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$79+ 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 8/27. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — HOU
Aug 2 — Aug 91
Sat 8/2
Sat 8/9
1 adult, Economy
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Cheapflights Tip: The best prices from Chicago Midway to Houston Hobby are usually found in February or September, 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 July 28, 2025.

Round-trip from

$157
(Southwest)

One-way from

$79
(Southwest)

Popular in

July

Cheapest in

February

Average price

$335

Good round-trip deal

$286 or less

Good one-way deal

$141 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. 10% potential increase in price ($29 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 July 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 July 28, 2025.

This Southwest deal was found by Cheapflights users on 7/26. 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 10/85:15 amMDW - HOU
Nonstop2h 35mSouthwest
Tue 10/146:50 pmHOU - MDW
Nonstop2h 30mSouthwest
Deal found 7/26$157
This Delta deal was found by Cheapflights users on 7/26. 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 9/94:25 pmMDW - HOU
1 stop6h 06mDelta
Tue 9/166:00 amHOU - MDW
1 stop5h 48mDelta
Deal found 7/26$217

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 July 28, 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

Tue 10/14

6:50 pm-9:20 pm

Nonstop2h 30m

$157

ChicagoHouston

MDW - HOU

MDWHOU

Chicago Midway

Tue 9/9

4:25 pm-10:31 pm

1 stop6h 06m

Houston Hobby

Tue 9/16

6:00 am-11:48 am

1 stop5h 48m

$217

ChicagoHouston

MDW - HOU

MDWHOU

Chicago Midway

Wed 8/27

8:25 pm-10:55 pm

Nonstop2h 30m

$79

ChicagoHouston

MDW - HOU

MDWHOU

Chicago Midway

Tue 8/26

10:31 am-5:39 pm

1 stop7h 08m

$109

ChicagoHouston

MDW - HOU

MDWHOU

Chicago Midway

Fri 8/8

1:11 pm-7:13 pm

1 stop6h 02m

$123

ChicagoHouston

MDW - HOU

MDWHOU

Chicago Midway

Thu 10/16

11:07 am-11:28 am

2 stops24h 21m

$270

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/28

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 July 25, 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 July 28, 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 44% 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 July 20, 2025.

Travelers seeking maximum savings on their Chicago Midway Airport to Houston Hobby Airport flight should consider departing on Wednesday 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 July 28, 2025.
Read reviews from past customers who have flown Southwest, Delta, and Allegiant Air 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
4,237 reviews

Comfort

8.0

Overall

8.0

Food

7.0

Crew

8.6

Boarding

8.1

Entertainment

7.5

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
Southwest
8.0
Very good
4,237 reviews
Southwest
8.0
Very good
4,237 reviews

Comfort

8.0

Overall

8.0

Food

7.0

Crew

8.6

Boarding

8.1

Entertainment

7.5

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
Delta
8.0
Very good
7,971 reviews
Southwest
8.0
Very good
4,237 reviews

Comfort

8.0

Overall

8.0

Food

7.0

Crew

8.6

Boarding

8.1

Entertainment

7.5

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
Allegiant Air
7.2
Good
702 reviews
Southwest
8.0
Very good
4,237 reviews

Comfort

8.0

Overall

8.0

Food

7.0

Crew

8.6

Boarding

8.1

Entertainment

7.5

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.

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.

  • 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 $157. Another airline that can offer you cheap pricing is Delta. Southwest is priced at 37% 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 Southwest ($79), Delta ($115), and Allegiant Air ($123).

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

    Looking at all options, your cheapest flight can be booked for $88. While the most popular route (Chicago Midway - Houston Hobby) can be booked for $89 on average our data indicates $291 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
Pearland
Freeport
Texas City
Seabrook
Rosenberg
Webster
League City
Lake Jackson
La Marque
Missouri City
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.
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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 July 28, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$68Average$195FlexibilityNo cancel feeOn-time65%
FrontierCheapest$84Average$184FlexibilityNo cancel feeOn-time62%
SouthwestCheapest$179Average$335FlexibilityNo cancel feeOn-time63%

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