays on this route, whereas Sunday has historically faced a higher average of delays compared to other days of the week.

Which airline has the best punctuality record on Chicago to Houston flights?

Over the last year, Southwest have had the lowest number of delays on this route, with just 20% of flights being delayed.

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

Booking 64 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 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 July 11, 2026.

Travelers seeking maximum savings on their Chicago to Houston Hobby Airport flight should consider departing on Wednesday 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.

The best insider tips for Chicago to Houston Hobby Airport flights

AI-powered summary based on content written by travel experts. AI can make mistakes.
Cheapflights partnered with top experts to bring you the best recommendations for your Chicago to Houston Hobby Airport trip
Our travel experts
Ramsey Qubein

Ramsey Qubein

Expert on MDW

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

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

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 12, 2026.
Read through reviews of airlines operating flights from Chicago to Houston Hobby Airport, such as Southwest,United Airlines, andAmerican Airlines. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Southwest
7.9
Good
4,251 reviews

Entertainment

7.5

Comfort

8.0

Food

7.0

Crew

8.6

Boarding

8.1

Overall

7.9

Reviews

1 / 20
10.0
Excellent

Sarah,Aug 2024

MDW - AUS

My first time, surprisingly good! It was a good ride overall. Coming from Singapore, this budget flight is better than the budget airline for our national carrier Singapore Airlines.
Southwest
7.9
Good
4,251 reviews
Southwest
7.9
Good
4,251 reviews

Entertainment

7.5

Comfort

8.0

Food

7.0

Crew

8.6

Boarding

8.1

Overall

7.9

Reviews

1 / 20
10.0
Excellent

Sarah,Aug 2024

MDW - AUS

My first time, surprisingly good! It was a good ride overall. Coming from Singapore, this budget flight is better than the budget airline for our national carrier Singapore Airlines.
United Airlines
7.4
Good
9,981 reviews
Southwest
7.9
Good
4,251 reviews

Entertainment

7.5

Comfort

8.0

Food

7.0

Crew

8.6

Boarding

8.1

Overall

7.9

Reviews

1 / 20
10.0
Excellent

Sarah,Aug 2024

MDW - AUS

My first time, surprisingly good! It was a good ride overall. Coming from Singapore, this budget flight is better than the budget airline for our national carrier Singapore Airlines.
American Airlines
7.1
Good
11,815 reviews
Southwest
7.9
Good
4,251 reviews

Entertainment

7.5

Comfort

8.0

Food

7.0

Crew

8.6

Boarding

8.1

Overall

7.9

Reviews

1 / 20
10.0
Excellent

Sarah,Aug 2024

MDW - AUS

My first time, surprisingly good! It was a good ride overall. Coming from Singapore, this budget flight is better than the budget airline for our national carrier Singapore Airlines.
JetBlue
7.1
Good
3,011 reviews
Southwest
7.9
Good
4,251 reviews

Entertainment

7.5

Comfort

8.0

Food

7.0

Crew

8.6

Boarding

8.1

Overall

7.9

Reviews

1 / 20
10.0
Excellent

Sarah,Aug 2024

MDW - AUS

My first time, surprisingly good! It was a good ride overall. Coming from Singapore, this budget flight is better than the budget airline for our national carrier Singapore Airlines.
Frontier
5.6
Fair
2,821 reviews
Southwest
7.9
Good
4,251 reviews

Entertainment

7.5

Comfort

8.0

Food

7.0

Crew

8.6

Boarding

8.1

Overall

7.9

Reviews

1 / 20
10.0
Excellent

Sarah,Aug 2024

MDW - AUS

My first time, surprisingly good! It was a good ride overall. Coming from Singapore, this budget flight is better than the budget airline for our national carrier Singapore 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 5h 20m. Southwest provides one of the quickest options available for as low as $185. The distance between Chicago and Houston Hobby Airport is about 938 mi. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.

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

    Frontier, at $70, was found to be the cheapest airline from Chicago to Houston Hobby Airport.Alternate airlines to your destination round-trip include United Airlines and American Airlines. Frontier is priced at 70% 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?

    $29 is the cheapest one-way deal found within the past few days, from Frontier. You may also be able to find cheap deals on American Airlines and United Airlines, with prices starting from $78 and $88, 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 $45). Flying from Chicago to Houston Hobby Airport in July is currently the most expensive (average of $732). 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
Pasadena
Stafford
Pearland
Baytown
Webster
West University Place
Texas City
Seabrook
Freeport
Kemah
Lake Jackson
Rosenberg
Missouri City
League City

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 July 12, 2026.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$70Average$197FlexibilityNo cancel feeOn-time62%
United AirlinesCheapest$138Average$324FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$167Average$339FlexibilityNo cancel feeOn-time71%
JetBlueCheapest$203Average$298FlexibilityNo cancel feeOn-time62%
SouthwestCheapest$217Average$307FlexibilityNo cancel feeOn-time63%

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