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Cheap flights from Chicago Midway Airport to Houston from $72

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 3/5. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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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
8:55 am - 11:50 am
MDW
-
HOU
2h 55mnonstop
Southwest Logo
6:40 am - 9:05 am
HOU
-
MDW
2h 25mnonstop
$143Southwest
Wed, Feb 4 - Tue, Feb 10
Southwest Logo
1:20 pm - 5:50 pm
MDW
-
HOU
4h 30m1 stop
Southwest Logo
8:30 pm - 10:55 pm
HOU
-
MDW
2h 25mnonstop
$149Southwest
Wed, Feb 4 - Tue, Feb 10
Southwest Logo
4:25 pm - 7:15 pm
MDW
-
HOU
2h 50mnonstop
Southwest Logo
11:05 am - 1:30 pm
HOU
-
MDW
2h 25mnonstop
$150Southwest
Sat, Feb 7 - Wed, Feb 11
Southwest Logo
9:35 pm - 12:20 am
MDW
-
HOU
2h 45mnonstop
Southwest Logo
11:05 am - 5:00 pm
HOU
-
MDW
5h 55m1 stop
$153Southwest
Thu, Mar 5 - Wed, Mar 11
Southwest Logo
7:55 pm - 10:40 pm
MDW
-
HOU
2h 45mnonstop
Southwest Logo
2:15 pm - 4:40 pm
HOU
-
MDW
2h 25mnonstop
$157Southwest
Tue, Feb 10 - Wed, Feb 11
Southwest Logo
1:20 pm - 5:50 pm
MDW
-
HOU
4h 30m1 stop
Southwest Logo
12:50 pm - 6:05 pm
HOU
-
MDW
5h 15m1 stop
$159Southwest
Wed, Feb 4 - Tue, Feb 10
Southwest Logo
4:25 pm - 7:15 pm
MDW
-
HOU
2h 50mnonstop
Southwest Logo
11:20 am - 4:30 pm
HOU
-
MDW
5h 10m1 stop
$160Southwest
Sat, Feb 7 - Wed, Feb 11
Southwest Logo
1:20 pm - 5:50 pm
MDW
-
HOU
4h 30m1 stop
Southwest Logo
11:00 am - 4:35 pm
HOU
-
MDW
5h 35m2 stops
$164Southwest
Wed, Feb 4 - Tue, Feb 10
Southwest Logo
4:25 pm - 7:15 pm
MDW
-
HOU
2h 50mnonstop
Southwest Logo
9:00 am - 2:55 pm
HOU
-
MDW
5h 55m2 stops
$166Southwest
Sat, Feb 7 - Wed, Feb 11
Southwest Logo
5:40 pm - 11:55 pm
MDW
-
HOU
6h 15m1 stop
Southwest Logo
4:20 pm - 9:55 pm
HOU
-
MDW
5h 35m2 stops
$168Southwest
Thu, Mar 5 - Wed, Mar 11

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 4
MDW8:55 amChicago Midway
2h 55m
HOU11:50 amHouston Hobby
Feb 10
HOU6:40 amHouston Hobby
2h 25m
MDW9:05 amChicago Midway
$143
Southwest
Feb 4
MDW1:20 pmChicago Midway
4h 30m
1 stop
HOU5:50 pmHouston Hobby
Feb 10
HOU8:30 pmHouston Hobby
2h 25m
MDW10:55 pmChicago Midway
$149
Southwest
Feb 7
MDW4:25 pmChicago Midway
2h 50m
HOU7:15 pmHouston Hobby
Feb 11
HOU11:05 amHouston Hobby
2h 25m
MDW1:30 pmChicago Midway
$150

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
Jan 31
MDW4:30 pmChicago Midway
6h 03m
1 stop
HOU10:33 pmHouston Hobby
Feb 10
HOU5:04 pmHouston Hobby
5h 18m
1 stop
MDW10:22 pmChicago Midway
$207
Delta
Mar 17
MDW6:25 amChicago Midway
7h 03m
1 stop
HOU1:28 pmHouston Hobby
Mar 26
HOU6:00 amHouston Hobby
6h 02m
1 stop
MDW12:02 pmChicago Midway
$234
Delta
Mar 8
MDW5:40 pmChicago Midway
5h 02m
1 stop
HOU10:42 pmHouston Hobby
Mar 15
HOU5:22 pmHouston Hobby
5h 09m
1 stop
MDW10:31 pmChicago Midway
$237

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 January 11, 2026.
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

Wed 2/4

8:55 am-11:50 am

Nonstop2h 55m

Houston Hobby

Tue 2/10

6:40 am-9:05 am

Nonstop2h 25m

$143

ChicagoHouston

MDW - HOU

MDWHOU

Chicago Midway

Wed 2/4

1:20 pm-5:50 pm

1 stop4h 30m

Houston Hobby

Tue 2/10

8:30 pm-10:55 pm

Nonstop2h 25m

$149

ChicagoHouston

MDW - HOU

MDWHOU

Chicago Midway

Sat 2/7

4:25 pm-7:15 pm

Nonstop2h 50m

Houston Hobby

Wed 2/11

11:05 am-1:30 pm

Nonstop2h 25m

$150

ChicagoHouston

MDW - HOU

MDWHOU

Chicago Midway

Thu 3/5

9:35 pm-12:20 am

Nonstop2h 45m

Houston Hobby

Wed 3/11

11:05 am-5:00 pm

1 stop5h 55m

$153

ChicagoHouston

MDW - HOU

MDWHOU

Chicago Midway

Tue 2/10

7:55 pm-10:40 pm

Nonstop2h 45m

Houston Hobby

Wed 2/11

2:15 pm-4:40 pm

Nonstop2h 25m

$157

ChicagoHouston

MDW - HOU

MDWHOU

Chicago Midway

Wed 2/4

1:20 pm-5:50 pm

1 stop4h 30m

Houston Hobby

Tue 2/10

12:50 pm-6:05 pm

1 stop5h 15m

$159

ChicagoHouston

MDW - HOU

MDWHOU

Chicago Midway

Sat 2/7

4:25 pm-7:15 pm

Nonstop2h 50m

Houston Hobby

Wed 2/11

11:20 am-4:30 pm

1 stop5h 10m

$160

ChicagoHouston

MDW - HOU

MDWHOU

Chicago Midway

Wed 2/4

1:20 pm-5:50 pm

1 stop4h 30m

Houston Hobby

Tue 2/10

11:00 am-4:35 pm

2 stops5h 35m

$164

ChicagoHouston

MDW - HOU

MDWHOU

Chicago Midway

Sat 2/7

4:25 pm-7:15 pm

Nonstop2h 50m

Houston Hobby

Wed 2/11

9:00 am-2:55 pm

2 stops5h 55m

$166

ChicagoHouston

MDW - HOU

MDWHOU

Chicago Midway

Thu 3/5

5:40 pm-11:55 pm

1 stop6h 15m

Houston Hobby

Wed 3/11

4:20 pm-9:55 pm

2 stops5h 35m

$168

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 February 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 $337. 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 $578.

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 $262. 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 $371. 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 $257 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 $191 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 January 2026, prices for Chicago Midway Airport to Houston Hobby Airport flights are approximately 2% 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

$210

Fastest flight time

2h 35m

Direct flights

Every day
The best one-way flight to Houston Hobby Airport from Chicago Midway Airport in the past 72 hours is $210. The best round-trip flight deal from Chicago Midway Airport to Houston Hobby Airport found on momondo in the last 72 hours is $233.
The fastest flight from Chicago Midway Airport to Houston Hobby Airport takes 2h 35m
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 35m.

  • 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
5.7
3,057 reviews
Search Frontier flights
Spirit AirlinesPriceFrom $116Free CancellationRating
6.3
8,300 reviews
Search Spirit Airlines flights
SouthwestPriceFrom $180Free CancellationRating
8.0
4,252 reviews
Search Southwest flights

  • Southwest Flights From Chicago Midway Airport to Houston Hobby Airport

    Across 36 Southwest flights from Chicago Midway Airport to Houston Hobby Airport this week, the average price was $332, with the best Southwest deals starting from $180 round-trip. 4,252 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
Sugar Land
Kemah
Pasadena
Baytown
Texas City
Webster
Rosenberg
Pearland
League City
Freeport
Lake Jackson
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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