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Midway

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

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 2/11. Fares are subject to change and may not be available on all flights or dates of travel.
HOU — MDW
Dec 18 — Dec 251
Thu 12/18
Thu 12/25
1 adult, Economy
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Cheapflights Tip: The best prices from Houston Hobby to Chicago Midway are usually found in September or October, booked 90 days in advance, depart on a Wednesday or Saturday and return on a Wednesday

Cheap flight deals from Hobby to Midway

Discover tips and strategies to find the most affordable flight options for your journey from Hobby (HOU) to Midway (MDW). 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 November 18, 2025.

Most accurate provider

CheapOair
3 stars

Most trusted provider

CheapOair
3 stars

Round-trip from

$117
(Southwest)

One-way from

$59
(Southwest)

Popular in

May

Cheapest in

September

Average price

$210

Good round-trip deal

$208 or less

Good one-way deal

$138 or less
Provider with most accurate pricing for Houston Hobby-Chicago Midway flight deals.
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Provider most trusted by Cheapflights users for Houston Hobby-Chicago Midway flights.
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From Houston Hobby to Chicago Midway
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One-way flight from Houston Hobby to Chicago Midway
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Highest demand for flights based on searches. 13% potential increase in price ($35 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($6 potential savings vs. average RT price).
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Average for round-trip flights in November 2025
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Price to beat on a round-trip flight from Houston Hobby to Chicago Midway.
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Price to beat on a one-way flight from Houston Hobby to Chicago Midway.
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Find flight deals from Hobby to Midway

Cheapest flights from Hobby to Midway
Explore the most affordable flight options available from Hobby to Midway. Find the lowest fares from popular airlines and budget airlines, with prices last updated on November 18, 2025.

This Southwest deal was found by Cheapflights users on 11/18. 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 12/242:35 pmHOU - MDW
Nonstop2h 25mSouthwest
Tue 1/66:15 amMDW - HOU
Nonstop3h 00mSouthwest
Deal found 11/18$117
This Southwest deal was found by Cheapflights users on 11/18. 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 12/242:35 pmHOU - MDW
Nonstop2h 25mSouthwest
Wed 12/3112:00 pmMDW - HOU
1 stop5h 40mSouthwest
Deal found 11/18$127
This Southwest deal was found by Cheapflights users on 11/16. 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 11/2411:00 amHOU - MDW
1 stop5h 30mSouthwest
Thu 11/276:10 amMDW - HOU
1 stop8h 15mSouthwest
Deal found 11/16$137
This Southwest deal was found by Cheapflights users on 11/16. 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 12/106:35 amHOU - MDW
Nonstop2h 25mSouthwest
Wed 12/1010:15 amMDW - HOU
Nonstop2h 55mSouthwest
Deal found 11/16$179
This Southwest deal was found by Cheapflights users on 11/17. 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 12/3010:45 pmHOU - MDW
Nonstop2h 25mSouthwest
Tue 1/67:55 pmMDW - HOU
Nonstop2h 45mSouthwest
Deal found 11/17$188
This Delta deal was found by Cheapflights users on 11/17. 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.
Mon 11/246:48 pmHOU - MDW
1 stop4h 52mDelta
Thu 11/275:34 pmMDW - HOU
1 stop5h 33mDelta
Deal found 11/17$197
This Delta deal was found by Cheapflights users on 11/17. 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.
Wed 12/106:00 amHOU - MDW
1 stop5h 55mDelta
Wed 12/1712:50 pmMDW - HOU
1 stop5h 02mDelta
Deal found 11/17$198
This Delta deal was found by Cheapflights users on 11/16. 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.
Wed 12/106:00 amHOU - MDW
1 stop5h 55mDelta
Wed 12/105:29 pmMDW - HOU
1 stop5h 19mDelta
Deal found 11/16$199
This Southwest deal was found by Cheapflights users on 11/16. 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 12/1111:10 amHOU - MDW
1 stop5h 25mSouthwest
Tue 12/165:15 pmMDW - HOU
Nonstop2h 45mSouthwest
Deal found 11/16$207
This Southwest deal was found by Cheapflights users on 11/17. 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 12/106:35 amHOU - MDW
Nonstop2h 25mSouthwest
Fri 12/129:55 pmMDW - HOU
Nonstop2h 40mSouthwest
Deal found 11/17$208

Cheapflights Fare Finder

 
Customize your flight search to find flights from Hobby to Midway 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 November 18, 2025.
Use the filters below to find and compare flights from Houston Hobby Airport to Chicago Midway Airport that are best for you.

Fly from

Hobby

Fly to

Midway

Route

Depart

Return

Price

HoustonChicago

HOU - MDW

HOUMDW

Houston Hobby

Tue 2/3

5:45 am-11:59 am

1 stop6h 14m

Chicago Midway

Wed 2/4

10:46 am-4:10 pm

1 stop5h 24m

$197

HoustonChicago

HOU - MDW

HOUMDW

Houston Hobby

Tue 1/27

5:04 pm-10:22 pm

1 stop5h 18m

Chicago Midway

Tue 2/3

10:48 am-4:10 pm

1 stop5h 22m

$197

HoustonChicago

HOU - MDW

HOUMDW

Houston Hobby

Sun 12/7

7:25 pm-9:50 pm

Nonstop2h 25m

Chicago Midway

Sun 12/14

9:55 pm-12:35 am

Nonstop2h 40m

$237

HoustonChicago

HOU - MDW

HOUMDW

Houston Hobby

Wed 12/3

2:35 pm-5:00 pm

Nonstop2h 25m

Chicago Midway

Thu 12/11

7:00 am-9:40 am

Nonstop2h 40m

$243

HoustonChicago

HOU - MDW

HOUMDW

Houston Hobby

Wed 12/17

7:45 pm-10:10 pm

Nonstop2h 25m

Chicago Midway

Sat 12/20

8:35 pm-11:20 pm

Nonstop2h 45m

$248

HoustonChicago

HOU - MDW

HOUMDW

Houston Hobby

Sun 12/7

10:39 am-4:18 pm

1 stop5h 39m

Chicago Midway

Mon 12/8

5:29 pm-10:48 pm

1 stop5h 19m

$257

HoustonChicago

HOU - MDW

HOUMDW

Houston Hobby

Mon 12/1

6:50 pm-9:15 pm

Nonstop2h 25m

Chicago Midway

Sat 12/13

1:45 pm-7:20 pm

1 stop5h 35m

$268

HoustonChicago

HOU - MDW

HOUMDW

Houston Hobby

Tue 12/2

6:47 pm-11:47 pm

1 stop5h 00m

Chicago Midway

Sat 12/6

6:00 am-1:28 pm

1 stop7h 28m

$269

HoustonChicago

HOU - MDW

HOUMDW

Houston Hobby

Wed 12/24

3:25 pm-10:22 pm

1 stop6h 57m

Chicago Midway

Wed 1/7

11:21 am-4:10 pm

1 stop4h 49m

$288

HoustonChicago

HOU - MDW

HOUMDW

Houston Hobby

Wed 2/11

11:05 am-1:30 pm

Nonstop2h 25m

$59

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/18

Showing 1-10 of 19 results
1
2

Compare providers for flights from Hobby to Midway

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 Hobby to Midway in November.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy2 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*1 star
eDreamsPrice Accuracy3 starsTrust Score*3 stars
CheapflightsfaresPrice Accuracy3 starsTrust Score*2 stars
CheapOairPrice Accuracy3 starsTrust Score*3 stars
MytripPrice Accuracy3 starsTrust Score*3 stars
JustAirTicketPrice Accuracy-Trust Score*1 star

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

Have a flexible travel schedule? Discover the best time to fly to Midway from Hobby 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 Houston Hobby Airport to Chicago Midway Airport

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

Use this chart to determine the optimal time to book a round-trip flight from Hobby to Midway. Price data was last updated on November 14, 2025.

The price you pay for your flight from Houston Hobby Airport to Chicago Midway Airport may vary depending on when you book. For the best chance of a lower fare, look to book 90 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 Houston Hobby Airport to Chicago Midway Airport?

Currently, January is the cheapest month in which you can book a flight from Houston Hobby Airport to Chicago Midway Airport (average of $53). Flying from Houston Hobby Airport to Chicago Midway Airport in April is currently the most expensive (average of $142). 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 HOU to MDW?

Find hourly flight availability from Hobby to Midway. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated November 18, 2025.

Unlike in the afternoon, when flights are generally more expensive, you can save up to 33% on flights from Houston Hobby Airport to Chicago Midway Airport by exploring options for tickets in the evening.

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

Use this chart to determine the cheapest time to fly round-trip from Hobby to Midway. Price data was last updated on November 2, 2025.

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

The best insider tips for Houston Hobby Airport to Chicago Midway 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 Houston Hobby Airport to Chicago Midway Airport trip
Airports
HOU

HOU offers three types of parking: Valet, Garage, and Economy. Valet is convenient and not much more expensive than Garage.

Read more about HOUby Scott Laird
MDW

Use the Orange Line for a quick, 30-minute ride from MDW to downtown Chicago, operating almost 24 hours a day.

Read more about MDWby Ramsey Qubein
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 Midway

Get insights into the airlines that provide service to Midway. 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 Midway. Reviews last updated November 18, 2025.
Peruse reviews from past customers who have flown with Southwest and Frontier from Houston Hobby Airport to Chicago Midway Airport to help guide your decision. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,245 reviews

Crew

8.6

Comfort

8.0

Entertainment

7.5

Overall

8.0

Boarding

8.1

Food

7.0

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
4,245 reviews
Southwest
8.0
Very good
4,245 reviews

Crew

8.6

Comfort

8.0

Entertainment

7.5

Overall

8.0

Boarding

8.1

Food

7.0

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.
Frontier
5.8
Fair
3,103 reviews
Southwest
8.0
Very good
4,245 reviews

Crew

8.6

Comfort

8.0

Entertainment

7.5

Overall

8.0

Boarding

8.1

Food

7.0

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 Hobby to Midway. 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 Houston Hobby Airport to Chicago Midway Airport?

    Airlines like Delta and Southwest fly from Houston Hobby Airport to Chicago Midway Airport in about 2h 25m. The time it takes to get you to your destination can typically vary by up to 3h 49m. The distance between Houston Hobby Airport and Chicago Midway Airport is about 938 mi. This flight may include one or multiple stops.

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

    Our cheapest airline available from Houston Hobby Airport to Chicago Midway Airport is Frontier. Our recent data shows that you can find tickets from as low as $87 on this airline. An additional option worth looking into is Southwest, starting at $171. You may be able to fly from Houston Hobby Airport to Chicago Midway Airport for 62% less than the average price by searching for these airlines.

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

    Looking for the cheapest flight from Houston Hobby Airport to Chicago Midway Airport? While on average our users pay $249, our data indicates the cheapest price to be $89. The most popular route (Houston Hobby - Chicago Midway), is priced around $99.

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

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

  • How can I find direct flights from Hobby to Midway?

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

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

    Yes. Cheapflights offers flight deals from Hobby to Midway 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 Houston Hobby Airport to Chicago Midway Airport?

    Currently, January is the cheapest month in which you can book a flight from Houston Hobby Airport to Chicago Midway Airport (average of $53). Flying from Houston Hobby Airport to Chicago Midway Airport in April is currently the most expensive (average of $142). 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 Chicago Midway Airport?

Book flights to Chicago Midway Airport if you plan to visit one of these locations
Lansing
Hammond
Porter
Benton Harbor
Merrillville

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Alternative routes for Hobby to Midway

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

Top 2 airlines flying from Hobby to Midway

Discover the top 2 airlines that operate flights from Hobby to Midway. 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 November 18, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$87Average$181FlexibilityNo cancel feeOn-time62%
SouthwestCheapest$171Average$281FlexibilityNo cancel feeOn-time63%

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