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Cheap flights from Chicago Midway Airport 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 Midway Airport to Houston departing on 1/17. 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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Find the cheapest flights from Chicago Midway Airport to Houston

Cheap round-trip flights

Enter your travel dates to find the best prices.
Southwest Logo
7:35 pm - 10:25 pm
MDW
-
HOU
2h 50mnonstop
Southwest Logo
5:55 am - 8:20 am
HOU
-
MDW
2h 25mnonstop
$157Southwest
Sat, Feb 7 - Sat, Feb 14
Southwest Logo
6:15 am - 9:15 am
MDW
-
HOU
3h 00mnonstop
Southwest Logo
6:40 am - 9:05 am
HOU
-
MDW
2h 25mnonstop
$177Southwest
Tue, Jan 27 - Thu, Jan 29
Southwest Logo
8:30 pm - 11:15 pm
MDW
-
HOU
2h 45mnonstop
Southwest Logo
6:40 am - 9:05 am
HOU
-
MDW
2h 25mnonstop
$187Southwest
Thu, Jan 15 - Sun, Jan 18
Southwest Logo
6:15 am - 9:15 am
MDW
-
HOU
3h 00mnonstop
Southwest Logo
5:00 am - 7:25 am
HOU
-
MDW
2h 25mnonstop
$197Southwest
Fri, Jan 23 - Sun, Feb 1
Southwest Logo
2:10 pm - 7:35 pm
MDW
-
HOU
5h 25m1 stop
Southwest Logo
6:35 am - 9:00 am
HOU
-
MDW
2h 25mnonstop
$202Southwest
Wed, Dec 31 - Thu, Jan 1
Delta Logo
10:53 am - 4:28 pm
MDW
-
HOU
5h 35m1 stop
Delta Logo
5:25 am - 9:56 am
HOU
-
MDW
4h 31m1 stop
$207Delta
Thu, Feb 19 - Tue, Feb 24
Southwest Logo
8:55 am - 11:50 am
MDW
-
HOU
2h 55mnonstop
Southwest Logo
9:00 am - 2:55 pm
HOU
-
MDW
5h 55m2 stops
$212Southwest
Sun, Jan 18 - Wed, Jan 21
Southwest Logo
8:55 pm - 11:45 pm
MDW
-
HOU
2h 50mnonstop
Southwest Logo
4:30 pm - 8:40 pm
HOU
-
MDW
4h 10m1 stop
$213Southwest
Sat, Feb 14 - Wed, Feb 18
Southwest Logo
6:15 am - 9:15 am
MDW
-
HOU
3h 00mnonstop
Southwest Logo
8:30 pm - 10:55 pm
HOU
-
MDW
2h 25mnonstop
$217Southwest
Mon, Jan 12 - Wed, Jan 14
Southwest Logo
7:35 pm - 10:25 pm
MDW
-
HOU
2h 50mnonstop
Southwest Logo
5:05 am - 7:30 am
HOU
-
MDW
2h 25mnonstop
$218Southwest
Sat, Jan 17 - Mon, Jan 19

Southwest flights from Chicago Midway Airport to Houston Hobby Airport

Our best Southwest deals on Chicago Midway Airport to Houston Hobby Airport flight tickets
Southwest
Feb 7
MDW7:35 pmChicago Midway
2h 50m
HOU10:25 pmHouston Hobby
Feb 14
HOU5:55 amHouston Hobby
2h 25m
MDW8:20 amChicago Midway
$157
Find similar
Southwest
Jan 27
MDW7:55 pmChicago Midway
2h 45m
HOU10:40 pmHouston Hobby
Feb 1
HOU5:00 amHouston Hobby
2h 25m
MDW7:25 amChicago Midway
$177
Find similar
Southwest
Jan 15
MDW8:30 pmChicago Midway
2h 45m
HOU11:15 pmHouston Hobby
Jan 18
HOU6:40 amHouston Hobby
2h 25m
MDW9:05 amChicago Midway
$187
Find similar

Delta flights from Chicago Midway Airport to Houston Hobby Airport

Our best Delta deals on Chicago Midway Airport to Houston Hobby Airport flight tickets
Delta
Feb 19
MDW10:53 amChicago Midway
5h 35m
1 stop
HOU4:28 pmHouston Hobby
Feb 24
HOU1:06 pmHouston Hobby
4h 39m
1 stop
MDW5:45 pmChicago Midway
$207
Find similar
Delta
Jan 6
MDW11:21 amChicago Midway
4h 49m
1 stop
HOU4:10 pmHouston Hobby
Jan 14
HOU5:45 amHouston Hobby
4h 42m
1 stop
MDW10:27 amChicago Midway
$247
Find similar
Delta
Feb 12
MDW6:00 amChicago Midway
6h 20m
1 stop
HOU12:20 pmHouston Hobby
Feb 19
HOU10:50 amHouston Hobby
6h 55m
1 stop
MDW5:45 pmChicago Midway
$248
Find similar

momondo Fare Finder

 
Customize your flight search to find flights from Chicago Midway Airport 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 December 18, 2025.
Use the filters below to find and compare flights from Chicago Midway Airport to Houston Hobby Airport that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

ChicagoHouston

MDW - HOU

MDWHOU

Chicago Midway

Sat 2/7

7:35 pm-10:25 pm

Nonstop2h 50m

Houston Hobby

Sat 2/14

5:55 am-8:20 am

Nonstop2h 25m

$157

ChicagoHouston

MDW - HOU

MDWHOU

Chicago Midway

Tue 1/27

6:15 am-9:15 am

Nonstop3h 00m

Houston Hobby

Thu 1/29

6:40 am-9:05 am

Nonstop2h 25m

$177

ChicagoHouston

MDW - HOU

MDWHOU

Chicago Midway

Thu 1/15

8:30 pm-11:15 pm

Nonstop2h 45m

Houston Hobby

Sun 1/18

6:40 am-9:05 am

Nonstop2h 25m

$187

ChicagoHouston

MDW - HOU

MDWHOU

Chicago Midway

Fri 1/23

6:15 am-9:15 am

Nonstop3h 00m

Houston Hobby

Sun 2/1

5:00 am-7:25 am

Nonstop2h 25m

$197

ChicagoHouston

MDW - HOU

MDWHOU

Chicago Midway

Wed 12/31

2:10 pm-7:35 pm

1 stop5h 25m

Houston Hobby

Thu 1/1

6:35 am-9:00 am

Nonstop2h 25m

$202

ChicagoHouston

MDW - HOU

MDWHOU

Chicago Midway

Thu 2/19

10:53 am-4:28 pm

1 stop5h 35m

Houston Hobby

Tue 2/24

5:25 am-9:56 am

1 stop4h 31m

$207

ChicagoHouston

MDW - HOU

MDWHOU

Chicago Midway

Sun 1/18

8:55 am-11:50 am

Nonstop2h 55m

Houston Hobby

Wed 1/21

9:00 am-2:55 pm

2 stops5h 55m

$212

ChicagoHouston

MDW - HOU

MDWHOU

Chicago Midway

Sat 2/14

8:55 pm-11:45 pm

Nonstop2h 50m

Houston Hobby

Wed 2/18

4:30 pm-8:40 pm

1 stop4h 10m

$213

ChicagoHouston

MDW - HOU

MDWHOU

Chicago Midway

Mon 1/12

6:15 am-9:15 am

Nonstop3h 00m

Houston Hobby

Wed 1/14

8:30 pm-10:55 pm

Nonstop2h 25m

$217

ChicagoHouston

MDW - HOU

MDWHOU

Chicago Midway

Sat 1/17

7:35 pm-10:25 pm

Nonstop2h 50m

Houston Hobby

Mon 1/19

5:05 am-7:30 am

Nonstop2h 25m

$218

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 Midway Airport 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 cheapest month to fly to Houston Hobby Airport?

In general, September is the cheapest month to fly from Chicago Midway Airport to Houston Hobby Airport. Due to it being the ‘off-season’ during this time, you can expect flight prices to be around $125. The month of August is another great option to travel to Houston Hobby Airport, with average flight prices from Chicago Midway Airport averaging around $202.

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 $334. 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 $589.

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 Midway Airport to Houston Hobby Airport in the evening for as low as $272. 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 $375. Of course, these prices can vary depending on the time of year and what airport you fly to.

What is the cheapest Chicago Midway to Houston Hobby flight route?

Fly from Chicago Midway to Houston Hobby for the best Chicago Midway - 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 Midway Airport when booking weeks ahead of your departure date. In general, you can expect to find flights to Houston Hobby Airport for around $256 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 Midway Airport for as low as $177 on momondo.

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

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

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

As of December 2025, prices for Chicago Midway Airport to Houston Hobby Airport flights are approximately 20% more expensive when compared to flights at the same time last year.

When to book flights from Chicago Midway Airport to Houston Hobby Airport

Are you open to changing your travel dates? Check out the ideal times to fly from Chicago Midway Airport 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 Midway Airport to Houston Hobby Airport (MDW to HOU) flight deals and tips

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

Best Price Found

$148

Fastest flight time

2h 40m

Direct flights

Every day
The best one-way flight to Houston Hobby Airport from Chicago Midway Airport in the past 72 hours is $148. The best round-trip flight deal from Chicago Midway Airport to Houston Hobby Airport found on momondo in the last 72 hours is $279.
The fastest flight from Chicago Midway Airport to Houston Hobby Airport takes 2h 40m
Direct flights go from Chicago Midway Airport to Houston Hobby Airport every day.
Search flight deals

  • How far is Chicago Midway to Houston Hobby by plane?

    A flight from Chicago Midway to Houston Hobby will travel around 937.5 mi. By plane, this route typically takes 2h 40m.

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

    Prices for flights from Chicago Midway Airport to Houston Hobby Airport are refreshed on a daily basis.

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

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

    The minimum age for a child to fly alone is five, but airlines offering an unaccompanied minor (UNMR) service may have their age restrictions, such as regulations concerning flight duration, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Chicago Midway Airport to Houston Hobby Airport.

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

    The travel and health documents required for your trip to Houston Hobby Airport can vary based on your itinerary and personal situation. As a rule, consider having multiple documents such as a national ID card or driver’s license, and a passport valid for six-months after you plan to arrive at Houston Hobby Airport. We always recommend checking with your airline or a trusted third party such as IATA to get advice.

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

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

Best airlines flying from Chicago Midway Airport to Houston Hobby Airport

Compare and see reviews for airlines that fly from Chicago Midway Airport to Houston Hobby Airport with momondo
Airline
Rating
Free Cancellation
Price
FrontierPriceFrom $86Free CancellationRating
5.8
3,081 reviews
Search Frontier flights
Spirit AirlinesPriceFrom $116Free CancellationRating
6.3
8,190 reviews
Search Spirit Airlines flights
SouthwestPriceFrom $178Free CancellationRating
7.9
4,250 reviews
Search Southwest flights

  • Southwest Flights From Chicago Midway Airport to Houston Hobby Airport

    Across 12 Southwest flights from Chicago Midway Airport to Houston Hobby Airport this week, the average price was $333, with the best Southwest deals starting from $178 round-trip. 4,250 users have rated Southwest on momondo, with an average score of 7.9/10.

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
Webster
Pearland
Freeport
Lake Jackson
League City
Stafford
Missouri City
Seabrook
La Marque
West University Place
Nassau Bay

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?

Yes. All flights to Houston from Chicago on momondo can be compared and filtered by various policies on offer, including flexible booking.

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

Once you have performed a search in the form on the page, momondo provides useful filters and insights. We can show you the cheapest days and times to fly as well as help filter your options to help you make an informed choice when booking flights to Houston from Chicago.

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

Of course. momondo tracks the price of Chicago to Houston flights. All you need is a valid email address and we will do the rest; it is that quick and easy.

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