Is Southwest the cheapest airline to fly with from Chicago to Houston Hobby Airport?

With an average price of $348 return, Southwest is not the cheapest airline to fly from Chicago to Houston Hobby Airport with. Instead, for the lowest price, our data suggests flying with Spirit Airlines, where a return flight costs $178 on average.

Does Southwest fly direct to Houston Hobby Airport from Chicago?

Yes, Southwest does offer direct flights for the route, with around 7 flights per week.

What’s the cheapest day of the week to fly from Chicago to Houston Hobby Airport with Southwest?

On average, the cheapest day of the week to fly from Chicago to Houston Hobby Airport with Southwest is Friday, when prices are around $77. The most expensive day is generally Saturday, where the average price is around $102.

What’s the cheapest month to fly from Chicago to Houston Hobby Airport with Southwest?

The cheapest month for Southwest flights to Houston Hobby Airport from Chicago is generally January, where plane tickets cost $89 on average. If possible, try to avoid the most expensive months of June and August, where tickets cost $297 and $418 respectively.

$59 Cheap Southwest Flights from Chicago to Houston Hobby Airport

CHI - HOU

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Flight Deals

Cheap Southwest Flight Deals from Chicago to Houston Hobby Airport

Here are some of the best deals found on KAYAK recently from Southwest for round-trip flights from Chicago to Houston Hobby Airport that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.

Discover the best prices for you by selecting your travel dates on KAYAK.

Round-trip

One-way

Last minute

Direct

Recent round-trip Southwest flight deals from Chicago to Houston Hobby Airport

Sat, Jan 10 - Sun, Jan 11

8:20 am - 11:20 amMDW-HOU

3h 00mnonstop

6:30 am - 8:50 amHOU-MDW

2h 20mnonstop

$117Southwest

Find Deal

Tue, Dec 2 - Tue, Dec 9

1:05 pm - 3:50 pmMDW-HOU

2h 45mnonstop

2:35 pm - 5:00 pmHOU-MDW

2h 25mnonstop

$158Southwest

Find Deal

Thu, Dec 4 - Sat, Dec 6

8:35 pm - 11:20 pmMDW-HOU

2h 45mnonstop

2:00 pm - 4:25 pmHOU-MDW

2h 25mnonstop

$177Southwest

Find Deal

Thu, Dec 4 - Sat, Dec 6

10:50 am - 3:15 pmMDW-HOU

4h 25m1 stop

6:10 pm - 8:35 pmHOU-MDW

2h 25mnonstop

$187Southwest

Find Deal

Tue, Dec 2 - Tue, Dec 9

1:05 pm - 3:50 pmMDW-HOU

2h 45mnonstop

1:15 pm - 5:15 pmHOU-MDW

4h 00m1 stop

$188Southwest

Find Deal

Fri, Feb 20 - Mon, Feb 23

9:55 pm - 12:40 amMDW-HOU

2h 45mnonstop

2:00 pm - 7:30 pmHOU-MDW

5h 30m1 stop

$193Southwest

Find Deal

Fri, Dec 5 - Sun, Dec 7

8:35 pm - 11:20 pmMDW-HOU

2h 45mnonstop

9:50 pm - 12:10 amHOU-MDW

2h 20mnonstop

$197Southwest

Find Deal

Wed, Jan 14 - Wed, Jan 14

6:15 am - 9:15 amMDW-HOU

3h 00mnonstop

11:00 am - 4:35 pmHOU-MDW

5h 35m2 stops

$198Southwest

Find Deal

Thu, Nov 27 - Thu, Dec 4

9:25 am - 2:40 pmMDW-HOU

5h 15m1 stop

10:20 am - 12:45 pmHOU-MDW

2h 25mnonstop

$202Southwest

Find Deal

Fri, Dec 5 - Sun, Dec 7

6:20 pm - 11:00 pmMDW-HOU

4h 40m1 stop

9:50 pm - 12:10 amHOU-MDW

2h 20mnonstop

$207Southwest

Find Deal

Useful Info

Low season	September
High season	March
Cheapest flight	$59
Average price round-trip	$189
Good deal one-way	$193

Best time to beat the crowds with an average 19% drop in price.

Most popular time to fly with an average 17% increase in price.

Flight from Chicago Midway Airport to Houston Hobby Airport

(avg. price over the last 2 weeks)

or less

When to Book Flights with Southwest from Chicago to Houston Hobby Airport

Average price per month

Flight prices as travel date approaches

Is Southwest the cheapest airline to fly with from Chicago to Houston Hobby Airport?
With an average price of $348 return, Southwest is not the cheapest airline to fly from Chicago to Houston Hobby Airport with. Instead, for the lowest price, our data suggests flying with Spirit Airlines, where a return flight costs $178 on average.
What is the cheapest Southwest flight from Chicago to Houston Hobby Airport?
In the last 3 days, the lowest price for a flight with Southwest from Chicago to Houston Hobby Airport was $157 for a return flight and $78 for a one-way flight.
Does Southwest fly direct to Houston Hobby Airport from Chicago?
Yes, Southwest does offer direct flights for the route, with around 7 flights per week.
What’s the cheapest day of the week to fly from Chicago to Houston Hobby Airport with Southwest?
On average, the cheapest day of the week to fly from Chicago to Houston Hobby Airport with Southwest is Friday, when prices are around $77. The most expensive day is generally Saturday, where the average price is around $102.
What’s the cheapest month to fly from Chicago to Houston Hobby Airport with Southwest?
The cheapest month for Southwest flights to Houston Hobby Airport from Chicago is generally January, where plane tickets cost $89 on average. If possible, try to avoid the most expensive months of June and August, where tickets cost $297 and $418 respectively.

8.0

Very good4,241 verified ratings

8.0Comfort

7.5Entertainment

7.0Food

8.1Boarding

8.6Crew

Pros +

Cons -

Show reviews that mention

10.0 Wonderful

James, Oct 2025

TUS-LAS

Very good

8.0 Very good

Greg, Oct 2025

OAK-BUR

Ever since Southwest starting charging for bags, passengers don't want to pay to check their bags, so the gate agents have to beg people to check their roller bags now because there's "not enough space". This was a terrible business move by Southwest.

8.0 Very good

Margaret, Oct 2025

SAV-HOU

Full cans of soda would be nice. A choice between two snacks would be appreciated.

8.0 Very good

TODD, Oct 2025

CMH-HOU

Tried watching free movie and it kept freezing so I couldn’t finish.

10.0 Wonderful

Antonio, Oct 2025

PVD-MCO

Always reliable

10.0 Wonderful

Verified traveler, Oct 2025

MDW-BWI

All was good. I just had a hard time getting connected to the WiFi/internet during the flight

4.0 Mediocre

Mike, Oct 2025

GRR-MDW

Staff/crew very good. 4 hour delay not good.

10.0 Wonderful

Stacy, Oct 2025

SMF-DEN

Sacrament staff are always polite and helpful. Airport is easy to maneuver and boarding is straightforward.

2.0 Poor

Verified traveler, Oct 2025

DAL-LIT

Delayed 5.5 hours

10.0 Wonderful

Verified traveler, Oct 2025

BOS-BWI

Great flight. Outstanding Service. Southwest was able to put us on a direct flight to Denver when the connection could have been affected by a later arrival to Baltimore. The direct flight was less expensive that the flight with the connection in Baltimore.

Everything you need to know for your flight from Chicago to Houston Hobby Airport

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Cabin class types available on flights to Houston Hobby Airport

First Class flights from Chicago to Houston Hobby Airport

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CHI - HOU

$59 Find Cheap Southwest Flights from Chicago to Houston Hobby Airport

Search hundreds of travel sites at once for deals on Southwest flights from Chicago to Houston Hobby Airport

Cheap Southwest Flight Deals from Chicago to Houston Hobby Airport

Recent round-trip Southwest flight deals from Chicago to Houston Hobby Airport

Recent one-way Southwest flight deals from Chicago to Houston Hobby Airport

Recent last minute Southwest flight deals from Chicago to Houston Hobby Airport

Recent direct Southwest flight deals from Chicago to Houston Hobby Airport

Good to know

When to Book Flights with Southwest from Chicago to Houston Hobby Airport

FAQs for flying to Houston Hobby Airport with Southwest

Is Southwest the cheapest airline to fly with from Chicago to Houston Hobby Airport?

What is the cheapest Southwest flight from Chicago to Houston Hobby Airport?

Does Southwest fly direct to Houston Hobby Airport from Chicago?

What’s the cheapest day of the week to fly from Chicago to Houston Hobby Airport with Southwest?

What’s the cheapest month to fly from Chicago to Houston Hobby Airport with Southwest?

Southwest Customer Reviews

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Everything you need to know for your flight from Chicago to Houston Hobby Airport

Cabin class types available on flights to Houston Hobby Airport

Cabin classes available on flights to Chicago. Prices are the lowest found on KAYAK over the last 7 days. Price and availability is not guaranteed.

Complete your trip to Houston Hobby Airport with a hotel stay or car rental

Flights to other popular destinations

The most popular flights on KAYAK according to clicks in the last 2 weeks. Prices are the lowest found on KAYAK over the last 7 days. Price and availability is not guaranteed.

Find deals for your return flight

Top Southwest flights

The most popular destinations for flights with Southwest according to clicks from KAYAK users. Prices are the lowest found on KAYAK over the last 7 days. Price and availability is not guaranteed.