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Midway

$79+ 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 9/23. Fares are subject to change and may not be available on all flights or dates of travel.
HOU — MDW
Aug 26 — Sep 21
Tue 8/26
Tue 9/2
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 Tuesday 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 August 21, 2025.

Round-trip from

$157
(Southwest)

One-way from

$79
(Southwest)

Popular in

May

Cheapest in

September

Average price

$217

Good round-trip deal

$208 or less

Good one-way deal

$188 or less
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. 8% potential increase in price ($24 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 August 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 August 21, 2025.

This Southwest deal was found by Cheapflights users on 8/19. 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 9/204:20 pmHOU - MDW
Nonstop2h 25mSouthwest
Sat 9/277:20 pmMDW - HOU
Nonstop2h 30mSouthwest
Deal found 8/19$157
This Southwest deal was found by Cheapflights users on 8/19. 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 10/2710:25 pmHOU - MDW
Nonstop2h 20mSouthwest
Tue 10/285:15 amMDW - HOU
Nonstop2h 35mSouthwest
Deal found 8/19$177
This Southwest deal was found by Cheapflights users on 8/19. 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 9/204:20 pmHOU - MDW
Nonstop2h 25mSouthwest
Mon 9/228:45 pmMDW - HOU
Nonstop2h 30mSouthwest
Deal found 8/19$188
This Southwest deal was found by Cheapflights users on 8/19. 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 9/166:35 amHOU - MDW
Nonstop2h 25mSouthwest
Fri 9/198:45 pmMDW - HOU
Nonstop2h 30mSouthwest
Deal found 8/19$197
This Southwest deal was found by Cheapflights users on 8/19. 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 10/43:10 pmHOU - MDW
1 stop3h 55mSouthwest
Sat 11/15:35 pmMDW - HOU
Nonstop2h 35mSouthwest
Deal found 8/19$198
This Southwest deal was found by Cheapflights users on 8/19. 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.
Fri 9/197:00 pmHOU - MDW
1 stop4h 50mSouthwest
Mon 9/228:45 pmMDW - HOU
Nonstop2h 30mSouthwest
Deal found 8/19$207
This Southwest deal was found by Cheapflights users on 8/21. 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 9/225:55 amHOU - MDW
Nonstop2h 25mSouthwest
Tue 9/238:25 pmMDW - HOU
Nonstop2h 30mSouthwest
Deal found 8/21$208
This Delta deal was found by Cheapflights users on 8/19. 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.
Sat 9/1310:44 amHOU - MDW
1 stop4h 42mDelta
Wed 9/1712:43 pmMDW - HOU
1 stop4h 57mDelta
Deal found 8/19$217
This Southwest deal was found by Cheapflights users on 8/20. 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 11/65:05 amHOU - MDW
1 stop4h 50mSouthwest
Mon 11/105:10 amMDW - HOU
Nonstop2h 45mSouthwest
Deal found 8/20$218
This Southwest deal was found by Cheapflights users on 8/20. 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.
Sun 9/2810:05 pmHOU - MDW
Nonstop2h 20mSouthwest
Thu 10/25:30 amMDW - HOU
Nonstop2h 30mSouthwest
Deal found 8/20$219
This Southwest deal was found by Cheapflights users on 8/19. 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 11/156:30 amHOU - MDW
Nonstop2h 25mSouthwest
Sat 11/1510:10 amMDW - HOU
2 stops6h 00mSouthwest
Deal found 8/19$223

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 August 21, 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

Sat 11/15

2:00 pm-4:25 pm

Nonstop2h 25m

Chicago Midway

Sat 11/15

7:30 pm-10:15 pm

Nonstop2h 45m

$157

HoustonChicago

HOU - MDW

HOUMDW

Houston Hobby

Sat 9/20

4:20 pm-6:45 pm

Nonstop2h 25m

Chicago Midway

Sat 9/27

7:20 pm-9:50 pm

Nonstop2h 30m

$157

HoustonChicago

HOU - MDW

HOUMDW

Houston Hobby

Sat 10/4

5:55 pm-8:20 pm

Nonstop2h 25m

Chicago Midway

Sat 11/1

7:45 pm-10:20 pm

Nonstop2h 35m

$157

HoustonChicago

HOU - MDW

HOUMDW

Houston Hobby

Sat 10/25

6:25 am-8:50 am

Nonstop2h 25m

Chicago Midway

Sun 11/2

5:10 am-7:55 am

Nonstop2h 45m

$177

HoustonChicago

HOU - MDW

HOUMDW

Houston Hobby

Sat 9/20

4:20 pm-6:45 pm

Nonstop2h 25m

Chicago Midway

Mon 9/22

8:45 pm-11:15 pm

Nonstop2h 30m

$177

HoustonChicago

HOU - MDW

HOUMDW

Houston Hobby

Thu 10/16

10:25 pm-12:45 am

Nonstop2h 20m

Chicago Midway

Tue 10/21

8:50 pm-11:25 pm

Nonstop2h 35m

$177

HoustonChicago

HOU - MDW

HOUMDW

Houston Hobby

Thu 11/13

7:25 pm-9:50 pm

Nonstop2h 25m

Chicago Midway

Sat 11/15

12:40 pm-3:25 pm

Nonstop2h 45m

$177

HoustonChicago

HOU - MDW

HOUMDW

Houston Hobby

Wed 11/5

7:45 pm-10:10 pm

Nonstop2h 25m

Chicago Midway

Sun 11/9

5:10 am-7:55 am

Nonstop2h 45m

$177

HoustonChicago

HOU - MDW

HOUMDW

Houston Hobby

Mon 9/29

7:35 am-10:05 am

Nonstop2h 30m

Chicago Midway

Wed 10/1

8:25 pm-10:55 pm

Nonstop2h 30m

$177

HoustonChicago

HOU - MDW

HOUMDW

Houston Hobby

Sat 11/1

8:10 pm-10:30 pm

Nonstop2h 20m

Chicago Midway

Sun 11/2

5:10 am-7:55 am

Nonstop2h 45m

$177

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/19

Showing 1-10 of 15 results
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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

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 August 8, 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, April is the cheapest month in which you can book a flight from Houston Hobby Airport to Chicago Midway Airport (average of $160). Flying from Houston Hobby Airport to Chicago Midway Airport in November is currently the most expensive (average of $249). 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 August 21, 2025.

Unlike in the afternoon, when flights are generally more expensive, you can save up to 31% 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 August 17, 2025.

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

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 August 21, 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

Comfort

8.0

Overall

8.0

Crew

8.6

Entertainment

7.5

Food

7.0

Boarding

8.1

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

Comfort

8.0

Overall

8.0

Crew

8.6

Entertainment

7.5

Food

7.0

Boarding

8.1

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
3,207 reviews
Southwest
8.0
Very good
4,245 reviews

Comfort

8.0

Overall

8.0

Crew

8.6

Entertainment

7.5

Food

7.0

Boarding

8.1

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 Southwest fly from Houston Hobby Airport to Chicago Midway Airport in about 2h 25m. The time it takes to get you to your destination is usually consistent. The distance between Houston Hobby Airport and Chicago Midway Airport is about 938 mi. All flights are typically nonstop.

  • 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 $83 on this airline. An additional option worth looking into is Southwest, starting at $177. You may be able to fly from Houston Hobby Airport to Chicago Midway Airport for 65% 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 $287, our data indicates the cheapest price to be $78. The most popular route (Houston Hobby - Chicago Midway), is priced around $50.

  • 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, April is the cheapest month in which you can book a flight from Houston Hobby Airport to Chicago Midway Airport (average of $160). Flying from Houston Hobby Airport to Chicago Midway Airport in November is currently the most expensive (average of $249). 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
Merrillville
Lansing
Hammond
Benton Harbor
Porter
Chesterton

Browse thousands of different options on Cheapflights for your next trip

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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 August 21, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$83Average$168FlexibilityNo cancel feeOn-time62%
SouthwestCheapest$177Average$290FlexibilityNo cancel feeOn-time63%

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