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$67+ 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 2/4. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — HOU
Oct 11 — Oct 181
Sat 10/11
Sat 10/18
1 adult, Economy
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Cheapflights Tip: The best prices from Chicago Midway to Houston Hobby are usually found in February or August, booked 53 days in advance, depart on a Wednesday or Thursday and return on a Wednesday

Cheap 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 September 11, 2025.

Round-trip from

$133
(Southwest)

One-way from

$67
(Southwest)

Popular in

July

Cheapest in

February

Average price

$204

Good round-trip deal

$267 or less

Good one-way deal

$195 or less
From Chicago Midway to Houston Hobby
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One-way flight from Chicago Midway to Houston Hobby
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Highest demand for flights based on searches. 9% potential increase in price ($24 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($8 potential savings vs. average RT price).
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Average for round-trip flights in September 2025
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Price to beat on a round-trip flight from Chicago Midway to Houston Hobby.
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Price to beat on a one-way flight from Chicago Midway to Houston Hobby.
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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 September 11, 2025.

This Southwest deal was found by Cheapflights users on 9/11. 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.
Wed 10/16:25 amMDW - HOU
Nonstop2h 30mSouthwest
Tue 10/79:15 pmHOU - MDW
Nonstop2h 20mSouthwest
Deal found 9/11$133
This Southwest deal was found by Cheapflights users on 9/11. 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.
Sat 10/258:25 amMDW - HOU
1 stop4h 05mSouthwest
Tue 10/289:15 pmHOU - MDW
Nonstop2h 20mSouthwest
Deal found 9/11$139
This Southwest deal was found by Cheapflights users on 9/11. 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.
Wed 10/81:00 pmMDW - HOU
Nonstop2h 35mSouthwest
Tue 10/145:00 pmHOU - MDW
1 stop5h 05mSouthwest
Deal found 9/11$143
This Southwest deal was found by Cheapflights users on 9/11. 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.
Sat 10/47:00 amMDW - HOU
Nonstop2h 35mSouthwest
Mon 10/610:25 pmHOU - MDW
Nonstop2h 20mSouthwest
Deal found 9/11$149
This Southwest deal was found by Cheapflights users on 9/11. 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.
Sat 10/1812:15 pmMDW - HOU
Nonstop2h 40mSouthwest
Sat 10/255:20 amHOU - MDW
1 stop6h 20mSouthwest
Deal found 9/11$155
This Southwest deal was found by Cheapflights users on 9/11. 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.
Wed 10/151:00 pmMDW - HOU
Nonstop2h 35mSouthwest
Sat 11/18:10 pmHOU - MDW
Nonstop2h 20mSouthwest
Deal found 9/11$157
This Southwest deal was found by Cheapflights users on 9/10. 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.
Thu 10/25:30 amMDW - HOU
Nonstop2h 30mSouthwest
Mon 10/610:25 pmHOU - MDW
Nonstop2h 20mSouthwest
Deal found 9/10$165

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 September 11, 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

Wed 10/8

5:15 am-7:50 am

Nonstop2h 35m

Houston Hobby

Wed 10/15

9:15 pm-11:35 pm

Nonstop2h 20m

$133

ChicagoHouston

MDW - HOU

MDWHOU

Chicago Midway

Sat 10/4

7:45 pm-10:20 pm

Nonstop2h 35m

Houston Hobby

Wed 10/8

3:35 pm-8:15 pm

1 stop4h 40m

$143

ChicagoHouston

MDW - HOU

MDWHOU

Chicago Midway

Sat 11/8

4:30 pm-7:15 pm

Nonstop2h 45m

Houston Hobby

Mon 11/10

9:50 pm-12:10 am

Nonstop2h 20m

$149

ChicagoHouston

MDW - HOU

MDWHOU

Chicago Midway

Sat 10/4

12:15 pm-2:55 pm

Nonstop2h 40m

Houston Hobby

Mon 10/6

10:25 pm-12:45 am

Nonstop2h 20m

$149

ChicagoHouston

MDW - HOU

MDWHOU

Chicago Midway

Sat 10/4

2:10 pm-7:25 pm

1 stop5h 15m

Houston Hobby

Sun 10/5

10:10 pm-12:30 am

Nonstop2h 20m

$159

ChicagoHouston

MDW - HOU

MDWHOU

Chicago Midway

Fri 12/5

8:35 pm-11:20 pm

Nonstop2h 45m

Houston Hobby

Mon 12/8

5:35 am-11:25 am

1 stop5h 50m

$175

ChicagoHouston

MDW - HOU

MDWHOU

Chicago Midway

Wed 11/19

7:00 am-9:40 am

Nonstop2h 40m

Houston Hobby

Sat 11/22

5:55 pm-8:20 pm

Nonstop2h 25m

$192

ChicagoHouston

MDW - HOU

MDWHOU

Chicago Midway

Wed 10/8

12:40 pm-4:55 pm

1 stop4h 15m

Houston Hobby

Sat 10/11

8:05 pm-10:25 pm

Nonstop2h 20m

$195

ChicagoHouston

MDW - HOU

MDWHOU

Chicago Midway

Mon 10/20

9:30 pm-12:05 am

Nonstop2h 35m

Houston Hobby

Sun 10/26

10:10 pm-12:30 am

Nonstop2h 20m

$197

ChicagoHouston

MDW - HOU

MDWHOU

Chicago Midway

Wed 2/4

8:55 am-11:50 am

Nonstop2h 55m

$67

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/11

Showing 1-10 of 20 results
1
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The best insider tips for Chicago Midway Airport to Houston Hobby Airport flights

Snippets provided in this section are AI-generated based on a summarization of Cheapflights-commissioned articles. The articles are presented as-is, for general informational purposes only, and may not be up-to-date. The opinions contained in the articles are original to the author and reflect their authentic experience, which may vary significantly from the experience of others.
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

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 August 29, 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 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, September is the cheapest month in which you can book a flight from Chicago Midway Airport to Houston Hobby Airport (average of $230). Flying from Chicago Midway Airport to Houston Hobby Airport in March is currently the most expensive (average of $331). 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 September 11, 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 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?

Use this chart to determine the cheapest time to fly round-trip from Midway to Hobby. Price data was last updated on September 7, 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.

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 September 11, 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
4,248 reviews

Entertainment

7.5

Crew

8.6

Boarding

8.1

Comfort

8.0

Overall

8.0

Food

7.0

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
4,248 reviews
Southwest
8.0
Very good
4,248 reviews

Entertainment

7.5

Crew

8.6

Boarding

8.1

Comfort

8.0

Overall

8.0

Food

7.0

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
8,023 reviews
Southwest
8.0
Very good
4,248 reviews

Entertainment

7.5

Crew

8.6

Boarding

8.1

Comfort

8.0

Overall

8.0

Food

7.0

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
3,177 reviews
Southwest
8.0
Very good
4,248 reviews

Entertainment

7.5

Crew

8.6

Boarding

8.1

Comfort

8.0

Overall

8.0

Food

7.0

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 35m. Fly via Southwest to get the fastest option. The distance from Chicago Midway Airport to Houston Hobby Airport is about 938 mi. Most flights are nonstop.

  • 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 $91, and Southwest, from $184. Spirit Airlines is priced at 72% 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 $56 on average, our data indicates $342 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, September is the cheapest month in which you can book a flight from Chicago Midway Airport to Houston Hobby Airport (average of $230). Flying from Chicago Midway Airport to Houston Hobby Airport in March is currently the most expensive (average of $331). 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
Texas City
Seabrook
Rosenberg
Webster
League City
Lake Jackson
La Marque
Missouri City
Pearland
West University Place
Nassau Bay

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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 Hobby flights
O'Hare Intl to George Bush Intcntl 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 September 11, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$68Average$195FlexibilityNo cancel feeOn-time65%
FrontierCheapest$91Average$189FlexibilityNo cancel feeOn-time62%
SouthwestCheapest$184Average$335FlexibilityNo cancel feeOn-time63%

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