$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 2/16. Fares are subject to change and may not be available on all flights or dates of travel.
Find cheap flights from Houston to Midway with Cheapflights
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Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”2. Select your favorite providers
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Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.Cheap flight deals from Houston to Midway
Cheapest flights from Houston to MidwayExplore 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 January 28, 2026.
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 January 28, 2026.
This Kiwi.com deal was found by Cheapflights users on 1/26. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
This Kiwi.com deal was found by Cheapflights users on 1/27. 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.
This Super.com deal was found by Cheapflights users on 1/26. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
This Super.com deal was found by Cheapflights users on 1/26. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
This Expedia deal was found by Cheapflights users on 1/26. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
This Super.com deal was found by Cheapflights users on 1/28. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
This Frontier deal was found by Cheapflights users on 1/26. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
This Southwest deal was found by Cheapflights users on 1/27. 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.
This Southwest deal was found by Cheapflights users on 1/25. 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.
This Southwest deal was found by Cheapflights users on 1/26. 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.
This Southwest deal was found by Cheapflights users on 1/25. 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.
This Southwest deal was found by Cheapflights users on 1/26. 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.
Find 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 January 28, 2026.
Round-trip from | $84 (Kiwi.com) |
|---|---|
One-way from | $53 (Kiwi.com) |
Popular in | March |
Cheapest in | September |
Average price | $292 |
Cheapflights Fare Finder
Use the filters below to find and compare flights from Houston to Chicago Midway Airport that are best for you.
Fly from
Fly to
Route
Depart
Return
Price
HoustonChicago
IAH - MDW
IAHMDW
Houston George Bush Intcntl
Fri 4/10
1:27 pm-3:59 pm
Nonstop2h 32m
Chicago Midway
Mon 4/13
9:20 am-12:32 pm
Nonstop3h 12m
HoustonChicago
IAH - MDW
IAHMDW
Houston George Bush Intcntl
Fri 2/20
6:15 am-5:53 pm
1 stop11h 38m
Chicago Midway
Sun 2/22
3:00 pm-6:06 pm
Nonstop3h 06m
HoustonChicago
IAH - MDW
IAHMDW
Houston George Bush Intcntl
Mon 2/16
10:30 am-1:08 pm
Nonstop2h 38m
Chicago Midway
Tue 2/17
6:00 am-5:12 pm
1 stop11h 12m
HoustonChicago
IAH - MDW
IAHMDW
Houston George Bush Intcntl
Thu 4/9
8:24 am-8:07 pm
1 stop11h 43m
Chicago Midway
Mon 4/13
9:04 pm-8:38 am
1 stop11h 34m
HoustonChicago
HOU - MDW
HOUMDW
Houston Hobby
Wed 4/22
7:10 am-9:35 am
Nonstop2h 25m
Chicago Midway
Sat 4/25
6:05 pm-8:50 pm
Nonstop2h 45m
HoustonChicago
IAH - MDW
IAHMDW
Houston George Bush Intcntl
Tue 3/3
6:15 am-7:07 pm
1 stop12h 52m
Chicago Midway
Mon 3/9
2:41 pm-4:22 pm
1 stop25h 41m
HoustonChicago
HOU - MDW
HOUMDW
Houston Hobby
Fri 2/27
6:20 am-8:40 am
Nonstop2h 20m
Chicago Midway
Mon 3/2
8:30 pm-11:15 pm
Nonstop2h 45m
HoustonChicago
HOU - MDW
HOUMDW
Houston Hobby
Thu 2/26
8:45 pm-11:10 pm
Nonstop2h 25m
Chicago Midway
Sun 3/1
9:55 pm-12:40 am
Nonstop2h 45m
HoustonChicago
HOU - MDW
HOUMDW
Houston Hobby
Thu 2/26
6:20 am-8:40 am
Nonstop2h 20m
Chicago Midway
Mon 3/2
8:30 pm-11:15 pm
Nonstop2h 45m
HoustonChicago
HOU - MDW
HOUMDW
Houston Hobby
Wed 3/4
6:40 am-9:05 am
Nonstop2h 25m
Chicago Midway
Sat 3/7
4:35 pm-9:35 pm
1 stop5h 00m
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.
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 January 23, 2026.
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, October is the cheapest month in which you can book a flight from Houston to Chicago Midway Airport (average of $63). Flying from Houston to Chicago Midway Airport in December 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 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 January 28, 2026.
Unlike at noon, when flights are generally more expensive, you can save up to 20% 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 January 24, 2026.
Travelers seeking maximum savings on their Houston to Chicago Midway Airport flight should consider departing on Wednesday afternoons 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.
How often are flights from Houston to Chicago delayed?
About 17% of weekly flights between Houston and Chicago have experienced delays in the past year, with the average delay time being 126 minutes.
What is the most punctual flight time for Houston to Chicago flights?
Historically, flights departing in the morning are less likely to be delayed, whereas flights leaving in the evening tend to experience delays more often.
What day of the week experiences the fewest flight delays on this route?
Tuesday tends to have the lowest number of delays on this route, whereas Sunday has historically faced a higher average of delays compared to other days of the week.
Which airline has the best punctuality record on Houston to Chicago flights?
Over the last year, Southwest have had the lowest number of delays on this route, with just 16% of flights being delayed.
The best insider tips for Houston to Chicago Midway Airport flights
AI-powered summary based on content written by travel experts. AI can make mistakes.
Cheapflights partnered with top experts to bring you the best recommendations for your Houston to Chicago Midway Airport trip
Our travel experts
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 January 28, 2026.
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.
Boarding
Comfort
Entertainment
Overall
Crew
Food
Reviews
Ila,Mar 2025
HOU - DAL
Boarding
Comfort
Entertainment
Overall
Crew
Food
Reviews
Ila,Mar 2025
HOU - DAL
Boarding
Comfort
Entertainment
Overall
Crew
Food
Reviews
Ila,Mar 2025
HOU - DAL
Boarding
Comfort
Entertainment
Overall
Crew
Food
Reviews
Ila,Mar 2025
HOU - DAL
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.
Traveling to a place near Chicago Midway Airport?
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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.
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 January 28, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$87 | Average$195 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$167 | Average$276 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$216 | Average$306 | FlexibilityNo cancel fee | On-timeN/A |