$103+ 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 8/19. Fares are subject to change and may not be available on all flights or dates of travel.
HOU — MDW
Aug 2 — Aug 91
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 October or November, booked 38 days in advance, depart on a Saturday or Wednesday and return on a Monday
Cheap flight deals from Houston to Midway
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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 July 3, 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 July 3, 2026.
This Southwest deal was found by Cheapflights users on 6/29. 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 8/175:00 am
HOU
- MDW
Nonstop2h 25m
Southwest
Wed 8/197:50 am
MDW
- HOU
Nonstop2h 35m
Southwest
Deal found 6/29![Southwest logo]()
$205
This Southwest deal was found by Cheapflights users on 6/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/219:25 pm
HOU
- MDW
Nonstop2h 30m
Southwest
Tue 7/289:00 pm
MDW
- HOU
Nonstop2h 40m
Southwest
Deal found 6/30![Southwest logo]()
$209
This Frontier deal was found by Cheapflights users on 6/28. 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.
Tue 8/410:53 am
IAH
- MDW
1 stop11h 10m
Frontier
Tue 8/1111:06 am
MDW
- IAH
1 stop11h 23m
Frontier
Deal found 6/28![Frontier logo]()
$210
This Southwest deal was found by Cheapflights users on 7/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/252:10 pm
HOU
- MDW
1 stop5h 25m
Southwest
Wed 7/299:00 pm
MDW
- HOU
Nonstop2h 40m
Southwest
Deal found 7/1![Southwest logo]()
$215
This Southwest deal was found by Cheapflights users on 6/29. 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
Wed 8/1910:10 am
MDW
- HOU
1 stop3h 50m
Southwest
Deal found 6/29![Southwest logo]()
$216
This Southwest deal was found by Cheapflights users on 6/30. 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 8/18:45 pm
HOU
- MDW
Nonstop2h 30m
Southwest
Sat 8/86:45 am
MDW
- HOU
1 stop6h 05m
Southwest
Deal found 6/30![Southwest logo]()
$217
This Southwest deal was found by Cheapflights users on 7/1. 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 8/18:45 pm
HOU
- MDW
Nonstop2h 30m
Southwest
Tue 8/44:40 pm
MDW
- HOU
1 stop6h 05m
Southwest
Deal found 7/1![Southwest logo]()
$219
This Southwest deal was found by Cheapflights users on 7/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/258:45 pm
HOU
- MDW
Nonstop2h 30m
Southwest
Tue 7/283:10 pm
MDW
- HOU
2 stops5h 30m
Southwest
Deal found 7/1![Southwest logo]()
$220
This Frontier deal was found by Cheapflights users on 6/28. 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 7/2910:53 am
IAH
- MDW
1 stop11h 10m
Frontier
Wed 8/511:06 am
MDW
- IAH
1 stop11h 23m
Frontier
Deal found 6/28![Frontier logo]()
$220
This Southwest deal was found by Cheapflights users on 6/28. 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
HOU
- MDW
Nonstop2h 20m
Southwest
Thu 9/1010:05 am
MDW
- HOU
1 stop3h 50m
Southwest
Deal found 6/28![Southwest logo]()
$221
This Southwest deal was found by Cheapflights users on 6/29. 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 8/18:45 pm
HOU
- MDW
Nonstop2h 30m
Southwest
Wed 8/57:40 am
MDW
- HOU
2 stops6h 05m
Southwest
Deal found 6/29![Southwest logo]()
$222
This Southwest deal was found by Cheapflights users on 7/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/1510:25 am
HOU
- MDW
1 stop3h 50m
Southwest
Mon 8/175:25 am
MDW
- HOU
Nonstop2h 25m
Southwest
Deal found 7/1![Southwest logo]()
$223
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 July 3, 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 July 3, 2026.
This Delta deal was found by Cheapflights users on 6/28. 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 10/1711:22 am
IAH
- MDW
1 stop6h 43m
Delta
Mon 10/195:15 pm
MDW
- IAH
1 stop6h 42m
Delta
Deal found 6/28![Delta logo]()
$225
This Southwest deal was found by Cheapflights users on 6/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/63:05 pm
HOU
- MDW
1 stop4h 45m
Southwest
Mon 8/105:25 am
MDW
- HOU
Nonstop2h 25m
Southwest
Deal found 6/28![Southwest logo]()
$235
This Delta deal was found by Cheapflights users on 6/29. 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.
Mon 8/246:00 am
HOU
- MDW
1 stop5h 51m
Delta
Wed 8/261:25 pm
MDW
- HOU
2 stops8h 40m
Delta
Deal found 6/29![Delta logo]()
$230
This Southwest deal was found by Cheapflights users on 7/1. 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 8/2611:25 am
HOU
- MDW
2 stops5h 30m
Southwest
Thu 8/2710:05 am
MDW
- HOU
1 stop3h 50m
Southwest
Deal found 7/1![Southwest logo]()
$238
This Delta deal was found by Cheapflights users on 6/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/44:37 pm
IAH
- MDW
1 stop5h 59m
Delta
Tue 8/111:25 pm
MDW
- IAH
2 stops10h 27m
Delta
Deal found 6/28![Delta logo]()
$230
This Southwest deal was found by Cheapflights users on 6/29. 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 8/18:45 pm
HOU
- MDW
Nonstop2h 30m
Southwest
Tue 8/48:25 pm
MDW
- HOU
Nonstop2h 25m
Southwest
Deal found 6/29![Southwest logo]()
$243
This Delta deal was found by Cheapflights users on 6/28. 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.
Mon 9/146:10 am
IAH
- MDW
1 stop7h 10m
Delta
Wed 9/169:29 am
MDW
- IAH
2 stops8h 10m
Delta
Deal found 6/28![Delta logo]()
$230
This Southwest deal was found by Cheapflights users on 7/2. 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 8/48:50 pm
HOU
- MDW
Nonstop2h 20m
Southwest
Wed 8/52:05 pm
MDW
- HOU
Nonstop2h 30m
Southwest
Deal found 7/2![Southwest logo]()
$244
This Delta deal was found by Cheapflights users on 6/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/1210:50 am
HOU
- MDW
2 stops7h 43m
Delta
Wed 8/199:24 am
MDW
- HOU
2 stops12h 41m
Delta
Deal found 6/28![Delta logo]()
$235
This Southwest deal was found by Cheapflights users on 7/2. 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 9/2811:30 am
HOU
- MDW
2 stops5h 25m
Southwest
Mon 10/52:10 pm
MDW
- HOU
1 stop5h 20m
Southwest
Deal found 7/2![Southwest logo]()
$246
This Delta deal was found by Cheapflights users on 7/2. 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 8/275:20 am
IAH
- MDW
1 stop7h 19m
Delta
Tue 9/19:24 am
MDW
- IAH
2 stops10h 44m
Delta
Deal found 7/2![Delta logo]()
$242
This Southwest deal was found by Cheapflights users on 7/1. 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 9/57:00 am
HOU
- MDW
Nonstop2h 25m
Southwest
Mon 9/75:30 am
MDW
- HOU
1 stop4h 05m
Southwest
Deal found 7/1![Southwest logo]()
$254
This Southwest deal was found by Cheapflights users on 6/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/711:05 am
HOU
- MDW
1 stop4h 20m
Southwest
Tue 8/115:15 pm
MDW
- HOU
Nonstop2h 30m
Southwest
Deal found 6/28![Southwest logo]()
$262
This Delta deal was found by Cheapflights users on 7/2. 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 9/55:09 pm
IAH
- MDW
1 stop5h 27m
Delta
Tue 9/86:05 am
MDW
- IAH
1 stop7h 27m
Delta
Deal found 7/2![Delta logo]()
$274
This Delta deal was found by Cheapflights users on 6/28. 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 10/29:44 am
IAH
- MDW
2 stops8h 49m
Delta
Mon 10/56:05 am
MDW
- IAH
1 stop5h 02m
Delta
Deal found 6/28![Delta logo]()
$277
This Delta deal was found by Cheapflights users on 7/1. 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 8/137:00 am
IAH
- MDW
1 stop4h 51m
Delta
Sat 8/151:25 pm
MDW
- IAH
2 stops10h 27m
Delta
Deal found 7/1![Delta logo]()
$279
This Delta deal was found by Cheapflights users on 6/29. 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 8/2010:50 am
HOU
- MDW
1 stop5h 25m
Delta
Mon 8/245:10 pm
MDW
- HOU
1 stop4h 55m
Delta
Deal found 6/29![Delta logo]()
$282
This Delta deal was found by Cheapflights users on 6/30. 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 9/185:26 pm
HOU
- MDW
1 stop5h 19m
Delta
Mon 9/211:19 pm
MDW
- HOU
2 stops9h 21m
Delta
Deal found 6/30![Delta logo]()
$287
This Delta deal was found by Cheapflights users on 7/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/1511:28 am
IAH
- MDW
2 stops11h 08m
Delta
Mon 8/171:25 pm
MDW
- IAH
2 stops10h 27m
Delta
Deal found 7/2![Delta logo]()
$292
This Delta deal was found by Cheapflights users on 7/2. 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 10/1110:57 am
IAH
- MDW
1 stop5h 42m
Delta
Tue 10/135:15 pm
MDW
- IAH
1 stop6h 42m
Delta
Deal found 7/2![Delta logo]()
$293
Last-minute flights from Houston to MidwayDiscover last-minute flight deals from Houston to Midway. Data last updated July 3, 2026 and is based on user searches.
Discover last-minute flight deals from Houston to Midway. Data last updated July 3, 2026 and is based on user searches.
This Southwest deal was found by Cheapflights users on 6/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/219:25 pm
HOU
- MDW
Nonstop2h 30m
Southwest
Tue 7/289:00 pm
MDW
- HOU
Nonstop2h 40m
Southwest
Deal found 6/30![Southwest logo]()
$209
This Southwest deal was found by Cheapflights users on 7/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/252:10 pm
HOU
- MDW
1 stop5h 25m
Southwest
Wed 7/299:00 pm
MDW
- HOU
Nonstop2h 40m
Southwest
Deal found 7/1![Southwest logo]()
$215
This Southwest deal was found by Cheapflights users on 7/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/258:45 pm
HOU
- MDW
Nonstop2h 30m
Southwest
Tue 7/283:10 pm
MDW
- HOU
2 stops5h 30m
Southwest
Deal found 7/1![Southwest logo]()
$220
This Frontier deal was found by Cheapflights users on 6/28. 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 7/2910:53 am
IAH
- MDW
1 stop11h 10m
Frontier
Wed 8/511:06 am
MDW
- IAH
1 stop11h 23m
Frontier
Deal found 6/28![Frontier logo]()
$220
This Southwest deal was found by Cheapflights users on 6/30. 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 8/18:45 pm
HOU
- MDW
Nonstop2h 30m
Southwest
Sat 8/86:45 am
MDW
- HOU
1 stop6h 05m
Southwest
Deal found 6/30![Southwest logo]()
$217
This Southwest deal was found by Cheapflights users on 7/2. 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 8/18:45 pm
HOU
- MDW
Nonstop2h 30m
Southwest
Tue 8/41:15 pm
MDW
- HOU
1 stop4h 10m
Southwest
Deal found 7/2![Southwest logo]()
$219
This Frontier deal was found by Cheapflights users on 6/28. 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.
Tue 8/410:53 am
IAH
- MDW
1 stop11h 10m
Frontier
Tue 8/1111:06 am
MDW
- IAH
1 stop11h 23m
Frontier
Deal found 6/28![Frontier logo]()
$210
This Frontier deal was found by Cheapflights users on 6/28. 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 8/512:16 pm
IAH
- MDW
1 stop9h 47m
Frontier
Sat 8/811:06 am
MDW
- IAH
1 stop11h 23m
Frontier
Deal found 6/28![Frontier logo]()
$225
This Southwest deal was found by Cheapflights users on 6/29. 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
Wed 8/1910:10 am
MDW
- HOU
1 stop3h 50m
Southwest
Deal found 6/29![Southwest logo]()
$216
This Southwest deal was found by Cheapflights users on 6/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/1510:25 am
HOU
- MDW
1 stop3h 50m
Southwest
Mon 8/175:25 am
MDW
- HOU
Nonstop2h 25m
Southwest
Deal found 6/30![Southwest logo]()
$223
This Southwest deal was found by Cheapflights users on 6/29. 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 8/175:00 am
HOU
- MDW
Nonstop2h 25m
Southwest
Wed 8/197:50 am
MDW
- HOU
Nonstop2h 35m
Southwest
Deal found 6/29![Southwest logo]()
$205
This Southwest deal was found by Cheapflights users on 6/28. 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
HOU
- MDW
Nonstop2h 20m
Southwest
Thu 9/1010:05 am
MDW
- HOU
1 stop3h 50m
Southwest
Deal found 6/28![Southwest logo]()
$221
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 July 3, 2026.
Search for one-way flight options from Houston to Midway. Find affordable one-way fares based on user searches. Data last updated July 3, 2026.
This Southwest deal was found by Cheapflights users on 6/29. 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 8/198:50 pm
HOU
- MDW
Nonstop2h 20m
Southwest
Deal found 6/29![Southwest logo]()
$103
This Super.com deal was found by Cheapflights users on 6/30. 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.
Wed 8/194:32 pm
IAH
- MDW
1 stop6h 15m
Frontier
Deal found 6/30![Frontier logo]()
$104
This Southwest deal was found by Cheapflights users on 6/30. 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 8/18:45 pm
HOU
- MDW
Nonstop2h 30m
Southwest
Deal found 6/30![Southwest logo]()
$105
This Frontier deal was found by Cheapflights users on 6/28. 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.
Tue 8/254:32 pm
IAH
- MDW
1 stop6h 15m
Frontier
Deal found 6/28![Frontier logo]()
$105
This Trip.com deal was found by Cheapflights users on 7/1. 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.
Wed 9/24:32 pm
IAH
- MDW
1 stop6h 15m
Frontier
Deal found 7/1![Frontier logo]()
$109
This Southwest deal was found by Cheapflights users on 7/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/252:10 pm
HOU
- MDW
1 stop5h 25m
Southwest
Deal found 7/1![Southwest logo]()
$110
This Southwest deal was found by Cheapflights users on 6/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/137:55 pm
HOU
- MDW
Nonstop2h 20m
Southwest
Deal found 6/30![Southwest logo]()
$113
This Delta deal was found by Cheapflights users on 6/29. 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.
Mon 8/242:37 pm
IAH
- MDW
1 stop7h 59m
Delta
Deal found 6/29![Delta logo]()
$113
This Trip.com deal was found by Cheapflights users on 6/29. 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.
Tue 8/410:53 am
IAH
- MDW
1 stop11h 10m
Frontier
Deal found 6/29![Frontier logo]()
$114
This Delta deal was found by Cheapflights users on 7/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/15:17 pm
HOU
- MDW
1 stop4h 58m
Delta
Deal found 7/1![Delta logo]()
$115
This Delta deal was found by Cheapflights users on 7/1. 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 7/286:30 am
IAH
- MDW
1 stop6h 39m
Delta
Deal found 7/1![Delta logo]()
$115
This Delta deal was found by Cheapflights users on 6/28. 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
2 stops7h 43m
Delta
Deal found 6/28![Delta logo]()
$118
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 July 3, 2026.
Round-trip from | $205 (Southwest) |
|---|---|
One-way from | $103 (Southwest) |
Popular in | January |
Cheapest in | October |
Average price | $322 |
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 July 3, 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
IAH - MDW
IAHMDW
Houston George Bush Intcntl
Sat 10/17
11:22 am-6:05 pm
1 stop6h 43m
Chicago Midway
Mon 10/19
5:15 pm-11:57 pm
1 stop6h 42m
$225
HoustonChicago
HOU - MDW
HOUMDW
Houston Hobby
Mon 8/24
6:00 am-11:51 am
1 stop5h 51m
Chicago Midway
Wed 8/26
1:25 pm-10:05 pm
2 stops8h 40m
$230
HoustonChicago
IAH - MDW
IAHMDW
Houston George Bush Intcntl
Tue 8/4
4:37 pm-10:36 pm
1 stop5h 59m
Chicago Midway
Tue 8/11
1:25 pm-11:52 pm
2 stops10h 27m
$230
HoustonChicago
IAH - MDW
IAHMDW
Houston George Bush Intcntl
Mon 9/14
6:10 am-1:20 pm
1 stop7h 10m
Chicago Midway
Wed 9/16
9:29 am-5:39 pm
2 stops8h 10m
$230
HoustonChicago
HOU - MDW
HOUMDW
Houston Hobby
Thu 8/6
3:05 pm-7:50 pm
1 stop4h 45m
Chicago Midway
Mon 8/10
5:25 am-7:50 am
Nonstop2h 25m
$235
HoustonChicago
HOU - MDW
HOUMDW
Houston Hobby
Wed 8/12
10:50 am-6:33 pm
2 stops7h 43m
Chicago Midway
Wed 8/19
9:24 am-10:05 pm
2 stops12h 41m
$235
HoustonChicago
HOU - MDW
HOUMDW
Houston Hobby
Wed 8/26
11:25 am-4:55 pm
2 stops5h 30m
Chicago Midway
Thu 8/27
10:05 am-1:55 pm
1 stop3h 50m
$238
HoustonChicago
IAH - MDW
IAHMDW
Houston George Bush Intcntl
Thu 8/27
5:20 am-12:39 pm
1 stop7h 19m
Chicago Midway
Tue 9/1
9:24 am-8:08 pm
2 stops10h 44m
$242
HoustonChicago
HOU - MDW
HOUMDW
Houston Hobby
Sat 8/1
8:45 pm-11:15 pm
Nonstop2h 30m
Chicago Midway
Tue 8/4
8:25 pm-10:50 pm
Nonstop2h 25m
$243
Quickest round-trip
HoustonChicago
HOU - MDW
HOUMDW
Houston Hobby
Tue 8/4
8:50 pm-11:10 pm
Nonstop2h 20m
Chicago Midway
Wed 8/5
2:05 pm-4:35 pm
Nonstop2h 30m
$244
Showing 1-10 of 41 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, October is the cheapest month in which you can book a flight from Houston to Chicago Midway Airport (average of $56). Flying from Houston to Chicago Midway Airport in May is currently the most expensive (average of $188). 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 July 3, 2026.
Unlike at noon, when flights are generally more expensive, you can save up to 17% 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?
How often are flights from Houston to Chicago delayed?
About 21% 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 20% 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 June 27, 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 July 3, 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.
Overall
7.9
Comfort
8.0
Entertainment
7.5
Food
7.0
Boarding
8.1
Crew
8.6
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Overall
7.9
Comfort
8.0
Entertainment
7.5
Food
7.0
Boarding
8.1
Crew
8.6
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Overall
7.9
Comfort
8.0
Entertainment
7.5
Food
7.0
Boarding
8.1
Crew
8.6
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Overall
7.9
Comfort
8.0
Entertainment
7.5
Food
7.0
Boarding
8.1
Crew
8.6
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
Hammond
Lansing
Merrillville
Valparaiso
Porter
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Complete your trip
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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 July 3, 2026.
Houston and Midway flights
Browse other Houston and Midway flight options. Last updated on July 3, 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 July 3, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$84 | Average$183 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$177 | Average$362 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$216 | Average$331 | FlexibilityNo cancel fee | On-timeN/A |