$76+ Cheap flights from Chicago (CHI) to Hobby (HOU)
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 4/18. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — HOU
Mar 25 — Apr 11
1 adult, Economy
We work with more than 300 partners to bring you better travel deals
Find cheap flights from Chicago to Hobby 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 Chicago to Houston Hobby are usually found in September or January, booked 86 days in advance, depart on a Wednesday or Saturday and return on a Wednesday
Cheap flight deals from Chicago to Hobby
Cheapest
Best
Last-minute
One-way
Cheapest flights from Chicago to HobbyExplore the most affordable flight options available from Chicago to Hobby. Find the lowest fares from popular airlines and budget airlines, with prices last updated on February 23, 2026.
Explore the most affordable flight options available from Chicago to Hobby. Find the lowest fares from popular airlines and budget airlines, with prices last updated on February 23, 2026.
This Southwest deal was found by Cheapflights users on 2/19. 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.
Wed 4/157:25 am
MDW
- HOU
Nonstop2h 40m
Southwest
Tue 4/218:40 pm
HOU
- MDW
Nonstop2h 25m
Southwest
Deal found 2/19![Southwest logo]()
$157
This Southwest deal was found by Cheapflights users on 2/22. 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.
Sun 4/126:50 am
MDW
- HOU
Nonstop2h 40m
Southwest
Sat 4/183:25 pm
HOU
- MDW
Nonstop2h 25m
Southwest
Deal found 2/22![Southwest logo]()
$166
This Southwest deal was found by Cheapflights users on 2/22. 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.
Sat 5/25:00 am
MDW
- HOU
Nonstop2h 40m
Southwest
Sun 5/35:00 am
HOU
- MDW
Nonstop2h 25m
Southwest
Deal found 2/22![Southwest logo]()
$177
This Southwest deal was found by Cheapflights users on 2/20. 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.
Thu 4/169:40 pm
MDW
- HOU
Nonstop2h 40m
Southwest
Sun 4/195:00 am
HOU
- MDW
Nonstop2h 25m
Southwest
Deal found 2/20![Southwest logo]()
$181
This Southwest deal was found by Cheapflights users on 2/19. 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.
Mon 4/69:35 pm
MDW
- HOU
Nonstop2h 45m
Southwest
Thu 4/95:10 am
HOU
- MDW
Nonstop2h 25m
Southwest
Deal found 2/19![Southwest logo]()
$191
This Delta deal was found by Cheapflights users on 2/20. 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.
Sat 4/189:48 am
ORD
- HOU
1 stop6h 40m
Delta
Sat 4/256:00 am
HOU
- ORD
1 stop7h 14m
Delta
Deal found 2/20![Delta logo]()
$197
This Southwest deal was found by Cheapflights users on 2/22. 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 5/16:55 am
MDW
- HOU
Nonstop2h 40m
Southwest
Sun 5/35:00 am
HOU
- MDW
Nonstop2h 25m
Southwest
Deal found 2/22![Southwest logo]()
$197
This Delta deal was found by Cheapflights users on 2/22. 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.
Fri 4/245:53 pm
ORD
- HOU
1 stop5h 14m
Delta
Sat 4/2510:48 am
HOU
- ORD
1 stop8h 00m
Delta
Deal found 2/22![Delta logo]()
$199
This Delta deal was found by Cheapflights users on 2/22. 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.
Sat 4/255:21 pm
MDW
- HOU
1 stop5h 46m
Delta
Mon 4/275:23 pm
HOU
- MDW
1 stop5h 05m
Delta
Deal found 2/22![Delta logo]()
$199
This Southwest deal was found by Cheapflights users on 2/22. 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 3/255:35 pm
MDW
- HOU
Nonstop2h 45m
Southwest
Fri 3/278:25 pm
HOU
- MDW
Nonstop2h 25m
Southwest
Deal found 2/22![Southwest logo]()
$200
This Delta deal was found by Cheapflights users on 2/22. 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 3/249:50 am
ORD
- HOU
1 stop6h 46m
Delta
Wed 3/255:22 pm
HOU
- ORD
1 stop6h 32m
Delta
Deal found 2/22![Delta logo]()
$201
This Delta deal was found by Cheapflights users on 2/20. 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.
Fri 4/245:21 pm
MDW
- HOU
1 stop5h 46m
Delta
Mon 4/275:23 pm
HOU
- MDW
1 stop5h 05m
Delta
Deal found 2/20![Delta logo]()
$201
Best flights from Chicago to HobbyDiscover carefully curated flight deals from Chicago to Hobby that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated February 23, 2026.
Discover carefully curated flight deals from Chicago to Hobby that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated February 23, 2026.
This Southwest deal was found by Cheapflights users on 2/22. 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.
Mon 3/239:35 pm
MDW
- HOU
Nonstop2h 45m
Southwest
Thu 3/265:05 am
HOU
- MDW
Nonstop2h 20m
Southwest
Deal found 2/22![Southwest logo]()
$237
This Delta deal was found by Cheapflights users on 2/20. 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 4/95:30 am
ORD
- HOU
1 stop7h 58m
Delta
Mon 4/131:31 pm
HOU
- ORD
1 stop7h 54m
Delta
Deal found 2/20![Delta logo]()
$257
This Southwest deal was found by Cheapflights users on 2/22. 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 4/167:45 am
MDW
- HOU
1 stop4h 30m
Southwest
Sun 4/195:00 am
HOU
- MDW
Nonstop2h 25m
Southwest
Deal found 2/22![Southwest logo]()
$248
This Southwest deal was found by Cheapflights users on 2/19. 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.
Thu 6/185:00 am
MDW
- HOU
Nonstop2h 35m
Southwest
Mon 6/225:00 am
HOU
- MDW
Nonstop2h 25m
Southwest
Deal found 2/19![Southwest logo]()
$259
This Southwest deal was found by Cheapflights users on 2/21. 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.
Fri 4/109:40 pm
MDW
- HOU
Nonstop2h 40m
Southwest
Sun 4/128:15 pm
HOU
- MDW
1 stop4h 05m
Southwest
Deal found 2/21![Southwest logo]()
$262
This Southwest deal was found by Cheapflights users on 2/19. 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.
Sat 4/116:05 pm
MDW
- HOU
Nonstop2h 45m
Southwest
Sun 4/198:10 pm
HOU
- MDW
1 stop4h 05m
Southwest
Deal found 2/19![Southwest logo]()
$267
This Southwest deal was found by Cheapflights users on 2/19. 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.
Mon 4/62:40 pm
ORD
- HOU
2 stops7h 05m
Southwest
Thu 4/99:30 am
HOU
- ORD
1 stop6h 00m
Southwest
Deal found 2/19![Southwest logo]()
$273
This Southwest deal was found by Cheapflights users on 2/22. 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 4/2110:30 am
ORD
- HOU
2 stops8h 20m
Southwest
Sat 4/258:25 am
HOU
- ORD
2 stops15h 00m
Southwest
Deal found 2/22![Southwest logo]()
$275
This Southwest deal was found by Cheapflights users on 2/19. 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 4/178:00 am
ORD
- HOU
2 stops10h 50m
Southwest
Mon 4/201:40 pm
HOU
- ORD
1 stop10h 15m
Southwest
Deal found 2/19![Southwest logo]()
$275
This Southwest deal was found by Cheapflights users on 2/21. 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.
Tue 3/106:25 pm
MDW
- HOU
1 stop4h 15m
Southwest
Wed 3/1111:30 am
HOU
- MDW
2 stops5h 30m
Southwest
Deal found 2/21![Southwest logo]()
$278
This Southwest deal was found by Cheapflights users on 2/19. 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.
Thu 3/2611:15 am
MDW
- HOU
1 stop4h 55m
Southwest
Thu 4/25:05 am
HOU
- MDW
Nonstop2h 20m
Southwest
Deal found 2/19![Southwest logo]()
$280
This Southwest deal was found by Cheapflights users on 2/20. 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.
Sun 4/52:40 pm
ORD
- HOU
2 stops7h 00m
Southwest
Sat 4/118:25 am
HOU
- ORD
2 stops15h 00m
Southwest
Deal found 2/20![Southwest logo]()
$284
This Southwest deal was found by Cheapflights users on 2/22. 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.
Sat 3/289:40 pm
MDW
- HOU
Nonstop2h 45m
Southwest
Sat 4/49:35 am
HOU
- MDW
Nonstop2h 25m
Southwest
Deal found 2/22![Southwest logo]()
$285
This Southwest deal was found by Cheapflights users on 2/19. 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.
Wed 4/1510:30 am
ORD
- HOU
2 stops8h 20m
Southwest
Sat 4/188:25 am
HOU
- ORD
2 stops15h 00m
Southwest
Deal found 2/19![Southwest logo]()
$286
This Southwest deal was found by Cheapflights users on 2/19. 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.
Thu 5/289:40 pm
MDW
- HOU
Nonstop2h 40m
Southwest
Sun 5/315:00 am
HOU
- MDW
Nonstop2h 25m
Southwest
Deal found 2/19![Southwest logo]()
$288
This Southwest deal was found by Cheapflights users on 2/22. 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 3/279:35 pm
MDW
- HOU
Nonstop2h 45m
Southwest
Wed 4/16:15 am
HOU
- MDW
Nonstop2h 20m
Southwest
Deal found 2/22![Southwest logo]()
$294
This Southwest deal was found by Cheapflights users on 2/19. 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.
Wed 5/138:00 am
MDW
- HOU
2 stops5h 55m
Southwest
Wed 6/312:50 pm
HOU
- MDW
1 stop5h 25m
Southwest
Deal found 2/19![Southwest logo]()
$294
This Southwest deal was found by Cheapflights users on 2/19. 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.
Thu 6/186:40 am
MDW
- HOU
Nonstop2h 35m
Southwest
Sun 6/219:20 pm
HOU
- MDW
Nonstop2h 25m
Southwest
Deal found 2/19![Southwest logo]()
$295
This Southwest deal was found by Cheapflights users on 2/19. 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.
Wed 3/252:40 pm
ORD
- HOU
1 stop5h 25m
Southwest
Sat 3/288:55 pm
HOU
- ORD
1 stop12h 50m
Southwest
Deal found 2/19![Southwest logo]()
$299
This Southwest deal was found by Cheapflights users on 2/19. 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.
Thu 4/234:15 pm
ORD
- HOU
1 stop5h 00m
Southwest
Sun 4/268:35 pm
HOU
- ORD
1 stop13h 10m
Southwest
Deal found 2/19![Southwest logo]()
$304
This Southwest deal was found by Cheapflights users on 2/19. 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 5/12:40 pm
ORD
- HOU
2 stops6h 30m
Southwest
Mon 5/46:00 am
HOU
- ORD
2 stops7h 15m
Southwest
Deal found 2/19![Southwest logo]()
$309
This Southwest deal was found by Cheapflights users on 2/21. 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.
Mon 6/87:20 pm
ORD
- HOU
2 stops14h 25m
Southwest
Sat 6/135:00 am
HOU
- ORD
1 stop9h 25m
Southwest
Deal found 2/21![Southwest logo]()
$311
This Southwest deal was found by Cheapflights users on 2/19. 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.
Thu 6/183:20 pm
ORD
- HOU
1 stop8h 25m
Southwest
Mon 6/223:35 pm
HOU
- ORD
2 stops8h 20m
Southwest
Deal found 2/19![Southwest logo]()
$313
Last-minute flights from Chicago to HobbyDiscover last-minute flight deals from Chicago to Hobby. Data last updated February 23, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to Hobby. Data last updated February 23, 2026 and is based on user searches.
This Southwest deal was found by Cheapflights users on 2/20. 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.
Mon 3/169:35 pm
MDW
- HOU
Nonstop2h 45m
Southwest
Tue 3/179:30 pm
HOU
- MDW
Nonstop2h 25m
Southwest
Deal found 2/20![Southwest logo]()
$211
This Southwest deal was found by Cheapflights users on 2/22. 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.
Mon 3/169:35 pm
MDW
- HOU
Nonstop2h 45m
Southwest
Wed 3/189:30 pm
HOU
- MDW
Nonstop2h 25m
Southwest
Deal found 2/22![Southwest logo]()
$242
This Southwest deal was found by Cheapflights users on 2/22. 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 3/175:35 pm
MDW
- HOU
Nonstop2h 45m
Southwest
Fri 3/203:10 pm
HOU
- MDW
Nonstop2h 20m
Southwest
Deal found 2/22![Southwest logo]()
$181
This Southwest deal was found by Cheapflights users on 2/19. 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.
Wed 3/183:20 pm
MDW
- HOU
1 stop5h 15m
Southwest
Tue 3/249:30 pm
HOU
- MDW
Nonstop2h 25m
Southwest
Deal found 2/19![Southwest logo]()
$230
This Southwest deal was found by Cheapflights users on 2/19. 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.
Wed 3/182:00 pm
ORD
- HOU
1 stop6h 30m
Southwest
Tue 3/246:45 am
HOU
- ORD
1 stop6h 05m
Southwest
Deal found 2/19![Southwest logo]()
$247
This Southwest deal was found by Cheapflights users on 2/21. 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.
Sat 3/219:40 pm
MDW
- HOU
Nonstop2h 45m
Southwest
Wed 4/16:15 am
HOU
- MDW
Nonstop2h 20m
Southwest
Deal found 2/21![Southwest logo]()
$237
This Southwest deal was found by Cheapflights users on 2/21. 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.
Mon 3/239:35 pm
MDW
- HOU
Nonstop2h 45m
Southwest
Fri 3/275:05 am
HOU
- MDW
Nonstop2h 20m
Southwest
Deal found 2/21![Southwest logo]()
$209
This Delta deal was found by Cheapflights users on 2/22. 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 3/249:50 am
ORD
- HOU
1 stop6h 46m
Delta
Wed 3/255:22 pm
HOU
- ORD
1 stop6h 32m
Delta
Deal found 2/22![Delta logo]()
$201
This Southwest deal was found by Cheapflights users on 2/20. 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.
Tue 3/242:40 pm
ORD
- HOU
2 stops5h 55m
Southwest
Thu 3/266:00 am
HOU
- ORD
1 stop5h 10m
Southwest
Deal found 2/20![Southwest logo]()
$252
This Southwest deal was found by Cheapflights users on 2/19. 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.
Wed 3/255:35 pm
MDW
- HOU
Nonstop2h 45m
Southwest
Thu 3/265:05 am
HOU
- MDW
Nonstop2h 20m
Southwest
Deal found 2/19![Southwest logo]()
$199
This Southwest deal was found by Cheapflights users on 2/22. 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 3/255:35 pm
MDW
- HOU
Nonstop2h 45m
Southwest
Fri 3/278:25 pm
HOU
- MDW
Nonstop2h 25m
Southwest
Deal found 2/22![Southwest logo]()
$200
This Southwest deal was found by Cheapflights users on 2/22. 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.
Sat 3/289:40 pm
MDW
- HOU
Nonstop2h 45m
Southwest
Tue 3/316:15 am
HOU
- MDW
Nonstop2h 20m
Southwest
Deal found 2/22![Southwest logo]()
$205
One-way flights from Chicago to HobbySearch for one-way flight options from Chicago to Hobby. Find affordable one-way fares based on user searches. Data last updated February 23, 2026.
Search for one-way flight options from Chicago to Hobby. Find affordable one-way fares based on user searches. Data last updated February 23, 2026.
This Southwest deal was found by Cheapflights users on 2/22. 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.
Sat 4/185:00 am
MDW
- HOU
Nonstop2h 40m
Southwest
Deal found 2/22![Southwest logo]()
$76
This Southwest deal was found by Cheapflights users on 2/20. 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.
Tue 4/218:40 pm
MDW
- HOU
Nonstop2h 40m
Southwest
Deal found 2/20![Southwest logo]()
$79
This Southwest deal was found by Cheapflights users on 2/22. 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.
Sat 4/43:00 pm
MDW
- HOU
Nonstop2h 50m
Southwest
Deal found 2/22![Southwest logo]()
$80
This Southwest deal was found by Cheapflights users on 2/20. 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.
Mon 4/66:10 pm
MDW
- HOU
Nonstop2h 50m
Southwest
Deal found 2/20![Southwest logo]()
$91
This Delta deal was found by Cheapflights users on 2/20. 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.
Sat 5/25:59 pm
ORD
- HOU
1 stop5h 08m
Delta
Deal found 2/20![Delta logo]()
$99
This Delta deal was found by Cheapflights users on 2/20. 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.
Sat 5/25:21 pm
MDW
- HOU
1 stop5h 46m
Delta
Deal found 2/20![Delta logo]()
$99
This Delta deal was found by Cheapflights users on 2/22. 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 4/79:40 am
ORD
- HOU
1 stop6h 52m
Delta
Deal found 2/22![Delta logo]()
$101
This Delta deal was found by Cheapflights users on 2/22. 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 3/3110:45 am
MDW
- HOU
1 stop5h 47m
Delta
Deal found 2/22![Delta logo]()
$101
This Delta deal was found by Cheapflights users on 2/19. 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 4/42:59 pm
ORD
- HOU
1 stop7h 52m
Delta
Deal found 2/19![Delta logo]()
$106
This Delta deal was found by Cheapflights users on 2/19. 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 4/44:30 pm
MDW
- HOU
1 stop6h 21m
Delta
Deal found 2/19![Delta logo]()
$106
This Southwest deal was found by Cheapflights users on 2/22. 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.
Sat 5/165:00 am
MDW
- HOU
Nonstop2h 40m
Southwest
Deal found 2/22![Southwest logo]()
$107
This Delta deal was found by Cheapflights users on 2/20. 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.
Tue 3/319:40 am
ORD
- HOU
1 stop6h 52m
Delta
Deal found 2/20![Delta logo]()
$109
Find flight deals from Chicago to Hobby
Discover tips and strategies to find the most affordable flight options for your journey from Chicago (CHI) to Hobby (HOU). 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 February 23, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $157 (Southwest) |
One-way from | $76 (Southwest) |
Popular in | March |
Cheapest in | September |
Average price | $210 |
Good round-trip deal | $316 or less |
Good one-way deal | $184 or less |
Cheapflights Fare Finder
Customize your flight search to find flights from Chicago to Hobby 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 February 23, 2026.
Use the filters below to find and compare flights from Chicago to Houston Hobby Airport that are best for you.
Fly from
Chicago
Fly to
Hobby
Route
Depart
Return
Price
ChicagoHouston
MDW - HOU
MDWHOU
Chicago Midway
Mon 3/23
9:35 pm-12:20 am
Nonstop2h 45m
Houston Hobby
Thu 3/26
5:05 am-7:25 am
Nonstop2h 20m
$237
ChicagoHouston
MDW - HOU
MDWHOU
Chicago Midway
Thu 4/16
7:45 am-12:15 pm
1 stop4h 30m
Houston Hobby
Sun 4/19
5:00 am-7:25 am
Nonstop2h 25m
$248
ChicagoHouston
ORD - HOU
ORDHOU
Chicago O'Hare Intl
Thu 4/9
5:30 am-1:28 pm
1 stop7h 58m
Houston Hobby
Mon 4/13
1:31 pm-9:25 pm
1 stop7h 54m
$257
ChicagoHouston
MDW - HOU
MDWHOU
Chicago Midway
Thu 6/18
5:00 am-7:35 am
Nonstop2h 35m
Houston Hobby
Mon 6/22
5:00 am-7:25 am
Nonstop2h 25m
$259
ChicagoHouston
MDW - HOU
MDWHOU
Chicago Midway
Fri 4/10
9:40 pm-12:20 am
Nonstop2h 40m
Houston Hobby
Sun 4/12
8:15 pm-12:20 am
1 stop4h 05m
$262
ChicagoHouston
MDW - HOU
MDWHOU
Chicago Midway
Sat 4/11
6:05 pm-8:50 pm
Nonstop2h 45m
Houston Hobby
Sun 4/19
8:10 pm-12:15 am
1 stop4h 05m
$267
ChicagoHouston
ORD - HOU
ORDHOU
Chicago O'Hare Intl
Mon 4/6
2:40 pm-9:45 pm
2 stops7h 05m
Houston Hobby
Thu 4/9
9:30 am-3:30 pm
1 stop6h 00m
$273
ChicagoHouston
ORD - HOU
ORDHOU
Chicago O'Hare Intl
Tue 4/21
10:30 am-6:50 pm
2 stops8h 20m
Houston Hobby
Sat 4/25
8:25 am-11:25 pm
2 stops15h 00m
$275
ChicagoHouston
ORD - HOU
ORDHOU
Chicago O'Hare Intl
Fri 4/17
8:00 am-6:50 pm
2 stops10h 50m
Houston Hobby
Mon 4/20
1:40 pm-11:55 pm
1 stop10h 15m
$275
ChicagoHouston
MDW - HOU
MDWHOU
Chicago Midway
Tue 3/10
6:25 pm-10:40 pm
1 stop4h 15m
Houston Hobby
Wed 3/11
11:30 am-5:00 pm
2 stops5h 30m
$278
Showing 1-10 of 45 results
Compare providers for flights from Chicago to Hobby
Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Chicago to Hobby in February.
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy2 stars | Trust Score*2 stars | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy- | Trust Score*1 star | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy2 stars | Trust Score*3 stars | |
| Price Accuracy- | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars |
- Most accurate provider: When it comes to deals on Chicago-Houston Hobby Airport flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Chicago-Houston Hobby Airport flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Chicago-Houston Hobby Airport flight searches over the past month and is updated monthly.
- Most trusted provider: When it comes to deals on Chicago-Houston Hobby Airport flights, Cheapflights users trust FlightHub the most. FlightHub has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Chicago-Houston Hobby Airport flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.
Best time to book a flight from Chicago to Hobby
Have a flexible travel schedule? Discover the best time to fly to Hobby from Chicago with our price prediction graph.
CHI-HOU
MDW-HOU
ORD-HOU
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 Chicago to Houston Hobby Airport
CHI-HOU
MDW-HOU
ORD-HOU
How far ahead should I book a flight from Chicago to Houston Hobby Airport?
Use this chart to determine the optimal time to book a round-trip flight from Chicago to Hobby. Price data was last updated on February 20, 2026.
Booking 86 days in advance of your planned departure date is, on average, the best time to get cheap flights from Chicago to Houston Hobby Airport. The general trend is that the closer you book to the departure date, the more expensive your flight will be.
What is the cheapest month to book a flight from Chicago to Houston Hobby Airport?
Currently, January is the cheapest month in which you can book a flight from Chicago to Houston Hobby Airport (average of $72). Flying from Chicago to Houston Hobby Airport in July is currently the most expensive (average of $131). 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 CHI to HOU?
Find hourly flight availability from Chicago to Hobby. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated February 23, 2026.
Unlike in the morning, when flights are generally more expensive, you can save up to 26% on flights from Chicago to Houston Hobby Airport by exploring options for tickets in the evening.
What is the cheapest day to fly from Chicago to Houston Hobby Airport?
Use this chart to determine the cheapest time to fly round-trip from Chicago to Hobby. Price data was last updated on February 21, 2026.
Travelers seeking maximum savings on their Chicago to Houston Hobby Airport flight should consider departing on Saturday 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 much does it cost to fly round-trip from Chicago to Houston Hobby Airport?
How often are flights from Chicago to Houston delayed?
About 19% of weekly flights between Chicago and Houston have experienced delays in the past year, with the average delay time being 116 minutes.
What is the most punctual flight time for Chicago to Houston 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?
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 Chicago to Houston flights?
Over the last year, Southwest have had the lowest number of delays on this route, with just 18% of flights being delayed.
The best insider tips for Chicago to Houston Hobby 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 Chicago to Houston Hobby Airport trip
Our travel experts
Reviews of airlines servicing Hobby
Get insights into the airlines that provide service to Hobby. 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 Hobby. Reviews last updated February 23, 2026.
Read through reviews of airlines operating flights from Chicago to Houston Hobby Airport, such as Southwest, United Airlines, and American Airlines. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Entertainment
7.5
Boarding
8.1
Crew
8.6
Food
7.0
Comfort
8.0
Overall
8.0
Reviews
1 / 20
2.0
MediocreMike,Aug 2025
OKC - AUS
Entertainment
7.5
Boarding
8.1
Crew
8.6
Food
7.0
Comfort
8.0
Overall
8.0
Reviews
1 / 20
2.0
MediocreMike,Aug 2025
OKC - AUS
Entertainment
7.5
Boarding
8.1
Crew
8.6
Food
7.0
Comfort
8.0
Overall
8.0
Reviews
1 / 20
2.0
MediocreMike,Aug 2025
OKC - AUS
Entertainment
7.5
Boarding
8.1
Crew
8.6
Food
7.0
Comfort
8.0
Overall
8.0
Reviews
1 / 20
2.0
MediocreMike,Aug 2025
OKC - AUS
Entertainment
7.5
Boarding
8.1
Crew
8.6
Food
7.0
Comfort
8.0
Overall
8.0
Reviews
1 / 20
2.0
MediocreMike,Aug 2025
OKC - AUS
Entertainment
7.5
Boarding
8.1
Crew
8.6
Food
7.0
Comfort
8.0
Overall
8.0
Reviews
1 / 20
2.0
MediocreMike,Aug 2025
OKC - AUS
Related info for your journey
Find useful and relevant information for your journey from Chicago to Hobby. 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 Houston Hobby Airport?
Book flights to Houston Hobby Airport if you plan to visit one of these locationsStafford
Pasadena
Kemah
Sugar Land
Pearland
Freeport
Webster
West University Place
Seabrook
Baytown
Texas City
Lake Jackson
Rosenberg
Missouri City
League City
Nassau Bay
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
Hobby flight routes
Other flight options
Other flights from Chicago
Popular flights
Alternative routes for Chicago to Hobby
See prices for flight routes from nearby airports that may be better suited for you.
Complete your trip
Complete your trip to Hobby by adding a car rental and/or hotel reservation to your travel itinerary.
Search flights from Chicago to Hobby by cabin class
Find flights from Chicago to Hobby, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Other flights to Hobby
Explore flights to Hobby departing from other origins. Flights are based on user searches made on Cheapflights and were last updated on February 23, 2026.
Chicago and Hobby flights
Browse other Chicago and Hobby flight options. Last updated on February 23, 2026.
Other flights from Chicago
Browse through other flights departing from Chicago. Flights are based on user searches made on Cheapflights and were last updated on February 23, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Top 5 airlines flying from Chicago to Hobby
Discover the top 5 airlines that operate flights from Chicago to Hobby. 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 February 23, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$67 | Average$188 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$76 | Average$154 | FlexibilityNo cancel fee | On-time65% | |
| Cheapest$134 | Average$318 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$163 | Average$269 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$188 | Average$326 | FlexibilityNo cancel fee | On-time63% |