$103+ Cheap flights from Midway (MDW) to Hobby (HOU)
This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 12/16. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — HOU
Nov 25 — Dec 21
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
We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.3. Compare prices and book
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 November or May, booked 76 days in advance, depart on a Wednesday or Thursday 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 October 26, 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 October 26, 2026.
This Southwest deal was found by Cheapflights users on 10/23. 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 12/78:50 pm -
Nonstop2h 40m
Tue 12/87:20 am -
Nonstop2h 30m
Deal found 10/23![Southwest logo]()
$209
This Southwest deal was found by Cheapflights users on 10/21. 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.
Fri 12/119:20 pm -
Nonstop2h 50m
Thu 12/1710:40 pm -
Nonstop2h 30m
Deal found 10/21![Southwest logo]()
$211
This Southwest deal was found by Cheapflights users on 10/21. 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.
Fri 12/1810:05 am -
1 stop4h 40m
Mon 12/2110:30 pm -
Nonstop2h 30m
Deal found 10/21![Southwest logo]()
$217
This Southwest deal was found by Cheapflights users on 10/23. 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 12/48:50 pm -
Nonstop2h 40m
Mon 12/76:30 pm -
1 stop4h 10m
Deal found 10/23![Southwest logo]()
$219
This Southwest deal was found by Cheapflights users on 10/22. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/129:20 pm -
Nonstop2h 50m
Sun 11/1510:40 pm -
Nonstop2h 30m
Deal found 10/22![Southwest logo]()
$222
This Southwest deal was found by Cheapflights users on 10/26. 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.
Thu 11/198:50 pm -
Nonstop2h 40m
Tue 11/2410:30 pm -
Nonstop2h 30m
Deal found 10/26![Southwest logo]()
$227
This Southwest deal was found by Cheapflights users on 10/21. 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.
Fri 11/134:50 pm -
1 stop4h 10m
Sun 11/1510:40 pm -
Nonstop2h 30m
Deal found 10/21![Southwest logo]()
$228
This Delta deal was found by Cheapflights users on 10/21. 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.
Sat 11/1411:27 am -
1 stop5h 02m
Tue 11/1710:27 am -
1 stop5h 51m
Deal found 10/21![Delta logo]()
$231
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 October 26, 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 October 26, 2026.
This Southwest deal was found by Cheapflights users on 10/23. 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 11/128:30 am -
1 stop5h 45m
Sun 11/1510:40 pm -
Nonstop2h 30m
Deal found 10/23![Southwest logo]()
$231
This Delta deal was found by Cheapflights users on 10/22. 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.
Thu 11/1910:34 am -
2 stops12h 47m
Thu 11/265:34 pm -
1 stop5h 20m
Deal found 10/22![Delta logo]()
$315
This Southwest deal was found by Cheapflights users on 10/26. 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.
Fri 12/115:20 pm -
Nonstop2h 40m
Mon 12/148:40 pm -
Nonstop2h 30m
Deal found 10/26![Southwest logo]()
$247
This Southwest deal was found by Cheapflights users on 10/26. 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.
Fri 12/185:10 am -
Nonstop2h 35m
Mon 1/46:00 pm -
Nonstop2h 25m
Deal found 10/26![Southwest logo]()
$275
This Delta deal was found by Cheapflights users on 10/25. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/35:12 pm -
1 stop6h 19m
Sun 12/66:12 am -
1 stop5h 52m
Deal found 10/25![Delta logo]()
$333
This Southwest deal was found by Cheapflights users on 10/24. 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 12/48:50 pm -
Nonstop2h 40m
Mon 12/74:00 pm -
1 stop3h 55m
Deal found 10/24![Southwest logo]()
$285
This KAYAK deal was found by Cheapflights users on 10/26. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/165:13 pm -
1 stop6h 08m
Thu 11/196:00 am -
1 stop5h 59m
Deal found 10/26![Delta logo]()
$341
This Southwest deal was found by Cheapflights users on 10/24. 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 11/219:25 pm -
Nonstop2h 45m
Sun 11/2212:55 pm -
1 stop4h 05m
Deal found 10/24![Southwest logo]()
$357
This Southwest deal was found by Cheapflights users on 10/23. 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 12/248:50 pm -
Nonstop2h 40m
Tue 12/295:10 am -
Nonstop2h 25m
Deal found 10/23![Southwest logo]()
$359
This Southwest deal was found by Cheapflights users on 10/24. 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 11/279:20 pm -
Nonstop2h 50m
Thu 12/37:20 am -
Nonstop2h 30m
Deal found 10/24![Southwest logo]()
$371
This Southwest deal was found by Cheapflights users on 10/26. 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.
Tue 11/2410:05 am -
1 stop4h 40m
Tue 12/111:15 am -
2 stops5h 50m
Deal found 10/26![Southwest logo]()
$390
This Southwest deal was found by Cheapflights users on 10/22. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/227:20 pm -
1 stop5h 45m
Sun 12/272:15 pm -
2 stops5h 55m
Deal found 10/22![Southwest logo]()
$394
Last-minute flights from Midway to HobbyDiscover last-minute flight deals from Midway to Hobby. Data last updated October 26, 2026 and is based on user searches.
Discover last-minute flight deals from Midway to Hobby. Data last updated October 26, 2026 and is based on user searches.
This Southwest deal was found by Cheapflights users on 10/22. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/99:20 pm -
Nonstop2h 50m
Wed 11/118:40 pm -
Nonstop2h 30m
Deal found 10/22![Southwest logo]()
$211
This Southwest deal was found by Cheapflights users on 10/22. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/99:20 pm -
Nonstop2h 50m
Fri 11/1312:55 pm -
1 stop4h 05m
Deal found 10/22![Southwest logo]()
$217
This Southwest deal was found by Cheapflights users on 10/22. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/129:20 pm -
Nonstop2h 50m
Sun 11/1510:40 pm -
Nonstop2h 30m
Deal found 10/22![Southwest logo]()
$222
This Southwest deal was found by Cheapflights users on 10/23. 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 11/134:50 pm -
1 stop4h 10m
Sun 11/1510:40 pm -
Nonstop2h 30m
Deal found 10/23![Southwest logo]()
$228
This Delta deal was found by Cheapflights users on 10/22. 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.
Sat 11/1411:27 am -
1 stop5h 02m
Tue 11/1710:27 am -
1 stop5h 51m
Deal found 10/22![Delta logo]()
$231
This Southwest deal was found by Cheapflights users on 10/26. 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.
Thu 11/198:50 pm -
Nonstop2h 40m
Tue 11/2410:30 pm -
Nonstop2h 30m
Deal found 10/26![Southwest logo]()
$227
This Southwest deal was found by Cheapflights users on 10/21. 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.
Sat 11/217:55 am -
1 stop5h 55m
Wed 11/2510:30 pm -
Nonstop2h 30m
Deal found 10/21![Southwest logo]()
$221
This Southwest deal was found by Cheapflights users on 10/23. 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 11/216:55 pm -
2 stops6h 10m
Sun 11/2210:40 pm -
Nonstop2h 30m
Deal found 10/23![Southwest logo]()
$237
This Southwest deal was found by Cheapflights users on 10/23. 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 11/263:50 pm -
Nonstop2h 45m
Tue 12/15:30 pm -
1 stop4h 05m
Deal found 10/23![Southwest logo]()
$235
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 October 26, 2026.
Search for one-way flight options from Midway to Hobby. Find affordable one-way fares based on user searches. Data last updated October 26, 2026.
This Southwest deal was found by Cheapflights users on 10/23. 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 12/168:00 am -
2 stops6h 00m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/23![Southwest logo]()
$103
This Southwest deal was found by Cheapflights users on 10/23. 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 12/38:50 pm -
Nonstop2h 40m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/23![Southwest logo]()
$105
This Southwest deal was found by Cheapflights users on 10/22. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/118:50 pm -
Nonstop2h 40m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/22![Southwest logo]()
$106
This Southwest deal was found by Cheapflights users on 10/21. 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.
Thu 1/147:50 pm -
Nonstop2h 45m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/21![Southwest logo]()
$111
This Southwest deal was found by Cheapflights users on 10/23. 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 11/187:05 am -
1 stop5h 40m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/23![Southwest logo]()
$115
This Southwest deal was found by Cheapflights users on 10/21. 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.
Sun 12/69:20 pm -
Nonstop2h 50m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/21![Southwest logo]()
$117
This Delta deal was found by Cheapflights users on 10/23. 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 11/181:31 pm -
2 stops9h 50m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/23![Delta logo]()
$120
This Southwest deal was found by Cheapflights users on 10/22. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/18:00 am -
2 stops6h 00m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/22![Southwest logo]()
$126
This Southwest deal was found by Cheapflights users on 10/26. 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.
Mon 11/239:20 pm -
Nonstop2h 50m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/26![Southwest logo]()
$134
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 October 26, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $209 (Southwest) |
One-way from | $103 (Southwest) |
Popular in | August |
Cheapest in | November |
Average price | $371 |
Good round-trip deal | $368 or less |
Good one-way deal | $257 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 7,457,451 searches. Data last updated October 26, 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 Chicago Midway - HOU Houston Hobby
MDWHOU
Chicago Midway
Wed 12/16
8:00 am-2:00 pm
2 stops6h 00m
Houston Hobby
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$103
Quickest round-trip
ChicagoHouston
MDW Chicago Midway - HOU Houston Hobby
MDWHOU
Chicago Midway
Sat 12/12
2:55 pm-5:35 pm
Nonstop2h 40m
Houston Hobby
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$106
ChicagoHouston
MDW Chicago Midway - HOU Houston Hobby
MDWHOU
Chicago Midway
Wed 11/11
5:15 pm-11:00 pm
1 stop5h 45m
Houston Hobby
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$116
ChicagoHouston
MDW Chicago Midway - HOU Houston Hobby
MDWHOU
Chicago Midway
Tue 1/5
5:20 pm-11:00 pm
1 stop5h 40m
Houston Hobby
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$116
ChicagoHouston
MDW Chicago Midway - HOU Houston Hobby
MDWHOU
Chicago Midway
Mon 12/14
12:50 pm-7:00 pm
1 stop6h 10m
Houston Hobby
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$116
ChicagoHouston
MDW Chicago Midway - HOU Houston Hobby
MDWHOU
Chicago Midway
Thu 12/17
5:12 pm-11:31 pm
1 stop6h 19m
Houston Hobby
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$148
ChicagoHouston
MDW Chicago Midway - HOU Houston Hobby
MDWHOU
Chicago Midway
Wed 11/25
7:20 pm-1:05 am
1 stop5h 45m
Houston Hobby
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$185
ChicagoHouston
MDW Chicago Midway - HOU Houston Hobby
MDWHOU
Chicago Midway
Fri 12/4
8:00 am-2:00 pm
2 stops6h 00m
Houston Hobby
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$191
ChicagoHouston
MDW Chicago Midway - HOU Houston Hobby
MDWHOU
Chicago Midway
Thu 11/12
8:30 am-2:15 pm
1 stop5h 45m
Houston Hobby
Sun 11/15
10:40 pm-1:10 am
Nonstop2h 30m
$231
ChicagoHouston
MDW Chicago Midway - HOU Houston Hobby
MDWHOU
Chicago Midway
Fri 12/11
5:20 pm-8:00 pm
Nonstop2h 40m
Houston Hobby
Mon 12/14
8:40 pm-11:10 pm
Nonstop2h 30m
$247
Showing 1-10 of 20 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 October.
| 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 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, November is the cheapest month in which you can book a flight from Chicago Midway Airport to Houston Hobby Airport (average of $266). Flying from Chicago Midway Airport to Houston Hobby Airport in August is currently the most expensive (average of $450). 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 October 26, 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 20% 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 October 24, 2026.
Travelers seeking maximum savings on their Chicago Midway Airport to Houston Hobby Airport flight should consider departing on Saturday at noon 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 21% 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?
Wednesday 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 October 26, 2026.
Read reviews from past customers who have flown Southwest,United Airlines, andFrontier 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
Crew
8.6
Entertainment
7.4
Comfort
8.0
Boarding
8.1
Overall
7.9
Reviews
1 / 20
10.0
ExcellentSarah,Aug 2024
MDW - AUS
Food
7.0
Crew
8.6
Entertainment
7.4
Comfort
8.0
Boarding
8.1
Overall
7.9
Reviews
1 / 20
10.0
ExcellentSarah,Aug 2024
MDW - AUS
Food
7.0
Crew
8.6
Entertainment
7.4
Comfort
8.0
Boarding
8.1
Overall
7.9
Reviews
1 / 20
10.0
ExcellentSarah,Aug 2024
MDW - AUS
Food
7.0
Crew
8.6
Entertainment
7.4
Comfort
8.0
Boarding
8.1
Overall
7.9
Reviews
1 / 20
10.0
ExcellentSarah,Aug 2024
MDW - 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
Pearland
Kemah
Webster
West University Place
Texas City
Stafford
Pasadena
Seabrook
Baytown
Freeport
Lake Jackson
Missouri City
Rosenberg
League City
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Top 3 airlines flying from Midway to Hobby
Discover the top 3 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 7,457,451 searches. Data last updated October 26, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$104 | Average$233 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$213 | Average$519 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$224 | Average$388 | FlexibilityNo cancel fee | On-time63% |