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$53+ 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 5/16. Fares are subject to change and may not be available on all flights or dates of travel.
HOU — MDW
Apr 27 — May 41
Sun 4/27
Sun 5/4
1 adult, Economy
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Cheapflights Tip: The best prices from Houston to Chicago Midway are usually found in August or June, booked 90 days in advance, depart on a Wednesday or Friday 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 April 22, 2025.

Round-trip from

$96
(Cheapflightsfares)

One-way from

$53
(Cheapflightsfares)

Popular in

December

Cheapest in

August

Average price

$256
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. 14% potential increase in price ($37 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 April 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 April 22, 2025.

This Cheapflightsfares deal was found by Cheapflights users on 4/21. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/167:40 pmIAH - MDW
Nonstop2h 33mFrontier
Wed 5/2112:21 pmMDW - IAH
Nonstop2h 57mFrontier
Deal found 4/21$96
This Southwest deal was found by Cheapflights users on 4/20. 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.
Wed 5/215:45 pmHOU - MDW
Nonstop2h 30mSouthwest
Wed 5/281:25 pmMDW - HOU
Nonstop2h 40mSouthwest
Deal found 4/20$187
This Delta deal was found by Cheapflights users on 4/22. 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 7/167:15 amIAH - MDW
1 stop7h 41mDelta
Wed 7/239:30 amMDW - IAH
1 stop6h 13mDelta
Deal found 4/22$217
This Delta deal was found by Cheapflights users on 4/21. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/136:00 amHOU - MDW
1 stop5h 53mDelta
Wed 5/1410:25 amMDW - HOU
1 stop7h 32mDelta
Deal found 4/21$219
This Mytrip deal was found by Cheapflights users on 4/21. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/176:36 amIAH - MDW
3 stops31h 37mMultiple Airlines
Mon 5/199:42 amMDW - IAH
3 stops27h 06mMultiple Airlines
Deal found 4/21$364

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 April 22, 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

IAH - MDW

IAHMDW

Houston George Bush Intcntl

Fri 5/16

7:40 pm-10:13 pm

Nonstop2h 33m

Chicago Midway

Wed 5/21

12:21 pm-3:18 pm

Nonstop2h 57m

$96

HoustonChicago

HOU - MDW

HOUMDW

Houston Hobby

Wed 5/21

5:45 pm-8:15 pm

Nonstop2h 30m

Chicago Midway

Wed 5/28

1:25 pm-4:05 pm

Nonstop2h 40m

$187

HoustonChicago

IAH - MDW

IAHMDW

Houston George Bush Intcntl

Wed 7/16

7:15 am-2:56 pm

1 stop7h 41m

Chicago Midway

Wed 7/23

9:30 am-3:43 pm

1 stop6h 13m

$217

HoustonChicago

HOU - MDW

HOUMDW

Houston Hobby

Tue 5/13

6:00 am-11:53 am

1 stop5h 53m

Chicago Midway

Wed 5/14

10:25 am-5:57 pm

1 stop7h 32m

$219

HoustonChicago

IAH - MDW

IAHMDW

Houston George Bush Intcntl

Sat 5/17

6:36 am-2:13 pm

3 stops31h 37m

Chicago Midway

Mon 5/19

9:42 am-12:48 pm

3 stops27h 06m

$364

HoustonChicago

IAH - MDW

IAHMDW

Houston George Bush Intcntl

Fri 5/16

7:40 pm-10:13 pm

Nonstop2h 33m

$53

HoustonChicago

HOU - MDW

HOUMDW

Houston Hobby

Wed 5/21

5:45 pm-8:15 pm

Nonstop2h 30m

$89

HoustonChicago

IAH - MDW

IAHMDW

Houston George Bush Intcntl

Thu 5/15

7:05 am-11:39 pm

1 stop16h 34m

$97

HoustonChicago

HOU - MDW

HOUMDW

Houston Hobby

Wed 5/28

6:00 am-11:53 am

1 stop5h 53m

$109

HoustonChicago

IAH - MDW

IAHMDW

Houston George Bush Intcntl

Wed 5/28

7:05 am-11:53 am

1 stop4h 48m

$109

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/21

Showing 1-10 of 12 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

Enjoy free snacks and non-alcoholic beverages on board, enhancing your short-haul flight experience.


Southwest offers two free checked bags, including oversized items like skis or golf clubs.

Read more about Southwestby Marisa Garcia
Airports
IAH

Check security wait times on the IAH website to ensure a smooth departure process.

Read more about IAHby Evie Carrick
MDW

Use the Orange Line train for a quick, affordable trip 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 April 18, 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 April 22, 2025.

Unlike at noon, when flights are generally more expensive, you can save up to 39% 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 March 30, 2025.

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

Rainfall in Midway by month

Plan your trip to Midway by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Chicago Midway Airport ranges from 1.7 - 4.9 inches per month. August is typically the wettest month, when rainfall can reach 4.9 in. January is typically the driest time to visit Chicago Midway Airport when rainfall is around 1.7 in.

Temperature in Midway by month

Plan your trip to Midway by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Chicago Midway Airport, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 73.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 23.0 F).

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 April 22, 2025.
Read through reviews of airlines operating flights from Houston to Chicago, such as Southwest, Delta and Allegiant Air. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,287 reviews

Food

7.1

Boarding

8.2

Comfort

8.0

Crew

8.6

Entertainment

7.6

Overall

8.0

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
4,287 reviews
Southwest
8.0
Very good
4,287 reviews

Food

7.1

Boarding

8.2

Comfort

8.0

Crew

8.6

Entertainment

7.6

Overall

8.0

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.
Delta
8.0
Very good
7,920 reviews
Southwest
8.0
Very good
4,287 reviews

Food

7.1

Boarding

8.2

Comfort

8.0

Crew

8.6

Entertainment

7.6

Overall

8.0

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.
Allegiant Air
7.3
Good
734 reviews
Southwest
8.0
Very good
4,287 reviews

Food

7.1

Boarding

8.2

Comfort

8.0

Crew

8.6

Entertainment

7.6

Overall

8.0

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
6.0
Okay
3,283 reviews
Southwest
8.0
Very good
4,287 reviews

Food

7.1

Boarding

8.2

Comfort

8.0

Crew

8.6

Entertainment

7.6

Overall

8.0

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 Houston to Midway. 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 Houston to Chicago Midway Airport round-trip?

    Currently priced at $96, 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 $188 and $217, respectively. Frontier is currently priced 56% 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 $53. Southwest flights start at $89 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 $88. While the most popular route (Houston Hobby - Chicago Midway) can be booked for $106 on average our data indicates $257 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 Houston?

Book flights to Houston if you plan to visit one of these locations
Merrillville
Hammond
Benton Harbor
Porter
Lansing
Valparaiso
Chesterton

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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 April 22, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$67Average$152FlexibilityNo cancel feeOn-time62%
SouthwestCheapest$190Average$339FlexibilityNo cancel feeOn-time63%
DeltaCheapest$216Average$395FlexibilityNo cancel feeOn-timeN/A

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