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Cheap flights from Chicago Midway Airport to Houston from $90

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 8/24. 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
1 adult, Economy, 0 bags

Discover deals from 900+ travel sites with momondo.

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
5:25 am - 7:50 am
MDW
-
HOU
2h 25mnonstop
Southwest Logo
7:55 pm - 10:15 pm
HOU
-
MDW
2h 20mnonstop
$179Southwest
Thu, Aug 13 - Mon, Aug 17
Southwest Logo
5:25 am - 7:50 am
MDW
-
HOU
2h 25mnonstop
Southwest Logo
7:55 pm - 10:15 pm
HOU
-
MDW
2h 20mnonstop
$180Southwest
Thu, Aug 6 - Thu, Aug 13
Southwest Logo
1:05 pm - 6:25 pm
MDW
-
HOU
5h 20m
1 stop
Southwest Logo
7:55 pm - 10:15 pm
HOU
-
MDW
2h 20mnonstop
$185Southwest
Thu, Aug 6 - Thu, Aug 13
Southwest Logo
5:25 am - 7:50 am
MDW
-
HOU
2h 25mnonstop
Southwest Logo
6:00 pm - 11:20 pm
HOU
-
MDW
5h 20m
1 stop
$189Southwest
Thu, Aug 6 - Thu, Aug 13
Southwest Logo
7:25 am - 9:55 am
MDW
-
HOU
2h 30mnonstop
Southwest Logo
11:30 am - 4:55 pm
HOU
-
MDW
5h 25m
2 stops
$190Southwest
Mon, Aug 24 - Mon, Aug 31
Southwest Logo
1:05 pm - 6:25 pm
MDW
-
HOU
5h 20m
1 stop
Southwest Logo
5:00 am - 7:25 am
HOU
-
MDW
2h 25mnonstop
$191Southwest
Mon, Aug 10 - Mon, Aug 17
Southwest Logo
1:05 pm - 6:25 pm
MDW
-
HOU
5h 20m
1 stop
Southwest Logo
12:10 pm - 5:00 pm
HOU
-
MDW
4h 50m
1 stop
$194Southwest
Thu, Aug 6 - Tue, Aug 11
Southwest Logo
1:05 pm - 6:25 pm
MDW
-
HOU
5h 20m
1 stop
Southwest Logo
3:20 pm - 8:05 pm
HOU
-
MDW
4h 45m
1 stop
$195Southwest
Thu, Aug 13 - Mon, Aug 17
Southwest Logo
10:05 am - 1:55 pm
MDW
-
HOU
3h 50m
1 stop
Southwest Logo
11:30 am - 4:55 pm
HOU
-
MDW
5h 25m
2 stops
$196Southwest
Thu, Aug 20 - Mon, Aug 24
Delta Logo
10:54 am - 4:25 pm
MDW
-
HOU
5h 31m
1 stop
Delta Logo
6:00 am - 11:51 am
HOU
-
MDW
5h 51m
1 stop
$199Delta
Wed, Aug 5 - Wed, Aug 12

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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
Aug 13
MDW5:25 amChicago Midway
2h 25m
HOU7:50 amHouston Hobby
Aug 17
HOU7:55 pmHouston Hobby
2h 20m
MDW10:15 pmChicago Midway
$179
Southwest
Aug 6
MDW5:25 amChicago Midway
2h 25m
HOU7:50 amHouston Hobby
Aug 13
HOU7:55 pmHouston Hobby
2h 20m
MDW10:15 pmChicago Midway
$180
Southwest
Aug 6
MDW1:05 pmChicago Midway
5h 20m
1 stop
HOU6:25 pmHouston Hobby
Aug 13
HOU7:55 pmHouston Hobby
2h 20m
MDW10:15 pmChicago Midway
$185

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
Aug 5
MDW10:54 amChicago Midway
5h 31m
1 stop
HOU4:25 pmHouston Hobby
Aug 12
HOU6:00 amHouston Hobby
5h 51m
1 stop
MDW11:51 amChicago Midway
$199
Delta
Aug 21
MDW5:10 pmChicago Midway
4h 55m
1 stop
HOU10:05 pmHouston Hobby
Aug 25
HOU10:50 amHouston Hobby
5h 25m
1 stop
MDW4:15 pmChicago Midway
$224
Delta
Aug 21
MDW5:10 pmChicago Midway
4h 55m
1 stop
HOU10:05 pmHouston Hobby
Aug 25
HOU10:50 amHouston Hobby
7h 43m
2 stops
MDW6:33 pmChicago Midway
$229

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 July 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

Cheapest round-trip
Quickest round-trip

ChicagoHouston

MDW - HOU

MDWHOU

Chicago Midway

Thu 8/13

5:25 am-7:50 am

Nonstop2h 25m

Houston Hobby

Mon 8/17

7:55 pm-10:15 pm

Nonstop2h 20m

$179

ChicagoHouston

MDW - HOU

MDWHOU

Chicago Midway

Thu 8/6

5:25 am-7:50 am

Nonstop2h 25m

Houston Hobby

Thu 8/13

7:55 pm-10:15 pm

Nonstop2h 20m

$180

ChicagoHouston

MDW - HOU

MDWHOU

Chicago Midway

Thu 8/6

1:05 pm-6:25 pm

1 stop5h 20m

Houston Hobby

Thu 8/13

7:55 pm-10:15 pm

Nonstop2h 20m

$185

ChicagoHouston

MDW - HOU

MDWHOU

Chicago Midway

Thu 8/6

5:25 am-7:50 am

Nonstop2h 25m

Houston Hobby

Thu 8/13

6:00 pm-11:20 pm

1 stop5h 20m

$189

ChicagoHouston

MDW - HOU

MDWHOU

Chicago Midway

Mon 8/24

7:25 am-9:55 am

Nonstop2h 30m

Houston Hobby

Mon 8/31

11:30 am-4:55 pm

2 stops5h 25m

$190

ChicagoHouston

MDW - HOU

MDWHOU

Chicago Midway

Mon 8/10

1:05 pm-6:25 pm

1 stop5h 20m

Houston Hobby

Mon 8/17

5:00 am-7:25 am

Nonstop2h 25m

$191

ChicagoHouston

MDW - HOU

MDWHOU

Chicago Midway

Thu 8/6

1:05 pm-6:25 pm

1 stop5h 20m

Houston Hobby

Tue 8/11

12:10 pm-5:00 pm

1 stop4h 50m

$194

ChicagoHouston

MDW - HOU

MDWHOU

Chicago Midway

Thu 8/13

1:05 pm-6:25 pm

1 stop5h 20m

Houston Hobby

Mon 8/17

3:20 pm-8:05 pm

1 stop4h 45m

$195

ChicagoHouston

MDW - HOU

MDWHOU

Chicago Midway

Thu 8/20

10:05 am-1:55 pm

1 stop3h 50m

Houston Hobby

Mon 8/24

11:30 am-4:55 pm

2 stops5h 25m

$196

ChicagoHouston

MDW - HOU

MDWHOU

Chicago Midway

Wed 8/5

10:54 am-4:25 pm

1 stop5h 31m

Houston Hobby

Wed 8/12

6:00 am-11:51 am

1 stop5h 51m

$199

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
1
2

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 typical price of a round-trip flight between Chicago Midway Airport and Houston Hobby Airport?

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 $163. The month of January is another great option to travel to Houston Hobby Airport, with average flight prices from Chicago Midway Airport averaging around $259.

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 $340. 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 $466.

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 afternoon. momondo users have found flights departing from Chicago Midway Airport to Houston Hobby Airport in the afternoon for as low as $319. 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 $390. 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 from Chicago Midway Airport 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 $301 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 $226 on momondo.

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

There is only 1 cabin class available to choose from on Chicago Midway Airport to Houston Hobby Airport 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 July 2026, prices for Chicago Midway Airport to Houston Hobby Airport flights are approximately 276% 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

$175

Fastest flight time

2h 25m

Direct flights

Every day
The best one-way flight to Houston Hobby Airport from Chicago Midway Airport in the past 72 hours is $175. The best round-trip flight deal from Chicago Midway Airport to Houston Hobby Airport found on momondo in the last 72 hours is $347.
The fastest flight from Chicago Midway Airport to Houston Hobby Airport takes 2h 25m
Direct flights go from Chicago Midway Airport to Houston Hobby Airport every day.
Search flight deals

Frequently asked questions about flying from Chicago Midway Airport to Houston Hobby Airport

  • 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 25m.

  • 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 $90Free CancellationRating
5.6
2,827 reviews
Search Frontier flights
SouthwestPriceFrom $224Free CancellationRating
7.9
4,250 reviews
Search Southwest flights

  • Southwest Flights From Chicago Midway Airport to Houston Hobby Airport

    Across 37 Southwest flights from Chicago Midway Airport to Houston Hobby Airport this week, the average price was $374, with the best Southwest deals starting from $224 round-trip. 4,248 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
Sugar Land
Pasadena
Texas City
Baytown
Rosenberg
Webster
Kemah
Pearland
League City
Freeport
Lake Jackson
Stafford
Seabrook
Missouri City
West University Place
La Marque
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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