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$46+ 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 1/22. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — HOU
Jan 3 — Jan 101
Sat 1/3
Sat 1/10
1 adult, Economy
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1. Tell us where you want to go

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Cheapflights Tip: The best prices from Chicago Midway to Houston Hobby are usually found in September or February, booked 26 days in advance, depart on a Wednesday or Thursday and return on a Wednesday

Cheap 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 December 4, 2025.

This Southwest deal was found by Cheapflights users on 12/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/167:00 amMDW - HOU
Nonstop2h 40mSouthwest
Tue 12/162:35 pmHOU - MDW
Nonstop2h 25mSouthwest
Deal found 12/2$257
This Delta deal was found by Cheapflights users on 12/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/165:39 pmMDW - HOU
1 stop5h 09mDelta
Wed 12/176:47 pmHOU - MDW
1 stop5h 00mDelta
Deal found 12/2$269
This Delta deal was found by Cheapflights users on 12/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/115:13 pmMDW - HOU
1 stop5h 35mDelta
Sat 1/105:45 amHOU - MDW
1 stop4h 47mDelta
Deal found 12/4$292
This Southwest deal was found by Cheapflights users on 12/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/168:35 pmMDW - HOU
Nonstop2h 45mSouthwest
Wed 12/178:45 amHOU - MDW
1 stop5h 25mSouthwest
Deal found 12/3$302
This Southwest deal was found by Cheapflights users on 12/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/155:15 pmMDW - HOU
Nonstop2h 45mSouthwest
Wed 12/176:35 amHOU - MDW
Nonstop2h 25mSouthwest
Deal found 12/3$312
This Southwest deal was found by Cheapflights users on 12/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/158:35 pmMDW - HOU
Nonstop2h 45mSouthwest
Mon 1/59:50 pmHOU - MDW
Nonstop2h 20mSouthwest
Deal found 12/2$313

Find flight deals from Midway to Hobby

Discover tips and strategies to find the most affordable flight options for your journey from Midway (MDW) to Hobby (HOU). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated December 4, 2025.

Most accurate provider

CheapOair
3 stars

Most trusted provider

CheapOair
3 stars

Round-trip from

$168
(Southwest)

One-way from

$46
(Southwest)

Popular in

July

Cheapest in

September

Average price

$220

Good round-trip deal

$277 or less

Good one-way deal

$124 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.
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From Chicago Midway to Houston Hobby
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One-way flight from Chicago Midway to Houston Hobby
Search Deals
Highest demand for flights based on searches. 10% potential increase in price ($28 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($8 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in December 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.
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Cheapflights Fare Finder

 
Customize your flight search to find flights from Midway to Hobby 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, Cheapflights users made 2,558,603 searches. Data last updated December 4, 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

Midway

Fly to

Hobby

Route

Depart

Return

Price

ChicagoHouston

MDW - HOU

MDWHOU

Chicago Midway

Sat 2/28

8:55 pm-11:45 pm

Nonstop2h 50m

Houston Hobby

Fri 3/6

1:55 pm-5:45 pm

1 stop3h 50m

$191

ChicagoHouston

MDW - HOU

MDWHOU

Chicago Midway

Wed 2/18

1:20 pm-5:50 pm

1 stop4h 30m

Houston Hobby

Tue 2/24

9:00 am-2:55 pm

2 stops5h 55m

$194

ChicagoHouston

MDW - HOU

MDWHOU

Chicago Midway

Sun 2/1

5:55 am-8:50 am

Nonstop2h 55m

Houston Hobby

Tue 2/3

11:20 am-4:30 pm

1 stop5h 10m

$196

ChicagoHouston

MDW - HOU

MDWHOU

Chicago Midway

Sat 1/17

11:21 am-4:10 pm

1 stop4h 49m

Houston Hobby

Mon 1/19

5:45 am-11:59 am

1 stop6h 14m

$197

ChicagoHouston

MDW - HOU

MDWHOU

Chicago Midway

Sat 1/17

11:21 am-4:10 pm

1 stop4h 49m

Houston Hobby

Sat 1/24

11:09 am-3:38 pm

1 stop4h 29m

$197

ChicagoHouston

MDW - HOU

MDWHOU

Chicago Midway

Tue 1/6

11:21 am-4:10 pm

1 stop4h 49m

Houston Hobby

Thu 1/8

5:45 am-10:27 am

1 stop4h 42m

$197

ChicagoHouston

MDW - HOU

MDWHOU

Chicago Midway

Tue 1/6

11:21 am-4:10 pm

1 stop4h 49m

Houston Hobby

Wed 1/7

5:04 pm-10:07 pm

1 stop5h 03m

$197

ChicagoHouston

MDW - HOU

MDWHOU

Chicago Midway

Mon 2/23

5:55 am-8:50 am

Nonstop2h 55m

Houston Hobby

Thu 2/26

8:45 pm-11:10 pm

Nonstop2h 25m

$204

ChicagoHouston

MDW - HOU

MDWHOU

Chicago Midway

Thu 1/29

1:20 pm-5:50 pm

1 stop4h 30m

Houston Hobby

Mon 2/2

9:00 am-2:55 pm

2 stops5h 55m

$209

ChicagoHouston

MDW - HOU

MDWHOU

Chicago Midway

Wed 12/17

5:15 pm-10:25 pm

1 stop5h 10m

Houston Hobby

Wed 1/7

3:00 pm-7:00 pm

1 stop4h 00m

$231

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/2

Showing 1-10 of 20 results
1
2

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 December.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy2 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*1 star
eDreamsPrice Accuracy3 starsTrust Score*3 stars
JustAirTicketPrice Accuracy-Trust Score*1 star
CheapflightsfaresPrice Accuracy3 starsTrust Score*2 stars
CheapOairPrice Accuracy3 starsTrust Score*3 stars
PricelinePrice Accuracy1 starTrust Score*3 stars
CheapTicketsDealPrice Accuracy3 starsTrust Score*3 stars
CheapfaremartPrice Accuracy-Trust Score*1 star
Justfly.comPrice Accuracy3 starsTrust 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

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

Use this chart to determine the optimal time to book a round-trip flight from Midway to Hobby. Price data was last updated on November 28, 2025.

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 26 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?

Find hourly flight availability from Midway to Hobby. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated December 4, 2025.

It’s typically best to fly out from Chicago Midway Airport to Houston Hobby Airport in the evening. Doing so could potentially save you 40% 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?

Use this chart to determine the cheapest time to fly round-trip from Midway to Hobby. Price data was last updated on November 29, 2025.

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

AI-powered summary based on content written by travel experts. AI can make mistakes.
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.

Read more about MDWby Ramsey Qubein
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.

Read more about HOUby Scott Laird
Our travel experts
Ramsey Qubein

Ramsey Qubein

Expert on MDW

Ramsey Qubein

Ramsey Qubein

An avid traveler and aviation expert who has visited 173 countries, all 50 states and seven continents, Ramsey Qubein flies nearly 400,000 miles a year. As a North Carolina-based freelance journalist for publications including Conde Nast Traveler, Forbes, USA Today and Bloomberg among others, he explores the latest trends in aviation, hospitality, cruises and business.

Read more
Scott Laird

Scott Laird

Expert on HOU

Scott Laird

Scott Laird

Originally from Anchorage, Alaska, Scott is a frequent contributor to Fodor’s Travel Guide, Conde Nast Traveler, TravelAge West, and TravelPulse. He holds a Bachelor of Science in Organizational Management from Alaska Pacific University and a Master of Science in Airline Management from Embry-Riddle Aeronautical University, and has worked in the airline and hotel industries and as a travel consultant.

Read more

Reviews of airlines servicing Hobby

Get insights into the airlines that provide service to Hobby. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Hobby. Reviews last updated December 4, 2025.
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
4,255 reviews

Crew

8.6

Boarding

8.1

Food

7.0

Comfort

8.0

Overall

8.0

Entertainment

7.5

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
4,255 reviews
Southwest
8.0
Very good
4,255 reviews

Crew

8.6

Boarding

8.1

Food

7.0

Comfort

8.0

Overall

8.0

Entertainment

7.5

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
8,160 reviews
Southwest
8.0
Very good
4,255 reviews

Crew

8.6

Boarding

8.1

Food

7.0

Comfort

8.0

Overall

8.0

Entertainment

7.5

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
3,092 reviews
Southwest
8.0
Very good
4,255 reviews

Crew

8.6

Boarding

8.1

Food

7.0

Comfort

8.0

Overall

8.0

Entertainment

7.5

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

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?

    There are many flights that can get you from Chicago Midway Airport to Houston Hobby Airport in 2h 50m. 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 $68. Other airlines that can offer you cheap pricing are Frontier, from $86, and Southwest, from $178. Spirit Airlines is priced at 72% lower than the current average price of a flight leaving 3 months from now.

  • What are the cheapest airlines to fly from Chicago Midway Airport to Houston Hobby Airport one-way?

    The cheapest airlines for a one-way flight from Chicago Midway Airport to Houston Hobby Airport are Frontier ($49), Southwest ($82), and Delta ($423).

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

    Looking at all options, your cheapest flight can be booked for $58. While the most popular route (Chicago Midway - Houston Hobby) can be booked for $94 on average, our data indicates $268 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

Traveling to a place near Houston Hobby Airport?

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

Browse thousands of different options on Cheapflights for your next trip

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Alternative routes for Midway to Hobby

See prices for flight routes from nearby airports that may be better suited for you.
O'Hare Intl to George Bush Intcntl flights
O'Hare Intl to Hobby flights
Midway to George Bush Intcntl flights

Top 3 airlines flying from Midway to Hobby

Discover the top 3 airlines that operate flights from Midway to Hobby. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated December 4, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$86Average$186FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$116Average$195FlexibilityNo cancel feeOn-time65%
SouthwestCheapest$178Average$332FlexibilityNo cancel feeOn-time63%

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