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Cheap flights from Chicago to Houston from $79

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Chicago to Houston departing on 10/21. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
1 adult
0 bags

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Cheap round-trip flights

Southwest Logo
7:45 pm - 10:20 pmMDW-HOU
2h 35mnonstop
Southwest Logo
6:55 am - 9:20 amHOU-MDW
2h 25mnonstop
$157Southwest
Find Deal
Sat, Oct 18 - Tue, Oct 21
Southwest Logo
8:25 am - 12:30 pmMDW-HOU
4h 05m1 stop
Southwest Logo
11:10 am - 1:35 pmHOU-MDW
2h 25mnonstop
$163Southwest
Find Deal
Sat, Oct 18 - Wed, Oct 22
Southwest Logo
9:55 pm - 12:35 amMDW-HOU
2h 40mnonstop
Southwest Logo
1:15 pm - 5:15 pmHOU-MDW
4h 00m1 stop
$167Southwest
Find Deal
Thu, Nov 13 - Mon, Nov 17
Southwest Logo
8:25 am - 12:30 pmMDW-HOU
4h 05m1 stop
Southwest Logo
10:30 am - 2:45 pmHOU-MDW
4h 15m1 stop
$172Southwest
Find Deal
Sat, Oct 18 - Wed, Oct 22
Southwest Logo
4:25 pm - 12:10 amORD-HOU
7h 45m1 stop
Southwest Logo
7:15 am - 12:15 pmHOU-ORD
5h 00m1 stop
$177Southwest
Find Deal
Thu, Nov 13 - Mon, Nov 17
Delta Logo
6:45 am - 1:27 pmORD-HOU
6h 42m1 stop
Delta Logo
6:44 pm - 11:58 pmHOU-ORD
5h 14m1 stop
$217Delta
Find Deal
Sat, Oct 18 - Tue, Oct 21
Delta Logo
6:00 am - 12:18 pmMDW-HOU
6h 18m1 stop
Delta Logo
1:13 pm - 9:10 pmHOU-MDW
7h 57m1 stop
$249Delta
Find Deal
Wed, Oct 1 - Sat, Oct 4
American Airlines Logo
1:22 pm - 6:07 pmORD-HOU
4h 45m1 stop
American Airlines Logo
4:41 pm - 11:13 pmHOU-ORD
6h 32m1 stop
$264American Airlines
Find Deal
Sat, Oct 18 - Mon, Oct 20
Sun Country Air Logo
7:45 pm - 12:04 pmORD-HOU
16h 19m1 stop
Sun Country Air Logo
9:34 am - 10:39 amHOU-ORD
25h 05m1 stop
$265Sun Country Air
Find Deal
Thu, Oct 2 - Sun, Oct 5
Sun Country Air Logo
7:45 pm - 12:16 pmORD-HOU
16h 31m1 stop
Sun Country Air Logo
9:34 am - 5:21 pmHOU-ORD
7h 47m1 stop
$273Sun Country Air
Find Deal
Thu, Oct 23 - Sun, Oct 26

Southwest flights from Chicago to Houston Hobby Airport

Our best Southwest deals on Chicago to Houston Hobby Airport flight tickets
Southwest
Oct 18
MDW7:45 pmChicago Midway
2h 35m
HOU10:20 pmHouston Hobby
Oct 21
HOU6:55 amHouston Hobby
2h 25m
MDW9:20 amChicago Midway
$157
Find similar
Southwest
Oct 18
MDW8:25 amChicago Midway
4h 05m
1 stop
HOU12:30 pmHouston Hobby
Oct 22
HOU11:10 amHouston Hobby
2h 25m
MDW1:35 pmChicago Midway
$163
Find similar
Southwest
Nov 13
MDW9:55 pmChicago Midway
2h 40m
HOU12:35 amHouston Hobby
Nov 17
HOU1:15 pmHouston Hobby
4h 00m
1 stop
MDW5:15 pmChicago Midway
$167
Find similar

Delta flights from Chicago to Houston Hobby Airport

Our best Delta deals on Chicago to Houston Hobby Airport flight tickets
Delta
Oct 18
ORD6:45 amChicago O'Hare Intl
6h 42m
1 stop
HOU1:27 pmHouston Hobby
Oct 21
HOU6:44 pmHouston Hobby
5h 14m
1 stop
ORD11:58 pmChicago O'Hare Intl
$217
Find similar
Delta
Oct 1
MDW6:00 amChicago Midway
6h 18m
1 stop
HOU12:18 pmHouston Hobby
Oct 4
HOU1:13 pmHouston Hobby
7h 57m
1 stop
MDW9:10 pmChicago Midway
$249
Find similar
Delta
Oct 16
ORD6:45 amChicago O'Hare Intl
6h 42m
1 stop
HOU1:27 pmHouston Hobby
Oct 23
HOU6:44 pmHouston Hobby
5h 14m
1 stop
ORD11:58 pmChicago O'Hare Intl
$258
Find similar

momondo Fare Finder

 
Customize your flight search to find flights from Chicago to Houston Hobby Airport 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, momondo users made 832,500 searches. Data last updated September 17, 2025.
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

ChicagoHouston

MDW - HOU

MDWHOU

Chicago Midway

Sat 10/18

7:45 pm-10:20 pm

Nonstop2h 35m

Houston Hobby

Tue 10/21

6:55 am-9:20 am

Nonstop2h 25m

$157

ChicagoHouston

MDW - HOU

MDWHOU

Chicago Midway

Sat 10/18

8:25 am-12:30 pm

1 stop4h 05m

Houston Hobby

Wed 10/22

11:10 am-1:35 pm

Nonstop2h 25m

$163

ChicagoHouston

MDW - HOU

MDWHOU

Chicago Midway

Thu 11/13

9:55 pm-12:35 am

Nonstop2h 40m

Houston Hobby

Mon 11/17

1:15 pm-5:15 pm

1 stop4h 00m

$167

ChicagoHouston

MDW - HOU

MDWHOU

Chicago Midway

Sat 10/18

8:25 am-12:30 pm

1 stop4h 05m

Houston Hobby

Wed 10/22

10:30 am-2:45 pm

1 stop4h 15m

$172

ChicagoHouston

ORD - HOU

ORDHOU

Chicago O'Hare Intl

Thu 11/13

4:25 pm-12:10 am

1 stop7h 45m

Houston Hobby

Mon 11/17

7:15 am-12:15 pm

1 stop5h 00m

$177

ChicagoHouston

ORD - HOU

ORDHOU

Chicago O'Hare Intl

Sat 10/18

6:45 am-1:27 pm

1 stop6h 42m

Houston Hobby

Tue 10/21

6:44 pm-11:58 pm

1 stop5h 14m

$217

ChicagoHouston

MDW - HOU

MDWHOU

Chicago Midway

Wed 10/1

6:00 am-12:18 pm

1 stop6h 18m

Houston Hobby

Sat 10/4

1:13 pm-9:10 pm

1 stop7h 57m

$249

ChicagoHouston

ORD - HOU

ORDHOU

Chicago O'Hare Intl

Sat 10/18

1:22 pm-6:07 pm

1 stop4h 45m

Houston Hobby

Mon 10/20

4:41 pm-11:13 pm

1 stop6h 32m

$264

ChicagoHouston

ORD - HOU

ORDHOU

Chicago O'Hare Intl

Thu 10/2

7:45 pm-12:04 pm

1 stop16h 19m

Houston Hobby

Sun 10/5

9:34 am-10:39 am

1 stop25h 05m

$265

ChicagoHouston

ORD - HOU

ORDHOU

Chicago O'Hare Intl

Thu 10/23

7:45 pm-12:16 pm

1 stop16h 31m

Houston Hobby

Sun 10/26

9:34 am-5:21 pm

1 stop7h 47m

$273

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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See travel insights to Houston from

How to get the cheapest flight ticket from Chicago to Houston Hobby Airport

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

What is the typical price of a round-trip flight between Chicago and Houston Hobby Airport?

What is the cheapest month to fly to Houston Hobby Airport?

In general, October is the cheapest month to fly from Chicago to Houston Hobby Airport. Due to it being the ‘off-season’ during this time, you can expect flight prices to be around $164. The month of September is another great option to travel to Houston Hobby Airport, with average flight prices from Chicago averaging around $177.

What is the cheapest day to depart on your flight to Houston Hobby Airport?

Our data shows that Wednesday is the least expensive day to fly to Houston Hobby Airport. Tickets to fly out on this day can be as low as $384. Be sure to avoid booking your departure on a Sunday as prices are generally higher than usual. According to our data, the average ticket price to Houston Hobby Airport on Sunday is $604.

What is the cheapest time of day to depart on your flight to Houston Hobby Airport?

According to our data, the cheapest time of day to fly to Houston Hobby Airport is in the evening. momondo users have found flights departing from Chicago to Houston Hobby Airport in the evening for as low as $274. Keep in mind that these prices may fluctuate based on what airline you choose and the time of year you plan to travel. Try not to purchase tickets in the morning because they tend to be around $377. Of course, these prices can vary depending on the time of year and what airport you fly to.

What is the cheapest Chicago to Houston Hobby flight route?

Fly from Chicago Midway to Houston Hobby for the best Chicago - Houston Hobby flight prices

How far in advance should I book a flight to Houston Hobby Airport?

You are more likely to see cheaper flights to Houston Hobby Airport from Chicago when booking weeks ahead of your departure date. In general, you can expect to find flights to Houston Hobby Airport for around $229 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Houston Hobby Airport from Chicago for as low as $160 on momondo.

What cabin class options are available on Chicago to Houston Hobby flights?

There is only 1 cabin class available to choose from on Chicago to Houston Hobby flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

Can stopping save me money on Chicago to Houston Hobby Airport flights?

No. A direct flight is the cheapest option for a flight between Chicago to Houston Hobby Airport.

How have Chicago to Houston Hobby Airport flight prices changed over time?

As of September 2025, prices for Chicago to Houston Hobby Airport flights are approximately 16% more expensive when compared to flights at the same time last year.

When to book flights from Chicago to Houston Hobby Airport

Are you open to changing your travel dates? Check out the ideal times to fly from Chicago to Houston Hobby Airport according to our flight data. Find out which month and days have the cheapest flights.
Estimated round-trip price

Cheap Chicago to Houston Hobby Airport (CHI to HOU) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Chicago to Houston Hobby Airport

Best Price Found

$118

Fastest flight time

2h 30m

Direct flights

Every day
The best one-way flight to Houston Hobby Airport from Chicago in the past 72 hours is $118. The best round-trip flight deal from Chicago to Houston Hobby Airport found on momondo in the last 72 hours is $228.
The fastest flight from Chicago to Houston Hobby Airport takes 2h 30m
Direct flights go from Chicago to Houston Hobby Airport every day.
Search flight deals

  • How far is Chicago to Houston Hobby by plane?

    The distance between Chicago and Houston Hobby is about 945.8 mi. Flights usually cover this in 2h 30m, depending on flying conditions and air traffic around both airports.

  • When did momondo last update prices for flights from Chicago to Houston Hobby Airport?

    Prices for flights from Chicago to Houston Hobby Airport are updated daily.

  • How many operators does momondo search for flights from Chicago to Houston Hobby Airport?

  • How old do you have to be to fly from Chicago to Houston Hobby Airport?

    Although the minimum age for a child to fly alone is five, airlines that offer an unaccompanied minor (UMNR) service may have their own age limits, which could be impacted by factors such as flight length, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Chicago to Houston Hobby Airport.

  • What documentation or ID do you need to fly to Houston Hobby Airport?

    The required travel and health documents for your Houston Hobby Airport trip may vary depending on your itinerary and personal circumstances. As a general rule, you should carry multiple documents, including a national ID card or driver's license and a passport valid for six months after your intended arrival at Houston Hobby Airport. We recommend that you seek guidance from your airline or a reliable third party such as IATA.

  • What is the most popular plane model from Chicago to Houston Hobby Airport?

  • What is the most popular airline from Chicago to Houston Hobby Airport?

Best airlines flying from Chicago to Houston Hobby Airport

Compare and see reviews for airlines that fly from Chicago to Houston Hobby Airport with momondo
Airline
Rating
Free Cancellation
Price
Spirit AirlinesPriceFrom $68Free CancellationRating
6.3
8,023 reviews
Search Spirit Airlines flights
FrontierPriceFrom $75Free CancellationRating
5.8
3,173 reviews
Search Frontier flights
American AirlinesPriceFrom $158Free CancellationRating
7.2
10,000 reviews
Search American Airlines flights
United AirlinesPriceFrom $170Free CancellationRating
7.4
8,926 reviews
Search United Airlines flights
SouthwestPriceFrom $182Free CancellationRating
8.0
4,242 reviews
Search Southwest flights

  • Southwest Flights From Chicago to Houston Hobby Airport

    Across 31 Southwest flights from Chicago to Houston Hobby Airport this week, the average price was $349, with the best Southwest deals starting from $182 round-trip. 4,242 users have rated Southwest on momondo, with an average score of 8.0/10.

Traveling to a place near Houston?

Book flights to Houston if you plan to visit one of these locations
Galveston
Kemah
Sugar Land
Pasadena
Baytown
Texas City
Rosenberg
Pearland
Webster
Stafford
Lake Jackson
Freeport
League City
Missouri City
La Marque
Seabrook
Nassau Bay
West University Place

Why use momondo?

Why should I use momondo to find a flight deal from Chicago to Houston?

momondo compares prices from hundreds of airlines and agents so you can find and book the best deal on flights from Chicago to Houston. Millions of users trust and use momondo every year so you are in good hands.

Can I find flights from Chicago to Houston with flexible booking policies on momondo?

All flight searches from Chicago to Houston on momondo can be filtered to show those which offer flexible booking policies.

How can momondo help me find flights from Chicago to Houston?

Once all potential Chicago to Houston flight options are in front of you, momondo lets you sort and filter flights based on preferences such as airline, price and flight times amongst many other options.

I’m not ready to book a flight from Chicago to Houston right now. Can momondo alert me if prices change?

If you are simply researching potential flights to Houston, momondo offers a useful price alert feature which will track prices for flights to Houston from Chicago and alert you when they change.

An easier way to manage your Houston Hobby Airport trip

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