What day of the week experiences the fewest flight delays on this route?

Saturday tends to have the lowest number of delays on this route, whereas Friday has historically faced a higher average of delays compared to other days of the week.

How often are flights from Chicago to Houston delayed?

About 16% of weekly flights between Chicago and Houston have experienced delays in the past year, with the average delay time being 114 minutes.

Which airline has the best punctuality record on Chicago to Houston flights?

Over the last year, Southwest have had the lowest number of delays on this route, with just 16% of flights being delayed.

What is the most punctual flight time for Chicago to Houston flights?

Historically, flights departing in the morning are less likely to be delayed, whereas flights leaving in the early afternoon tend to experience delays more often.

How long is the flight from Chicago Midway Airport to Houston Hobby Airport?

There are many flights that can get you from Chicago Midway Airport to Houston Hobby Airport in 3h. Fly via Southwest or Delta to get the fastest option. The distance from Chicago Midway Airport to Houston Hobby Airport is about 938 mi. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.

What are the cheapest airlines flying from Chicago Midway Airport to Houston Hobby Airport round-trip?

Cheapflights users have booked flights from Chicago Midway Airport to Houston Hobby Airport round-trip from $91. Other airlines that can offer you cheap pricing are Spirit Airlines, from $116, and Southwest, from $178. Frontier is priced at 62% lower than the current average price of a flight leaving 3 months from now.

In terms of precipitation, rainfall in Houston Hobby Airport ranges from 3.2 - 5.9 inches per month. June is typically the wettest month, when rainfall can reach 5.9 in. February is typically the driest time to visit Houston Hobby Airport when rainfall is around 3.2 in.

If weather is an important factor for your trip to Houston Hobby Airport, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 84.2 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 53.6 F).

What are the cheapest flights from Chicago Midway Airport to Houston Hobby Airport?

Looking at all options, your cheapest flight can be booked for $78. While the most popular route (Chicago Midway - Houston Hobby) can be booked for $83 on average, our data indicates $271 when flying from Chicago Midway Airport to Houston Hobby Airport.

What are the most popular airlines that fly from Chicago Midway Airport to Houston Hobby Airport?

Consider Southwest, Frontier or Spirit Airlines when booking your flight. These represent the most popular airlines when flying from Chicago Midway Airport to Houston Hobby Airport.

Most accurate provider : When it comes to deals on Chicago Midway Airport-Houston Hobby Airport flights, users find the pricing of CheapOair to be most consistent on Cheapflights vs. CheapOair Users can find the same prices on Chicago Midway Airport-Houston Hobby Airport flight deals on Cheapflights vs. CheapOair >95% of the time. Price accuracy is based on data collected from Chicago Midway Airport-Houston Hobby Airport flight searches over the past month and is updated monthly.

Most trusted provider : When it comes to deals on Chicago Midway Airport-Houston Hobby Airport flights, Cheapflights users trust CheapOair the most. CheapOair has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Chicago Midway Airport-Houston Hobby Airport flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

Can I find deals for flights from Midway to Hobby that include hotel bookings?

Yes. In addition to deals on Midway to Hobby flights, Cheapflights offers vacation packages that include both flights and hotel.

How can I find direct flights from Midway to Hobby?

After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Midway to Hobby.

Can I find deals for business class flights from Midway to Hobby?

Yes. Cheapflights offers flight deals from Midway to Hobby by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

$59+ Cheap Flights from Chicago Midway Airport to Houston Hobby Airport

Home Search by date Vacation packages Hotels Flight deals Car rental Travel tips & news

Find cheap flights from Midway to Hobby with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

Cheapflights Tip: The best prices from Chicago Midway to Houston Hobby are usually found in September or February, booked 53 days in advance, depart on a Wednesday or Thursday and return on a Wednesday

Cheap flight deals from Midway to Hobby

Most accurate provider	CheapOair 3 stars
Most trusted provider	CheapOair 3 stars
Round-trip from	$117 (Southwest)
One-way from	$59 (Southwest)
Popular in	July
Cheapest in	September
Average price	$237
Good round-trip deal	$259 or less
Good one-way deal	$193 or less

Provider with most accurate pricing for Chicago Midway-Houston Hobby flight deals.

Search Deals

Provider most trusted by Cheapflights users for Chicago Midway-Houston Hobby flights.

Search Deals

From Chicago Midway to Houston Hobby

Search Deals

One-way flight from Chicago Midway to Houston Hobby

Search Deals

Highest demand for flights based on searches. 11% potential increase in price ($32 potential increase over avg. RT price).

Search Deals

Cheapest flight prices on average. 3% potential price decrease ($9 potential savings vs. average RT price).

Search Deals

Average for round-trip flights in October 2025

Search Deals

Price to beat on a round-trip flight from Chicago Midway to Houston Hobby.

Search Deals

Price to beat on a one-way flight from Chicago Midway to Houston Hobby.

Search Deals

Find flight deals from Midway to Hobby

Cheapest flights from Midway to Hobby
Explore the most affordable flight options available from Midway to Hobby. Find the lowest fares from popular airlines and budget airlines, with prices last updated on October 30, 2025.

Thu 12/117:00 amMDW - HOU

Nonstop2h 40mSouthwest

Sat 1/106:00 pmHOU - MDW

Nonstop2h 25mSouthwest

Deal found 10/30

$157

Tue 12/21:05 pmMDW - HOU

Nonstop2h 45mSouthwest

Tue 12/92:35 pmHOU - MDW

Nonstop2h 25mSouthwest

Deal found 10/30

$158

Thu 12/48:35 pmMDW - HOU

Nonstop2h 45mSouthwest

Sat 12/62:00 pmHOU - MDW

Nonstop2h 25mSouthwest

Deal found 10/29

$177

Fri 12/58:35 pmMDW - HOU

Nonstop2h 45mSouthwest

Sun 12/79:50 pmHOU - MDW

Nonstop2h 20mSouthwest

Deal found 10/28

$197

Thu 11/279:25 amMDW - HOU

1 stop5h 15mSouthwest

Thu 12/410:20 amHOU - MDW

Nonstop2h 25mSouthwest

Deal found 10/28

$202

Tue 12/98:35 pmMDW - HOU

Nonstop2h 45mSouthwest

Thu 12/184:50 pmHOU - MDW

Nonstop2h 25mSouthwest

Deal found 10/30

$205

Tue 11/117:00 amMDW - HOU

Nonstop2h 40mSouthwest

Tue 11/187:45 pmHOU - MDW

Nonstop2h 25mSouthwest

Deal found 10/28

$214

Best flights from Midway to Hobby
Discover carefully curated flight deals from Midway to Hobby that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated October 30, 2025.

Wed 1/146:15 amMDW - HOU

Nonstop3h 00mSouthwest

Wed 1/141:35 pmHOU - MDW

1 stop5h 15mSouthwest

Deal found 10/30

$193

Thu 11/275:34 pmMDW - HOU

1 stop5h 33mDelta

Tue 12/26:47 pmHOU - MDW

1 stop5h 00mDelta

Deal found 10/29

$207

Fri 12/58:35 pmMDW - HOU

Nonstop2h 45mSouthwest

Sun 12/77:10 amHOU - MDW

1 stop5h 35mSouthwest

Deal found 10/29

$207

Thu 11/276:00 amMDW - HOU

1 stop7h 28mDelta

Thu 12/46:47 pmHOU - MDW

1 stop5h 00mDelta

Deal found 10/28

$207

Fri 12/56:00 amMDW - HOU

1 stop7h 28mDelta

Sun 12/76:00 amHOU - MDW

1 stop5h 55mDelta

Deal found 10/29

$217

Fri 1/165:55 amMDW - HOU

Nonstop2h 55mSouthwest

Sat 1/2411:25 amHOU - MDW

Nonstop2h 25mSouthwest

Deal found 10/28

$217

Wed 12/318:35 pmMDW - HOU

Nonstop2h 45mSouthwest

Thu 1/16:35 amHOU - MDW

Nonstop2h 25mSouthwest

Deal found 10/29

$220

Tue 11/185:34 pmMDW - HOU

1 stop5h 33mDelta

Wed 11/1910:40 amHOU - MDW

1 stop5h 59mDelta

Deal found 10/29

$234

Sat 11/156:00 amMDW - HOU

1 stop7h 28mDelta

Mon 11/176:48 pmHOU - MDW

1 stop4h 52mDelta

Deal found 10/28

$273

Wed 11/125:15 pmMDW - HOU

Nonstop2h 45mSouthwest

Thu 11/132:10 pmHOU - MDW

1 stop4h 20mSouthwest

Deal found 10/29

$283

Last-minute flights from Midway to Hobby
Discover last-minute flight deals from Midway to Hobby. Data last updated October 30, 2025 and is based on user searches.

Tue 11/117:00 amMDW - HOU

Nonstop2h 40mSouthwest

Tue 11/187:45 pmHOU - MDW

Nonstop2h 25mSouthwest

Deal found 10/28

$214

Fri 11/145:34 pmMDW - HOU

1 stop5h 33mDelta

Wed 12/36:47 pmHOU - MDW

1 stop5h 00mDelta

Deal found 10/28

$257

Sat 11/1510:10 amMDW - HOU

2 stops6h 00mSouthwest

Wed 11/197:45 pmHOU - MDW

Nonstop2h 25mSouthwest

Deal found 10/28

$229

Tue 11/185:34 pmMDW - HOU

1 stop5h 33mDelta

Wed 11/1910:40 amHOU - MDW

1 stop5h 59mDelta

Deal found 10/29

$234

Tue 11/188:35 pmMDW - HOU

Nonstop2h 45mSouthwest

Wed 11/196:35 amHOU - MDW

Nonstop2h 25mSouthwest

Deal found 10/28

$249

Thu 11/275:34 pmMDW - HOU

1 stop5h 33mDelta

Tue 12/26:47 pmHOU - MDW

1 stop5h 00mDelta

Deal found 10/28

$197

Thu 11/279:25 amMDW - HOU

1 stop5h 15mSouthwest

Thu 12/410:20 amHOU - MDW

Nonstop2h 25mSouthwest

Deal found 10/28

$202

Thu 11/279:25 amMDW - HOU

1 stop5h 15mSouthwest

Fri 11/288:30 amHOU - MDW

Nonstop2h 30mSouthwest

Deal found 10/28

$218

One-way flights from Midway to Hobby
Search for one-way flight options from Midway to Hobby. Find affordable one-way fares based on user searches. Data last updated October 30, 2025.

Wed 1/283:30 pmMDW - HOU

Nonstop2h 50mSouthwest

Deal found 10/28

$59

Wed 12/310:20 amMDW - HOU

Nonstop2h 50mSouthwest

Deal found 10/28

$79

Tue 12/25:15 pmMDW - HOU

Nonstop2h 45mSouthwest

Deal found 10/28

$80

Wed 11/198:35 pmMDW - HOU

Nonstop2h 45mSouthwest

Deal found 10/29

$90

Mon 11/245:10 amMDW - HOU

Nonstop2h 45mSouthwest

Deal found 10/29

$94

Fri 12/58:35 pmMDW - HOU

Nonstop2h 45mSouthwest

Deal found 10/29

$99

Wed 11/196:00 amMDW - HOU

1 stop7h 28mDelta

Deal found 10/29

$100

Thu 1/112:00 pmMDW - HOU

1 stop5h 40mSouthwest

Deal found 10/28

$104

Sat 12/610:10 amMDW - HOU

2 stops6h 00mSouthwest

Deal found 10/28

$114

Mon 12/15:00 amMDW - HOU

Nonstop2h 50mSouthwest

Deal found 10/30

$115

Mon 12/85:15 pmMDW - HOU

Nonstop2h 45mSouthwest

Deal found 10/28

$120

Cheapflights Fare Finder

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 1/14

6:15 am-9:15 am

Nonstop3h 00m

Houston Hobby

Wed 1/14

1:35 pm-6:50 pm

1 stop5h 15m

$193

ChicagoHouston

MDW - HOU

MDWHOU

Chicago Midway

Thu 11/27

5:34 pm-11:07 pm

1 stop5h 33m

Houston Hobby

Tue 12/2

6:47 pm-11:47 pm

1 stop5h 00m

$207

ChicagoHouston

MDW - HOU

MDWHOU

Chicago Midway

Fri 12/5

8:35 pm-11:20 pm

Nonstop2h 45m

Houston Hobby

Sun 12/7

7:10 am-12:45 pm

1 stop5h 35m

$207

ChicagoHouston

MDW - HOU

MDWHOU

Chicago Midway

Thu 11/27

6:00 am-1:28 pm

1 stop7h 28m

Houston Hobby

Thu 12/4

6:47 pm-11:47 pm

1 stop5h 00m

$207

ChicagoHouston

MDW - HOU

MDWHOU

Chicago Midway

Fri 12/5

6:00 am-1:28 pm

1 stop7h 28m

Houston Hobby

Sun 12/7

6:00 am-11:55 am

1 stop5h 55m

$217

ChicagoHouston

MDW - HOU

MDWHOU

Chicago Midway

Fri 1/16

5:55 am-8:50 am

Nonstop2h 55m

Houston Hobby

Sat 1/24

11:25 am-1:50 pm

Nonstop2h 25m

$217

ChicagoHouston

MDW - HOU

MDWHOU

Chicago Midway

Wed 12/31

8:35 pm-11:20 pm

Nonstop2h 45m

Houston Hobby

Thu 1/1

6:35 am-9:00 am

Nonstop2h 25m

$220

ChicagoHouston

MDW - HOU

MDWHOU

Chicago Midway

Tue 11/18

5:34 pm-11:07 pm

1 stop5h 33m

Houston Hobby

Wed 11/19

10:40 am-4:39 pm

1 stop5h 59m

$234

ChicagoHouston

MDW - HOU

MDWHOU

Chicago Midway

Sat 11/15

6:00 am-1:28 pm

1 stop7h 28m

Houston Hobby

Mon 11/17

6:48 pm-11:40 pm

1 stop4h 52m

$273

ChicagoHouston

MDW - HOU

MDWHOU

Chicago Midway

Wed 11/12

5:15 pm-8:00 pm

Nonstop2h 45m

Houston Hobby

Thu 11/13

2:10 pm-6:30 pm

1 stop4h 20m

$283

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/30

Showing 1-10 of 21 results

Compare providers for flights from Midway to Hobby

Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Midway to Hobby in October.

Provider	Price Accuracy	Trust Score*
Expedia	Price Accuracy2 stars	Trust Score*3 stars
FlightHub	Price Accuracy3 stars	Trust Score*1 star
eDreams	Price Accuracy3 stars	Trust Score*3 stars
Cheapflightsfares	Price Accuracy3 stars	Trust Score*2 stars
JustAirTicket	Price Accuracy-	Trust Score*1 star
CheapOair	Price Accuracy3 stars	Trust Score*3 stars
Priceline	Price Accuracy1 star	Trust Score*3 stars
CheapTicketsDeal	Price Accuracy3 stars	Trust Score*3 stars
Cheapfaremart	Price Accuracy-	Trust Score*1 star
Justfly.com	Price Accuracy3 stars	Trust Score*3 stars

*The Trust Score is based on feedback from users after their booking experience. It measures overall satisfaction, helping us identify issues like hidden fees, problems during the ticketing process, and the quality of customer service. This score is our best indicator of the provider's quality and reliability.

Most accurate provider: When it comes to deals on Chicago Midway Airport-Houston Hobby Airport flights, users find the pricing of CheapOair to be most consistent on Cheapflights vs. CheapOair Users can find the same prices on Chicago Midway Airport-Houston Hobby Airport flight deals on Cheapflights vs. CheapOair >95% of the time. Price accuracy is based on data collected from Chicago Midway Airport-Houston Hobby Airport flight searches over the past month and is updated monthly.
Most trusted provider: When it comes to deals on Chicago Midway Airport-Houston Hobby Airport flights, Cheapflights users trust CheapOair the most. CheapOair has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Chicago Midway Airport-Houston Hobby Airport flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

Best time to book a flight from Midway to Hobby

Have a flexible travel schedule? Discover the best time to fly to Hobby from Midway with our price prediction graph.

Estimated round-trip price

Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

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

Prices

Delays

How far ahead should I book a flight from Chicago Midway Airport to Houston Hobby Airport?

The price you pay for your flight from Chicago Midway Airport to Houston Hobby Airport may vary depending on when you book. For the best chance of a lower fare, look to book 53 days in advance of your trip. Fares are likely to increase a fortnight or so before your departure date.

What is the cheapest month to book a flight from Chicago Midway Airport to Houston Hobby Airport?

Currently, April is the cheapest month in which you can book a flight from Chicago Midway Airport to Houston Hobby Airport (average of $81). Flying from Chicago Midway Airport to Houston Hobby Airport in July is currently the most expensive (average of $205). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

What is the cheapest time of day to fly from MDW to HOU?

It’s typically best to fly out from Chicago Midway Airport to Houston Hobby Airport in the evening. Doing so could potentially save you 42% on the flight price compared to flying in the morning, which is usually more expensive.

What is the cheapest day to fly from Chicago Midway Airport to Houston Hobby Airport?

Travelers seeking maximum savings on their Chicago Midway Airport to Houston Hobby Airport flight should consider departing on Saturday evenings when fares are most often at their lowest. Sunday at noon flights should be avoided if possible as fares are typically the most expensive at this time.

The best insider tips for Chicago Midway Airport to Houston Hobby Airport flights

Cheapflights partnered with top experts to bring you the best recommendations for your Chicago Midway Airport to Houston Hobby Airport trip

Airports

MDW

Use the Orange Line train for a quick, cost-effective way to reach MDW. It connects directly to the airport and operates almost 24 hours.

HOU

HOU is easy to navigate with a single terminal. Consider using a map app for real-time traffic updates when traveling to or from the airport.

Our travel experts

Ramsey Qubein

Expert on MDW

Scott Laird

Expert on HOU

Reviews of airlines servicing Hobby

Read reviews from past customers who have flown Southwest, Spirit Airlines, and Frontier from Chicago Midway Airport to Houston Hobby Airport. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.

Southwest

8.0

Very good

4,243 reviews

Reviews

1 / 20

2.0

Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines

Southwest

8.0

Very good

4,243 reviews

Southwest

8.0

Very good

4,243 reviews

Reviews

1 / 20

2.0

Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines

Spirit Airlines

6.3

Okay

8,116 reviews

Southwest

8.0

Very good

4,243 reviews

Reviews

1 / 20

2.0

Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines

Frontier

5.8

Fair

3,123 reviews

Southwest

8.0

Very good

4,243 reviews

Reviews

1 / 20

2.0

Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines

Related info for your journey

How long is the flight from Chicago Midway Airport to Houston Hobby Airport?
There are many flights that can get you from Chicago Midway Airport to Houston Hobby Airport in 3h. Fly via Southwest or Delta to get the fastest option. The distance from Chicago Midway Airport to Houston Hobby Airport is about 938 mi. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.
What are the cheapest airlines flying from Chicago Midway Airport to Houston Hobby Airport round-trip?
Cheapflights users have booked flights from Chicago Midway Airport to Houston Hobby Airport round-trip from $91. Other airlines that can offer you cheap pricing are Spirit Airlines, from $116, and Southwest, from $178. Frontier is priced at 62% lower than the current average price of a flight leaving 3 months from now.
What are the cheapest flights from Chicago Midway Airport to Houston Hobby Airport?
Looking at all options, your cheapest flight can be booked for $78. While the most popular route (Chicago Midway - Houston Hobby) can be booked for $83 on average, our data indicates $271 when flying from Chicago Midway Airport to Houston Hobby Airport.
Can I find deals for flights from Midway to Hobby that include hotel bookings?
Yes. In addition to deals on Midway to Hobby flights, Cheapflights offers vacation packages that include both flights and hotel.
How can I find direct flights from Midway to Hobby?
After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Midway to Hobby.
Can I find deals for business class flights from Midway to Hobby?
Yes. Cheapflights offers flight deals from Midway to Hobby by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.
What is the cheapest month to book a flight from Chicago Midway Airport to Houston Hobby Airport?
Currently, April is the cheapest month in which you can book a flight from Chicago Midway Airport to Houston Hobby Airport (average of $81). Flying from Chicago Midway Airport to Houston Hobby Airport in July is currently the most expensive (average of $205). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

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Top 3 airlines flying from Midway to Hobby

Airline	Cheapest	Average	Flexibility	On-time
Frontier	Cheapest$91	Average$192	FlexibilityNo cancel fee	On-time62%
Spirit Airlines	Cheapest$116	Average$195	FlexibilityNo cancel fee	On-time65%
Southwest	Cheapest$178	Average$333	FlexibilityNo cancel fee	On-time63%

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$59+ Cheap flights from Midway (MDW) to Hobby (HOU)

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 1/28. Fares are subject to change and may not be available on all flights or dates of travel.

Find cheap flights from Midway to Hobby with Cheapflights

1. Tell us where you want to go

2. Select your favorite providers

3. Compare prices and book

Cheapflights Tip: The best prices from Chicago Midway to Houston Hobby are usually found in September or February, booked 53 days in advance, depart on a Wednesday or Thursday and return on a Wednesday

Cheap flight deals from Midway to Hobby

Most accurate provider

Most trusted provider

Round-trip from

One-way from

Popular in

Cheapest in

Average price

Good round-trip deal

Good one-way deal

Find flight deals from Midway to Hobby

Cheapest flights from Midway to HobbyExplore the most affordable flight options available from Midway to Hobby. Find the lowest fares from popular airlines and budget airlines, with prices last updated on October 30, 2025.

Explore the most affordable flight options available from Midway to Hobby. Find the lowest fares from popular airlines and budget airlines, with prices last updated on October 30, 2025.

Cheapflights Fare Finder

Use the filters below to find and compare flights from Chicago Midway Airport to Houston Hobby Airport that are best for you.

Compare providers for flights from Midway to Hobby

Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.

Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Midway to Hobby in October.

Best time to book a flight from Midway to Hobby

Have a flexible travel schedule? Discover the best time to fly to Hobby from Midway with our price prediction graph.

Cheapflights Insights

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

How far ahead should I book a flight from Chicago Midway Airport to Houston Hobby Airport?

What is the cheapest month to book a flight from Chicago Midway Airport to Houston Hobby Airport?

What is the cheapest time of day to fly from MDW to HOU?

What is the cheapest day to fly from Chicago Midway Airport to Houston Hobby Airport?

How often are flights from Chicago to Houston delayed?

What is the most punctual flight time for Chicago to Houston flights?

What day of the week experiences the fewest flight delays on this route?

Which airline has the best punctuality record on Chicago to Houston flights?

The best insider tips for Chicago Midway Airport to Houston Hobby Airport flights

Cheapflights partnered with top experts to bring you the best recommendations for your Chicago Midway Airport to Houston Hobby Airport trip

Airports

MDW

HOU

Our travel experts

Reviews of airlines servicing Hobby

Read reviews from past customers who have flown Southwest, Spirit Airlines, and Frontier from Chicago Midway Airport to Houston Hobby Airport. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.

Related info for your journey

Find useful and relevant information for your journey from Midway to Hobby. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

How long is the flight from Chicago Midway Airport to Houston Hobby Airport?

What are the cheapest airlines flying from Chicago Midway Airport to Houston Hobby Airport round-trip?

What are the cheapest flights from Chicago Midway Airport to Houston Hobby Airport?

Can I find deals for flights from Midway to Hobby that include hotel bookings?

How can I find direct flights from Midway to Hobby?

Can I find deals for business class flights from Midway to Hobby?

What is the cheapest month to book a flight from Chicago Midway Airport to Houston Hobby Airport?

Traveling to a place near Houston Hobby Airport?

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for Midway to Hobby

See prices for flight routes from nearby airports that may be better suited for you.

Top 3 airlines flying from Midway to Hobby

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Cheapest flights from Midway to Hobby
Explore the most affordable flight options available from Midway to Hobby. Find the lowest fares from popular airlines and budget airlines, with prices last updated on October 30, 2025.