$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 6/3. Fares are subject to change and may not be available on all flights or dates of travel.
HOU — MDW
Jun 6 — Jun 131
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 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 May 7, 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 May 7, 2026.
This Kiwi.com deal was found by Cheapflights users on 5/4. 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 5/3010:52 am
IAH
- MDW
1 stop11h 10m
Frontier
Tue 6/212:27 pm
MDW
- IAH
1 stop10h 23m
Frontier
Deal found 5/4![Frontier logo]()
$147
This Kiwi.com deal was found by Cheapflights users on 5/6. 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 6/35:45 am
IAH
- MDW
1 stop16h 17m
Frontier
Mon 6/812:04 pm
MDW
- IAH
1 stop10h 46m
Frontier
Deal found 5/6![Frontier logo]()
$148
This Kiwi.com deal was found by Cheapflights users on 5/4. 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 5/3010:52 am
IAH
- MDW
1 stop11h 10m
Frontier
Mon 6/16:00 am
MDW
- IAH
1 stop16h 50m
Frontier
Deal found 5/4![Frontier logo]()
$153
This Kiwi.com deal was found by Cheapflights users on 5/4. 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 6/610:52 am
IAH
- MDW
1 stop11h 10m
Frontier
Tue 6/912:27 pm
MDW
- IAH
1 stop18h 56m
Frontier
Deal found 5/4![Frontier logo]()
$166
This Southwest deal was found by Cheapflights users on 5/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/236:20 pm
HOU
- MDW
Nonstop2h 25m
Southwest
Tue 6/309:00 pm
MDW
- HOU
Nonstop2h 35m
Southwest
Deal found 5/6![Southwest logo]()
$169
This Kiwi.com deal was found by Cheapflights users on 5/7. 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 6/168:02 pm
IAH
- MDW
1 stop15h 07m
Frontier
Tue 6/236:00 am
MDW
- IAH
1 stop25h 23m
Frontier
Deal found 5/7![Frontier logo]()
$169
This Kiwi.com deal was found by Cheapflights users on 5/4. 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 5/288:02 pm
IAH
- MDW
1 stop15h 07m
Frontier
Tue 6/212:27 pm
MDW
- IAH
1 stop10h 23m
Frontier
Deal found 5/4![Frontier logo]()
$173
This Southwest deal was found by Cheapflights users on 5/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/89:25 pm
HOU
- MDW
Nonstop2h 25m
Southwest
Tue 7/149:10 am
MDW
- HOU
1 stop4h 40m
Southwest
Deal found 5/7![Southwest logo]()
$175
This Southwest deal was found by Cheapflights users on 5/6. 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 6/38:40 pm
HOU
- MDW
Nonstop2h 25m
Southwest
Wed 6/106:30 am
MDW
- HOU
1 stop5h 45m
Southwest
Deal found 5/6![Southwest logo]()
$179
This Expedia deal was found by Cheapflights users on 5/3. 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.
Wed 5/2711:12 am
IAH
- MDW
1 stop10h 50m
Frontier
Thu 5/2812:27 pm
MDW
- IAH
1 stop10h 23m
Frontier
Deal found 5/3![Frontier logo]()
$180
This Southwest deal was found by Cheapflights users on 5/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/22:40 pm
HOU
- MDW
2 stops5h 40m
Southwest
Tue 6/912:00 pm
MDW
- HOU
Nonstop2h 35m
Southwest
Deal found 5/6![Southwest logo]()
$184
This Kiwi.com deal was found by Cheapflights users on 5/5. 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 5/268:02 pm
IAH
- MDW
1 stop15h 07m
Frontier
Sat 5/306:00 am
MDW
- IAH
1 stop16h 50m
Frontier
Deal found 5/5![Frontier logo]()
$188
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 May 7, 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 May 7, 2026.
This Southwest deal was found by Cheapflights users on 5/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/1610:25 am
HOU
- MDW
1 stop5h 30m
Southwest
Tue 6/2310:15 am
MDW
- HOU
1 stop3h 50m
Southwest
Deal found 5/6![Southwest logo]()
$184
This Delta deal was found by Cheapflights users on 5/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/236:30 am
IAH
- MDW
1 stop6h 39m
Delta
Tue 6/306:00 am
MDW
- IAH
1 stop7h 38m
Delta
Deal found 5/6![Delta logo]()
$197
This Southwest deal was found by Cheapflights users on 5/5. 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
Sat 6/65:05 am
MDW
- HOU
Nonstop2h 35m
Southwest
Deal found 5/5![Southwest logo]()
$184
This Southwest deal was found by Cheapflights users on 5/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/16:30 pm
HOU
- MDW
1 stop5h 25m
Southwest
Wed 7/2210:15 am
MDW
- HOU
1 stop4h 30m
Southwest
Deal found 5/6![Southwest logo]()
$199
This Southwest deal was found by Cheapflights users on 5/4. 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 5/285:05 am
HOU
- MDW
Nonstop2h 25m
Southwest
Mon 6/16:55 am
MDW
- HOU
Nonstop2h 40m
Southwest
Deal found 5/4![Southwest logo]()
$199
This Southwest deal was found by Cheapflights users on 5/6. 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 5/2810:25 am
HOU
- MDW
1 stop5h 25m
Southwest
Sat 5/3010:00 am
MDW
- HOU
1 stop3h 55m
Southwest
Deal found 5/6![Southwest logo]()
$214
This Delta deal was found by Cheapflights users on 5/4. 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 6/124:20 pm
IAH
- MDW
1 stop5h 57m
Delta
Tue 6/165:11 pm
MDW
- IAH
1 stop6h 45m
Delta
Deal found 5/4![Delta logo]()
$299
This Delta deal was found by Cheapflights users on 5/2. 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.
Fri 6/194:20 pm
IAH
- MDW
1 stop5h 57m
Delta
Sat 6/276:00 am
MDW
- IAH
1 stop5h 18m
Delta
Deal found 5/2![Delta logo]()
$309
This Southwest deal was found by Cheapflights users on 5/2. 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 5/304:05 pm
HOU
- MDW
1 stop4h 00m
Southwest
Sat 6/67:05 am
MDW
- HOU
Nonstop2h 35m
Southwest
Deal found 5/2![Southwest logo]()
$249
This Delta deal was found by Cheapflights users on 5/5. 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 7/67:02 am
IAH
- MDW
1 stop5h 03m
Delta
Fri 7/179:19 am
MDW
- IAH
1 stop5h 11m
Delta
Deal found 5/5![Delta logo]()
$309
This Southwest deal was found by Cheapflights users on 5/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/84:05 pm
HOU
- MDW
Nonstop2h 25m
Southwest
Sun 7/128:30 am
MDW
- HOU
Nonstop2h 40m
Southwest
Deal found 5/5![Southwest logo]()
$260
This Delta deal was found by Cheapflights users on 5/3. 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 5/276:00 am
HOU
- MDW
1 stop5h 56m
Delta
Sun 5/3110:59 am
MDW
- HOU
1 stop5h 10m
Delta
Deal found 5/3![Delta logo]()
$320
This Southwest deal was found by Cheapflights users on 5/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/612:15 pm
HOU
- MDW
1 stop5h 30m
Southwest
Tue 6/93:10 pm
MDW
- HOU
2 stops5h 30m
Southwest
Deal found 5/4![Southwest logo]()
$265
This Delta deal was found by Cheapflights users on 5/3. 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 5/286:00 am
IAH
- MDW
1 stop7h 19m
Delta
Sun 5/3110:59 am
MDW
- IAH
1 stop6h 31m
Delta
Deal found 5/3![Delta logo]()
$322
This Delta deal was found by Cheapflights users on 5/5. 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 7/34:20 pm
IAH
- MDW
1 stop5h 57m
Delta
Sun 7/56:00 am
MDW
- IAH
1 stop5h 23m
Delta
Deal found 5/5![Delta logo]()
$328
This Southwest deal was found by Cheapflights users on 5/2. 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 5/2310:50 am
HOU
- MDW
2 stops6h 00m
Southwest
Tue 5/268:40 pm
MDW
- HOU
Nonstop2h 40m
Southwest
Deal found 5/2![Southwest logo]()
$282
This Delta deal was found by Cheapflights users on 5/3. 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 5/176:00 am
IAH
- MDW
1 stop7h 19m
Delta
Tue 5/1910:59 am
MDW
- IAH
1 stop6h 31m
Delta
Deal found 5/3![Delta logo]()
$357
This Delta deal was found by Cheapflights users on 5/2. 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 5/168:29 am
IAH
- MDW
1 stop8h 03m
Delta
Mon 5/186:23 am
MDW
- IAH
1 stop6h 51m
Delta
Deal found 5/2![Delta logo]()
$357
This Delta deal was found by Cheapflights users on 5/2. 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.
Fri 5/2910:45 am
IAH
- MDW
1 stop7h 11m
Delta
Sun 5/3110:59 am
MDW
- IAH
1 stop6h 31m
Delta
Deal found 5/2![Delta logo]()
$363
This Delta deal was found by Cheapflights users on 5/6. 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 5/2211:34 am
IAH
- MDW
1 stop6h 59m
Delta
Sun 5/246:23 am
MDW
- IAH
1 stop6h 51m
Delta
Deal found 5/6![Delta logo]()
$371
This Delta deal was found by Cheapflights users on 5/4. 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 7/22:43 pm
IAH
- MDW
1 stop7h 34m
Delta
Sun 7/56:00 am
MDW
- IAH
1 stop5h 23m
Delta
Deal found 5/4![Delta logo]()
$397
This Delta deal was found by Cheapflights users on 5/4. 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
Sun 6/76:00 am
MDW
- IAH
1 stop7h 43m
Delta
Deal found 5/4![Delta logo]()
$397
Last-minute flights from Houston to MidwayDiscover last-minute flight deals from Houston to Midway. Data last updated May 7, 2026 and is based on user searches.
Discover last-minute flight deals from Houston to Midway. Data last updated May 7, 2026 and is based on user searches.
This Kiwi.com deal was found by Cheapflights users on 5/5. 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 5/268:02 pm
IAH
- MDW
1 stop15h 07m
Frontier
Sat 5/306:00 am
MDW
- IAH
1 stop16h 50m
Frontier
Deal found 5/5![Frontier logo]()
$188
This Expedia deal was found by Cheapflights users on 5/3. 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.
Wed 5/2711:12 am
IAH
- MDW
1 stop10h 50m
Frontier
Thu 5/2812:27 pm
MDW
- IAH
1 stop10h 23m
Frontier
Deal found 5/3![Frontier logo]()
$180
This Kiwi.com deal was found by Cheapflights users on 5/4. 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 5/288:02 pm
IAH
- MDW
1 stop15h 07m
Frontier
Tue 6/212:27 pm
MDW
- IAH
1 stop10h 23m
Frontier
Deal found 5/4![Frontier logo]()
$173
This Kiwi.com deal was found by Cheapflights users on 5/4. 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 5/3010:52 am
IAH
- MDW
1 stop11h 10m
Frontier
Tue 6/212:27 pm
MDW
- IAH
1 stop10h 23m
Frontier
Deal found 5/4![Frontier logo]()
$147
This Kiwi.com deal was found by Cheapflights users on 5/4. 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 5/3010:52 am
IAH
- MDW
1 stop11h 10m
Frontier
Mon 6/16:00 am
MDW
- IAH
1 stop16h 50m
Frontier
Deal found 5/4![Frontier logo]()
$153
This Southwest deal was found by Cheapflights users on 5/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/26:10 pm
HOU
- MDW
Nonstop2h 25m
Southwest
Wed 6/39:40 am
MDW
- HOU
1 stop4h 20m
Southwest
Deal found 5/4![Southwest logo]()
$175
This Southwest deal was found by Cheapflights users on 5/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/22:40 pm
HOU
- MDW
2 stops5h 40m
Southwest
Tue 6/912:00 pm
MDW
- HOU
Nonstop2h 35m
Southwest
Deal found 5/6![Southwest logo]()
$184
This Kiwi.com deal was found by Cheapflights users on 5/6. 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 6/35:45 am
IAH
- MDW
1 stop16h 17m
Frontier
Mon 6/812:04 pm
MDW
- IAH
1 stop10h 46m
Frontier
Deal found 5/6![Frontier logo]()
$148
This Southwest deal was found by Cheapflights users on 5/6. 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 6/38:40 pm
HOU
- MDW
Nonstop2h 25m
Southwest
Wed 6/106:30 am
MDW
- HOU
1 stop5h 45m
Southwest
Deal found 5/6![Southwest logo]()
$179
This Kiwi.com deal was found by Cheapflights users on 5/4. 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 6/610:52 am
IAH
- MDW
1 stop11h 10m
Frontier
Tue 6/912:27 pm
MDW
- IAH
1 stop18h 56m
Frontier
Deal found 5/4![Frontier logo]()
$166
This Kiwi.com deal was found by Cheapflights users on 5/7. 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 6/168:02 pm
IAH
- MDW
1 stop15h 07m
Frontier
Tue 6/236:00 am
MDW
- IAH
1 stop25h 23m
Frontier
Deal found 5/7![Frontier logo]()
$169
This Southwest deal was found by Cheapflights users on 5/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/236:20 pm
HOU
- MDW
Nonstop2h 25m
Southwest
Tue 6/309:00 pm
MDW
- HOU
Nonstop2h 35m
Southwest
Deal found 5/6![Southwest logo]()
$169
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 May 7, 2026.
Search for one-way flight options from Houston to Midway. Find affordable one-way fares based on user searches. Data last updated May 7, 2026.
This Kiwi.com deal was found by Cheapflights users on 5/5. 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 6/35:45 am
IAH
- MDW
1 stop16h 17m
Frontier
Deal found 5/5![Frontier logo]()
$67
This Kiwi.com deal was found by Cheapflights users on 5/6. 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 7/111:12 am
IAH
- MDW
1 stop10h 59m
Frontier
Deal found 5/6![Frontier logo]()
$70
This Trip.com deal was found by Cheapflights users on 5/3. 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 5/2711:12 am
IAH
- MDW
1 stop10h 50m
Frontier
Deal found 5/3![Frontier logo]()
$71
This Kiwi.com deal was found by Cheapflights users on 5/4. 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 5/258:50 pm
IAH
- MDW
1 stop14h 22m
Frontier
Deal found 5/4![Frontier logo]()
$74
This Kiwi.com deal was found by Cheapflights users on 5/3. 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 5/268:02 pm
IAH
- MDW
1 stop26h 00m
Frontier
Deal found 5/3![Frontier logo]()
$76
This Kiwi.com deal was found by Cheapflights users on 5/4. 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 5/3010:52 am
IAH
- MDW
1 stop11h 10m
Frontier
Deal found 5/4![Frontier logo]()
$82
This Kiwi.com deal was found by Cheapflights users on 5/5. 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 6/610:52 am
IAH
- MDW
1 stop11h 10m
Frontier
Deal found 5/5![Frontier logo]()
$84
This Southwest deal was found by Cheapflights users on 5/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/27:10 am
HOU
- MDW
Nonstop2h 25m
Southwest
Deal found 5/5![Southwest logo]()
$85
This Kiwi.com deal was found by Cheapflights users on 5/7. 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 7/2210:52 am
IAH
- MDW
1 stop11h 16m
Frontier
Deal found 5/7![Frontier logo]()
$88
This CheapOair deal was found by Cheapflights users on 5/4. 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.
Mon 6/15:45 am
IAH
- MDW
1 stop5h 24m
Frontier
Deal found 5/4![Frontier logo]()
$90
This Southwest deal was found by Cheapflights users on 5/7. 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
1 stop5h 30m
Southwest
Deal found 5/7![Southwest logo]()
$95
This Super.com deal was found by Cheapflights users on 5/3. 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 6/811:12 am
IAH
- MDW
1 stop10h 50m
Frontier
Deal found 5/3![Frontier logo]()
$95
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 May 7, 2026.
Round-trip from | $147 (Kiwi.com) |
|---|---|
One-way from | $67 (Kiwi.com) |
Popular in | January |
Cheapest in | October |
Average price | $302 |
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 May 7, 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
Tue 6/16
10:25 am-3:55 pm
1 stop5h 30m
Chicago Midway
Tue 6/23
10:15 am-2:05 pm
1 stop3h 50m
$184
Quickest round-trip
HoustonChicago
HOU - MDW
HOUMDW
Houston Hobby
Wed 6/3
6:10 pm-8:35 pm
Nonstop2h 25m
Chicago Midway
Sat 6/6
5:05 am-7:40 am
Nonstop2h 35m
$184
HoustonChicago
IAH - MDW
IAHMDW
Houston George Bush Intcntl
Tue 6/23
6:30 am-1:09 pm
1 stop6h 39m
Chicago Midway
Tue 6/30
6:00 am-1:38 pm
1 stop7h 38m
$197
HoustonChicago
HOU - MDW
HOUMDW
Houston Hobby
Mon 6/1
6:30 pm-11:55 pm
1 stop5h 25m
Chicago Midway
Wed 7/22
10:15 am-2:45 pm
1 stop4h 30m
$199
HoustonChicago
HOU - MDW
HOUMDW
Houston Hobby
Thu 5/28
5:05 am-7:30 am
Nonstop2h 25m
Chicago Midway
Mon 6/1
6:55 am-9:35 am
Nonstop2h 40m
$199
HoustonChicago
HOU - MDW
HOUMDW
Houston Hobby
Thu 5/28
10:25 am-3:50 pm
1 stop5h 25m
Chicago Midway
Sat 5/30
10:00 am-1:55 pm
1 stop3h 55m
$214
HoustonChicago
HOU - MDW
HOUMDW
Houston Hobby
Sat 5/30
4:05 pm-8:05 pm
1 stop4h 00m
Chicago Midway
Sat 6/6
7:05 am-9:40 am
Nonstop2h 35m
$249
HoustonChicago
HOU - MDW
HOUMDW
Houston Hobby
Wed 7/8
4:05 pm-6:30 pm
Nonstop2h 25m
Chicago Midway
Sun 7/12
8:30 am-11:10 am
Nonstop2h 40m
$260
HoustonChicago
HOU - MDW
HOUMDW
Houston Hobby
Sat 6/6
12:15 pm-5:45 pm
1 stop5h 30m
Chicago Midway
Tue 6/9
3:10 pm-8:40 pm
2 stops5h 30m
$265
HoustonChicago
HOU - MDW
HOUMDW
Houston Hobby
Sat 5/23
10:50 am-4:50 pm
2 stops6h 00m
Chicago Midway
Tue 5/26
8:40 pm-11:20 pm
Nonstop2h 40m
$282
Showing 1-10 of 44 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
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 10 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, July is the cheapest month in which you can book a flight from Houston to Chicago Midway Airport (average of $51). Flying from Houston to Chicago Midway Airport in January is currently the most expensive (average of $186). 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 May 7, 2026.
Unlike at noon, when flights are generally more expensive, you can save up to 25% 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 May 2, 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 afternoons flights should be avoided if possible as fares are typically the most expensive at this time.
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 20% of weekly flights between Houston and Chicago have experienced delays in the past year, with the average delay time being 120 minutes.
What is the most punctual flight time for Houston to Chicago flights?
Historically, flights departing in the morning are less likely to be delayed, whereas flights leaving in the early afternoon tend to experience delays more often.
What day of the week experiences the fewest flight delays on this route?
Saturday tends to have the lowest number of delays on this route, whereas Sunday has historically faced a higher average of delays compared to other days of the week.
Which airline has the best punctuality record on Houston to Chicago flights?
Over the last year, Southwest have had the lowest number of delays on this route, with just 19% 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 May 7, 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
Crew
8.6
Boarding
8.1
Comfort
8.0
Overall
7.9
Entertainment
7.5
Reviews
1 / 20
6.0
GoodScott,Feb 2026
HOU - FLL
Food
7.0
Crew
8.6
Boarding
8.1
Comfort
8.0
Overall
7.9
Entertainment
7.5
Reviews
1 / 20
6.0
GoodScott,Feb 2026
HOU - FLL
Food
7.0
Crew
8.6
Boarding
8.1
Comfort
8.0
Overall
7.9
Entertainment
7.5
Reviews
1 / 20
6.0
GoodScott,Feb 2026
HOU - FLL
Food
7.0
Crew
8.6
Boarding
8.1
Comfort
8.0
Overall
7.9
Entertainment
7.5
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 locationsBenton Harbor
Lansing
Merrillville
Hammond
Porter
Browse thousands of different options on Cheapflights for your next trip
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Alternative routes for Houston to Midway
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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 May 7, 2026.
Houston and Midway flights
Browse other Houston and Midway flight options. Last updated on May 7, 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 May 7, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$84 | Average$183 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$162 | Average$314 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$216 | Average$358 | FlexibilityNo cancel fee | On-timeN/A |