$67+ 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 4/16. Fares are subject to change and may not be available on all flights or dates of travel.
HOU — MDW
Apr 22 — Apr 291
Round-trip
1 adult, Economy
We work with more than 300 partners to bring you better travel deals
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 September or October, booked 11 days in advance, depart on a Wednesday or Saturday 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 March 23, 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 March 23, 2026.
This Frontier deal was found by Cheapflights users on 3/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/164:06 pm
IAH
- MDW
1 stop6h 13m
Frontier
Tue 4/212:15 pm
MDW
- IAH
1 stop8h 35m
Frontier
Deal found 3/23![Frontier logo]()
$140
This Kiwi.com deal was found by Cheapflights users on 3/20. 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 4/2512:35 pm
IAH
- MDW
1 stop6h 02m
Multiple Airlines
Tue 4/282:15 pm
MDW
- IAH
1 stop8h 35m
Multiple Airlines
Deal found 3/20![Multiple Airlines logo]()
$148
This Kiwi.com deal was found by Cheapflights users on 3/18. 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 4/304:06 pm
IAH
- MDW
1 stop6h 13m
Multiple Airlines
Sat 5/27:34 pm
MDW
- IAH
1 stop15h 37m
Multiple Airlines
Deal found 3/18![Multiple Airlines logo]()
$150
This Super.com deal was found by Cheapflights users on 3/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/101:27 pm
IAH
- MDW
Nonstop2h 32m
Frontier
Tue 4/142:15 pm
MDW
- IAH
1 stop8h 35m
Frontier
Deal found 3/22![Frontier logo]()
$154
This Super.com deal was found by Cheapflights users on 3/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/101:27 pm
IAH
- MDW
Nonstop2h 32m
Frontier
Mon 4/139:20 am
MDW
- IAH
Nonstop3h 12m
Frontier
Deal found 3/22![Frontier logo]()
$156
This Expedia deal was found by Cheapflights users on 3/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/101:27 pm
IAH
- MDW
Nonstop2h 32m
Frontier
Sun 4/125:05 am
MDW
- IAH
1 stop25h 57m
Frontier
Deal found 3/22![Frontier logo]()
$159
This Super.com deal was found by Cheapflights users on 3/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/164:06 pm
IAH
- MDW
1 stop6h 13m
Frontier
Thu 4/232:15 pm
MDW
- IAH
1 stop8h 35m
Frontier
Deal found 3/22![Frontier logo]()
$160
This Kiwi.com deal was found by Cheapflights users on 3/20. 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 4/164:06 pm
IAH
- MDW
1 stop6h 13m
Frontier
Sun 4/196:00 am
MDW
- IAH
1 stop11h 19m
Frontier
Deal found 3/20![Frontier logo]()
$168
This Southwest deal was found by Cheapflights users on 3/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/218:40 pm
HOU
- MDW
Nonstop2h 25m
Southwest
Tue 4/287:25 am
MDW
- HOU
Nonstop2h 40m
Southwest
Deal found 3/22![Southwest logo]()
$180
This Southwest deal was found by Cheapflights users on 3/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/168:20 pm
HOU
- MDW
Nonstop2h 25m
Southwest
Tue 5/198:40 pm
MDW
- HOU
Nonstop2h 40m
Southwest
Deal found 3/23![Southwest logo]()
$189
This Southwest deal was found by Cheapflights users on 3/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/62:40 pm
HOU
- MDW
2 stops5h 40m
Southwest
Wed 5/138:00 am
MDW
- HOU
2 stops5h 55m
Southwest
Deal found 3/22![Southwest logo]()
$210
This Southwest deal was found by Cheapflights users on 3/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/75:10 am
HOU
- MDW
Nonstop2h 25m
Southwest
Sat 5/912:55 pm
MDW
- HOU
1 stop4h 20m
Southwest
Deal found 3/22![Southwest logo]()
$213
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 March 23, 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 March 23, 2026.
This Southwest deal was found by Cheapflights users on 3/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/66:10 pm
HOU
- MDW
Nonstop2h 25m
Southwest
Wed 5/138:00 am
MDW
- HOU
2 stops5h 55m
Southwest
Deal found 3/21![Southwest logo]()
$232
This Delta deal was found by Cheapflights users on 3/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/219:43 am
IAH
- MDW
1 stop6h 43m
Delta
Tue 4/2810:41 am
MDW
- IAH
1 stop5h 03m
Delta
Deal found 3/22![Delta logo]()
$237
This Southwest deal was found by Cheapflights users on 3/18. 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 5/210:50 am
HOU
- MDW
2 stops6h 00m
Southwest
Tue 5/59:40 am
MDW
- HOU
1 stop4h 20m
Southwest
Deal found 3/18![Southwest logo]()
$233
This Delta deal was found by Cheapflights users on 3/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/910:27 am
HOU
- MDW
1 stop5h 45m
Delta
Mon 5/115:10 pm
MDW
- HOU
1 stop5h 16m
Delta
Deal found 3/21![Delta logo]()
$257
This Southwest deal was found by Cheapflights users on 3/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/293:30 pm
HOU
- MDW
1 stop4h 50m
Southwest
Sun 5/35:00 am
MDW
- HOU
1 stop4h 30m
Southwest
Deal found 3/22![Southwest logo]()
$238
This Delta deal was found by Cheapflights users on 3/19. 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 5/201:06 pm
HOU
- MDW
1 stop8h 03m
Delta
Wed 5/276:23 am
MDW
- HOU
1 stop5h 48m
Delta
Deal found 3/19![Delta logo]()
$266
This Southwest deal was found by Cheapflights users on 3/19. 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 4/1712:55 pm
HOU
- MDW
Nonstop2h 30m
Southwest
Mon 4/209:40 pm
MDW
- HOU
Nonstop2h 40m
Southwest
Deal found 3/19![Southwest logo]()
$257
This Delta deal was found by Cheapflights users on 3/18. 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 4/235:20 am
IAH
- MDW
1 stop7h 23m
Delta
Sun 4/266:00 am
MDW
- IAH
1 stop5h 14m
Delta
Deal found 3/18![Delta logo]()
$277
This Southwest deal was found by Cheapflights users on 3/18. 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 5/712:55 pm
HOU
- MDW
Nonstop2h 30m
Southwest
Sun 5/105:00 am
MDW
- HOU
1 stop4h 30m
Southwest
Deal found 3/18![Southwest logo]()
$267
This Delta deal was found by Cheapflights users on 3/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/142:59 pm
IAH
- MDW
1 stop7h 29m
Delta
Wed 4/156:00 am
MDW
- IAH
1 stop7h 51m
Delta
Deal found 3/21![Delta logo]()
$277
This Southwest deal was found by Cheapflights users on 3/18. 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 4/172:45 pm
HOU
- MDW
1 stop5h 35m
Southwest
Sun 4/196:55 am
MDW
- HOU
1 stop4h 55m
Southwest
Deal found 3/18![Southwest logo]()
$277
This Delta deal was found by Cheapflights users on 3/19. 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 5/265:55 am
IAH
- MDW
1 stop6h 01m
Delta
Wed 5/275:12 pm
MDW
- IAH
1 stop6h 42m
Delta
Deal found 3/19![Delta logo]()
$295
This Southwest deal was found by Cheapflights users on 3/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/36:10 pm
HOU
- MDW
Nonstop2h 25m
Southwest
Tue 6/99:10 am
MDW
- HOU
1 stop4h 40m
Southwest
Deal found 3/21![Southwest logo]()
$285
This Delta deal was found by Cheapflights users on 3/19. 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 5/265:55 am
IAH
- MDW
1 stop6h 01m
Delta
Tue 5/265:12 pm
MDW
- IAH
1 stop6h 42m
Delta
Deal found 3/19![Delta logo]()
$295
This Southwest deal was found by Cheapflights users on 3/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/32:40 pm
HOU
- MDW
2 stops5h 40m
Southwest
Wed 6/109:10 am
MDW
- HOU
1 stop4h 40m
Southwest
Deal found 3/21![Southwest logo]()
$300
This Delta deal was found by Cheapflights users on 3/18. 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 4/84:56 pm
IAH
- MDW
1 stop5h 35m
Delta
Sat 4/1110:45 am
MDW
- IAH
1 stop7h 13m
Delta
Deal found 3/18![Delta logo]()
$301
This Southwest deal was found by Cheapflights users on 3/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/316:50 pm
HOU
- MDW
Nonstop2h 25m
Southwest
Tue 8/410:10 am
MDW
- HOU
1 stop3h 50m
Southwest
Deal found 3/22![Southwest logo]()
$305
This Delta deal was found by Cheapflights users on 3/20. 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 7/2011:30 am
IAH
- MDW
1 stop7h 01m
Delta
Sun 7/269:30 am
MDW
- IAH
1 stop5h 09m
Delta
Deal found 3/20![Delta logo]()
$317
This Southwest deal was found by Cheapflights users on 3/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/1612:55 pm
HOU
- MDW
Nonstop2h 30m
Southwest
Sun 4/196:55 am
MDW
- HOU
1 stop6h 00m
Southwest
Deal found 3/21![Southwest logo]()
$307
This Delta deal was found by Cheapflights users on 3/19. 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 6/136:30 am
IAH
- MDW
1 stop6h 41m
Delta
Sun 8/96:00 am
MDW
- IAH
1 stop6h 16m
Delta
Deal found 3/19![Delta logo]()
$327
This Delta deal was found by Cheapflights users on 3/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/52:20 pm
IAH
- MDW
1 stop6h 49m
Delta
Mon 6/89:17 am
MDW
- IAH
1 stop5h 08m
Delta
Deal found 3/21![Delta logo]()
$328
This Delta deal was found by Cheapflights users on 3/18. 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 4/172:59 pm
IAH
- MDW
1 stop7h 29m
Delta
Sun 4/196:00 am
MDW
- IAH
1 stop7h 51m
Delta
Deal found 3/18![Delta logo]()
$378
This Delta deal was found by Cheapflights users on 3/20. 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 7/306:30 am
IAH
- MDW
1 stop6h 41m
Delta
Mon 8/36:00 am
MDW
- IAH
1 stop6h 16m
Delta
Deal found 3/20![Delta logo]()
$389
This Delta deal was found by Cheapflights users on 3/18. 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 4/311:39 am
IAH
- MDW
1 stop6h 15m
Delta
Tue 4/76:07 pm
MDW
- IAH
1 stop5h 52m
Delta
Deal found 3/18![Delta logo]()
$418
Last-minute flights from Houston to MidwayDiscover last-minute flight deals from Houston to Midway. Data last updated March 23, 2026 and is based on user searches.
Discover last-minute flight deals from Houston to Midway. Data last updated March 23, 2026 and is based on user searches.
This Super.com deal was found by Cheapflights users on 3/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/101:27 pm
IAH
- MDW
Nonstop2h 32m
Frontier
Tue 4/142:15 pm
MDW
- IAH
1 stop8h 35m
Frontier
Deal found 3/22![Frontier logo]()
$154
This Super.com deal was found by Cheapflights users on 3/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/101:27 pm
IAH
- MDW
Nonstop2h 32m
Frontier
Mon 4/139:20 am
MDW
- IAH
Nonstop3h 12m
Frontier
Deal found 3/22![Frontier logo]()
$156
This Expedia deal was found by Cheapflights users on 3/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/101:27 pm
IAH
- MDW
Nonstop2h 32m
Frontier
Sun 4/125:05 am
MDW
- IAH
1 stop25h 57m
Frontier
Deal found 3/22![Frontier logo]()
$159
This Frontier deal was found by Cheapflights users on 3/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/164:06 pm
IAH
- MDW
1 stop6h 13m
Frontier
Tue 4/212:15 pm
MDW
- IAH
1 stop8h 35m
Frontier
Deal found 3/23![Frontier logo]()
$140
This Super.com deal was found by Cheapflights users on 3/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/164:06 pm
IAH
- MDW
1 stop6h 13m
Frontier
Thu 4/232:15 pm
MDW
- IAH
1 stop8h 35m
Frontier
Deal found 3/22![Frontier logo]()
$160
This Kiwi.com deal was found by Cheapflights users on 3/20. 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 4/164:06 pm
IAH
- MDW
1 stop6h 13m
Frontier
Sun 4/196:00 am
MDW
- IAH
1 stop11h 19m
Frontier
Deal found 3/20![Frontier logo]()
$168
This Southwest deal was found by Cheapflights users on 3/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/165:10 am
HOU
- MDW
Nonstop2h 25m
Southwest
Tue 4/218:40 pm
MDW
- HOU
Nonstop2h 40m
Southwest
Deal found 3/22![Southwest logo]()
$225
This Southwest deal was found by Cheapflights users on 3/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/218:40 pm
HOU
- MDW
Nonstop2h 25m
Southwest
Tue 4/287:25 am
MDW
- HOU
Nonstop2h 40m
Southwest
Deal found 3/22![Southwest logo]()
$180
This Southwest deal was found by Cheapflights users on 3/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/227:10 am
HOU
- MDW
Nonstop2h 25m
Southwest
Fri 4/2412:10 pm
MDW
- HOU
Nonstop2h 40m
Southwest
Deal found 3/22![Southwest logo]()
$219
This Kiwi.com deal was found by Cheapflights users on 3/20. 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 4/2512:35 pm
IAH
- MDW
1 stop6h 02m
Multiple Airlines
Tue 4/282:15 pm
MDW
- IAH
1 stop8h 35m
Multiple Airlines
Deal found 3/20![Multiple Airlines logo]()
$148
This Southwest deal was found by Cheapflights users on 3/20. 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 4/2510:50 am
HOU
- MDW
2 stops6h 00m
Southwest
Tue 4/288:40 pm
MDW
- HOU
Nonstop2h 40m
Southwest
Deal found 3/20![Southwest logo]()
$228
This Kiwi.com deal was found by Cheapflights users on 3/18. 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 4/304:06 pm
IAH
- MDW
1 stop6h 13m
Multiple Airlines
Sat 5/27:34 pm
MDW
- IAH
1 stop15h 37m
Multiple Airlines
Deal found 3/18![Multiple Airlines logo]()
$150
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 March 23, 2026.
Search for one-way flight options from Houston to Midway. Find affordable one-way fares based on user searches. Data last updated March 23, 2026.
This Trip.com deal was found by Cheapflights users on 3/19. 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.
Thu 4/166:00 am
IAH
- MDW
1 stop13h 31m
Frontier
Deal found 3/19![Frontier logo]()
$67
This Kiwi.com deal was found by Cheapflights users on 3/18. 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 4/156:05 am
IAH
- MDW
1 stop13h 26m
Frontier
Deal found 3/18![Frontier logo]()
$69
This Frontier deal was found by Cheapflights users on 3/20. 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 4/234:06 pm
IAH
- MDW
1 stop6h 13m
Frontier
Deal found 3/20![Frontier logo]()
$70
This Kiwi.com deal was found by Cheapflights users on 3/19. 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 4/216:10 am
IAH
- MDW
1 stop13h 21m
Frontier
Deal found 3/19![Frontier logo]()
$72
This Kiwi.com deal was found by Cheapflights users on 3/19. 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 4/86:20 am
IAH
- MDW
1 stop15h 59m
Frontier
Deal found 3/19![Frontier logo]()
$76
This Kiwi.com deal was found by Cheapflights users on 3/19. 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 4/76:14 pm
IAH
- MDW
1 stop28h 05m
Frontier
Deal found 3/19![Frontier logo]()
$79
This WAYA deal was found by Cheapflights users on 3/19. 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 WAYA is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/2512:35 pm
IAH
- MDW
1 stop6h 02m
Multiple Airlines
Deal found 3/19![Multiple Airlines logo]()
$80
This Kiwi.com deal was found by Cheapflights users on 3/18. 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 4/2312:35 pm
IAH
- MDW
1 stop9h 44m
Multiple Airlines
Deal found 3/18![Multiple Airlines logo]()
$81
This Kiwi.com deal was found by Cheapflights users on 3/20. 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.
Fri 4/177:04 pm
IAH
- MDW
1 stop20h 56m
Frontier
Deal found 3/20![Frontier logo]()
$83
This Kiwi.com deal was found by Cheapflights users on 3/18. 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.
Mon 5/412:32 pm
IAH
- MDW
1 stop22h 40m
Multiple Airlines
Deal found 3/18![Multiple Airlines logo]()
$84
This Southwest deal was found by Cheapflights users on 3/19. 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 4/216:10 pm
HOU
- MDW
Nonstop2h 25m
Southwest
Deal found 3/19![Southwest logo]()
$109
This Southwest deal was found by Cheapflights users on 3/18. 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 4/258:10 am
HOU
- MDW
1 stop4h 00m
Southwest
Deal found 3/18![Southwest logo]()
$114
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 March 23, 2026.
Round-trip from | $140 (Expedia) |
|---|---|
One-way from | $67 (Trip.com) |
Popular in | January |
Cheapest in | September |
Average price | $354 |
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 March 23, 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 - MDW
HOUMDW
Houston Hobby
Wed 5/6
6:10 pm-8:35 pm
Nonstop2h 25m
Chicago Midway
Wed 5/13
8:00 am-1:55 pm
2 stops5h 55m
$232
HoustonChicago
HOU - MDW
HOUMDW
Houston Hobby
Sat 5/2
10:50 am-4:50 pm
2 stops6h 00m
Chicago Midway
Tue 5/5
9:40 am-2:00 pm
1 stop4h 20m
$233
HoustonChicago
IAH - MDW
IAHMDW
Houston George Bush Intcntl
Tue 4/21
9:43 am-4:26 pm
1 stop6h 43m
Chicago Midway
Tue 4/28
10:41 am-3:44 pm
1 stop5h 03m
$237
HoustonChicago
HOU - MDW
HOUMDW
Houston Hobby
Wed 4/29
3:30 pm-8:20 pm
1 stop4h 50m
Chicago Midway
Sun 5/3
5:00 am-9:30 am
1 stop4h 30m
$238
HoustonChicago
HOU - MDW
HOUMDW
Houston Hobby
Sat 5/9
10:27 am-4:12 pm
1 stop5h 45m
Chicago Midway
Mon 5/11
5:10 pm-10:26 pm
1 stop5h 16m
$257
Quickest round-trip
HoustonChicago
HOU - MDW
HOUMDW
Houston Hobby
Fri 4/17
12:55 pm-3:25 pm
Nonstop2h 30m
Chicago Midway
Mon 4/20
9:40 pm-12:20 am
Nonstop2h 40m
$257
HoustonChicago
HOU - MDW
HOUMDW
Houston Hobby
Wed 5/20
1:06 pm-9:09 pm
1 stop8h 03m
Chicago Midway
Wed 5/27
6:23 am-12:11 pm
1 stop5h 48m
$266
HoustonChicago
HOU - MDW
HOUMDW
Houston Hobby
Thu 5/7
12:55 pm-3:25 pm
Nonstop2h 30m
Chicago Midway
Sun 5/10
5:00 am-9:30 am
1 stop4h 30m
$267
HoustonChicago
IAH - MDW
IAHMDW
Houston George Bush Intcntl
Thu 4/23
5:20 am-12:43 pm
1 stop7h 23m
Chicago Midway
Sun 4/26
6:00 am-11:14 am
1 stop5h 14m
$277
HoustonChicago
IAH - MDW
IAHMDW
Houston George Bush Intcntl
Tue 4/14
2:59 pm-10:28 pm
1 stop7h 29m
Chicago Midway
Wed 4/15
6:00 am-1:51 pm
1 stop7h 51m
$277
Showing 1-10 of 42 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
IAH-MDW
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 to Chicago Midway Airport
HO1-MDW
IAH-MDW
HOU-MDW
How far ahead should I book a flight from Houston to Chicago Midway Airport?
Use this chart to determine the optimal time to book a round-trip flight from Houston to Midway. Price data was last updated on March 13, 2026.
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 11 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 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 $63). Flying from Houston to Chicago Midway Airport in January is currently the most expensive (average of $192). 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 March 23, 2026.
Unlike at noon, when flights are generally more expensive, you can save up to 26% on flights from Houston to Chicago Midway Airport by exploring options for tickets in the evening.
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 March 14, 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. 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 18% of weekly flights between Houston and Chicago have experienced delays in the past year, with the average delay time being 122 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 17% of flights being delayed.
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 March 23, 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.
Food
7.0
Entertainment
7.5
Boarding
8.1
Comfort
8.0
Crew
8.6
Overall
8.0
Reviews
1 / 20
6.0
GoodScott,Feb 2026
HOU - FLL
Food
7.0
Entertainment
7.5
Boarding
8.1
Comfort
8.0
Crew
8.6
Overall
8.0
Reviews
1 / 20
6.0
GoodScott,Feb 2026
HOU - FLL
Food
7.0
Entertainment
7.5
Boarding
8.1
Comfort
8.0
Crew
8.6
Overall
8.0
Reviews
1 / 20
6.0
GoodScott,Feb 2026
HOU - FLL
Food
7.0
Entertainment
7.5
Boarding
8.1
Comfort
8.0
Crew
8.6
Overall
8.0
Reviews
1 / 20
6.0
GoodScott,Feb 2026
HOU - FLL
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 locationsLansing
Merrillville
Hammond
Porter
Benton Harbor
Browse thousands of different options on Cheapflights for your next trip
Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.
Alternative routes
Complete your trip
Flights by cabin class
Midway flight routes
Other flight options
Popular flights
Alternative routes for Houston to Midway
See prices for flight routes from nearby airports that may be better suited for you.
Complete your trip
Complete your trip to Midway by adding a car rental and/or hotel reservation to your travel itinerary.
Search flights from Houston to Midway by cabin class
Find flights from Houston to Midway, based on your preferred cabin class, be it economy, premium economy, business, or first class.
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 March 23, 2026.
Houston and Midway flights
Browse other Houston and Midway flight options. Last updated on March 23, 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 March 23, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$84 | Average$185 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$162 | Average$272 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$216 | Average$358 | FlexibilityNo cancel fee | On-timeN/A |