$111+ Cheap flights from Hobby (HOU) to Chicago (CHI)
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 11/12. Fares are subject to change and may not be available on all flights or dates of travel.
HOU — CHI
Nov 25 — Dec 21
Round-trip
1 adult, Economy
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Find cheap flights from Hobby to Chicago 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 Hobby to Chicago are usually found in January or April, booked 79 days in advance, depart on a Saturday or Wednesday and return on a Wednesday
Cheap flight deals from Hobby to Chicago
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Cheapest flights from Hobby to ChicagoExplore the most affordable flight options available from Hobby to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on October 26, 2026.
Explore the most affordable flight options available from Hobby to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on October 26, 2026.
This Southwest deal was found by Cheapflights users on 10/24. Clicking the “Pick Dates” 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 12/87:20 am -
Nonstop2h 30m
Tue 12/158:00 am -
2 stops6h 00m
Deal found 10/24![Southwest logo]()
$190
This Southwest deal was found by Cheapflights users on 10/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/145:00 am -
Nonstop2h 25m
Sat 11/146:20 pm -
Nonstop2h 50m
Deal found 10/23![Southwest logo]()
$209
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.
Thu 11/1210:40 pm -
Nonstop2h 30m
Mon 11/168:50 pm -
Nonstop2h 40m
Deal found 10/21![Southwest logo]()
$211
This Southwest deal was found by Cheapflights users on 10/25. Clicking the “Pick Dates” 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 11/2310:40 pm -
Nonstop2h 30m
Tue 12/18:50 pm -
Nonstop2h 40m
Deal found 10/25![Southwest logo]()
$219
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 12/47:20 am -
Nonstop2h 30m
Mon 12/74:15 pm -
1 stop5h 50m
Deal found 10/21![Southwest logo]()
$221
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 12/58:50 am -
1 stop4h 05m
Sat 12/1210:20 am -
1 stop6h 35m
Deal found 10/20![Southwest logo]()
$226
This Delta deal was found by Cheapflights users on 10/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/86:08 am -
1 stop6h 16m
Tue 12/158:04 am -
1 stop6h 09m
Deal found 10/23![Delta logo]()
$229
This Delta deal was found by Cheapflights users on 10/22. 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 11/106:00 am -
1 stop6h 20m
Sat 11/146:15 pm -
1 stop5h 06m
Deal found 10/22![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.
Thu 11/126:00 am -
2 stops12h 30m
Tue 11/173:59 pm -
1 stop7h 22m
Deal found 10/21![Delta logo]()
$236
This Delta deal was found by Cheapflights users on 10/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/2611:05 am -
2 stops8h 34m
Tue 12/812:34 pm -
2 stops10h 57m
Deal found 10/23![Delta logo]()
$239
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 11/146:00 am -
2 stops10h 41m
Tue 11/1712:38 pm -
2 stops10h 43m
Deal found 10/21![Delta logo]()
$241
This Delta deal was found by Cheapflights users on 10/22. 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 12/511:15 am -
1 stop5h 51m
Sun 12/66:49 am -
1 stop7h 24m
Deal found 10/22![Delta logo]()
$242
Best flights from Hobby to ChicagoDiscover carefully curated flight deals from Hobby to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated October 26, 2026.
Discover carefully curated flight deals from Hobby to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated October 26, 2026.
This Southwest deal was found by Cheapflights users on 10/22. 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 12/58:50 am -
1 stop4h 05m
Mon 12/76:40 am -
Nonstop2h 40m
Deal found 10/22![Southwest logo]()
$217
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 11/196:00 am -
1 stop5h 59m
Sat 11/215:13 pm -
1 stop6h 08m
Deal found 10/21![Delta logo]()
$231
This Southwest deal was found by Cheapflights users on 10/22. 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 12/1611:30 am -
2 stops5h 45m
Thu 12/175:15 am -
Nonstop2h 40m
Deal found 10/22![Southwest logo]()
$222
This Delta deal was found by Cheapflights users on 10/22. 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 11/135:24 pm -
1 stop6h 30m
Sat 11/146:15 pm -
1 stop5h 06m
Deal found 10/22![Delta logo]()
$231
This Delta deal was found by Cheapflights users on 10/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/73:11 pm -
1 stop5h 42m
Tue 12/83:59 pm -
1 stop7h 32m
Deal found 10/23![Delta logo]()
$231
This Southwest deal was found by Cheapflights users on 10/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/1312:55 pm -
1 stop4h 05m
Sun 11/155:20 am -
1 stop5h 50m
Deal found 10/23![Southwest logo]()
$236
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 1/1210:38 am -
2 stops7h 59m
Tue 1/261:00 pm -
2 stops8h 43m
Deal found 10/20![Delta logo]()
$241
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 11/204:00 pm -
1 stop4h 25m
Sun 11/229:20 pm -
Nonstop2h 50m
Deal found 10/21![Southwest logo]()
$277
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 12/410:41 am -
1 stop6h 25m
Mon 12/73:59 pm -
1 stop7h 32m
Deal found 10/21![Delta logo]()
$265
This Southwest deal was found by Cheapflights users on 10/24. Clicking the “Pick Dates” 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 11/2210:40 pm -
Nonstop2h 30m
Tue 12/18:50 pm -
Nonstop2h 40m
Deal found 10/24![Southwest logo]()
$281
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 11/196:00 am -
2 stops10h 41m
Sat 11/2112:38 pm -
2 stops10h 43m
Deal found 10/21![Delta logo]()
$275
This Southwest deal was found by Cheapflights users on 10/22. 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 11/3010:30 pm -
Nonstop2h 30m
Wed 12/26:40 am -
Nonstop2h 40m
Deal found 10/22![Southwest logo]()
$310
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 12/411:30 am -
2 stops5h 45m
Mon 12/78:00 am -
2 stops6h 00m
Deal found 10/21![Southwest logo]()
$316
This Delta deal was found by Cheapflights users on 10/24. Clicking the “Pick Dates” 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 11/236:00 am -
1 stop6h 20m
Wed 12/211:39 am -
2 stops11h 52m
Deal found 10/24![Delta logo]()
$329
This Southwest deal was found by Cheapflights users on 10/22. 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 12/1011:30 am -
2 stops5h 45m
Sun 12/1310:05 am -
2 stops5h 35m
Deal found 10/22![Southwest logo]()
$317
This Delta deal was found by Cheapflights users on 10/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/106:08 am -
2 stops10h 09m
Tue 6/15:30 am -
1 stop6h 44m
Deal found 10/23![Delta logo]()
$339
This Southwest deal was found by Cheapflights users on 10/25. Clicking the “Pick Dates” 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 12/3111:15 am -
2 stops5h 50m
Mon 1/44:50 pm -
1 stop4h 10m
Deal found 10/25![Southwest logo]()
$333
This Delta deal was found by Cheapflights users on 10/25. Clicking the “Pick Dates” 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 12/156:12 am -
2 stops10h 05m
Fri 12/186:49 am -
1 stop7h 24m
Deal found 10/25![Delta logo]()
$390
This Delta deal was found by Cheapflights users on 10/25. Clicking the “Pick Dates” 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 11/206:00 am -
2 stops10h 41m
Sun 11/226:49 am -
1 stop7h 22m
Deal found 10/25![Delta logo]()
$400
This Delta deal was found by Cheapflights users on 10/22. 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.
Thu 11/56:09 am -
1 stop6h 04m
Wed 11/112:44 pm -
2 stops8h 37m
Deal found 10/22![Delta logo]()
$440
This Delta deal was found by Cheapflights users on 10/22. 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 12/1810:41 am -
1 stop6h 25m
Sun 12/206:23 am -
2 stops11h 43m
Deal found 10/22![Delta logo]()
$490
Last-minute flights from Hobby to ChicagoDiscover last-minute flight deals from Hobby to Chicago. Data last updated October 26, 2026 and is based on user searches.
Discover last-minute flight deals from Hobby to Chicago. Data last updated October 26, 2026 and is based on user searches.
This Southwest deal was found by Cheapflights users on 10/22. 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 11/107:20 am -
Nonstop2h 30m
Tue 11/103:50 pm -
1 stop6h 40m
Deal found 10/22![Southwest logo]()
$221
This Southwest deal was found by Cheapflights users on 10/22. 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 11/101:20 pm -
1 stop5h 45m
Fri 11/134:50 pm -
1 stop4h 10m
Deal found 10/22![Southwest logo]()
$226
This Delta deal was found by Cheapflights users on 10/22. 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 11/106:00 am -
1 stop6h 20m
Tue 11/106:15 pm -
1 stop5h 06m
Deal found 10/22![Delta logo]()
$231
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.
Thu 11/1210:40 pm -
Nonstop2h 30m
Mon 11/168:50 pm -
Nonstop2h 40m
Deal found 10/21![Southwest logo]()
$211
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.
Thu 11/1212:55 pm -
1 stop4h 05m
Tue 11/178:50 pm -
Nonstop2h 40m
Deal found 10/21![Southwest logo]()
$217
This Southwest deal was found by Cheapflights users on 10/22. 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 11/1210:40 pm -
Nonstop2h 30m
Sun 11/159:20 pm -
Nonstop2h 50m
Deal found 10/22![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.
Thu 11/126:00 am -
2 stops12h 30m
Tue 11/173:59 pm -
1 stop7h 22m
Deal found 10/21![Delta logo]()
$236
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 11/135:24 pm -
1 stop5h 30m
Mon 11/165:13 pm -
1 stop6h 08m
Deal found 10/21![Delta logo]()
$231
This Southwest deal was found by Cheapflights users on 10/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/145:00 am -
Nonstop2h 25m
Sat 11/146:20 pm -
Nonstop2h 50m
Deal found 10/23![Southwest logo]()
$209
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 11/146:00 am -
2 stops10h 41m
Tue 11/1712:38 pm -
2 stops10h 43m
Deal found 10/21![Delta logo]()
$241
This Southwest deal was found by Cheapflights users on 10/25. Clicking the “Pick Dates” 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 11/2310:40 pm -
Nonstop2h 30m
Tue 12/18:50 pm -
Nonstop2h 40m
Deal found 10/25![Southwest logo]()
$219
This Delta deal was found by Cheapflights users on 10/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/2611:05 am -
1 stop5h 35m
Tue 12/88:04 am -
1 stop6h 09m
Deal found 10/23![Delta logo]()
$229
One-way flights from Hobby to ChicagoSearch for one-way flight options from Hobby to Chicago. Find affordable one-way fares based on user searches. Data last updated October 26, 2026.
Search for one-way flight options from Hobby to Chicago. Find affordable one-way fares based on user searches. Data last updated October 26, 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.
Thu 11/1212:55 pm -
1 stop4h 05m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/21![Southwest logo]()
$111
This Southwest deal was found by Cheapflights users on 10/25. Clicking the “Pick Dates” 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 11/2310:40 pm -
Nonstop2h 30m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/25![Southwest logo]()
$114
This Delta deal was found by Cheapflights users on 10/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/145:24 pm -
1 stop6h 30m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/23![Delta logo]()
$115
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.
Wed 12/211:30 am -
2 stops5h 40m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/21![Southwest logo]()
$116
This Southwest deal was found by Cheapflights users on 10/22. 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 11/1510:40 pm -
Nonstop2h 30m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/22![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.
Thu 11/126:00 am -
2 stops12h 04m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/21![Delta logo]()
$121
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 12/205:00 pm -
1 stop5h 20m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/21![Southwest logo]()
$127
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 12/102:07 pm -
1 stop5h 52m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/21![American Airlines logo]()
$127
This Southwest deal was found by Cheapflights users on 10/22. 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 11/910:40 pm -
Nonstop2h 30m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/22![Southwest logo]()
$131
This Southwest deal was found by Cheapflights users on 10/26. Clicking the “Pick Dates” 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 12/42:35 pm -
Nonstop2h 25m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/26![Southwest logo]()
$134
This Southwest deal was found by Cheapflights users on 10/24. Clicking the “Pick Dates” 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 11/145:00 am -
Nonstop2h 25m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/24![Southwest logo]()
$138
This Kissandfly.com deal was found by Cheapflights users on 10/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kissandfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/410:41 am -
1 stop7h 22m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/26![Frontier logo]()
$147
Find flight deals from Hobby to Chicago
Discover tips and strategies to find the most affordable flight options for your journey from Hobby (HOU) to Chicago (CHI). 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 26, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $190 (Southwest) |
One-way from | $111 (Southwest) |
Popular in | October |
Cheapest in | January |
Average price | $315 |
Good round-trip deal | $358 or less |
Good one-way deal | $257 or less |
Cheapflights Fare Finder
Customize your flight search to find flights from Hobby to Chicago 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 26, 2026.
Use the filters below to find and compare flights from Houston Hobby Airport to Chicago that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
HoustonChicago
HOU Houston Hobby - MDW Chicago Midway
HOUMDW
Houston Hobby
Thu 11/19
11:05 am-3:30 pm
1 stop4h 25m
Chicago Midway
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$116
HoustonChicago
HOU Houston Hobby - ORD Chicago O'Hare Intl
HOUORD
Houston Hobby
Wed 11/18
10:27 am-5:05 pm
1 stop6h 38m
Chicago O'Hare Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$116
HoustonChicago
HOU Houston Hobby - MDW Chicago Midway
HOUMDW
Houston Hobby
Fri 12/4
11:30 am-5:15 pm
2 stops5h 45m
Chicago Midway
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$116
HoustonChicago
HOU Houston Hobby - ORD Chicago O'Hare Intl
HOUORD
Houston Hobby
Sat 12/5
6:12 am-12:24 pm
1 stop6h 12m
Chicago O'Hare Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$116
HoustonChicago
HOU Houston Hobby - ORD Chicago O'Hare Intl
HOUORD
Houston Hobby
Fri 12/4
5:27 pm-11:56 pm
1 stop6h 29m
Chicago O'Hare Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$116
HoustonChicago
HOU Houston Hobby - ORD Chicago O'Hare Intl
HOUORD
Houston Hobby
Thu 11/26
11:05 am-7:05 pm
1 stop8h 00m
Chicago O'Hare Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$116
HoustonChicago
HOU Houston Hobby - MDW Chicago Midway
HOUMDW
Houston Hobby
Thu 11/12
6:00 am-6:04 pm
2 stops12h 04m
Chicago Midway
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$121
HoustonChicago
HOU Houston Hobby - ORD Chicago O'Hare Intl
HOUORD
Houston Hobby
Fri 12/18
10:41 am-7:45 pm
2 stops9h 04m
Chicago O'Hare Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$121
Quickest round-trip
HoustonChicago
HOU Houston Hobby - MDW Chicago Midway
HOUMDW
Houston Hobby
Mon 12/7
8:40 pm-11:10 pm
Nonstop2h 30m
Chicago Midway
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$138
HoustonChicago
HOU Houston Hobby - ORD Chicago O'Hare Intl
HOUORD
Houston Hobby
Mon 12/7
10:30 am-5:06 pm
1 stop6h 36m
Chicago O'Hare Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$148
Showing 1-10 of 43 resultsSorted by cheapest first
Compare providers for flights from Hobby to Chicago
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 Hobby to Chicago in October.
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy2 stars | Trust Score*3 stars | |
| Price Accuracy- | Trust Score*1 star | |
| Price Accuracy- | Trust Score*3 stars | |
| Price Accuracy2 stars | Trust Score*1 star | |
| 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 |
- Most accurate provider: When it comes to deals on Houston Hobby Airport-Chicago flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Houston Hobby Airport-Chicago flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Houston Hobby Airport-Chicago flight searches over the past month and is updated monthly.
- Most trusted provider: When it comes to deals on Houston Hobby Airport-Chicago 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 Houston Hobby Airport-Chicago 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 Hobby to Chicago
Have a flexible travel schedule? Discover the best time to fly to Chicago from Hobby with our price prediction graph.
HOU-CHI
HOU-MDW
HOU-ORD
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 Hobby Airport to Chicago
HOU-CHI
HOU-MDW
HOU-ORD
What is the cheapest month to book a flight from Houston Hobby Airport to Chicago?
Currently, January is the cheapest month in which you can book a flight from Houston Hobby Airport to Chicago (average of $181). Flying from Houston Hobby Airport to Chicago in June is currently the most expensive (average of $331). 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 CHI?
Find hourly flight availability from Hobby to Chicago. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated October 26, 2026.
A simple way to save on the total cost of your ticket is to fly from Houston Hobby Airport to Chicago in the evening. If you’re flexible enough to do this you can expect to save up to 22% on your trip compared to booking a flight at noon.
How much does it cost to fly round-trip from Houston Hobby Airport to Chicago?
Airfare is typical for this route at the moment.
Houston Hobby Airport to Chicago flights typically cost between $186 and $362 in December.The cheapest round-trip price found within the last 5 days was $190 on Southwest (Dec 8-Dec 15).
How often are flights from Houston to Chicago delayed?
About 24% of weekly flights between Houston and Chicago have experienced delays in the past year, with the average delay time being 113 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?
Tuesday tends to have the lowest number of delays on this route, whereas Sunday has historically faced a higher average of delays compared to other days of the week.
Which airline has the best punctuality record on Houston to Chicago flights?
Over the last year, Southwest have had the lowest number of delays on this route, with just 24% of flights being delayed.
How far ahead should I book a flight from Houston Hobby Airport to Chicago?
Booking 78 days in advance of your planned departure date is, on average, the best time to get cheap flights from Houston Hobby Airport to Chicago. 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 Houston Hobby Airport to Chicago?
Use this chart to determine the cheapest time to fly round-trip from Hobby to Chicago. Price data was last updated on October 24, 2026.
Travelers seeking maximum savings on their Houston Hobby Airport to Chicago flight should consider departing on Tuesday evenings 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 Houston Hobby Airport to Chicago 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 Hobby Airport to Chicago trip
Our travel experts
Reviews of airlines servicing Chicago
Get insights into the airlines that provide service to Chicago. 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 Chicago. Reviews last updated October 26, 2026.
Peruse reviews from past customers who have flown with Southwest,United Airlines, andJetBlue from Houston Hobby Airport to Chicago to help guide your decision. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Boarding
8.1
Entertainment
7.4
Overall
7.9
Crew
8.6
Comfort
8.0
Food
7.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Boarding
8.1
Entertainment
7.4
Overall
7.9
Crew
8.6
Comfort
8.0
Food
7.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Boarding
8.1
Entertainment
7.4
Overall
7.9
Crew
8.6
Comfort
8.0
Food
7.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Boarding
8.1
Entertainment
7.4
Overall
7.9
Crew
8.6
Comfort
8.0
Food
7.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Boarding
8.1
Entertainment
7.4
Overall
7.9
Crew
8.6
Comfort
8.0
Food
7.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Boarding
8.1
Entertainment
7.4
Overall
7.9
Crew
8.6
Comfort
8.0
Food
7.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Related info for your journey
Find useful and relevant information for your journey from Hobby to Chicago. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
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Top 5 airlines flying from Hobby to Chicago
Discover the top 5 airlines that operate flights from Hobby to Chicago. 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 26, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$64 | Average$198 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$160 | Average$375 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$177 | Average$309 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$209 | Average$425 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$268 | Average$309 | FlexibilityNo cancel fee | On-time62% |