$78+ Cheap flights from Houston to Midway (MDW)
This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 9/11. Fares are subject to change and may not be available on all flights or dates of travel.
HOU — MDW
Sep 17 — Sep 241
Round-trip
1 adult, Economy
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Find cheap flights from Houston 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 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 Houston to Midway
Cheapest
Best
Last-minute
One-way
Cheapest flights from Houston to MidwayExplore the most affordable flight options available from Houston to Midway. Find the lowest fares from popular airlines and budget airlines, with prices last updated on August 18, 2026.
Explore the most affordable flight options available from Houston to Midway. Find the lowest fares from popular airlines and budget airlines, with prices last updated on August 18, 2026.
This Kiwi.com deal was found by Cheapflights users on 8/14. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/24:32 pm -
1 stop6h 15m
Sat 9/511:45 am -
1 stop10h 29m
Deal found 8/14![Frontier logo]()
$155
This Frontier deal was found by Cheapflights users on 8/16. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/291:35 pm -
1 stop8h 18m
Tue 11/37:25 am -
1 stop7h 40m
Deal found 8/16![Frontier logo]()
$156
This Expedia deal was found by Cheapflights users on 8/13. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/54:32 pm -
1 stop6h 15m
Tue 9/811:50 am -
1 stop10h 24m
Deal found 8/13![Frontier logo]()
$158
This Kiwi.com deal was found by Cheapflights users on 8/13. 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.
Tue 9/159:04 pm -
1 stop20h 47m
Tue 9/226:25 am -
1 stop16h 05m
Deal found 8/13![Frontier logo]()
$159
This Kiwi.com deal was found by Cheapflights users on 8/13. 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.
Sat 9/54:32 pm -
1 stop6h 15m
Sat 9/126:25 am -
1 stop16h 05m
Deal found 8/13![Frontier logo]()
$162
This Orbitz deal was found by Cheapflights users on 8/13. 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 Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/31:35 pm -
1 stop8h 18m
Thu 11/512:03 pm -
1 stop10h 07m
Deal found 8/13![Frontier logo]()
$172
This Southwest deal was found by Cheapflights users on 8/12. 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.
Thu 9/107:55 pm -
Nonstop2h 25m
Thu 9/175:25 am -
Nonstop2h 25m
Deal found 8/12![Southwest logo]()
$185
This Kiwi.com deal was found by Cheapflights users on 8/13. 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 9/1012:08 pm -
1 stop5h 38m
Sat 9/126:25 am -
1 stop16h 05m
Deal found 8/13![Frontier logo]()
$186
This CheapOair deal was found by Cheapflights users on 8/13. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/311:35 pm -
1 stop8h 18m
Mon 11/212:03 pm -
1 stop10h 07m
Deal found 8/13![Frontier logo]()
$188
This Southwest deal was found by Cheapflights users on 8/13. 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 9/28:50 pm -
Nonstop2h 20m
Sat 9/51:20 pm -
1 stop5h 50m
Deal found 8/13![Southwest logo]()
$189
This Southwest deal was found by Cheapflights users on 8/13. 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 9/117:55 pm -
Nonstop2h 25m
Mon 9/145:25 am -
Nonstop2h 25m
Deal found 8/13![Southwest logo]()
$191
This Southwest deal was found by Cheapflights users on 8/13. 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 11/1111:30 am -
2 stops5h 40m
Sat 11/142:55 pm -
Nonstop2h 40m
Deal found 8/13![Southwest logo]()
$196
Best flights from Houston to MidwayDiscover carefully curated flight deals from Houston to Midway that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated August 18, 2026.
Discover carefully curated flight deals from Houston to Midway that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated August 18, 2026.
This Southwest deal was found by Cheapflights users on 8/13. 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 9/107:55 pm -
Nonstop2h 25m
Sat 9/125:55 am -
1 stop6h 00m
Deal found 8/13![Southwest logo]()
$195
This Delta deal was found by Cheapflights users on 8/13. 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.
Fri 10/165:00 pm -
1 stop5h 33m
Wed 10/2110:59 am -
1 stop4h 55m
Deal found 8/13![Delta logo]()
$231
This Southwest deal was found by Cheapflights users on 8/13. 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.
Sat 9/127:40 pm -
Nonstop2h 20m
Sat 9/192:15 pm -
1 stop4h 35m
Deal found 8/13![Southwest logo]()
$195
This Southwest deal was found by Cheapflights users on 8/16. 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.
Tue 9/88:50 pm -
Nonstop2h 25m
Thu 9/105:25 am -
Nonstop2h 25m
Deal found 8/16![Southwest logo]()
$209
This Delta deal was found by Cheapflights users on 8/15. 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 9/112:44 pm -
1 stop8h 00m
Tue 9/156:05 am -
1 stop7h 25m
Deal found 8/15![Delta logo]()
$242
This Southwest deal was found by Cheapflights users on 8/15. 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 9/107:55 pm -
Nonstop2h 25m
Tue 9/157:50 am -
Nonstop2h 35m
Deal found 8/15![Southwest logo]()
$209
This Delta deal was found by Cheapflights users on 8/15. 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.
Thu 10/298:05 am -
2 stops9h 55m
Fri 10/301:27 pm -
2 stops7h 50m
Deal found 8/15![Delta logo]()
$252
This Southwest deal was found by Cheapflights users on 8/14. 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.
Sat 9/197:00 am -
Nonstop2h 25m
Tue 9/228:40 am -
1 stop6h 20m
Deal found 8/14![Southwest logo]()
$219
This Delta deal was found by Cheapflights users on 8/17. 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 10/225:29 am -
2 stops7h 18m
Tue 10/275:09 pm -
1 stop6h 46m
Deal found 8/17![Delta logo]()
$269
This Southwest deal was found by Cheapflights users on 8/16. 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.
Wed 9/232:35 pm -
2 stops5h 35m
Mon 9/285:25 am -
Nonstop2h 25m
Deal found 8/16![Southwest logo]()
$224
This Southwest deal was found by Cheapflights users on 8/14. 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 9/107:55 pm -
Nonstop2h 25m
Fri 9/111:05 pm -
1 stop5h 20m
Deal found 8/14![Southwest logo]()
$228
This Delta deal was found by Cheapflights users on 8/14. 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 9/1811:26 am -
1 stop7h 07m
Sat 9/192:00 pm -
1 stop7h 30m
Deal found 8/14![Delta logo]()
$294
This Southwest deal was found by Cheapflights users on 8/17. 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 9/911:25 am -
1 stop4h 05m
Sat 9/1210:05 am -
2 stops6h 50m
Deal found 8/17![Southwest logo]()
$230
This Delta deal was found by Cheapflights users on 8/17. 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 9/84:59 pm -
1 stop5h 45m
Tue 9/229:29 am -
2 stops10h 04m
Deal found 8/17![Delta logo]()
$299
This Delta deal was found by Cheapflights users on 8/16. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/2211:26 am -
2 stops11h 18m
Mon 9/281:19 pm -
2 stops10h 35m
Deal found 8/16![Delta logo]()
$304
This Southwest deal was found by Cheapflights users on 8/16. 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.
Sat 9/57:40 pm -
Nonstop2h 25m
Wed 9/97:50 am -
Nonstop2h 35m
Deal found 8/16![Southwest logo]()
$270
This Delta deal was found by Cheapflights users on 8/16. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/2311:26 am -
2 stops11h 18m
Mon 9/281:19 pm -
2 stops10h 35m
Deal found 8/16![Delta logo]()
$304
This Southwest deal was found by Cheapflights users on 8/14. 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.
Sun 11/1512:55 pm -
1 stop4h 05m
Wed 11/183:50 pm -
1 stop6h 35m
Deal found 8/14![Southwest logo]()
$293
This Delta deal was found by Cheapflights users on 8/13. 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.
Wed 10/145:29 am -
2 stops7h 18m
Sat 10/171:27 pm -
2 stops7h 50m
Deal found 8/13![Delta logo]()
$343
This Delta deal was found by Cheapflights users on 8/15. 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.
Sun 10/186:00 am -
1 stop5h 47m
Tue 10/2010:01 am -
1 stop7h 49m
Deal found 8/15![Delta logo]()
$344
Last-minute flights from Houston to MidwayDiscover last-minute flight deals from Houston to Midway. Data last updated August 18, 2026 and is based on user searches.
Discover last-minute flight deals from Houston to Midway. Data last updated August 18, 2026 and is based on user searches.
This Southwest deal was found by Cheapflights users on 8/13. 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.
Mon 8/317:55 pm -
Nonstop2h 20m
Wed 9/302:45 pm -
2 stops5h 15m
Deal found 8/13![Southwest logo]()
$200
This Kiwi.com deal was found by Cheapflights users on 8/14. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/17:55 pm -
2 stops15h 00m
Tue 9/811:50 am -
1 stop19h 27m
Deal found 8/14![Frontier logo]()
$192
This Kiwi.com deal was found by Cheapflights users on 8/14. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/24:32 pm -
1 stop6h 15m
Sat 9/511:45 am -
1 stop10h 29m
Deal found 8/14![Frontier logo]()
$155
This Southwest deal was found by Cheapflights users on 8/13. 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 9/28:50 pm -
Nonstop2h 20m
Sat 9/51:20 pm -
1 stop5h 50m
Deal found 8/13![Southwest logo]()
$189
This Expedia deal was found by Cheapflights users on 8/13. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/54:32 pm -
1 stop6h 15m
Tue 9/811:50 am -
1 stop10h 24m
Deal found 8/13![Frontier logo]()
$158
This Kiwi.com deal was found by Cheapflights users on 8/13. 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.
Sat 9/54:32 pm -
1 stop6h 15m
Sat 9/126:25 am -
1 stop16h 05m
Deal found 8/13![Frontier logo]()
$162
This Southwest deal was found by Cheapflights users on 8/12. 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.
Thu 9/107:55 pm -
Nonstop2h 25m
Thu 9/175:25 am -
Nonstop2h 25m
Deal found 8/12![Southwest logo]()
$185
This Kiwi.com deal was found by Cheapflights users on 8/13. 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 9/1012:08 pm -
1 stop5h 38m
Sat 9/126:25 am -
1 stop16h 05m
Deal found 8/13![Frontier logo]()
$186
This Kiwi.com deal was found by Cheapflights users on 8/13. 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 9/1012:08 pm -
1 stop5h 38m
Mon 9/146:46 pm -
1 stop12h 31m
Deal found 8/13![Frontier logo]()
$193
This Southwest deal was found by Cheapflights users on 8/13. 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 9/107:55 pm -
Nonstop2h 25m
Mon 9/145:25 am -
Nonstop2h 25m
Deal found 8/13![Southwest logo]()
$197
This Southwest deal was found by Cheapflights users on 8/13. 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 9/117:55 pm -
Nonstop2h 25m
Mon 9/145:25 am -
Nonstop2h 25m
Deal found 8/13![Southwest logo]()
$191
This Kiwi.com deal was found by Cheapflights users on 8/13. 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.
Tue 9/159:04 pm -
1 stop20h 47m
Tue 9/226:25 am -
1 stop16h 05m
Deal found 8/13![Frontier logo]()
$159
One-way flights from Houston to MidwaySearch for one-way flight options from Houston to Midway. Find affordable one-way fares based on user searches. Data last updated August 18, 2026.
Search for one-way flight options from Houston to Midway. Find affordable one-way fares based on user searches. Data last updated August 18, 2026.
This Frontier deal was found by Cheapflights users on 8/14. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/1112:08 pm -
1 stop5h 43m
Deal found 8/14![Frontier logo]()
$78
This CheapOair deal was found by Cheapflights users on 8/17. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/2412:08 pm -
1 stop5h 38m
Deal found 8/17![Frontier logo]()
$79
This CheapOair deal was found by Cheapflights users on 8/13. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/1012:08 pm -
1 stop5h 38m
Deal found 8/13![Frontier logo]()
$80
This Super.com deal was found by Cheapflights users on 8/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/36:08 am -
1 stop11h 43m
Deal found 8/17![Frontier logo]()
$82
This Frontier deal was found by Cheapflights users on 8/13. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/24:32 pm -
1 stop6h 15m
Deal found 8/13![Frontier logo]()
$83
This Frontier deal was found by Cheapflights users on 8/14. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/2112:07 pm -
1 stop11h 36m
Deal found 8/14![Frontier logo]()
$84
This CheapOair deal was found by Cheapflights users on 8/16. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/2012:17 pm -
1 stop11h 26m
Deal found 8/16![Frontier logo]()
$85
This Super.com deal was found by Cheapflights users on 8/13. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/216:08 am -
1 stop11h 43m
Deal found 8/13![Frontier logo]()
$88
This Trip.com deal was found by Cheapflights users on 8/13. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/129:12 pm -
1 stop26h 31m
Deal found 8/13![Frontier logo]()
$90
This Trip.com deal was found by Cheapflights users on 8/14. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/138:44 pm -
1 stop14h 14m
Deal found 8/14![Frontier logo]()
$92
This Southwest deal was found by Cheapflights users on 8/13. 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 9/18:50 pm -
Nonstop2h 20m
Deal found 8/13![Southwest logo]()
$93
This CheapOair deal was found by Cheapflights users on 8/13. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/84:32 pm -
1 stop6h 15m
Deal found 8/13![Frontier logo]()
$94
Find flight deals from Houston to Midway
Discover tips and strategies to find the most affordable flight options for your journey from Houston (HO1) to Midway (MDW). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated August 18, 2026.
Round-trip from | $155 (Kiwi.com) |
|---|---|
One-way from | $78 (Frontier) |
Popular in | January |
Cheapest in | November |
Average price | $307 |
Cheapflights Fare Finder
Customize your flight search to find flights from Houston 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 August 18, 2026.
Use the filters below to find and compare flights from Houston to Chicago Midway Airport that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
HoustonChicago
HOU Houston Hobby - MDW Chicago Midway
HOUMDW
Houston Hobby
Thu 9/10
7:55 pm-10:20 pm
Nonstop2h 25m
Chicago Midway
Sat 9/12
5:55 am-11:55 am
1 stop6h 00m
$195
HoustonChicago
HOU Houston Hobby - MDW Chicago Midway
HOUMDW
Houston Hobby
Sat 9/12
7:40 pm-10:00 pm
Nonstop2h 20m
Chicago Midway
Sat 9/19
2:15 pm-6:50 pm
1 stop4h 35m
$195
Quickest round-trip
HoustonChicago
HOU Houston Hobby - MDW Chicago Midway
HOUMDW
Houston Hobby
Tue 9/8
8:50 pm-11:15 pm
Nonstop2h 25m
Chicago Midway
Thu 9/10
5:25 am-7:50 am
Nonstop2h 25m
$209
HoustonChicago
HOU Houston Hobby - MDW Chicago Midway
HOUMDW
Houston Hobby
Thu 9/10
7:55 pm-10:20 pm
Nonstop2h 25m
Chicago Midway
Tue 9/15
7:50 am-10:25 am
Nonstop2h 35m
$209
HoustonChicago
HOU Houston Hobby - MDW Chicago Midway
HOUMDW
Houston Hobby
Sat 9/19
7:00 am-9:25 am
Nonstop2h 25m
Chicago Midway
Tue 9/22
8:40 am-3:00 pm
1 stop6h 20m
$219
HoustonChicago
HOU Houston Hobby - MDW Chicago Midway
HOUMDW
Houston Hobby
Wed 9/23
2:35 pm-8:10 pm
2 stops5h 35m
Chicago Midway
Mon 9/28
5:25 am-7:50 am
Nonstop2h 25m
$224
HoustonChicago
HOU Houston Hobby - MDW Chicago Midway
HOUMDW
Houston Hobby
Thu 9/10
7:55 pm-10:20 pm
Nonstop2h 25m
Chicago Midway
Fri 9/11
1:05 pm-6:25 pm
1 stop5h 20m
$228
HoustonChicago
HOU Houston Hobby - MDW Chicago Midway
HOUMDW
Houston Hobby
Wed 9/9
11:25 am-3:30 pm
1 stop4h 05m
Chicago Midway
Sat 9/12
10:05 am-4:55 pm
2 stops6h 50m
$230
HoustonChicago
IAH Houston George Bush Intcntl - MDW Chicago Midway
IAHMDW
Houston George Bush Intcntl
Fri 10/16
5:00 pm-10:33 pm
1 stop5h 33m
Chicago Midway
Wed 10/21
10:59 am-3:54 pm
1 stop4h 55m
$231
HoustonChicago
IAH Houston George Bush Intcntl - MDW Chicago Midway
IAHMDW
Houston George Bush Intcntl
Fri 9/11
2:44 pm-10:44 pm
1 stop8h 00m
Chicago Midway
Tue 9/15
6:05 am-1:30 pm
1 stop7h 25m
$242
Showing 1-10 of 39 resultsSorted by cheapest first
Best time to book a flight from Houston to Midway
Have a flexible travel schedule? Discover the best time to fly to Midway from Houston with our price prediction graph.
HO1-MDW
HOU-MDW
IAH-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 to Chicago Midway Airport
HO1-MDW
HOU-MDW
IAH-MDW
What is the cheapest month to book a flight from Houston to Chicago Midway Airport?
Currently, February is the cheapest month in which you can book a flight from Houston to Chicago Midway Airport (average of $153). Flying from Houston to Chicago Midway Airport in January is currently the most expensive (average of $579). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.
What is the cheapest time of day to fly from HOU to MDW?
Find hourly flight availability from Houston to Midway. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated August 18, 2026.
Unlike at noon, when flights are generally more expensive, you can save up to 16% on flights from Houston to Chicago Midway Airport by exploring options for tickets in the evening.
How much does it cost to fly round-trip from Houston to Chicago Midway Airport?
Airfare is below average for this route at the moment.
Houston to Chicago Midway Airport flights typically cost between $227 and $514 in September.The cheapest round-trip price found within the last 5 days was $155 on Frontier (Sep 2-Sep 5).
How often are flights from Houston to Chicago delayed?
About 23% of weekly flights between Houston and Chicago have experienced delays in the past year, with the average delay time being 119 minutes.
What is the most punctual flight time for Houston to Chicago flights?
Historically, flights departing in the morning are less likely to be delayed, whereas flights leaving in the evening tend to experience delays more often.
What day of the week experiences the fewest flight delays on this route?
Tuesday tends to have the lowest number of delays on this route, whereas Sunday has historically faced a higher average of delays compared to other days of the week.
Which airline has the best punctuality record on Houston to Chicago flights?
Over the last year, Southwest have had the lowest number of delays on this route, with just 23% of flights being delayed.
How far ahead should I book a flight from Houston to Chicago Midway Airport?
The price you pay for your flight from Houston to Chicago Midway Airport may vary depending on when you book. For the best chance of a lower fare, look to book 37 days in advance of your trip. Fares are likely to increase a fortnight or so before your departure date.
What is the cheapest day to fly from Houston to Chicago Midway Airport?
Use this chart to determine the cheapest time to fly round-trip from Houston to Midway. Price data was last updated on August 15, 2026.
Travelers seeking maximum savings on their Houston to Chicago Midway Airport flight should consider departing on Wednesday afternoons when fares are most often at their lowest. Monday at noon flights should be avoided if possible as fares are typically the most expensive at this time.
The best insider tips for Houston to Chicago Midway Airport flights
AI-powered summary based on content written by travel experts. AI can make mistakes.
Cheapflights partnered with top experts to bring you the best recommendations for your Houston to Chicago Midway Airport trip
Our travel experts
Reviews of airlines servicing Midway
Get insights into the airlines that provide service to Midway. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Midway. Reviews last updated August 18, 2026.
Get a feel of what it's like to fly with Southwest,Delta, andFrontier from Houston to Chicago Midway Airport by reading reviews from past customers. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Entertainment
7.5
Food
7.0
Boarding
8.1
Overall
8.0
Crew
8.6
Comfort
8.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Entertainment
7.5
Food
7.0
Boarding
8.1
Overall
8.0
Crew
8.6
Comfort
8.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Entertainment
7.5
Food
7.0
Boarding
8.1
Overall
8.0
Crew
8.6
Comfort
8.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Entertainment
7.5
Food
7.0
Boarding
8.1
Overall
8.0
Crew
8.6
Comfort
8.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Related info for your journey
Find useful and relevant information for your journey from Houston to Midway. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
Traveling to a place near Chicago Midway Airport?
Book flights to Chicago Midway Airport if you plan to visit one of these locationsBenton Harbor
Lansing
Merrillville
Valparaiso
Hammond
Saint Joseph
Porter
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Complete your trip
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Search flights from Houston to Midway by cabin class
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Other flights to Midway
Explore flights to Midway departing from other origins. Flights are based on user searches made on Cheapflights and were last updated on August 18, 2026.
Houston and Midway flights
Browse other Houston and Midway flight options. Last updated on August 18, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Top 3 airlines flying from Houston to Midway
Discover the top 3 airlines that operate flights from Houston to Midway. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated August 18, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$84 | Average$178 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$197 | Average$386 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$228 | Average$327 | FlexibilityNo cancel fee | On-timeN/A |