$106+ Cheap flights from Chicago (CHI) to Hobby (HOU)
This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 12/4. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — HOU
Nov 20 — Nov 271
Round-trip
1 adult, Economy
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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 January or February, booked 90 days in advance, depart on a Wednesday or Saturday and return on a Saturday
Cheap flight deals from Chicago to Hobby
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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 October 21, 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 October 21, 2026.
This Southwest deal was found by Cheapflights users on 10/20. 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.
Fri 12/48:50 pm -
Nonstop2h 40m
Mon 12/78:40 pm -
Nonstop2h 30m
Deal found 10/20![Southwest logo]()
$211
This Southwest deal was found by Cheapflights users on 10/19. 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 12/18:50 pm -
Nonstop2h 40m
Sat 12/53:45 pm -
Nonstop2h 25m
Deal found 10/19![Southwest logo]()
$212
This Southwest deal was found by Cheapflights users on 10/21. 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 12/56:20 pm -
Nonstop2h 45m
Sat 12/128:50 am -
1 stop4h 05m
Deal found 10/21![Southwest logo]()
$217
This Southwest deal was found by Cheapflights users on 10/21. 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 11/139:20 pm -
Nonstop2h 50m
Sun 11/1510:40 pm -
Nonstop2h 30m
Deal found 10/21![Southwest logo]()
$222
This Southwest deal was found by Cheapflights users on 10/21. 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 12/1810:05 am -
1 stop4h 40m
Mon 12/215:00 pm -
1 stop5h 20m
Deal found 10/21![Southwest logo]()
$226
This Southwest deal was found by Cheapflights users on 10/19. 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 12/56:20 pm -
Nonstop2h 45m
Mon 12/74:00 pm -
1 stop3h 55m
Deal found 10/19![Southwest logo]()
$227
This Delta deal was found by Cheapflights users on 10/21. 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 12/56:16 pm -
1 stop5h 15m
Sat 12/1211:15 am -
1 stop7h 54m
Deal found 10/21![Delta logo]()
$231
This Delta deal was found by Cheapflights users on 10/19. 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 11/1011:27 am -
1 stop5h 02m
Tue 11/175:24 pm -
1 stop5h 30m
Deal found 10/19![Delta logo]()
$231
This Southwest deal was found by Cheapflights users on 10/18. 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 12/38:50 pm -
Nonstop2h 40m
Thu 12/1011:30 am -
2 stops5h 40m
Deal found 10/18![Southwest logo]()
$233
This Southwest deal was found by Cheapflights users on 10/20. 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 11/309:45 pm -
Nonstop2h 45m
Wed 12/27:20 am -
Nonstop2h 30m
Deal found 10/20![Southwest logo]()
$235
This Delta deal was found by Cheapflights users on 10/21. 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 11/1411:18 am -
2 stops12h 03m
Tue 11/176:00 am -
1 stop6h 20m
Deal found 10/21![Delta logo]()
$236
This Delta deal was found by Cheapflights users on 10/19. 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.
Sun 12/66:49 am -
1 stop7h 24m
Tue 12/86:08 am -
1 stop6h 16m
Deal found 10/19![Delta logo]()
$242
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 October 21, 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 October 21, 2026.
This Southwest deal was found by Cheapflights users on 10/19. 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 12/18:50 pm -
Nonstop2h 40m
Sat 12/53:45 pm -
Nonstop2h 25m
Deal found 10/19![Southwest logo]()
$212
This Delta deal was found by Cheapflights users on 10/20. 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 11/146:15 pm -
1 stop5h 06m
Tue 11/1710:27 am -
1 stop6h 38m
Deal found 10/20![Delta logo]()
$231
This Southwest deal was found by Cheapflights users on 10/20. 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 11/217:55 am -
1 stop5h 55m
Mon 11/2310:40 pm -
Nonstop2h 30m
Deal found 10/20![Southwest logo]()
$221
This Delta deal was found by Cheapflights users on 10/20. 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 11/1412:38 pm -
2 stops10h 43m
Wed 11/183:12 pm -
1 stop5h 37m
Deal found 10/20![Delta logo]()
$236
This Southwest deal was found by Cheapflights users on 10/20. 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 12/108:50 pm -
Nonstop2h 40m
Sat 12/128:45 am -
2 stops5h 50m
Deal found 10/20![Southwest logo]()
$222
This Southwest deal was found by Cheapflights users on 10/21. 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 12/48:50 pm -
Nonstop2h 40m
Sun 12/67:50 am -
Nonstop2h 30m
Deal found 10/21![Southwest logo]()
$222
This Southwest deal was found by Cheapflights users on 10/18. 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 12/56:20 pm -
Nonstop2h 45m
Mon 12/74:00 pm -
1 stop3h 55m
Deal found 10/18![Southwest logo]()
$227
This Delta deal was found by Cheapflights users on 10/21. 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 11/211:31 pm -
2 stops9h 50m
Sun 11/226:00 am -
2 stops10h 39m
Deal found 10/21![Delta logo]()
$325
This KAYAK deal was found by Cheapflights users on 10/21. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/146:16 pm -
1 stop5h 15m
Thu 12/1710:41 am -
1 stop6h 25m
Deal found 10/21![Delta logo]()
$359
This Southwest deal was found by Cheapflights users on 10/20. 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 11/198:50 pm -
Nonstop2h 40m
Sun 11/2210:40 pm -
Nonstop2h 30m
Deal found 10/20![Southwest logo]()
$301
This Delta deal was found by Cheapflights users on 10/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/711:19 am -
2 stops11h 44m
Mon 11/93:12 pm -
1 stop5h 37m
Deal found 10/16![Delta logo]()
$364
This Southwest deal was found by Cheapflights users on 10/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/2410:05 am -
1 stop4h 40m
Tue 12/15:00 pm -
1 stop5h 40m
Deal found 10/17![Southwest logo]()
$347
This Delta deal was found by Cheapflights users on 10/21. 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.
Thu 1/217:00 am -
2 stops9h 30m
Mon 1/255:35 pm -
1 stop6h 15m
Deal found 10/21![Delta logo]()
$390
This Southwest deal was found by Cheapflights users on 10/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/129:20 pm -
Nonstop2h 50m
Tue 11/1711:30 am -
2 stops5h 40m
Deal found 10/16![Southwest logo]()
$350
This Delta deal was found by Cheapflights users on 10/18. 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.
Sat 1/233:00 pm -
1 stop6h 43m
Sun 1/3110:38 am -
1 stop7h 54m
Deal found 10/18![Delta logo]()
$398
This Delta deal was found by Cheapflights users on 10/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/306:15 pm -
1 stop5h 06m
Thu 12/35:27 pm -
1 stop6h 29m
Deal found 10/17![Delta logo]()
$403
This Southwest deal was found by Cheapflights users on 10/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/45:25 pm -
1 stop5h 35m
Mon 12/711:30 am -
2 stops5h 40m
Deal found 10/17![Southwest logo]()
$380
This Delta deal was found by Cheapflights users on 10/19. 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 11/2112:38 pm -
2 stops10h 43m
Sun 11/225:24 pm -
1 stop6h 30m
Deal found 10/19![Delta logo]()
$403
This Southwest deal was found by Cheapflights users on 10/18. 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.
Sun 12/277:35 am -
1 stop5h 50m
Thu 12/318:40 pm -
Nonstop2h 30m
Deal found 10/18![Southwest logo]()
$384
This Delta deal was found by Cheapflights users on 10/20. 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 11/196:23 am -
2 stops10h 06m
Sun 11/223:12 pm -
1 stop5h 37m
Deal found 10/20![Delta logo]()
$404
This Delta deal was found by Cheapflights users on 10/19. 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.
Fri 1/223:00 pm -
1 stop6h 43m
Sun 1/245:35 pm -
1 stop6h 15m
Deal found 10/19![Delta logo]()
$408
This Southwest deal was found by Cheapflights users on 10/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/269:25 pm -
Nonstop2h 45m
Wed 12/305:00 pm -
1 stop4h 05m
Deal found 10/16![Southwest logo]()
$413
Last-minute flights from Chicago to HobbyDiscover last-minute flight deals from Chicago to Hobby. Data last updated October 21, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to Hobby. Data last updated October 21, 2026 and is based on user searches.
This Delta deal was found by Cheapflights users on 10/20. 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 11/105:13 pm -
1 stop6h 08m
Thu 11/126:00 am -
1 stop5h 59m
Deal found 10/20![Delta logo]()
$231
This Southwest deal was found by Cheapflights users on 10/19. 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 11/115:15 pm -
1 stop5h 45m
Wed 11/1811:30 am -
2 stops5h 40m
Deal found 10/19![Southwest logo]()
$232
This American Airlines deal was found by Cheapflights users on 10/21. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/125:00 am -
1 stop6h 05m
Fri 11/135:02 pm -
1 stop6h 57m
Deal found 10/21![American Airlines logo]()
$253
This Southwest deal was found by Cheapflights users on 10/21. 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 11/139:20 pm -
Nonstop2h 50m
Sun 11/1510:40 pm -
Nonstop2h 30m
Deal found 10/21![Southwest logo]()
$222
This Delta deal was found by Cheapflights users on 10/21. 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 11/136:15 pm -
1 stop5h 06m
Mon 11/165:24 pm -
1 stop6h 30m
Deal found 10/21![Delta logo]()
$265
This Delta deal was found by Cheapflights users on 10/21. 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 11/146:15 pm -
1 stop5h 06m
Tue 11/1710:27 am -
1 stop6h 38m
Deal found 10/21![Delta logo]()
$231
This Delta deal was found by Cheapflights users on 10/21. 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 11/1412:30 pm -
2 stops10h 51m
Tue 11/175:24 pm -
1 stop5h 30m
Deal found 10/21![Delta logo]()
$236
This Southwest deal was found by Cheapflights users on 10/19. 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 11/168:50 pm -
Nonstop2h 40m
Mon 11/2310:40 pm -
Nonstop2h 30m
Deal found 10/19![Southwest logo]()
$211
This Southwest deal was found by Cheapflights users on 10/20. 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.
Wed 11/188:00 am -
2 stops6h 00m
Wed 11/2510:30 pm -
Nonstop2h 30m
Deal found 10/20![Southwest logo]()
$226
This Southwest deal was found by Cheapflights users on 10/18. 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 11/266:10 am -
Nonstop2h 45m
Tue 12/111:50 am -
1 stop5h 05m
Deal found 10/18![Southwest logo]()
$227
This Southwest deal was found by Cheapflights users on 10/20. 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 11/309:45 pm -
Nonstop2h 45m
Wed 12/27:20 am -
Nonstop2h 30m
Deal found 10/20![Southwest logo]()
$235
This Delta deal was found by Cheapflights users on 10/19. 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.
Mon 11/306:15 pm -
1 stop5h 06m
Wed 12/26:08 am -
2 stops10h 09m
Deal found 10/19![Delta logo]()
$246
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 October 21, 2026.
Search for one-way flight options from Chicago to Hobby. Find affordable one-way fares based on user searches. Data last updated October 21, 2026.
This Southwest deal was found by Cheapflights users on 10/21. 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 12/119:20 pm -
Nonstop2h 50m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/21![Southwest logo]()
$106
This Southwest deal was found by Cheapflights users on 10/19. 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 12/38:50 pm -
Nonstop2h 40m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/19![Southwest logo]()
$111
This Delta deal was found by Cheapflights users on 10/20. 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 11/96:15 pm -
1 stop5h 06m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/20![Delta logo]()
$116
This Southwest deal was found by Cheapflights users on 10/21. 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.
Sun 12/69:20 pm -
Nonstop2h 50m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/21![Southwest logo]()
$117
This Delta deal was found by Cheapflights users on 10/21. 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.
Mon 11/162:44 pm -
2 stops8h 37m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/21![Delta logo]()
$121
This Southwest deal was found by Cheapflights users on 10/20. 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 12/2010:05 am -
1 stop4h 40m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/20![Southwest logo]()
$122
This Delta deal was found by Cheapflights users on 10/19. 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 12/912:34 pm -
2 stops10h 57m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/19![Delta logo]()
$126
This American Airlines deal was found by Cheapflights users on 10/21. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/225:00 am -
1 stop6h 04m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/21![American Airlines logo]()
$127
This Southwest deal was found by Cheapflights users on 10/19. 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.
Sun 12/1310:05 am -
2 stops5h 35m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/19![Southwest logo]()
$128
This Southwest deal was found by Cheapflights users on 10/18. 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.
Tue 11/178:50 pm -
Nonstop2h 40m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/18![Southwest logo]()
$129
This American Airlines deal was found by Cheapflights users on 10/18. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/51:43 pm -
1 stop4h 58m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/18![American Airlines logo]()
$139
This Delta deal was found by Cheapflights users on 10/19. 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 11/187:05 am -
2 stops9h 24m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/19![Delta logo]()
$144
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 October 21, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $211 (Southwest) |
One-way from | $106 (Southwest) |
Popular in | June |
Cheapest in | January |
Average price | $286 |
Good round-trip deal | $366 or less |
Good one-way deal | $255 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 7,457,451 searches. Data last updated October 21, 2026.
Use the filters below to find and compare flights from Chicago to Houston Hobby Airport that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
ChicagoHouston
MDW Chicago Midway - HOU Houston Hobby
MDWHOU
Chicago Midway
Fri 12/4
8:05 am-10:50 am
Nonstop2h 45m
Houston Hobby
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$106
ChicagoHouston
ORD Chicago O'Hare Intl - HOU Houston Hobby
ORDHOU
Chicago O'Hare Intl
Mon 2/1
3:00 pm-9:43 pm
1 stop6h 43m
Houston Hobby
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$116
ChicagoHouston
ORD Chicago O'Hare Intl - HOU Houston Hobby
ORDHOU
Chicago O'Hare Intl
Sat 12/12
6:16 pm-11:31 pm
1 stop5h 15m
Houston Hobby
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$116
ChicagoHouston
MDW Chicago Midway - HOU Houston Hobby
MDWHOU
Chicago Midway
Sat 12/5
6:00 am-12:55 pm
1 stop6h 55m
Houston Hobby
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$116
ChicagoHouston
MDW Chicago Midway - HOU Houston Hobby
MDWHOU
Chicago Midway
Fri 12/11
6:00 pm-11:20 pm
1 stop5h 20m
Houston Hobby
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$116
Quickest round-trip
ChicagoHouston
MDW Chicago Midway - HOU Houston Hobby
MDWHOU
Chicago Midway
Sun 12/20
9:05 am-11:45 am
Nonstop2h 40m
Houston Hobby
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$117
ChicagoHouston
ORD Chicago O'Hare Intl - HOU Houston Hobby
ORDHOU
Chicago O'Hare Intl
Mon 11/16
2:44 pm-11:21 pm
2 stops8h 37m
Houston Hobby
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$121
ChicagoHouston
ORD Chicago O'Hare Intl - HOU Houston Hobby
ORDHOU
Chicago O'Hare Intl
Wed 11/18
10:32 am-4:29 pm
1 stop5h 57m
Houston Hobby
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$139
ChicagoHouston
ORD Chicago O'Hare Intl - HOU Houston Hobby
ORDHOU
Chicago O'Hare Intl
Fri 12/4
6:16 pm-11:31 pm
1 stop5h 15m
Houston Hobby
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$148
ChicagoHouston
ORD Chicago O'Hare Intl - HOU Houston Hobby
ORDHOU
Chicago O'Hare Intl
Fri 12/11
6:16 pm-11:31 pm
1 stop5h 15m
Houston Hobby
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$150
Showing 1-10 of 38 resultsSorted by cheapest first
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 October.
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy- | Trust Score*1 star | |
| Price Accuracy2 stars | Trust Score*3 stars | |
| Price Accuracy- | Trust Score*3 stars | |
| Price Accuracy2 stars | Trust Score*1 star | |
| Price Accuracy2 stars | Trust Score*3 stars | |
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy- | Trust Score*1 star |
- 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
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 $199). Flying from Chicago to Houston Hobby Airport in June is currently the most expensive (average of $329). 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 October 21, 2026.
Unlike in the afternoon, when flights are generally more expensive, you can save up to 20% on flights from Chicago to Houston Hobby Airport by exploring options for tickets in the evening.
How much does it cost to fly round-trip from Chicago to Houston Hobby Airport?
Airfare is typical for this route at the moment.
Chicago to Houston Hobby Airport flights typically cost between $184 and $362 in December.The cheapest round-trip price found within the last 5 days was $211 on Southwest (Dec 4-Dec 7).
What’s the top layover airport for flights from Chicago to Houston Hobby Airport?
Share of 1-stop round-trip flights from Chicago to Houston Hobby Airport chosen by Cheapflights users in the past 12 months, using the same layover each way.
Orlando (MCO) – chosen by Cheapflights users on 50% of 1-stop itineraries from Chicago to Houston Hobby Airport on Cheapflights.
What’s the cheapest layover airport for flights from Chicago to Houston Hobby Airport?
Average round-trip fare for 1-stop flights from Chicago to Houston Hobby Airport, chosen by Cheapflights users in the past 12 months, with the same layover each way.
Orlando (MCO) is the most affordable 1-stop option, with an average round-trip price of $240.
What’s the fastest layover option from Chicago to Houston Hobby Airport?
Shortest average travel time for 1-stop one-way flights from Chicago to Houston Hobby Airport, based on itineraries clicked by Cheapflights users over the past 12 months, grouped by layover airport.
Flights via Atlanta (ATL) have the shortest average one-way travel time for 1-stop routes: 5h 31m.
Which airport typically offers the quickest layover for flights from Chicago to Houston Hobby Airport?
Average layover duration for 1-stop one-way flights from Chicago to Houston Hobby Airport, chosen by Cheapflights users in the last 12 months, grouped by stopover airport.
Flights via Atlanta (ATL) offer the fastest connection on this route, with an average layover time of 0h 57m.
How often are flights from Chicago to Houston delayed?
About 21% of weekly flights between Chicago and Houston have experienced delays in the past year, with the average delay time being 114 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?
Thursday 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 20% of flights being delayed.
How far ahead should I book a flight from Chicago to Houston Hobby Airport?
Booking 64 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 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 October 17, 2026.
Travelers seeking maximum savings on their Chicago to Houston Hobby Airport flight should consider departing on Saturday at noon 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.
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 October 21, 2026.
Read through reviews of airlines operating flights from Chicago to Houston Hobby Airport, such as Southwest,United Airlines, andJetBlue. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Comfort
8.0
Boarding
8.1
Crew
8.6
Food
7.0
Entertainment
7.4
Overall
7.9
Reviews
1 / 20
10.0
ExcellentSarah,Aug 2024
MDW - AUS
Comfort
8.0
Boarding
8.1
Crew
8.6
Food
7.0
Entertainment
7.4
Overall
7.9
Reviews
1 / 20
10.0
ExcellentSarah,Aug 2024
MDW - AUS
Comfort
8.0
Boarding
8.1
Crew
8.6
Food
7.0
Entertainment
7.4
Overall
7.9
Reviews
1 / 20
10.0
ExcellentSarah,Aug 2024
MDW - AUS
Comfort
8.0
Boarding
8.1
Crew
8.6
Food
7.0
Entertainment
7.4
Overall
7.9
Reviews
1 / 20
10.0
ExcellentSarah,Aug 2024
MDW - AUS
Comfort
8.0
Boarding
8.1
Crew
8.6
Food
7.0
Entertainment
7.4
Overall
7.9
Reviews
1 / 20
10.0
ExcellentSarah,Aug 2024
MDW - AUS
Comfort
8.0
Boarding
8.1
Crew
8.6
Food
7.0
Entertainment
7.4
Overall
7.9
Reviews
1 / 20
10.0
ExcellentSarah,Aug 2024
MDW - 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 locationsSugar Land
Pearland
Kemah
Webster
West University Place
Texas City
Stafford
Pasadena
Seabrook
Baytown
Freeport
Lake Jackson
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Rosenberg
League City
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Other flights to Hobby
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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 7,457,451 searches. Data last updated October 21, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$80 | Average$220 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$140 | Average$426 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$188 | Average$357 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$203 | Average$298 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$224 | Average$327 | FlexibilityNo cancel fee | On-time63% |