$86+ Cheap flights from Hobby (HOU) to Chicago (CHI)
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 7/8. Fares are subject to change and may not be available on all flights or dates of travel.
HOU — CHI
Jun 26 — Jul 31
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
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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 October, 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 May 27, 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 May 27, 2026.
This Southwest deal was found by Cheapflights users on 5/27. Clicking the “Pick Dates” 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 7/149:25 pm
HOU
- MDW
Nonstop2h 30m
Southwest
Tue 7/284:15 pm
MDW
- HOU
Nonstop2h 40m
Southwest
Deal found 5/27![Southwest logo]()
$171
This Southwest deal was found by Cheapflights users on 5/27. Clicking the “Pick Dates” 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 7/149:25 pm
HOU
- MDW
Nonstop2h 30m
Southwest
Wed 7/1510:15 am
MDW
- HOU
1 stop3h 50m
Southwest
Deal found 5/27![Southwest logo]()
$177
This Southwest deal was found by Cheapflights users on 5/26. 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.
Tue 6/2310:25 am
HOU
- MDW
1 stop5h 30m
Southwest
Wed 6/241:10 pm
MDW
- HOU
Nonstop2h 35m
Southwest
Deal found 5/26![Southwest logo]()
$181
This Southwest deal was found by Cheapflights users on 5/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/89:25 pm
HOU
- MDW
Nonstop2h 30m
Southwest
Tue 7/143:10 pm
MDW
- HOU
2 stops5h 30m
Southwest
Deal found 5/27![Southwest logo]()
$182
This Southwest deal was found by Cheapflights users on 5/26. 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.
Tue 7/149:25 pm
HOU
- MDW
Nonstop2h 30m
Southwest
Tue 8/47:40 am
MDW
- HOU
2 stops6h 05m
Southwest
Deal found 5/26![Southwest logo]()
$186
This Southwest deal was found by Cheapflights users on 5/25. 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.
Wed 8/128:50 pm
HOU
- MDW
Nonstop2h 20m
Southwest
Mon 8/175:55 am
MDW
- HOU
Nonstop2h 30m
Southwest
Deal found 5/25![Southwest logo]()
$187
This Southwest deal was found by Cheapflights users on 5/25. 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.
Wed 7/89:25 pm
HOU
- MDW
Nonstop2h 30m
Southwest
Wed 7/157:10 pm
MDW
- HOU
Nonstop2h 35m
Southwest
Deal found 5/25![Southwest logo]()
$189
This Southwest deal was found by Cheapflights users on 5/25. 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.
Wed 7/2910:25 am
HOU
- MDW
1 stop5h 30m
Southwest
Tue 8/42:00 pm
MDW
- HOU
1 stop5h 30m
Southwest
Deal found 5/25![Southwest logo]()
$191
This Southwest deal was found by Cheapflights users on 5/27. Clicking the “Pick Dates” 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 7/287:00 pm
HOU
- MDW
1 stop5h 10m
Southwest
Tue 8/47:40 am
MDW
- HOU
2 stops6h 05m
Southwest
Deal found 5/27![Southwest logo]()
$196
This Delta deal was found by Cheapflights users on 5/26. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/41:13 pm
HOU
- ORD
1 stop7h 37m
Delta
Tue 8/115:28 am
ORD
- HOU
1 stop6h 48m
Delta
Deal found 5/26![Delta logo]()
$197
This Delta deal was found by Cheapflights users on 5/25. 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.
Wed 9/306:00 am
HOU
- ORD
2 stops11h 23m
Delta
Tue 10/68:55 am
ORD
- HOU
2 stops7h 35m
Delta
Deal found 5/25![Delta logo]()
$208
This Delta deal was found by Cheapflights users on 5/25. 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.
Wed 8/121:13 pm
HOU
- ORD
1 stop5h 36m
Delta
Tue 8/183:31 pm
ORD
- HOU
1 stop6h 34m
Delta
Deal found 5/25![Delta logo]()
$209
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 May 27, 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 May 27, 2026.
This Delta deal was found by Cheapflights users on 5/26. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/1611:00 am
HOU
- ORD
2 stops10h 33m
Delta
Thu 9/2412:40 pm
ORD
- HOU
2 stops9h 55m
Delta
Deal found 5/26![Delta logo]()
$220
This Southwest deal was found by Cheapflights users on 5/24. 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 7/182:10 pm
HOU
- MDW
1 stop5h 25m
Southwest
Tue 7/219:00 pm
MDW
- HOU
Nonstop2h 40m
Southwest
Deal found 5/24![Southwest logo]()
$240
This Delta deal was found by Cheapflights users on 5/26. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/812:55 pm
HOU
- ORD
1 stop5h 50m
Delta
Tue 7/149:45 am
ORD
- HOU
1 stop6h 37m
Delta
Deal found 5/26![Delta logo]()
$238
This Delta deal was found by Cheapflights users on 5/22. 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 7/35:08 pm
HOU
- ORD
1 stop6h 51m
Delta
Tue 7/79:45 am
ORD
- HOU
1 stop6h 38m
Delta
Deal found 5/22![Delta logo]()
$255
This Southwest deal was found by Cheapflights users on 5/26. 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.
Thu 8/202:40 pm
HOU
- MDW
1 stop5h 05m
Southwest
Sun 8/236:05 am
MDW
- HOU
1 stop6h 05m
Southwest
Deal found 5/26![Southwest logo]()
$289
This Delta deal was found by Cheapflights users on 5/25. 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 8/256:00 am
HOU
- ORD
2 stops10h 24m
Delta
Mon 9/75:28 am
ORD
- HOU
1 stop6h 48m
Delta
Deal found 5/25![Delta logo]()
$259
This Southwest deal was found by Cheapflights users on 5/24. 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.
Thu 7/168:30 pm
HOU
- MDW
1 stop4h 35m
Southwest
Mon 7/209:40 pm
MDW
- HOU
Nonstop2h 35m
Southwest
Deal found 5/24![Southwest logo]()
$289
This Delta deal was found by Cheapflights users on 5/22. 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 6/2510:09 am
HOU
- ORD
1 stop6h 55m
Delta
Tue 6/305:30 am
ORD
- HOU
1 stop6h 42m
Delta
Deal found 5/22![Delta logo]()
$276
This Delta deal was found by Cheapflights users on 5/24. 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.
Wed 7/110:09 am
HOU
- ORD
2 stops10h 22m
Delta
Tue 7/79:45 am
ORD
- HOU
1 stop6h 37m
Delta
Deal found 5/24![Delta logo]()
$279
This Southwest deal was found by Cheapflights users on 5/24. 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.
Fri 8/2811:30 am
HOU
- MDW
2 stops5h 25m
Southwest
Sun 8/307:15 am
MDW
- HOU
1 stop5h 00m
Southwest
Deal found 5/24![Southwest logo]()
$338
This Delta deal was found by Cheapflights users on 5/22. 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.
Wed 7/296:00 am
HOU
- ORD
2 stops13h 30m
Delta
Mon 8/35:28 am
ORD
- HOU
1 stop6h 48m
Delta
Deal found 5/22![Delta logo]()
$294
This Southwest deal was found by Cheapflights users on 5/26. 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.
Mon 7/66:25 am
HOU
- MDW
Nonstop2h 25m
Southwest
Thu 7/97:15 pm
MDW
- HOU
Nonstop2h 35m
Southwest
Deal found 5/26![Southwest logo]()
$369
This Southwest deal was found by Cheapflights users on 5/24. 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.
Thu 8/2711:30 am
HOU
- MDW
2 stops5h 25m
Southwest
Sun 8/307:15 am
MDW
- HOU
1 stop5h 00m
Southwest
Deal found 5/24![Southwest logo]()
$372
This Delta deal was found by Cheapflights users on 5/26. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/256:00 am
HOU
- ORD
2 stops11h 26m
Delta
Tue 7/289:45 am
ORD
- HOU
1 stop6h 37m
Delta
Deal found 5/26![Delta logo]()
$313
This Southwest deal was found by Cheapflights users on 5/27. Clicking the “Pick Dates” 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 7/233:00 pm
HOU
- MDW
1 stop4h 35m
Southwest
Sun 7/265:40 pm
MDW
- HOU
1 stop4h 05m
Southwest
Deal found 5/27![Southwest logo]()
$383
This Delta deal was found by Cheapflights users on 5/22. 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 8/46:00 am
HOU
- ORD
2 stops8h 57m
Delta
Tue 8/1112:29 pm
ORD
- HOU
2 stops10h 17m
Delta
Deal found 5/22![Delta logo]()
$318
This Southwest deal was found by Cheapflights users on 5/22. 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 6/215:10 am
HOU
- MDW
Nonstop2h 25m
Southwest
Sun 6/285:00 am
MDW
- HOU
1 stop5h 35m
Southwest
Deal found 5/22![Southwest logo]()
$384
This Delta deal was found by Cheapflights users on 5/24. 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.
Wed 7/15:08 pm
HOU
- MDW
1 stop5h 09m
Delta
Sat 7/49:17 am
MDW
- HOU
2 stops7h 07m
Delta
Deal found 5/24![Delta logo]()
$324
This Southwest deal was found by Cheapflights users on 5/27. Clicking the “Pick Dates” 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 6/145:35 am
HOU
- MDW
1 stop5h 55m
Southwest
Tue 6/163:55 pm
MDW
- HOU
1 stop4h 50m
Southwest
Deal found 5/27![Southwest logo]()
$391
This Delta deal was found by Cheapflights users on 5/26. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/75:20 pm
HOU
- MDW
1 stop5h 16m
Delta
Sun 8/96:05 am
MDW
- HOU
1 stop6h 11m
Delta
Deal found 5/26![Delta logo]()
$337
This Delta deal was found by Cheapflights users on 5/24. 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.
Fri 8/2810:50 am
HOU
- ORD
1 stop7h 59m
Delta
Sun 8/306:40 am
ORD
- HOU
1 stop5h 36m
Delta
Deal found 5/24![Delta logo]()
$337
This Delta deal was found by Cheapflights users on 5/25. 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 9/116:00 am
HOU
- ORD
2 stops10h 48m
Delta
Sun 9/137:10 am
ORD
- HOU
1 stop4h 54m
Delta
Deal found 5/25![Delta logo]()
$342
This Delta deal was found by Cheapflights users on 5/23. 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 6/236:03 am
HOU
- ORD
1 stop14h 29m
Delta
Fri 6/266:35 am
ORD
- HOU
1 stop5h 37m
Delta
Deal found 5/23![Delta logo]()
$347
Last-minute flights from Hobby to ChicagoDiscover last-minute flight deals from Hobby to Chicago. Data last updated May 27, 2026 and is based on user searches.
Discover last-minute flight deals from Hobby to Chicago. Data last updated May 27, 2026 and is based on user searches.
This Southwest deal was found by Cheapflights users on 5/26. 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 5/294:25 pm
HOU
- MDW
1 stop4h 00m
Southwest
Tue 6/307:10 am
MDW
- HOU
Nonstop2h 35m
Southwest
Deal found 5/26![Southwest logo]()
$232
This Delta deal was found by Cheapflights users on 5/26. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/1610:09 am
HOU
- ORD
1 stop6h 55m
Delta
Tue 6/307:01 am
ORD
- HOU
2 stops9h 22m
Delta
Deal found 5/26![Delta logo]()
$202
This Southwest deal was found by Cheapflights users on 5/25. 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.
Tue 6/165:00 pm
HOU
- MDW
1 stop5h 00m
Southwest
Tue 7/79:30 am
MDW
- HOU
1 stop4h 15m
Southwest
Deal found 5/25![Southwest logo]()
$209
This Delta deal was found by Cheapflights users on 5/25. 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 6/166:03 am
HOU
- ORD
1 stop6h 33m
Delta
Tue 7/79:45 am
ORD
- HOU
1 stop6h 37m
Delta
Deal found 5/25![Delta logo]()
$244
This Southwest deal was found by Cheapflights users on 5/25. 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.
Sat 6/208:45 pm
HOU
- MDW
Nonstop2h 25m
Southwest
Wed 6/241:10 pm
MDW
- HOU
Nonstop2h 35m
Southwest
Deal found 5/25![Southwest logo]()
$226
This Southwest deal was found by Cheapflights users on 5/25. 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.
Sat 6/208:45 pm
HOU
- MDW
Nonstop2h 25m
Southwest
Tue 6/236:30 am
MDW
- HOU
1 stop5h 45m
Southwest
Deal found 5/25![Southwest logo]()
$236
This Southwest deal was found by Cheapflights users on 5/26. 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.
Tue 6/2310:25 am
HOU
- MDW
1 stop5h 30m
Southwest
Wed 6/241:10 pm
MDW
- HOU
Nonstop2h 35m
Southwest
Deal found 5/26![Southwest logo]()
$181
This Southwest deal was found by Cheapflights users on 5/26. 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.
Tue 6/236:00 pm
HOU
- MDW
1 stop4h 00m
Southwest
Tue 6/309:10 am
MDW
- HOU
1 stop4h 40m
Southwest
Deal found 5/26![Southwest logo]()
$186
This Southwest deal was found by Cheapflights users on 5/26. 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.
Tue 6/2310:25 am
HOU
- MDW
1 stop5h 30m
Southwest
Tue 6/239:00 pm
MDW
- HOU
Nonstop2h 35m
Southwest
Deal found 5/26![Southwest logo]()
$221
This Southwest deal was found by Cheapflights users on 5/26. 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.
Sat 6/278:45 pm
HOU
- MDW
Nonstop2h 25m
Southwest
Wed 7/17:10 am
MDW
- HOU
Nonstop2h 35m
Southwest
Deal found 5/26![Southwest logo]()
$225
This Delta deal was found by Cheapflights users on 5/26. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/275:12 pm
HOU
- ORD
1 stop6h 52m
Delta
Wed 7/15:30 am
ORD
- HOU
1 stop6h 42m
Delta
Deal found 5/26![Delta logo]()
$248
This Delta deal was found by Cheapflights users on 5/25. 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.
Mon 6/296:03 am
HOU
- ORD
1 stop8h 13m
Delta
Tue 6/307:01 am
ORD
- HOU
2 stops9h 22m
Delta
Deal found 5/25![Delta logo]()
$253
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 May 27, 2026.
Search for one-way flight options from Hobby to Chicago. Find affordable one-way fares based on user searches. Data last updated May 27, 2026.
This Southwest deal was found by Cheapflights users on 5/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/89:25 pm
HOU
- MDW
Nonstop2h 30m
Southwest
Deal found 5/27![Southwest logo]()
$86
This Southwest deal was found by Cheapflights users on 5/25. 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.
Tue 8/411:25 am
HOU
- MDW
1 stop4h 05m
Southwest
Deal found 5/25![Southwest logo]()
$91
This Southwest deal was found by Cheapflights users on 5/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/236:00 pm
HOU
- MDW
1 stop4h 00m
Southwest
Deal found 5/27![Southwest logo]()
$96
This Delta deal was found by Cheapflights users on 5/26. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/1910:50 am
HOU
- MDW
1 stop5h 25m
Delta
Deal found 5/26![Delta logo]()
$99
This Delta deal was found by Cheapflights users on 5/27. Clicking the “Pick Dates” 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 7/812:55 pm
HOU
- ORD
1 stop5h 50m
Delta
Deal found 5/27![Delta logo]()
$99
This Southwest deal was found by Cheapflights users on 5/26. 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.
Mon 8/105:45 pm
HOU
- MDW
Nonstop2h 25m
Southwest
Deal found 5/26![Southwest logo]()
$102
This Delta deal was found by Cheapflights users on 5/26. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/146:00 am
HOU
- ORD
2 stops9h 05m
Delta
Deal found 5/26![Delta logo]()
$104
This Delta deal was found by Cheapflights users on 5/22. 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 7/216:00 am
HOU
- MDW
1 stop5h 56m
Delta
Deal found 5/22![Delta logo]()
$105
This Delta deal was found by Cheapflights users on 5/25. 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 8/111:13 pm
HOU
- ORD
1 stop7h 37m
Delta
Deal found 5/25![Delta logo]()
$105
This Southwest deal was found by Cheapflights users on 5/26. 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.
Sat 8/1510:25 am
HOU
- MDW
1 stop3h 50m
Southwest
Deal found 5/26![Southwest logo]()
$107
This Delta deal was found by Cheapflights users on 5/24. 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.
Tue 7/146:00 am
HOU
- MDW
2 stops12h 18m
Delta
Deal found 5/24![Delta logo]()
$110
This Delta deal was found by Cheapflights users on 5/27. Clicking the “Pick Dates” 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 8/245:20 pm
HOU
- MDW
1 stop5h 16m
Delta
Deal found 5/27![Delta logo]()
$112
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 May 27, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $171 (Southwest) |
One-way from | $86 (Southwest) |
Popular in | May |
Cheapest in | January |
Average price | $284 |
Good round-trip deal | $298 or less |
Good one-way deal | $171 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 2,558,603 searches. Data last updated May 27, 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 - ORD
HOUORD
Houston Hobby
Wed 9/16
11:00 am-9:33 pm
2 stops10h 33m
Chicago O'Hare Intl
Thu 9/24
12:40 pm-10:35 pm
2 stops9h 55m
$220
HoustonChicago
HOU - ORD
HOUORD
Houston Hobby
Wed 7/8
12:55 pm-6:45 pm
1 stop5h 50m
Chicago O'Hare Intl
Tue 7/14
9:45 am-4:22 pm
1 stop6h 37m
$238
HoustonChicago
HOU - MDW
HOUMDW
Houston Hobby
Sat 7/18
2:10 pm-7:35 pm
1 stop5h 25m
Chicago Midway
Tue 7/21
9:00 pm-11:40 pm
Nonstop2h 40m
$240
HoustonChicago
HOU - ORD
HOUORD
Houston Hobby
Fri 7/3
5:08 pm-11:59 pm
1 stop6h 51m
Chicago O'Hare Intl
Tue 7/7
9:45 am-4:23 pm
1 stop6h 38m
$255
HoustonChicago
HOU - ORD
HOUORD
Houston Hobby
Tue 8/25
6:00 am-4:24 pm
2 stops10h 24m
Chicago O'Hare Intl
Mon 9/7
5:28 am-12:16 pm
1 stop6h 48m
$259
HoustonChicago
HOU - ORD
HOUORD
Houston Hobby
Thu 6/25
10:09 am-5:04 pm
1 stop6h 55m
Chicago O'Hare Intl
Tue 6/30
5:30 am-12:12 pm
1 stop6h 42m
$276
HoustonChicago
HOU - ORD
HOUORD
Houston Hobby
Wed 7/1
10:09 am-8:31 pm
2 stops10h 22m
Chicago O'Hare Intl
Tue 7/7
9:45 am-4:22 pm
1 stop6h 37m
$279
HoustonChicago
HOU - MDW
HOUMDW
Houston Hobby
Thu 8/20
2:40 pm-7:45 pm
1 stop5h 05m
Chicago Midway
Sun 8/23
6:05 am-12:10 pm
1 stop6h 05m
$289
HoustonChicago
HOU - MDW
HOUMDW
Houston Hobby
Thu 7/16
8:30 pm-1:05 am
1 stop4h 35m
Chicago Midway
Mon 7/20
9:40 pm-12:15 am
Nonstop2h 35m
$289
HoustonChicago
HOU - ORD
HOUORD
Houston Hobby
Wed 7/29
6:00 am-7:30 pm
2 stops13h 30m
Chicago O'Hare Intl
Mon 8/3
5:28 am-12:16 pm
1 stop6h 48m
$294
Showing 1-10 of 53 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 May.
| 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 Accuracy2 stars | Trust Score*1 star | |
| Price Accuracy- | Trust Score*1 star | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy- | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| 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
HOU-RFD
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
HOU-RFD
What is the cheapest month to book a flight from Houston Hobby Airport to Chicago?
Currently, February is the cheapest month in which you can book a flight from Houston Hobby Airport to Chicago (average of $29). Flying from Houston Hobby Airport to Chicago in November is currently the most expensive (average of $601). 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 May 27, 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 39% 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?
How often are flights from Houston to Chicago delayed?
About 20% of weekly flights between Houston and Chicago have experienced delays in the past year, with the average delay time being 116 minutes.
What is the most punctual flight time for Houston to Chicago flights?
Historically, flights departing in the morning are less likely to be delayed, whereas flights leaving in the early afternoon tend to experience delays more often.
What day of the week experiences the fewest flight delays on this route?
Saturday tends to have the lowest number of delays on this route, whereas Sunday has historically faced a higher average of delays compared to other days of the week.
Which airline has the best punctuality record on Houston to Chicago flights?
Over the last year, Southwest have had the lowest number of delays on this route, with just 20% 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 May 23, 2026.
Travelers seeking maximum savings on their Houston Hobby Airport to Chicago flight should consider departing on Sunday 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 May 27, 2026.
Peruse reviews from past customers who have flown with Southwest,United Airlines, andAmerican Airlines 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.
Entertainment
7.5
Crew
8.6
Food
7.0
Overall
7.9
Comfort
8.0
Boarding
8.1
Reviews
1 / 20
6.0
GoodScott,Feb 2026
HOU - FLL
Entertainment
7.5
Crew
8.6
Food
7.0
Overall
7.9
Comfort
8.0
Boarding
8.1
Reviews
1 / 20
6.0
GoodScott,Feb 2026
HOU - FLL
Entertainment
7.5
Crew
8.6
Food
7.0
Overall
7.9
Comfort
8.0
Boarding
8.1
Reviews
1 / 20
6.0
GoodScott,Feb 2026
HOU - FLL
Entertainment
7.5
Crew
8.6
Food
7.0
Overall
7.9
Comfort
8.0
Boarding
8.1
Reviews
1 / 20
6.0
GoodScott,Feb 2026
HOU - FLL
Spirit Airlines
Entertainment
7.5
Crew
8.6
Food
7.0
Overall
7.9
Comfort
8.0
Boarding
8.1
Reviews
1 / 20
6.0
GoodScott,Feb 2026
HOU - FLL
Entertainment
7.5
Crew
8.6
Food
7.0
Overall
7.9
Comfort
8.0
Boarding
8.1
Reviews
1 / 20
6.0
GoodScott,Feb 2026
HOU - FLL
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.
Traveling to a place near Chicago?
Book flights to Chicago if you plan to visit one of these locationsBenton Harbor
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Other flights to Chicago
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Hobby and Chicago flights
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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 2,558,603 searches. Data last updated May 27, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$60 | Average$190 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$71 | Average$157 | FlexibilityNo cancel fee | On-time65% | |
| Cheapest$157 | Average$337 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$167 | Average$323 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$177 | Average$258 | FlexibilityNo cancel fee | On-time71% |