$85+ Cheap flights from Hobby (HOU) 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 7/14. Fares are subject to change and may not be available on all flights or dates of travel.
HOU — MDW
Jun 14 — Jun 211
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 October or November, booked 84 days in advance, depart on a Wednesday or Saturday and return on a Monday
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 May 15, 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 May 15, 2026.
This Southwest deal was found by Cheapflights users on 5/13. 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.
Tue 7/289:25 pm
HOU
- MDW
Nonstop2h 25m
Southwest
Tue 8/48:25 pm
MDW
- HOU
Nonstop2h 25m
Southwest
Deal found 5/13![Southwest logo]()
$169
This Southwest deal was found by Cheapflights users on 5/13. 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 8/1211:25 am
HOU
- MDW
1 stop4h 05m
Southwest
Tue 8/188:25 pm
MDW
- HOU
Nonstop2h 25m
Southwest
Deal found 5/13![Southwest logo]()
$175
This Southwest deal was found by Cheapflights users on 5/11. 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.
Wed 7/84:05 pm
HOU
- MDW
Nonstop2h 25m
Southwest
Tue 7/143:10 pm
MDW
- HOU
2 stops5h 30m
Southwest
Deal found 5/11![Southwest logo]()
$180
This Southwest deal was found by Cheapflights users on 5/12. 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 10/245:00 am
HOU
- MDW
Nonstop2h 25m
Southwest
Tue 10/276:05 am
MDW
- HOU
Nonstop2h 30m
Southwest
Deal found 5/12![Southwest logo]()
$184
This Southwest deal was found by Cheapflights users on 5/14. 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 6/178:10 am
HOU
- MDW
2 stops7h 15m
Southwest
Tue 6/309:10 am
MDW
- HOU
1 stop4h 40m
Southwest
Deal found 5/14![Southwest logo]()
$185
This Southwest deal was found by Cheapflights users on 5/15. 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 7/89:25 pm
HOU
- MDW
Nonstop2h 25m
Southwest
Wed 7/159:00 pm
MDW
- HOU
Nonstop2h 35m
Southwest
Deal found 5/15![Southwest logo]()
$189
This Southwest deal was found by Cheapflights users on 5/12. 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.
Tue 6/25:30 pm
HOU
- MDW
1 stop4h 15m
Southwest
Wed 6/312:15 pm
MDW
- HOU
Nonstop2h 40m
Southwest
Deal found 5/12![Southwest logo]()
$194
This Southwest deal was found by Cheapflights users on 5/12. 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 8/2910:25 am
HOU
- MDW
1 stop3h 50m
Southwest
Tue 9/110:10 am
MDW
- HOU
1 stop3h 50m
Southwest
Deal found 5/12![Southwest logo]()
$195
This Delta deal was found by Cheapflights users on 5/13. 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.
Tue 7/286:00 am
HOU
- MDW
1 stop5h 56m
Delta
Wed 8/125:10 pm
MDW
- HOU
1 stop5h 36m
Delta
Deal found 5/13![Delta logo]()
$197
This Southwest deal was found by Cheapflights users on 5/14. 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 8/411:25 am
HOU
- MDW
1 stop4h 05m
Southwest
Thu 8/67:25 am
MDW
- HOU
Nonstop2h 30m
Southwest
Deal found 5/14![Southwest logo]()
$200
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 May 15, 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 May 15, 2026.
This Southwest deal was found by Cheapflights users on 5/10. 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 7/299:25 pm
HOU
- MDW
Nonstop2h 25m
Southwest
Tue 8/47:50 am
MDW
- HOU
Nonstop2h 35m
Southwest
Deal found 5/10![Southwest logo]()
$224
This Delta deal was found by Cheapflights users on 5/14. 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 7/215:14 pm
HOU
- MDW
1 stop5h 01m
Delta
Sat 7/254:22 pm
MDW
- HOU
1 stop5h 29m
Delta
Deal found 5/14![Delta logo]()
$248
This Southwest deal was found by Cheapflights users on 5/14. 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 7/149:25 pm
HOU
- MDW
Nonstop2h 25m
Southwest
Thu 7/162:45 pm
MDW
- HOU
1 stop5h 00m
Southwest
Deal found 5/14![Southwest logo]()
$234
This Delta deal was found by Cheapflights users on 5/10. 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.
Thu 8/1310:50 am
HOU
- MDW
1 stop5h 25m
Delta
Sun 8/166:05 am
MDW
- HOU
1 stop6h 11m
Delta
Deal found 5/10![Delta logo]()
$288
This Southwest deal was found by Cheapflights users on 5/14. 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 7/246:50 pm
HOU
- MDW
Nonstop2h 25m
Southwest
Mon 7/279:40 pm
MDW
- HOU
Nonstop2h 30m
Southwest
Deal found 5/14![Southwest logo]()
$289
This Southwest deal was found by Cheapflights users on 5/12. 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 6/266:50 pm
HOU
- MDW
Nonstop2h 25m
Southwest
Fri 7/311:35 am
MDW
- HOU
Nonstop2h 35m
Southwest
Deal found 5/12![Southwest logo]()
$290
This Southwest deal was found by Cheapflights users on 5/12. 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.
Mon 6/11:30 pm
HOU
- MDW
1 stop4h 05m
Southwest
Tue 6/309:10 am
MDW
- HOU
1 stop4h 40m
Southwest
Deal found 5/12![Southwest logo]()
$298
This Southwest deal was found by Cheapflights users on 5/10. 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 7/288:15 am
HOU
- MDW
1 stop5h 35m
Southwest
Tue 8/42:40 pm
MDW
- HOU
2 stops5h 15m
Southwest
Deal found 5/10![Southwest logo]()
$304
This Southwest deal was found by Cheapflights users on 5/13. 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.
Thu 7/92:55 pm
HOU
- MDW
1 stop3h 55m
Southwest
Sun 7/128:30 am
MDW
- HOU
Nonstop2h 40m
Southwest
Deal found 5/13![Southwest logo]()
$313
This Southwest deal was found by Cheapflights users on 5/10. 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 7/32:10 pm
HOU
- MDW
1 stop5h 00m
Southwest
Sun 7/56:55 am
MDW
- HOU
Nonstop2h 35m
Southwest
Deal found 5/10![Southwest logo]()
$326
This Southwest deal was found by Cheapflights users on 5/13. 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 5/272:40 pm
HOU
- MDW
1 stop4h 55m
Southwest
Sat 5/3010:30 am
MDW
- HOU
2 stops6h 30m
Southwest
Deal found 5/13![Southwest logo]()
$337
Last-minute flights from Hobby to MidwayDiscover last-minute flight deals from Hobby to Midway. Data last updated May 15, 2026 and is based on user searches.
Discover last-minute flight deals from Hobby to Midway. Data last updated May 15, 2026 and is based on user searches.
This Southwest deal was found by Cheapflights users on 5/12. 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.
Tue 6/25:30 pm
HOU
- MDW
1 stop4h 15m
Southwest
Wed 6/312:15 pm
MDW
- HOU
Nonstop2h 40m
Southwest
Deal found 5/12![Southwest logo]()
$194
This Southwest deal was found by Cheapflights users on 5/12. 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.
Tue 6/25:30 pm
HOU
- MDW
1 stop4h 15m
Southwest
Thu 6/49:40 pm
MDW
- HOU
Nonstop2h 30m
Southwest
Deal found 5/12![Southwest logo]()
$209
This Southwest deal was found by Cheapflights users on 5/14. 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 6/83:50 pm
HOU
- MDW
1 stop4h 50m
Southwest
Wed 6/101:10 pm
MDW
- HOU
Nonstop2h 35m
Southwest
Deal found 5/14![Southwest logo]()
$204
This Southwest deal was found by Cheapflights users on 5/15. 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 6/94:30 pm
HOU
- MDW
Nonstop2h 25m
Southwest
Wed 6/241:10 pm
MDW
- HOU
Nonstop2h 35m
Southwest
Deal found 5/15![Southwest logo]()
$189
This Southwest deal was found by Cheapflights users on 5/12. 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 6/106:20 pm
HOU
- MDW
Nonstop2h 25m
Southwest
Tue 6/169:10 am
MDW
- HOU
1 stop4h 40m
Southwest
Deal found 5/12![Southwest logo]()
$175
This Southwest deal was found by Cheapflights users on 5/12. 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.
Tue 6/169:25 pm
HOU
- MDW
Nonstop2h 25m
Southwest
Tue 6/234:15 pm
MDW
- HOU
Nonstop2h 35m
Southwest
Deal found 5/12![Southwest logo]()
$169
This Delta deal was found by Cheapflights users on 5/12. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/166:03 am
HOU
- MDW
1 stop6h 02m
Delta
Wed 6/2411:05 am
MDW
- HOU
1 stop5h 18m
Delta
Deal found 5/12![Delta logo]()
$197
This Southwest deal was found by Cheapflights users on 5/14. 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 6/178:10 am
HOU
- MDW
2 stops7h 15m
Southwest
Tue 6/305:50 pm
MDW
- HOU
Nonstop2h 35m
Southwest
Deal found 5/14![Southwest logo]()
$180
This Delta deal was found by Cheapflights users on 5/10. 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.
Tue 6/235:08 pm
HOU
- MDW
1 stop5h 09m
Delta
Sat 6/274:25 pm
MDW
- HOU
1 stop5h 18m
Delta
Deal found 5/10![Delta logo]()
$208
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 May 15, 2026.
Search for one-way flight options from Hobby to Midway. Find affordable one-way fares based on user searches. Data last updated May 15, 2026.
This Southwest deal was found by Cheapflights users on 5/13. 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.
Tue 7/148:15 am
HOU
- MDW
Nonstop2h 30m
Southwest
Deal found 5/13![Southwest logo]()
$85
This Southwest deal was found by Cheapflights users on 5/11. 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 8/2511:25 am
HOU
- MDW
1 stop4h 05m
Southwest
Deal found 5/11![Southwest logo]()
$90
This Southwest deal was found by Cheapflights users on 5/12. 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.
Tue 10/1312:00 pm
HOU
- MDW
1 stop4h 55m
Southwest
Deal found 5/12![Southwest logo]()
$95
This Delta deal was found by Cheapflights users on 5/13. 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.
Tue 7/145:14 pm
HOU
- MDW
1 stop5h 01m
Delta
Deal found 5/13![Delta logo]()
$99
This Southwest deal was found by Cheapflights users on 5/11. 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 6/68:45 pm
HOU
- MDW
Nonstop2h 25m
Southwest
Deal found 5/11![Southwest logo]()
$100
This Delta deal was found by Cheapflights users on 5/15. 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.
Tue 6/1610:09 am
HOU
- MDW
1 stop6h 07m
Delta
Deal found 5/15![Delta logo]()
$105
This Kiwi.com deal was found by Cheapflights users on 5/15. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 6/146:44 pm
HOU
- MDW
1 stop24h 46m
Allegiant Air
Deal found 5/15![Allegiant Air logo]()
$108
This Kiwi.com deal was found by Cheapflights users on 5/15. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/317:01 pm
HOU
- MDW
1 stop19h 51m
Allegiant Air
Deal found 5/15![Allegiant Air logo]()
$113
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 May 15, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $169 (Southwest) |
One-way from | $85 (Southwest) |
Popular in | January |
Cheapest in | October |
Average price | $337 |
Good round-trip deal | $281 or less |
Good one-way deal | $171 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 2,558,603 searches. Data last updated May 15, 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
HoustonChicago
HOU - MDW
HOUMDW
Houston Hobby
Wed 7/29
9:25 pm-11:50 pm
Nonstop2h 25m
Chicago Midway
Tue 8/4
7:50 am-10:25 am
Nonstop2h 35m
$224
HoustonChicago
HOU - MDW
HOUMDW
Houston Hobby
Tue 7/14
9:25 pm-11:50 pm
Nonstop2h 25m
Chicago Midway
Thu 7/16
2:45 pm-7:45 pm
1 stop5h 00m
$234
HoustonChicago
HOU - MDW
HOUMDW
Houston Hobby
Tue 7/21
5:14 pm-10:15 pm
1 stop5h 01m
Chicago Midway
Sat 7/25
4:22 pm-9:51 pm
1 stop5h 29m
$248
HoustonChicago
HOU - MDW
HOUMDW
Houston Hobby
Thu 8/13
10:50 am-4:15 pm
1 stop5h 25m
Chicago Midway
Sun 8/16
6:05 am-12:16 pm
1 stop6h 11m
$288
Quickest round-trip
HoustonChicago
HOU - MDW
HOUMDW
Houston Hobby
Fri 7/24
6:50 pm-9:15 pm
Nonstop2h 25m
Chicago Midway
Mon 7/27
9:40 pm-12:10 am
Nonstop2h 30m
$289
HoustonChicago
HOU - MDW
HOUMDW
Houston Hobby
Fri 6/26
6:50 pm-9:15 pm
Nonstop2h 25m
Chicago Midway
Fri 7/3
11:35 am-2:10 pm
Nonstop2h 35m
$290
HoustonChicago
HOU - MDW
HOUMDW
Houston Hobby
Mon 6/1
1:30 pm-5:35 pm
1 stop4h 05m
Chicago Midway
Tue 6/30
9:10 am-1:50 pm
1 stop4h 40m
$298
HoustonChicago
HOU - MDW
HOUMDW
Houston Hobby
Tue 7/28
8:15 am-1:50 pm
1 stop5h 35m
Chicago Midway
Tue 8/4
2:40 pm-7:55 pm
2 stops5h 15m
$304
HoustonChicago
HOU - MDW
HOUMDW
Houston Hobby
Thu 7/9
2:55 pm-6:50 pm
1 stop3h 55m
Chicago Midway
Sun 7/12
8:30 am-11:10 am
Nonstop2h 40m
$313
HoustonChicago
HOU - MDW
HOUMDW
Houston Hobby
Fri 7/3
2:10 pm-7:10 pm
1 stop5h 00m
Chicago Midway
Sun 7/5
6:55 am-9:30 am
Nonstop2h 35m
$326
Showing 1-10 of 22 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 May.
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy2 stars | Trust Score*3 stars | |
| Price Accuracy- | Trust Score*1 star | |
| Price Accuracy2 stars | Trust Score*1 star | |
| Price Accuracy2 stars | Trust Score*3 stars | |
| 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 83 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, October is the cheapest month in which you can book a flight from Houston Hobby Airport to Chicago Midway Airport (average of $202). Flying from Houston Hobby Airport to Chicago Midway Airport in January is currently the most expensive (average of $559). 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 May 15, 2026.
Unlike at noon, when flights are generally more expensive, you can save up to 44% 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 May 9, 2026.
Travelers seeking maximum savings on their Houston Hobby Airport to Chicago Midway Airport flight should consider departing on Sunday 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 20% of weekly flights between Houston and Chicago have experienced delays in the past year, with the average delay time being 116 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?
Saturday 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 20% 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
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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 May 15, 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.
Food
7.0
Overall
8.0
Comfort
8.0
Boarding
8.1
Entertainment
7.5
Crew
8.6
Reviews
1 / 20
6.0
GoodScott,Feb 2026
HOU - FLL
Food
7.0
Overall
8.0
Comfort
8.0
Boarding
8.1
Entertainment
7.5
Crew
8.6
Reviews
1 / 20
6.0
GoodScott,Feb 2026
HOU - FLL
Food
7.0
Overall
8.0
Comfort
8.0
Boarding
8.1
Entertainment
7.5
Crew
8.6
Reviews
1 / 20
6.0
GoodScott,Feb 2026
HOU - FLL
Related info for your journey
Find useful and relevant information for your journey from Hobby 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?
Book flights to Chicago Midway Airport if you plan to visit one of these locationsBenton Harbor
Lansing
Merrillville
Hammond
Porter
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Top 2 airlines flying from Hobby to Midway
Discover the top 2 airlines that operate flights from Hobby 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 May 15, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$94 | Average$202 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$162 | Average$318 | FlexibilityNo cancel fee | On-time63% |