$90+ Cheap flights from Midway (MDW) to Hobby (HOU)
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 8/4. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — HOU
Jul 15 — Jul 221
Round-trip
1 adult, Economy
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Find cheap flights from Midway to Hobby with Cheapflights
1. Tell us where you want to go
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.Cheapflights Tip: The best prices from Chicago Midway to Houston Hobby are usually found in September or August, booked 76 days in advance, depart on a Wednesday or Monday and return on a Saturday
Cheap flight deals from Midway to Hobby
Cheapest
Best
Last-minute
One-way
Cheapest flights from Midway to HobbyExplore the most affordable flight options available from Midway to Hobby. Find the lowest fares from popular airlines and budget airlines, with prices last updated on June 15, 2026.
Explore the most affordable flight options available from Midway to Hobby. Find the lowest fares from popular airlines and budget airlines, with prices last updated on June 15, 2026.
This Southwest deal was found by Cheapflights users on 6/10. 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 9/228:25 pm
MDW
- HOU
Nonstop2h 25m
Southwest
Wed 9/234:45 pm
HOU
- MDW
Nonstop2h 25m
Southwest
Deal found 6/10![Southwest logo]()
$179
This Southwest deal was found by Cheapflights users on 6/10. 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 8/1110:20 am
MDW
- HOU
1 stop4h 50m
Southwest
Wed 8/128:50 pm
HOU
- MDW
Nonstop2h 20m
Southwest
Deal found 6/10![Southwest logo]()
$189
This Southwest deal was found by Cheapflights users on 6/12. 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 8/81:45 pm
MDW
- HOU
Nonstop2h 30m
Southwest
Tue 8/114:45 pm
HOU
- MDW
Nonstop2h 25m
Southwest
Deal found 6/12![Southwest logo]()
$198
This Delta deal was found by Cheapflights users on 6/10. 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 8/125:10 pm
MDW
- HOU
1 stop4h 55m
Delta
Tue 8/1810:50 am
HOU
- MDW
1 stop5h 25m
Delta
Deal found 6/10![Delta logo]()
$199
This Southwest deal was found by Cheapflights users on 6/12. 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 7/297:10 pm
MDW
- HOU
Nonstop2h 35m
Southwest
Wed 8/1211:25 am
HOU
- MDW
1 stop4h 05m
Southwest
Deal found 6/12![Southwest logo]()
$200
This Southwest deal was found by Cheapflights users on 6/11. 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 10/89:55 pm
MDW
- HOU
Nonstop2h 35m
Southwest
Tue 10/136:00 am
HOU
- MDW
Nonstop2h 25m
Southwest
Deal found 6/11![Southwest logo]()
$202
This Southwest deal was found by Cheapflights users on 6/10. 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 7/299:00 pm
MDW
- HOU
Nonstop2h 40m
Southwest
Wed 8/57:35 am
HOU
- MDW
1 stop4h 15m
Southwest
Deal found 6/10![Southwest logo]()
$204
This Southwest deal was found by Cheapflights users on 6/11. 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 8/257:50 am
MDW
- HOU
Nonstop2h 35m
Southwest
Thu 9/242:40 pm
HOU
- MDW
1 stop5h 05m
Southwest
Deal found 6/11![Southwest logo]()
$208
This Southwest deal was found by Cheapflights users on 6/10. 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 7/84:15 pm
MDW
- HOU
Nonstop2h 40m
Southwest
Wed 7/89:25 pm
HOU
- MDW
Nonstop2h 30m
Southwest
Deal found 6/10![Southwest logo]()
$209
This Southwest deal was found by Cheapflights users on 6/12. 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 8/1510:05 am
MDW
- HOU
2 stops6h 45m
Southwest
Tue 8/182:45 pm
HOU
- MDW
Nonstop2h 25m
Southwest
Deal found 6/12![Southwest logo]()
$213
Best flights from Midway to HobbyDiscover carefully curated flight deals from Midway to Hobby that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated June 15, 2026.
Discover carefully curated flight deals from Midway to Hobby that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated June 15, 2026.
This Southwest deal was found by Cheapflights users on 6/11. 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 8/152:25 pm
MDW
- HOU
1 stop5h 25m
Southwest
Mon 8/176:10 am
HOU
- MDW
Nonstop2h 25m
Southwest
Deal found 6/11![Southwest logo]()
$227
This Delta deal was found by Cheapflights users on 6/11. 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 8/221:27 pm
MDW
- HOU
2 stops7h 56m
Delta
Sat 8/295:20 pm
HOU
- MDW
1 stop5h 16m
Delta
Deal found 6/11![Delta logo]()
$242
This Southwest deal was found by Cheapflights users on 6/10. 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 9/111:05 pm
MDW
- HOU
1 stop5h 20m
Southwest
Mon 9/145:45 pm
HOU
- MDW
Nonstop2h 25m
Southwest
Deal found 6/10![Southwest logo]()
$242
This Southwest deal was found by Cheapflights users on 6/14. 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 7/157:10 am
MDW
- HOU
Nonstop2h 35m
Southwest
Wed 7/229:25 pm
HOU
- MDW
Nonstop2h 30m
Southwest
Deal found 6/14![Southwest logo]()
$244
This Delta deal was found by Cheapflights users on 6/14. 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.
Fri 9/114:30 pm
MDW
- HOU
1 stop6h 10m
Delta
Tue 9/156:00 am
HOU
- MDW
2 stops12h 11m
Delta
Deal found 6/14![Delta logo]()
$279
This Southwest deal was found by Cheapflights users on 6/13. 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 7/227:10 am
MDW
- HOU
Nonstop2h 35m
Southwest
Sat 7/258:45 pm
HOU
- MDW
Nonstop2h 30m
Southwest
Deal found 6/13![Southwest logo]()
$244
This Southwest deal was found by Cheapflights users on 6/10. 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 7/114:05 pm
MDW
- HOU
1 stop4h 35m
Southwest
Tue 7/149:25 pm
HOU
- MDW
Nonstop2h 30m
Southwest
Deal found 6/10![Southwest logo]()
$254
This Southwest deal was found by Cheapflights users on 6/12. 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 10/148:40 pm
MDW
- HOU
Nonstop2h 25m
Southwest
Fri 10/168:30 pm
HOU
- MDW
1 stop4h 15m
Southwest
Deal found 6/12![Southwest logo]()
$264
This Southwest deal was found by Cheapflights users on 6/14. 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 8/71:05 pm
MDW
- HOU
1 stop5h 20m
Southwest
Mon 8/102:40 pm
HOU
- MDW
1 stop4h 50m
Southwest
Deal found 6/14![Southwest logo]()
$277
This Southwest deal was found by Cheapflights users on 6/10. 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 7/166:40 am
MDW
- HOU
1 stop5h 05m
Southwest
Sat 7/186:45 pm
HOU
- MDW
Nonstop2h 30m
Southwest
Deal found 6/10![Southwest logo]()
$289
Last-minute flights from Midway to HobbyDiscover last-minute flight deals from Midway to Hobby. Data last updated June 15, 2026 and is based on user searches.
Discover last-minute flight deals from Midway to Hobby. Data last updated June 15, 2026 and is based on user searches.
This Southwest deal was found by Cheapflights users on 6/10. 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 7/84:15 pm
MDW
- HOU
Nonstop2h 40m
Southwest
Wed 7/89:25 pm
HOU
- MDW
Nonstop2h 30m
Southwest
Deal found 6/10![Southwest logo]()
$209
This Southwest deal was found by Cheapflights users on 6/10. 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 7/143:10 pm
MDW
- HOU
2 stops5h 30m
Southwest
Tue 7/289:25 pm
HOU
- MDW
Nonstop2h 30m
Southwest
Deal found 6/10![Southwest logo]()
$220
This Southwest deal was found by Cheapflights users on 6/12. 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 7/1510:15 am
MDW
- HOU
1 stop3h 50m
Southwest
Tue 7/216:20 pm
HOU
- MDW
Nonstop2h 25m
Southwest
Deal found 6/12![Southwest logo]()
$215
This Southwest deal was found by Cheapflights users on 6/12. 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 7/297:10 pm
MDW
- HOU
Nonstop2h 35m
Southwest
Wed 8/1211:25 am
HOU
- MDW
1 stop4h 05m
Southwest
Deal found 6/12![Southwest logo]()
$200
This Southwest deal was found by Cheapflights users on 6/10. 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 7/299:00 pm
MDW
- HOU
Nonstop2h 40m
Southwest
Wed 8/57:35 am
HOU
- MDW
1 stop4h 15m
Southwest
Deal found 6/10![Southwest logo]()
$204
This Southwest deal was found by Cheapflights users on 6/14. 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 7/2910:15 am
MDW
- HOU
Nonstop2h 40m
Southwest
Thu 8/67:55 pm
HOU
- MDW
Nonstop2h 20m
Southwest
Deal found 6/14![Southwest logo]()
$217
One-way flights from Midway to HobbySearch for one-way flight options from Midway to Hobby. Find affordable one-way fares based on user searches. Data last updated June 15, 2026.
Search for one-way flight options from Midway to Hobby. Find affordable one-way fares based on user searches. Data last updated June 15, 2026.
This Southwest deal was found by Cheapflights users on 6/10. 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 8/47:50 am
MDW
- HOU
Nonstop2h 35m
Southwest
Deal found 6/10![Southwest logo]()
$90
This Southwest deal was found by Cheapflights users on 6/10. 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 8/1910:10 am
MDW
- HOU
1 stop3h 50m
Southwest
Deal found 6/10![Southwest logo]()
$96
This Delta deal was found by Cheapflights users on 6/11. 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 8/46:05 am
MDW
- HOU
1 stop6h 11m
Delta
Deal found 6/11![Delta logo]()
$100
This Southwest deal was found by Cheapflights users on 6/10. 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 7/219:00 pm
MDW
- HOU
Nonstop2h 40m
Southwest
Deal found 6/10![Southwest logo]()
$105
This Southwest deal was found by Cheapflights users on 6/10. 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 8/65:55 am
MDW
- HOU
Nonstop2h 30m
Southwest
Deal found 6/10![Southwest logo]()
$109
This Kiwi.com deal was found by Cheapflights users on 6/13. 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.
Thu 8/132:49 pm
MDW
- HOU
1 stop28h 24m
Allegiant Air
Deal found 6/13![Allegiant Air logo]()
$110
This Southwest deal was found by Cheapflights users on 6/10. 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 7/73:10 pm
MDW
- HOU
2 stops5h 30m
Southwest
Deal found 6/10![Southwest logo]()
$115
This Delta deal was found by Cheapflights users on 6/11. 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.
Thu 8/65:10 pm
MDW
- HOU
1 stop4h 55m
Delta
Deal found 6/11![Delta logo]()
$119
This Southwest deal was found by Cheapflights users on 6/13. 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 8/57:40 am
MDW
- HOU
2 stops6h 05m
Southwest
Deal found 6/13![Southwest logo]()
$120
Find flight deals from Midway to Hobby
Discover tips and strategies to find the most affordable flight options for your journey from Midway (MDW) to Hobby (HOU). 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 June 15, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $179 (Southwest) |
One-way from | $90 (Southwest) |
Popular in | June |
Cheapest in | September |
Average price | $374 |
Good round-trip deal | $303 or less |
Good one-way deal | $171 or less |
Cheapflights Fare Finder
Customize your flight search to find flights from Midway to Hobby 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 June 15, 2026.
Use the filters below to find and compare flights from Chicago Midway Airport to Houston Hobby Airport that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
ChicagoHouston
MDW - HOU
MDWHOU
Chicago Midway
Sat 8/15
2:25 pm-7:50 pm
1 stop5h 25m
Houston Hobby
Mon 8/17
6:10 am-8:35 am
Nonstop2h 25m
$227
ChicagoHouston
MDW - HOU
MDWHOU
Chicago Midway
Sat 8/22
1:27 pm-9:23 pm
2 stops7h 56m
Houston Hobby
Sat 8/29
5:20 pm-10:36 pm
1 stop5h 16m
$242
ChicagoHouston
MDW - HOU
MDWHOU
Chicago Midway
Fri 9/11
1:05 pm-6:25 pm
1 stop5h 20m
Houston Hobby
Mon 9/14
5:45 pm-8:10 pm
Nonstop2h 25m
$242
Quickest round-trip
ChicagoHouston
MDW - HOU
MDWHOU
Chicago Midway
Wed 7/15
7:10 am-9:45 am
Nonstop2h 35m
Houston Hobby
Wed 7/22
9:25 pm-11:55 pm
Nonstop2h 30m
$244
ChicagoHouston
MDW - HOU
MDWHOU
Chicago Midway
Wed 7/22
7:10 am-9:45 am
Nonstop2h 35m
Houston Hobby
Sat 7/25
8:45 pm-11:15 pm
Nonstop2h 30m
$244
ChicagoHouston
MDW - HOU
MDWHOU
Chicago Midway
Sat 7/11
4:05 pm-8:40 pm
1 stop4h 35m
Houston Hobby
Tue 7/14
9:25 pm-11:55 pm
Nonstop2h 30m
$254
ChicagoHouston
MDW - HOU
MDWHOU
Chicago Midway
Wed 10/14
8:40 pm-11:05 pm
Nonstop2h 25m
Houston Hobby
Fri 10/16
8:30 pm-12:45 am
1 stop4h 15m
$264
ChicagoHouston
MDW - HOU
MDWHOU
Chicago Midway
Fri 8/7
1:05 pm-6:25 pm
1 stop5h 20m
Houston Hobby
Mon 8/10
2:40 pm-7:30 pm
1 stop4h 50m
$277
ChicagoHouston
MDW - HOU
MDWHOU
Chicago Midway
Fri 9/11
4:30 pm-10:40 pm
1 stop6h 10m
Houston Hobby
Tue 9/15
6:00 am-6:11 pm
2 stops12h 11m
$279
ChicagoHouston
MDW - HOU
MDWHOU
Chicago Midway
Thu 7/16
6:40 am-11:45 am
1 stop5h 05m
Houston Hobby
Sat 7/18
6:45 pm-9:15 pm
Nonstop2h 30m
$289
Showing 1-10 of 21 resultsSorted by cheapest first
Compare providers for flights from Midway to Hobby
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 Midway to Hobby in June.
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy- | Trust Score*1 star | |
| Price Accuracy2 stars | Trust Score*1 star | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy- | Trust Score*3 stars | |
| Price Accuracy- | Trust Score*1 star |
- Most accurate provider: When it comes to deals on Chicago Midway Airport-Houston Hobby Airport flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Chicago Midway Airport-Houston Hobby Airport flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Chicago Midway Airport-Houston Hobby Airport flight searches over the past month and is updated monthly.
- Most trusted provider: When it comes to deals on Chicago Midway Airport-Houston Hobby Airport flights, Cheapflights users trust FlightHub the most. FlightHub 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 Chicago Midway Airport-Houston Hobby 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 Midway to Hobby
Have a flexible travel schedule? Discover the best time to fly to Hobby from Midway with our price prediction graph.
MDW-HOU
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 Chicago Midway Airport to Houston Hobby Airport
Prices
Delays
How far ahead should I book a flight from Chicago Midway Airport to Houston Hobby Airport?
The price you pay for your flight from Chicago Midway Airport to Houston Hobby Airport may vary depending on when you book. For the best chance of a lower fare, look to book 75 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 Chicago Midway Airport to Houston Hobby Airport?
Currently, September is the cheapest month in which you can book a flight from Chicago Midway Airport to Houston Hobby Airport (average of $144). Flying from Chicago Midway Airport to Houston Hobby Airport in June is currently the most expensive (average of $374). 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 MDW to HOU?
Find hourly flight availability from Midway to Hobby. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated June 15, 2026.
It’s typically best to fly out from Chicago Midway Airport to Houston Hobby Airport in the evening. Doing so could potentially save you 19% on the flight price compared to flying in the afternoon, which is usually more expensive.
What is the cheapest day to fly from Chicago Midway Airport to Houston Hobby Airport?
Use this chart to determine the cheapest time to fly round-trip from Midway to Hobby. Price data was last updated on June 8, 2026.
Travelers seeking maximum savings on their Chicago Midway Airport to Houston Hobby Airport flight should consider departing on Wednesday evenings when fares are most often at their lowest. Sunday at noon flights should be avoided if possible as fares are typically the most expensive at this time.
How often are flights from Chicago to Houston delayed?
About 20% of weekly flights between Chicago and Houston have experienced delays in the past year, with the average delay time being 114 minutes.
What is the most punctual flight time for Chicago to Houston flights?
Historically, flights departing in the morning are less likely to be delayed, whereas flights leaving in the early afternoon 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 Chicago to Houston flights?
Over the last year, Southwest have had the lowest number of delays on this route, with just 20% of flights being delayed.
The best insider tips for Chicago Midway Airport to Houston Hobby 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 Chicago Midway Airport to Houston Hobby Airport trip
Our travel experts
Reviews of airlines servicing Hobby
Get insights into the airlines that provide service to Hobby. 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 Hobby. Reviews last updated June 15, 2026.
Read reviews from past customers who have flown Southwest and Frontier from Chicago Midway Airport to Houston Hobby Airport. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Food
7.0
Comfort
8.0
Entertainment
7.5
Crew
8.6
Boarding
8.1
Overall
7.9
Reviews
1 / 20
2.0
MediocreMike,Aug 2025
OKC - AUS
Food
7.0
Comfort
8.0
Entertainment
7.5
Crew
8.6
Boarding
8.1
Overall
7.9
Reviews
1 / 20
2.0
MediocreMike,Aug 2025
OKC - AUS
Food
7.0
Comfort
8.0
Entertainment
7.5
Crew
8.6
Boarding
8.1
Overall
7.9
Reviews
1 / 20
2.0
MediocreMike,Aug 2025
OKC - AUS
Related info for your journey
Find useful and relevant information for your journey from Midway to Hobby. 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 Houston Hobby Airport?
Book flights to Houston Hobby Airport if you plan to visit one of these locationsSugar Land
Pasadena
Kemah
Stafford
Pearland
Baytown
West University Place
Seabrook
Freeport
Texas City
Lake Jackson
Rosenberg
Missouri City
Webster
League City
Nassau Bay
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Top 2 airlines flying from Midway to Hobby
Discover the top 2 airlines that operate flights from Midway to Hobby. 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 June 15, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$90 | Average$200 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$213 | Average$337 | FlexibilityNo cancel fee | On-time63% |