$105+ Cheap flights from Hobby (HOU) to Midway (MDW)
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 10/14. Fares are subject to change and may not be available on all flights or dates of travel.
HOU — MDW
Oct 16 — Oct 231
Round-trip
1 adult, Economy
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Find cheap flights from Hobby to Midway 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 Houston Hobby to Chicago Midway are usually found in November or December, booked 38 days in advance, depart on a Saturday or Wednesday and return on a Wednesday
Cheap flight deals from Hobby to Midway
Cheapest
Best
Last-minute
One-way
Cheapest flights from Hobby to MidwayExplore the most affordable flight options available from Hobby to Midway. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 16, 2026.
Explore the most affordable flight options available from Hobby to Midway. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 16, 2026.
This Southwest deal was found by Cheapflights users on 9/15. 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 10/134:00 pm -
Nonstop2h 25m
Tue 10/208:35 pm -
Nonstop2h 40m
Deal found 9/15![Southwest logo]()
$209
This Southwest deal was found by Cheapflights users on 9/14. 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 10/146:35 pm -
Nonstop2h 30m
Wed 10/216:25 am -
Nonstop2h 35m
Deal found 9/14![Southwest logo]()
$210
This Southwest deal was found by Cheapflights users on 9/14. 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.
Tue 12/16:30 pm -
1 stop4h 10m
Tue 12/86:40 am -
Nonstop2h 40m
Deal found 9/14![Southwest logo]()
$219
This Southwest deal was found by Cheapflights users on 9/13. 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 10/216:35 pm -
Nonstop2h 30m
Sat 10/248:05 am -
1 stop5h 10m
Deal found 9/13![Southwest logo]()
$220
This Southwest deal was found by Cheapflights users on 9/15. 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 11/75:00 am -
Nonstop2h 25m
Mon 11/99:20 pm -
Nonstop2h 50m
Deal found 9/15![Southwest logo]()
$224
This Southwest deal was found by Cheapflights users on 9/14. 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 10/2111:30 am -
1 stop5h 40m
Tue 10/271:30 pm -
1 stop5h 25m
Deal found 9/14![Southwest logo]()
$225
This Delta deal was found by Cheapflights users on 9/14. 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.
Tue 10/276:09 am -
1 stop5h 45m
Sat 11/74:19 pm -
1 stop6h 44m
Deal found 9/14![Delta logo]()
$229
This Southwest deal was found by Cheapflights users on 9/14. 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.
Mon 11/912:55 pm -
1 stop4h 05m
Tue 11/105:00 pm -
Nonstop2h 45m
Deal found 9/14![Southwest logo]()
$230
This Southwest deal was found by Cheapflights users on 9/15. 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 12/15:30 pm -
1 stop4h 05m
Thu 12/38:50 pm -
Nonstop2h 40m
Deal found 9/15![Southwest logo]()
$235
This Southwest deal was found by Cheapflights users on 9/14. 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.
Thu 10/297:55 pm -
Nonstop2h 25m
Mon 11/29:20 pm -
Nonstop2h 45m
Deal found 9/14![Southwest logo]()
$239
Best flights from Hobby to MidwayDiscover carefully curated flight deals from Hobby to Midway that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated September 16, 2026.
Discover carefully curated flight deals from Hobby to Midway that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated September 16, 2026.
This Southwest deal was found by Cheapflights users on 9/15. 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 12/15:30 pm -
1 stop4h 05m
Thu 12/38:50 pm -
Nonstop2h 40m
Deal found 9/15![Southwest logo]()
$235
This Delta deal was found by Cheapflights users on 9/15. 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 10/216:09 am -
2 stops10h 38m
Wed 10/281:27 pm -
2 stops9h 36m
Deal found 9/15![Delta logo]()
$239
This Southwest deal was found by Cheapflights users on 9/14. 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.
Thu 10/2912:55 pm -
Nonstop2h 25m
Thu 11/57:50 am -
Nonstop2h 45m
Deal found 9/14![Southwest logo]()
$240
This Southwest deal was found by Cheapflights users on 9/15. 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 10/226:35 pm -
1 stop5h 45m
Mon 10/267:10 am -
Nonstop2h 35m
Deal found 9/15![Southwest logo]()
$249
This Southwest deal was found by Cheapflights users on 9/14. 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 10/218:45 pm -
Nonstop2h 30m
Sun 10/257:00 am -
Nonstop2h 35m
Deal found 9/14![Southwest logo]()
$299
This Southwest deal was found by Cheapflights users on 9/15. 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 10/178:30 am -
2 stops6h 45m
Mon 10/194:30 pm -
2 stops5h 15m
Deal found 9/15![Southwest logo]()
$325
This Delta deal was found by Cheapflights users on 9/13. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/215:24 pm -
1 stop5h 30m
Sun 11/225:13 pm -
1 stop6h 08m
Deal found 9/13![Delta logo]()
$440
This Southwest deal was found by Cheapflights users on 9/15. 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 11/2510:30 pm -
Nonstop2h 30m
Mon 11/309:45 pm -
Nonstop2h 45m
Deal found 9/15![Southwest logo]()
$359
This Southwest deal was found by Cheapflights users on 9/14. 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.
Thu 10/86:45 pm -
Nonstop2h 25m
Fri 10/99:30 pm -
Nonstop2h 40m
Deal found 9/14![Southwest logo]()
$390
This Southwest deal was found by Cheapflights users on 9/12. 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.
Fri 10/96:45 pm -
Nonstop2h 25m
Sat 10/177:20 am -
Nonstop2h 35m
Deal found 9/12![Southwest logo]()
$420
Last-minute flights from Hobby to MidwayDiscover last-minute flight deals from Hobby to Midway. Data last updated September 16, 2026 and is based on user searches.
Discover last-minute flight deals from Hobby to Midway. Data last updated September 16, 2026 and is based on user searches.
This Southwest deal was found by Cheapflights users on 9/15. 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 10/134:00 pm -
Nonstop2h 25m
Tue 10/208:35 pm -
Nonstop2h 40m
Deal found 9/15![Southwest logo]()
$209
This Southwest deal was found by Cheapflights users on 9/14. 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.
Tue 10/133:20 pm -
1 stop4h 05m
Thu 10/299:30 pm -
Nonstop2h 40m
Deal found 9/14![Southwest logo]()
$234
This Southwest deal was found by Cheapflights users on 9/14. 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 10/146:35 pm -
Nonstop2h 30m
Wed 10/216:25 am -
Nonstop2h 35m
Deal found 9/14![Southwest logo]()
$210
This Southwest deal was found by Cheapflights users on 9/13. 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 10/216:35 pm -
Nonstop2h 30m
Sat 10/248:05 am -
1 stop5h 10m
Deal found 9/13![Southwest logo]()
$220
This Southwest deal was found by Cheapflights users on 9/14. 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 10/2111:30 am -
1 stop5h 40m
Tue 10/271:30 pm -
1 stop5h 25m
Deal found 9/14![Southwest logo]()
$225
This Southwest deal was found by Cheapflights users on 9/14. 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.
Thu 10/225:00 am -
Nonstop2h 25m
Tue 10/2710:10 am -
1 stop4h 00m
Deal found 9/14![Southwest logo]()
$230
This Delta deal was found by Cheapflights users on 9/14. 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.
Tue 10/276:09 am -
1 stop5h 45m
Sat 11/74:19 pm -
1 stop6h 44m
Deal found 9/14![Delta logo]()
$229
This Southwest deal was found by Cheapflights users on 9/14. 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.
Thu 10/297:55 pm -
Nonstop2h 25m
Mon 11/29:20 pm -
Nonstop2h 45m
Deal found 9/14![Southwest logo]()
$239
One-way flights from Hobby to MidwaySearch for one-way flight options from Hobby to Midway. Find affordable one-way fares based on user searches. Data last updated September 16, 2026.
Search for one-way flight options from Hobby to Midway. Find affordable one-way fares based on user searches. Data last updated September 16, 2026.
This Southwest deal was found by Cheapflights users on 9/14. 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.
Tue 10/138:45 pm -
Nonstop2h 30m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/14![Southwest logo]()
$105
This Southwest deal was found by Cheapflights users on 9/15. 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 11/148:50 am -
1 stop4h 05m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/15![Southwest logo]()
$110
This Southwest deal was found by Cheapflights users on 9/15. 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 11/1011:30 am -
2 stops5h 40m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/15![Southwest logo]()
$116
This Delta deal was found by Cheapflights users on 9/15. 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 11/146:00 am -
2 stops10h 39m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/15![Delta logo]()
$120
This Southwest deal was found by Cheapflights users on 9/16. 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 10/292:00 pm -
1 stop3h 50m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/16![Southwest logo]()
$125
This Southwest deal was found by Cheapflights users on 9/15. 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 12/111:15 am -
2 stops5h 50m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/15![Southwest logo]()
$126
This Southwest deal was found by Cheapflights users on 9/15. 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 10/226:35 pm -
1 stop5h 45m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/15![Southwest logo]()
$130
This Southwest deal was found by Cheapflights users on 9/15. 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 10/3012:55 pm -
Nonstop2h 25m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/15![Southwest logo]()
$135
This Southwest deal was found by Cheapflights users on 9/13. 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.
Fri 10/166:45 pm -
Nonstop2h 25m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/13![Southwest logo]()
$143
This Delta deal was found by Cheapflights users on 9/15. 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 11/135:24 pm -
1 stop5h 30m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/15![Delta logo]()
$145
Find flight deals from Hobby to Midway
Discover tips and strategies to find the most affordable flight options for your journey from Hobby (HOU) 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 September 16, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $209 (Southwest) |
One-way from | $105 (Southwest) |
Popular in | January |
Cheapest in | November |
Average price | $323 |
Good round-trip deal | $328 or less |
Good one-way deal | $209 or less |
Cheapflights Fare Finder
Customize your flight search to find flights from Hobby 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 7,457,451 searches. Data last updated September 16, 2026.
Use the filters below to find and compare flights from Houston Hobby Airport to Chicago Midway Airport that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
Quickest round-trip
HoustonChicago
HOU Houston Hobby - MDW Chicago Midway
HOUMDW
Houston Hobby
Wed 10/14
8:45 pm-11:15 pm
Nonstop2h 30m
Chicago Midway
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$105
HoustonChicago
HOU Houston Hobby - MDW Chicago Midway
HOUMDW
Houston Hobby
Sat 10/17
5:30 pm-8:00 pm
Nonstop2h 30m
Chicago Midway
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$105
HoustonChicago
HOU Houston Hobby - MDW Chicago Midway
HOUMDW
Houston Hobby
Tue 10/13
6:15 pm-10:00 pm
1 stop3h 45m
Chicago Midway
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$115
HoustonChicago
HOU Houston Hobby - MDW Chicago Midway
HOUMDW
Houston Hobby
Wed 10/7
8:45 pm-11:15 pm
Nonstop2h 30m
Chicago Midway
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$160
HoustonChicago
HOU Houston Hobby - MDW Chicago Midway
HOUMDW
Houston Hobby
Thu 12/10
7:20 am-9:50 am
Nonstop2h 30m
Chicago Midway
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$165
HoustonChicago
HOU Houston Hobby - MDW Chicago Midway
HOUMDW
Houston Hobby
Tue 11/10
5:24 pm-10:54 pm
1 stop5h 30m
Chicago Midway
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$175
HoustonChicago
HOU Houston Hobby - MDW Chicago Midway
HOUMDW
Houston Hobby
Mon 12/7
5:27 pm-10:55 pm
1 stop5h 28m
Chicago Midway
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$175
HoustonChicago
HOU Houston Hobby - MDW Chicago Midway
HOUMDW
Houston Hobby
Tue 10/13
5:28 pm-10:33 pm
1 stop5h 05m
Chicago Midway
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$175
HoustonChicago
HOU Houston Hobby - MDW Chicago Midway
HOUMDW
Houston Hobby
Wed 12/9
3:11 pm-10:55 pm
1 stop7h 44m
Chicago Midway
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$175
HoustonChicago
HOU Houston Hobby - MDW Chicago Midway
HOUMDW
Houston Hobby
Mon 10/12
8:30 pm-1:10 am
1 stop4h 40m
Chicago Midway
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$177
Showing 1-10 of 20 resultsSorted by cheapest first
Compare providers for flights from Hobby to Midway
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 Hobby to Midway in September.
| 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 Accuracy- | Trust Score*3 stars |
- Most accurate provider: When it comes to deals on Houston Hobby Airport-Chicago Midway Airport flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Houston Hobby Airport-Chicago Midway Airport flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Houston Hobby Airport-Chicago Midway Airport flight searches over the past month and is updated monthly.
- Most trusted provider: When it comes to deals on Houston Hobby Airport-Chicago Midway 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 Houston Hobby Airport-Chicago Midway 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 Hobby to Midway
Have a flexible travel schedule? Discover the best time to fly to Midway from Hobby with our price prediction graph.
HOU-MDW
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 Hobby Airport to Chicago Midway Airport
Prices
Delays
How far ahead should I book a flight from Houston Hobby Airport to Chicago Midway Airport?
The price you pay for your flight from Houston Hobby Airport to Chicago Midway Airport may vary depending on when you book. For the best chance of a lower fare, look to book 37 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 Hobby Airport to Chicago Midway Airport?
Currently, November is the cheapest month in which you can book a flight from Houston Hobby Airport to Chicago Midway Airport (average of $210). Flying from Houston Hobby Airport to Chicago Midway Airport in January is currently the most expensive (average of $706). 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 Hobby 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 September 16, 2026.
Unlike at noon, when flights are generally more expensive, you can save up to 27% on flights from Houston Hobby Airport to Chicago Midway Airport by exploring options for tickets in the evening.
What is the cheapest day to fly from Houston Hobby Airport to Chicago Midway Airport?
Use this chart to determine the cheapest time to fly round-trip from Hobby to Midway. Price data was last updated on September 12, 2026.
Travelers seeking maximum savings on their Houston Hobby Airport to Chicago Midway Airport flight should consider departing on Thursday 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 Houston to Chicago delayed?
About 24% of weekly flights between Houston and Chicago have experienced delays in the past year, with the average delay time being 114 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 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 Houston to Chicago flights?
Over the last year, Southwest have had the lowest number of delays on this route, with just 24% of flights being delayed.
The best insider tips for Houston Hobby Airport 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 Hobby Airport 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 September 16, 2026.
Peruse reviews from past customers who have flown with Southwest and Frontier from Houston Hobby Airport to Chicago Midway Airport to help guide your decision. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Comfort
8.0
Crew
8.6
Food
7.0
Boarding
8.1
Overall
8.0
Entertainment
7.5
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Comfort
8.0
Crew
8.6
Food
7.0
Boarding
8.1
Overall
8.0
Entertainment
7.5
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Comfort
8.0
Crew
8.6
Food
7.0
Boarding
8.1
Overall
8.0
Entertainment
7.5
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Related info for your journey
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Traveling to a place near Chicago Midway Airport?
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Top 2 airlines flying from Hobby to Midway
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| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$103 | Average$203 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$205 | Average$395 | FlexibilityNo cancel fee | On-time63% |