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Midway

$52+ Cheap flights from Houston 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 11/6. Fares are subject to change and may not be available on all flights or dates of travel.
HOU — MDW
Oct 31 — Nov 71
Fri 10/31
Fri 11/7
1 adult, Economy
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Cheapflights Tip: The best prices from Houston 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 Houston to Midway

Discover tips and strategies to find the most affordable flight options for your journey from Houston (HO1) 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 October 1, 2025.

Round-trip from

$97
(Trip.com)

One-way from

$52
(Trip.com)

Popular in

May

Cheapest in

September

Average price

$190
From Houston to Chicago Midway
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One-way flight from Houston to Chicago Midway
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Highest demand for flights based on searches. 10% potential increase in price ($27 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 October 2025
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Find flight deals from Houston to Midway

Cheapest flights from Houston to Midway
Explore the most affordable flight options available from Houston to Midway. Find the lowest fares from popular airlines and budget airlines, with prices last updated on October 1, 2025.

This Priceline deal was found by Cheapflights users on 9/28. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/232:12 pmIAH - MDW
Nonstop2h 30mFrontier
Sat 10/2510:00 amMDW - IAH
Nonstop2h 52mFrontier
Deal found 9/28$98
This Frontier deal was found by Cheapflights users on 9/29. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/110:04 amIAH - MDW
Nonstop2h 33mFrontier
Sun 11/25:30 amMDW - IAH
Nonstop2h 49mFrontier
Deal found 9/29$100
This Frontier deal was found by Cheapflights users on 9/29. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/251:39 pmIAH - MDW
Nonstop2h 30mFrontier
Fri 10/316:30 amMDW - IAH
Nonstop2h 49mFrontier
Deal found 9/29$102
This Frontier deal was found by Cheapflights users on 9/29. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/251:39 pmIAH - MDW
Nonstop2h 30mFrontier
Sun 11/25:30 amMDW - IAH
Nonstop2h 49mFrontier
Deal found 9/29$104
This Kiwi.com deal was found by Cheapflights users on 9/29. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/3110:04 amIAH - MDW
Nonstop2h 33mFrontier
Sat 11/16:30 amMDW - IAH
Nonstop2h 49mFrontier
Deal found 9/29$106
This Frontier deal was found by Cheapflights users on 9/29. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/3010:04 amIAH - MDW
Nonstop2h 33mFrontier
Fri 10/316:30 amMDW - IAH
Nonstop2h 49mFrontier
Deal found 9/29$110
This Cheapflightsfares deal was found by Cheapflights users on 9/30. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/111:39 pmIAH - MDW
Nonstop2h 30mFrontier
Sat 10/1810:00 amMDW - IAH
Nonstop2h 52mFrontier
Deal found 9/30$111
This Frontier deal was found by Cheapflights users on 9/29. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/232:12 pmIAH - MDW
Nonstop2h 30mFrontier
Sun 11/25:30 amMDW - IAH
Nonstop2h 49mFrontier
Deal found 9/29$112
This Cheapflightsfares deal was found by Cheapflights users on 9/30. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/111:39 pmIAH - MDW
Nonstop2h 30mFrontier
Thu 10/2310:30 amMDW - IAH
Nonstop2h 52mFrontier
Deal found 9/30$113
This Priceline deal was found by Cheapflights users on 10/1. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/181:39 pmIAH - MDW
Nonstop2h 30mFrontier
Fri 10/311:37 pmMDW - IAH
1 stop8h 29mFrontier
Deal found 10/1$115
This Frontier deal was found by Cheapflights users on 10/1. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/251:39 pmIAH - MDW
Nonstop2h 30mFrontier
Mon 10/279:45 amMDW - IAH
1 stop6h 58mFrontier
Deal found 10/1$116
This Southwest deal was found by Cheapflights users on 9/30. 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 10/312:40 pmHOU - MDW
Nonstop2h 25mSouthwest
Sat 11/17:45 pmMDW - HOU
Nonstop2h 35mSouthwest
Deal found 9/30$157

Cheapflights Fare Finder

 
Customize your flight search to find flights from Houston 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 October 1, 2025.
Use the filters below to find and compare flights from Houston to Chicago Midway Airport that are best for you.

Fly from

Houston

Fly to

Midway

Route

Depart

Return

Price

HoustonChicago

HOU - MDW

HOUMDW

Houston Hobby

Thu 10/30

6:15 am-8:40 am

Nonstop2h 25m

Chicago Midway

Wed 11/5

5:15 pm-8:00 pm

Nonstop2h 45m

$177

HoustonChicago

HOU - MDW

HOUMDW

Houston Hobby

Thu 10/30

6:15 am-8:40 am

Nonstop2h 25m

Chicago Midway

Tue 11/4

8:35 pm-11:20 pm

Nonstop2h 45m

$177

HoustonChicago

HOU - MDW

HOUMDW

Houston Hobby

Wed 12/3

6:35 am-9:00 am

Nonstop2h 25m

Chicago Midway

Sun 12/7

5:10 am-7:55 am

Nonstop2h 45m

$177

HoustonChicago

HOU - MDW

HOUMDW

Houston Hobby

Sat 11/8

4:10 pm-6:35 pm

Nonstop2h 25m

Chicago Midway

Mon 11/10

9:55 pm-12:35 am

Nonstop2h 40m

$177

HoustonChicago

HOU - MDW

HOUMDW

Houston Hobby

Sat 11/8

4:10 pm-6:35 pm

Nonstop2h 25m

Chicago Midway

Sun 11/9

5:10 am-7:55 am

Nonstop2h 45m

$177

HoustonChicago

HOU - MDW

HOUMDW

Houston Hobby

Tue 10/28

9:15 pm-11:35 pm

Nonstop2h 20m

Chicago Midway

Tue 11/4

5:15 pm-8:00 pm

Nonstop2h 45m

$177

HoustonChicago

HOU - MDW

HOUMDW

Houston Hobby

Tue 12/2

3:00 pm-7:05 pm

1 stop4h 05m

Chicago Midway

Sat 12/6

7:30 pm-10:15 pm

Nonstop2h 45m

$188

HoustonChicago

HOU - MDW

HOUMDW

Houston Hobby

Sat 11/15

2:00 pm-4:25 pm

Nonstop2h 25m

Chicago Midway

Sun 11/16

8:00 am-10:50 am

Nonstop2h 50m

$197

HoustonChicago

HOU - MDW

HOUMDW

Houston Hobby

Fri 12/5

7:45 pm-10:10 pm

Nonstop2h 25m

Chicago Midway

Mon 12/8

6:20 am-11:20 am

1 stop5h 00m

$207

HoustonChicago

IAH - MDW

IAHMDW

Houston George Bush Intcntl

Thu 10/30

6:40 am-1:08 pm

1 stop6h 28m

Chicago Midway

Tue 11/4

10:40 am-3:26 pm

1 stop4h 46m

$217

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/1

Showing 1-10 of 43 results
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The best insider tips for Houston 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 to Chicago Midway Airport trip
Airlines
Frontier

Frontier's UpFront Plus seats guarantee an empty middle seat for extra comfort.


Book early morning flights for better on-time performance and fewer delays.

Read more about Frontierby Marisa Garcia
Southwest

Southwest offers free snacks and non-alcoholic beverages, enhancing your short-haul flight experience.


Enjoy free messaging and in-flight entertainment on Southwest, perfect for short flights.

Read more about Southwestby Marisa Garcia
Airports
IAH

Check the IAH Depart tab for current security wait times to ensure a smooth departure.

Read more about IAHby Evie Carrick
MDW

Use the 'L' train for a quick, 30-minute ride to downtown Chicago from MDW.

Read more about MDWby Ramsey Qubein
Our travel experts
Marisa Garcia

Marisa Garcia

Expert on Frontier and Southwest

Marisa Garcia

Marisa Garcia

Marisa knows planes inside and out, spending 16 years working on aircraft in hangars at airports around the world. She is an aviation industry expert, specialized in airline interiors and regulations. Ten years ago, she pivoted to journalism. She shares her insights in leading aviation, travel, and business publications and on her site FlightChic.

Read more
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
Evie Carrick

Evie Carrick

Expert on IAH

Evie Carrick

Evie Carrick

Evie Carrick is a writer and editor who has lived in five countries and traveled to over 50, with extensive experience flying around the world. She was born in Colorado, but has spent time flying to both coasts to visit family. She writes regularly for Travel + Leisure, BuzzFeed, and SKI and recently published seven travel journals with Simon & Schuster.

Read more

Best time to book a flight from Houston to Midway

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

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

Use this chart to determine the optimal time to book a round-trip flight from Houston to Midway. Price data was last updated on September 26, 2025.

The price you pay for your flight from Houston 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 to Chicago Midway Airport?

Currently, April is the cheapest month in which you can book a flight from Houston to Chicago Midway Airport (average of $160). Flying from Houston 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 Houston 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 October 1, 2025.

Unlike in the afternoon, when flights are generally more expensive, you can save up to 36% on flights from Houston to Chicago Midway Airport by exploring options for tickets in the evening.

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

Use this chart to determine the cheapest time to fly round-trip from Houston to Midway. Price data was last updated on September 28, 2025.

Travelers seeking maximum savings on their Houston to Chicago Midway Airport flight should consider departing on Monday evenings 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.

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 October 1, 2025.
Get a feel of what it's like to fly with Southwest, Delta, and Frontier from Houston to Chicago Midway Airport by reading reviews from past customers. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,248 reviews

Comfort

8.0

Entertainment

7.5

Overall

8.0

Boarding

8.1

Food

7.0

Crew

8.6

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

Comfort

8.0

Entertainment

7.5

Overall

8.0

Boarding

8.1

Food

7.0

Crew

8.6

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
7,961 reviews
Southwest
8.0
Very good
4,248 reviews

Comfort

8.0

Entertainment

7.5

Overall

8.0

Boarding

8.1

Food

7.0

Crew

8.6

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
3,154 reviews
Southwest
8.0
Very good
4,248 reviews

Comfort

8.0

Entertainment

7.5

Overall

8.0

Boarding

8.1

Food

7.0

Crew

8.6

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 Houston 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 to Chicago Midway Airport?

    For as low as $177, Southwest can have you in Chicago Midway Airport from Houston in 2h 25m. Houston and Chicago Midway Airport are separated by a distance of 938 mi. Both multi-stop and nonstop flights can be found to your destination and back.

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

    Currently priced at $83, Frontier will fly you from Houston to Chicago Midway Airport and back. In addition to Frontier, many other airlines offer competitively priced options for your trip. Search Cheapflights for deals from Southwest and Delta - these airlines can fly you to your destination from $172 and $216, respectively. Frontier is currently priced 65% below the average price you’ll pay for this route.

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

    To fly one-way, consider booking your trip with Frontier, which is currently one of the cheapest options available, starting at $77. Southwest flights start at $79 while deals on Delta start at $109 one-way.

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

    Looking at all options, your cheapest flight can be booked for $78. While the most popular route (Houston Hobby - Chicago Midway) can be booked for $100 on average, our data indicates $286 when flying from Houston to Chicago Midway Airport.

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

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

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

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

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

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

    Currently, April is the cheapest month in which you can book a flight from Houston to Chicago Midway Airport (average of $160). Flying from Houston 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

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Alternative routes for Houston to Midway

See prices for flight routes from nearby airports that may be better suited for you.
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Top 3 airlines flying from Houston to Midway

Discover the top 3 airlines that operate flights from Houston 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 October 1, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$83Average$180FlexibilityNo cancel feeOn-time62%
SouthwestCheapest$172Average$283FlexibilityNo cancel feeOn-time63%
DeltaCheapest$216Average$331FlexibilityNo cancel feeOn-timeN/A

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