$77+ Cheap flights from Houston 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 9/14. Fares are subject to change and may not be available on all flights or dates of travel.
HOU — CHI
Jul 11 — Jul 181
Round-trip
1 adult, Economy
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Find cheap flights from Houston 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 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 Houston to Chicago
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Best
Last-minute
One-way
Cheapest flights from Houston to ChicagoExplore the most affordable flight options available from Houston to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on June 11, 2026.
Explore the most affordable flight options available from Houston to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on June 11, 2026.
This Frontier deal was found by Cheapflights users on 6/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/59:42 pm
IAH
- ORD
Nonstop2h 51m
Frontier
Sat 8/85:30 pm
ORD
- IAH
Nonstop3h 17m
Frontier
Deal found 6/6![Frontier logo]()
$131
This Kiwi.com deal was found by Cheapflights users on 6/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/159:42 pm
IAH
- ORD
Nonstop2h 51m
Frontier
Tue 8/185:29 pm
ORD
- IAH
Nonstop3h 28m
Frontier
Deal found 6/9![Frontier logo]()
$135
This Frontier deal was found by Cheapflights users on 6/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/289:52 pm
IAH
- ORD
Nonstop2h 50m
Frontier
Wed 9/25:29 pm
ORD
- IAH
Nonstop3h 28m
Frontier
Deal found 6/8![Frontier logo]()
$136
This Frontier deal was found by Cheapflights users on 6/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/146:42 pm
IAH
- ORD
Nonstop2h 52m
Frontier
Wed 9/162:46 pm
ORD
- IAH
Nonstop3h 01m
Frontier
Deal found 6/5![Frontier logo]()
$137
This Kiwi.com deal was found by Cheapflights users on 6/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/79:58 pm
IAH
- ORD
Nonstop2h 51m
Frontier
Sat 8/85:30 pm
ORD
- IAH
Nonstop3h 17m
Frontier
Deal found 6/5![Frontier logo]()
$138
This Kiwi.com deal was found by Cheapflights users on 6/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/279:52 pm
IAH
- ORD
Nonstop2h 50m
Frontier
Tue 9/15:29 pm
ORD
- IAH
Nonstop3h 28m
Frontier
Deal found 6/6![Frontier logo]()
$139
This Kiwi.com deal was found by Cheapflights users on 6/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/1212:16 pm
IAH
- ORD
1 stop7h 37m
Frontier
Tue 8/185:29 pm
ORD
- IAH
Nonstop3h 28m
Frontier
Deal found 6/9![Frontier logo]()
$140
This Frontier deal was found by Cheapflights users on 6/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/29:52 pm
IAH
- ORD
Nonstop2h 50m
Frontier
Sun 9/65:29 pm
ORD
- IAH
Nonstop3h 28m
Frontier
Deal found 6/9![Frontier logo]()
$141
This Kiwi.com deal was found by Cheapflights users on 6/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/269:52 pm
IAH
- ORD
Nonstop2h 50m
Frontier
Thu 9/35:29 pm
ORD
- IAH
Nonstop3h 28m
Frontier
Deal found 6/6![Frontier logo]()
$142
This Frontier deal was found by Cheapflights users on 6/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/139:42 pm
IAH
- ORD
Nonstop2h 51m
Frontier
Sat 8/155:30 pm
ORD
- IAH
Nonstop3h 17m
Frontier
Deal found 6/10![Frontier logo]()
$143
This Frontier deal was found by Cheapflights users on 6/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/289:58 pm
IAH
- ORD
Nonstop2h 51m
Frontier
Wed 8/55:30 pm
ORD
- IAH
Nonstop3h 17m
Frontier
Deal found 6/8![Frontier logo]()
$144
This Kiwi.com deal was found by Cheapflights users on 6/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/512:16 pm
IAH
- ORD
1 stop7h 37m
Frontier
Tue 8/115:30 pm
ORD
- IAH
Nonstop3h 17m
Frontier
Deal found 6/9![Frontier logo]()
$145
Best flights from Houston to ChicagoDiscover carefully curated flight deals from Houston to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated June 11, 2026.
Discover carefully curated flight deals from Houston to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated June 11, 2026.
This Delta deal was found by Cheapflights users on 6/8. Clicking the “Pick Dates” 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 8/47:00 am
IAH
- MDW
1 stop4h 51m
Delta
Tue 8/119:59 am
MDW
- IAH
1 stop7h 41m
Delta
Deal found 6/8![Delta logo]()
$199
This Southwest deal was found by Cheapflights users on 6/9. Clicking the “Pick Dates” 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
Mon 8/101:05 pm
MDW
- HOU
1 stop5h 20m
Southwest
Deal found 6/9![Southwest logo]()
$209
This United Airlines deal was found by Cheapflights users on 6/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/78:25 pm
IAH
- ORD
Nonstop2h 50m
United Airlines
Tue 7/149:40 pm
ORD
- IAH
Nonstop2h 54m
United Airlines
Deal found 6/9![United Airlines logo]()
$209
This Expedia deal was found by Cheapflights users on 6/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/1710:53 am
IAH
- MDW
1 stop11h 10m
Frontier
Mon 8/2412:04 pm
MDW
- IAH
1 stop10h 44m
Frontier
Deal found 6/10![Frontier logo]()
$264
This Kiwi.com deal was found by Cheapflights users on 6/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/118:20 am
IAH
- RFD
1 stop26h 17m
Multiple Airlines
Sun 7/1911:27 am
RFD
- IAH
2 stops43h 53m
Multiple Airlines
Deal found 6/8![Multiple Airlines logo]()
$271
This Delta deal was found by Cheapflights users on 6/9. Clicking the “Pick Dates” 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 8/410:50 am
HOU
- ORD
1 stop7h 59m
Delta
Tue 8/116:40 am
ORD
- HOU
1 stop5h 36m
Delta
Deal found 6/9![Delta logo]()
$199
This Delta deal was found by Cheapflights users on 6/10. Clicking the “Pick Dates” 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 8/2611:28 am
IAH
- ORD
2 stops9h 27m
Delta
Tue 9/11:59 pm
ORD
- IAH
2 stops8h 41m
Delta
Deal found 6/10![Delta logo]()
$210
This Southwest deal was found by Cheapflights users on 6/9. Clicking the “Pick Dates” 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 stop6h 40m
Southwest
Sat 8/221:20 pm
MDW
- HOU
1 stop5h 45m
Southwest
Deal found 6/9![Southwest logo]()
$237
This Delta deal was found by Cheapflights users on 6/10. Clicking the “Pick Dates” 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 9/293:20 pm
IAH
- ORD
1 stop5h 02m
Delta
Thu 10/13:42 pm
ORD
- IAH
1 stop5h 33m
Delta
Deal found 6/10![Delta logo]()
$218
This Southwest deal was found by Cheapflights users on 6/10. Clicking the “Pick Dates” 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 7/82:35 pm
HOU
- MDW
Nonstop2h 25m
Southwest
Wed 7/159:00 pm
MDW
- HOU
Nonstop2h 40m
Southwest
Deal found 6/10![Southwest logo]()
$244
This KAYAK deal was found by Cheapflights users on 6/8. Clicking the “Pick Dates” 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.
Sun 6/214:15 pm
HOU
- ORD
1 stop7h 17m
American Airlines
Wed 6/241:25 pm
ORD
- HOU
1 stop6h 26m
American Airlines
Deal found 6/8![American Airlines logo]()
$542
This Kiwi.com deal was found by Cheapflights users on 6/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/912:16 pm
IAH
- MDW
1 stop9h 47m
Frontier
Wed 8/1912:04 pm
MDW
- IAH
1 stop10h 44m
Frontier
Deal found 6/10![Frontier logo]()
$276
This United Airlines deal was found by Cheapflights users on 6/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/286:40 pm
IAH
- ORD
Nonstop2h 52m
United Airlines
Mon 8/316:29 pm
ORD
- IAH
Nonstop2h 51m
United Airlines
Deal found 6/8![United Airlines logo]()
$289
This Delta deal was found by Cheapflights users on 6/9. Clicking the “Pick Dates” 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 10/58:05 am
IAH
- ORD
2 stops11h 23m
Delta
Wed 10/77:05 am
ORD
- IAH
1 stop7h 39m
Delta
Deal found 6/9![Delta logo]()
$223
This Southwest deal was found by Cheapflights users on 6/9. Clicking the “Pick Dates” 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 7/159:25 pm
HOU
- MDW
Nonstop2h 30m
Southwest
Sat 7/188:25 pm
MDW
- HOU
Nonstop2h 40m
Southwest
Deal found 6/9![Southwest logo]()
$254
This Delta deal was found by Cheapflights users on 6/9. Clicking the “Pick Dates” 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 8/205:41 am
IAH
- ORD
2 stops12h 48m
Delta
Tue 8/257:00 am
ORD
- IAH
2 stops10h 40m
Delta
Deal found 6/9![Delta logo]()
$228
This Expedia deal was found by Cheapflights users on 6/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/2710:52 am
IAH
- MDW
1 stop11h 19m
Frontier
Tue 6/3012:27 pm
MDW
- IAH
1 stop10h 21m
Frontier
Deal found 6/10![Frontier logo]()
$310
This Kiwi.com deal was found by Cheapflights users on 6/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/118:20 am
IAH
- RFD
1 stop26h 17m
Multiple Airlines
Fri 7/177:50 pm
RFD
- IAH
1 stop12h 55m
Multiple Airlines
Deal found 6/10![Multiple Airlines logo]()
$364
This Southwest deal was found by Cheapflights users on 6/9. Clicking the “Pick Dates” 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 8/29:20 pm
HOU
- MDW
Nonstop2h 30m
Southwest
Thu 8/65:55 am
MDW
- HOU
Nonstop2h 30m
Southwest
Deal found 6/9![Southwest logo]()
$276
This Expedia deal was found by Cheapflights users on 6/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/2310:53 am
IAH
- MDW
1 stop11h 10m
Frontier
Mon 7/2712:11 pm
MDW
- IAH
1 stop10h 28m
Frontier
Deal found 6/10![Frontier logo]()
$318
This Delta deal was found by Cheapflights users on 6/9. Clicking the “Pick Dates” 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 9/25:09 pm
IAH
- MDW
1 stop5h 27m
Delta
Sun 9/66:05 am
MDW
- IAH
1 stop7h 22m
Delta
Deal found 6/9![Delta logo]()
$250
This Kiwi.com deal was found by Cheapflights users on 6/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/3010:09 pm
IAH
- RFD
2 stops22h 14m
Multiple Airlines
Mon 8/39:13 pm
RFD
- IAH
1 stop16h 46m
Multiple Airlines
Deal found 6/10![Multiple Airlines logo]()
$386
This Southwest deal was found by Cheapflights users on 6/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/42:35 pm
HOU
- MDW
2 stops5h 35m
Southwest
Wed 8/1210:10 am
MDW
- HOU
1 stop3h 50m
Southwest
Deal found 6/6![Southwest logo]()
$300
This Delta deal was found by Cheapflights users on 6/8. Clicking the “Pick Dates” 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 7/48:05 am
IAH
- MDW
1 stop7h 35m
Delta
Wed 7/81:49 pm
MDW
- IAH
2 stops8h 35m
Delta
Deal found 6/8![Delta logo]()
$270
This Southwest deal was found by Cheapflights users on 6/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/76:00 pm
HOU
- MDW
1 stop4h 00m
Southwest
Tue 7/143:10 pm
MDW
- HOU
2 stops5h 30m
Southwest
Deal found 6/7![Southwest logo]()
$300
This Kiwi.com deal was found by Cheapflights users on 6/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/2310:09 pm
IAH
- RFD
2 stops22h 14m
Multiple Airlines
Mon 7/277:50 pm
RFD
- IAH
1 stop22h 35m
Multiple Airlines
Deal found 6/6![Multiple Airlines logo]()
$424
This Southwest deal was found by Cheapflights users on 6/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/43:05 pm
HOU
- MDW
1 stop4h 45m
Southwest
Sun 9/67:50 am
MDW
- HOU
Nonstop2h 35m
Southwest
Deal found 6/5![Southwest logo]()
$300
This Delta deal was found by Cheapflights users on 6/10. Clicking the “Pick Dates” 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 8/54:37 pm
IAH
- MDW
1 stop5h 59m
Delta
Sun 8/96:05 am
MDW
- IAH
1 stop7h 26m
Delta
Deal found 6/10![Delta logo]()
$277
This Southwest deal was found by Cheapflights users on 6/8. Clicking the “Pick Dates” 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 8/2011:30 am
HOU
- MDW
2 stops5h 25m
Southwest
Mon 8/241:05 pm
MDW
- HOU
1 stop5h 20m
Southwest
Deal found 6/8![Southwest logo]()
$300
This Delta deal was found by Cheapflights users on 6/10. Clicking the “Pick Dates” 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 8/96:00 am
HOU
- ORD
1 stop6h 40m
Delta
Wed 8/193:25 pm
ORD
- HOU
1 stop6h 40m
Delta
Deal found 6/10![Delta logo]()
$277
Last-minute flights from Houston to ChicagoDiscover last-minute flight deals from Houston to Chicago. Data last updated June 11, 2026 and is based on user searches.
Discover last-minute flight deals from Houston to Chicago. Data last updated June 11, 2026 and is based on user searches.
This Kiwi.com deal was found by Cheapflights users on 6/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/159:58 pm
IAH
- ORD
Nonstop2h 50m
Frontier
Tue 7/75:46 pm
ORD
- IAH
Nonstop3h 17m
Frontier
Deal found 6/10![Frontier logo]()
$193
This deal was found by Cheapflights users on 6/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/159:58 pm
IAH
- ORD
Nonstop2h 50m
Frontier
Sat 7/255:46 pm
ORD
- IAH
Nonstop3h 17m
Frontier
Deal found 6/8![Frontier logo]()
$203
This deal was found by Cheapflights users on 6/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/169:58 pm
IAH
- ORD
Nonstop2h 50m
Frontier
Sat 7/255:46 pm
ORD
- IAH
Nonstop3h 17m
Frontier
Deal found 6/8![Frontier logo]()
$158
This Super.com deal was found by Cheapflights users on 6/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/169:58 pm
IAH
- ORD
Nonstop2h 50m
Frontier
Tue 7/75:46 pm
ORD
- IAH
Nonstop3h 17m
Frontier
Deal found 6/10![Frontier logo]()
$174
This Kiwi.com deal was found by Cheapflights users on 6/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/169:58 pm
IAH
- ORD
Nonstop2h 50m
Frontier
Tue 7/141:50 pm
ORD
- IAH
1 stop17h 30m
Frontier
Deal found 6/10![Frontier logo]()
$204
This Frontier deal was found by Cheapflights users on 6/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/169:58 pm
IAH
- ORD
Nonstop2h 50m
Frontier
Tue 6/235:29 pm
ORD
- IAH
Nonstop3h 23m
Frontier
Deal found 6/10![Frontier logo]()
$208
This deal was found by Cheapflights users on 6/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/199:58 pm
IAH
- ORD
Nonstop2h 50m
Frontier
Sat 7/255:46 pm
ORD
- IAH
Nonstop3h 17m
Frontier
Deal found 6/8![Frontier logo]()
$197
This Frontier deal was found by Cheapflights users on 6/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/209:58 pm
IAH
- ORD
Nonstop2h 50m
Frontier
Sat 6/275:29 pm
ORD
- IAH
Nonstop3h 23m
Frontier
Deal found 6/8![Frontier logo]()
$155
This Frontier deal was found by Cheapflights users on 6/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/209:58 pm
IAH
- ORD
Nonstop2h 50m
Frontier
Tue 6/235:29 pm
ORD
- IAH
Nonstop3h 23m
Frontier
Deal found 6/8![Frontier logo]()
$209
This Southwest deal was found by Cheapflights users on 6/10. Clicking the “Pick Dates” 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 7/76:20 pm
HOU
- MDW
Nonstop2h 25m
Southwest
Tue 7/149:00 pm
MDW
- HOU
Nonstop2h 40m
Southwest
Deal found 6/10![Southwest logo]()
$209
This Kiwi.com deal was found by Cheapflights users on 6/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/86:00 am
IAH
- MDW
1 stop16h 03m
Frontier
Wed 7/1512:11 pm
MDW
- IAH
1 stop10h 28m
Frontier
Deal found 6/10![Frontier logo]()
$203
This Southwest deal was found by Cheapflights users on 6/9. Clicking the “Pick Dates” 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 7/282:35 pm
HOU
- MDW
Nonstop2h 25m
Southwest
Tue 8/44:40 pm
MDW
- HOU
1 stop6h 05m
Southwest
Deal found 6/9![Southwest logo]()
$204
One-way flights from Houston to ChicagoSearch for one-way flight options from Houston to Chicago. Find affordable one-way fares based on user searches. Data last updated June 11, 2026.
Search for one-way flight options from Houston to Chicago. Find affordable one-way fares based on user searches. Data last updated June 11, 2026.
This Frontier deal was found by Cheapflights users on 6/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/146:42 pm
IAH
- ORD
Nonstop2h 52m
Frontier
Deal found 6/5![Frontier logo]()
$77
This Super.com deal was found by Cheapflights users on 6/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/259:58 pm
IAH
- ORD
Nonstop2h 51m
Frontier
Deal found 6/10![Frontier logo]()
$79
This Super.com deal was found by Cheapflights users on 6/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/79:42 pm
IAH
- ORD
Nonstop2h 51m
Frontier
Deal found 6/10![Frontier logo]()
$83
This Kiwi.com deal was found by Cheapflights users on 6/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/69:42 pm
IAH
- ORD
Nonstop2h 51m
Frontier
Deal found 6/8![Frontier logo]()
$84
This Frontier deal was found by Cheapflights users on 6/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/79:52 pm
IAH
- ORD
Nonstop2h 50m
Frontier
Deal found 6/9![Frontier logo]()
$85
This Super.com deal was found by Cheapflights users on 6/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/299:58 pm
IAH
- ORD
Nonstop2h 50m
Frontier
Deal found 6/6![Frontier logo]()
$88
This Southwest deal was found by Cheapflights users on 6/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/48:50 pm
HOU
- MDW
Nonstop2h 20m
Southwest
Deal found 6/7![Southwest logo]()
$90
This United Airlines deal was found by Cheapflights users on 6/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/126:15 am
IAH
- ORD
Nonstop2h 54m
United Airlines
Deal found 6/10![United Airlines logo]()
$90
This Kiwi.com deal was found by Cheapflights users on 6/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/196:30 am
IAH
- ORD
1 stop14h 23m
Frontier
Deal found 6/10![Frontier logo]()
$93
This Super.com deal was found by Cheapflights users on 6/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/99:58 pm
IAH
- ORD
Nonstop2h 51m
Frontier
Deal found 6/9![Frontier logo]()
$94
This Kiwi.com deal was found by Cheapflights users on 6/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/1212:16 pm
IAH
- MDW
1 stop9h 47m
Frontier
Deal found 6/9![Frontier logo]()
$94
This Super.com deal was found by Cheapflights users on 6/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/309:58 pm
IAH
- ORD
Nonstop2h 50m
Frontier
Deal found 6/10![Frontier logo]()
$95
Find flight deals from Houston to Chicago
Discover tips and strategies to find the most affordable flight options for your journey from Houston (HO1) 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 June 11, 2026.
Round-trip from | $131 (Frontier) |
|---|---|
One-way from | $77 (Frontier) |
Popular in | May |
Cheapest in | January |
Average price | $279 |
Cheapflights Fare Finder
Customize your flight search to find flights from Houston 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 June 11, 2026.
Use the filters below to find and compare flights from Houston to Chicago that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
HoustonChicago
IAH - MDW
IAHMDW
Houston George Bush Intcntl
Tue 8/4
7:00 am-11:51 am
1 stop4h 51m
Chicago Midway
Tue 8/11
9:59 am-5:40 pm
1 stop7h 41m
$199
HoustonChicago
HOU - ORD
HOUORD
Houston Hobby
Tue 8/4
10:50 am-6:49 pm
1 stop7h 59m
Chicago O'Hare Intl
Tue 8/11
6:40 am-12:16 pm
1 stop5h 36m
$199
HoustonChicago
HOU - MDW
HOUMDW
Houston Hobby
Tue 8/4
11:25 am-3:30 pm
1 stop4h 05m
Chicago Midway
Mon 8/10
1:05 pm-6:25 pm
1 stop5h 20m
$209
HoustonChicago
IAH - ORD
IAHORD
Houston George Bush Intcntl
Tue 7/7
8:25 pm-11:15 pm
Nonstop2h 50m
Chicago O'Hare Intl
Tue 7/14
9:40 pm-12:34 am
Nonstop2h 54m
$209
HoustonChicago
IAH - ORD
IAHORD
Houston George Bush Intcntl
Wed 8/26
11:28 am-8:55 pm
2 stops9h 27m
Chicago O'Hare Intl
Tue 9/1
1:59 pm-10:40 pm
2 stops8h 41m
$210
HoustonChicago
IAH - ORD
IAHORD
Houston George Bush Intcntl
Tue 9/29
3:20 pm-8:22 pm
1 stop5h 02m
Chicago O'Hare Intl
Thu 10/1
3:42 pm-9:15 pm
1 stop5h 33m
$218
HoustonChicago
IAH - ORD
IAHORD
Houston George Bush Intcntl
Mon 10/5
8:05 am-7:28 pm
2 stops11h 23m
Chicago O'Hare Intl
Wed 10/7
7:05 am-2:44 pm
1 stop7h 39m
$223
HoustonChicago
IAH - ORD
IAHORD
Houston George Bush Intcntl
Thu 8/20
5:41 am-6:29 pm
2 stops12h 48m
Chicago O'Hare Intl
Tue 8/25
7:00 am-5:40 pm
2 stops10h 40m
$228
HoustonChicago
HOU - MDW
HOUMDW
Houston Hobby
Sat 8/15
10:25 am-5:05 pm
1 stop6h 40m
Chicago Midway
Sat 8/22
1:20 pm-7:05 pm
1 stop5h 45m
$237
HoustonChicago
HOU - MDW
HOUMDW
Houston Hobby
Wed 7/8
2:35 pm-5:00 pm
Nonstop2h 25m
Chicago Midway
Wed 7/15
9:00 pm-11:40 pm
Nonstop2h 40m
$244
Showing 1-10 of 60 resultsSorted by cheapest first
Best time to book a flight from Houston to Chicago
Have a flexible travel schedule? Discover the best time to fly to Chicago from Houston with our price prediction graph.
HO1-CHI
IAH-ORD
IAH-MDW
HOU-MDW
IAH-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 to Chicago
HO1-CHI
IAH-ORD
IAH-MDW
HOU-MDW
IAH-RFD
What is the cheapest month to book a flight from Houston to Chicago?
Currently, September is the cheapest month in which you can book a flight from Houston to Chicago (average of $174). Flying from Houston to Chicago in January is currently the most expensive (average of $738). 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 Houston 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 June 11, 2026.
A simple way to save on the total cost of your ticket is to fly from Houston to Chicago in the evening. If you’re flexible enough to do this you can expect to save up to 50% on your trip compared to booking a flight at noon.
How much does it cost to fly round-trip from Houston to Chicago?
How often are flights from Houston to Chicago delayed?
About 15% of weekly flights between Houston and Chicago have experienced delays in the past year, with the average delay time being 144 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 evening tend to experience delays more often.
What day of the week experiences the fewest flight delays on this route?
Wednesday 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, United Airlines have had the lowest number of delays on this route, with just 10% of flights being delayed.
How far ahead should I book a flight from Houston to Chicago?
To ensure you get the cheapest price possible for a flight from Houston to Chicago, you should look to book at least 78 days in advance of your intended travel date. The price of your flight may increase if you delay and leave booking until a week or so before departure.
What is the cheapest day to fly from Houston to Chicago?
Use this chart to determine the cheapest time to fly round-trip from Houston to Chicago. Price data was last updated on August 31, 2025.
Travelers seeking maximum savings on their Houston to Chicago flight should consider departing on Wednesday afternoons when fares are most often at their lowest. Sunday afternoons flights should be avoided if possible as fares are typically the most expensive at this time.
The best insider tips for Houston 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 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 June 11, 2026.
Get a feel of what it's like to fly with Southwest,Delta, andUnited Airlines from Houston to Chicago by reading reviews from past customers. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Comfort
8.0
Overall
7.9
Boarding
8.1
Entertainment
7.5
Food
7.0
Crew
8.6
Reviews
1 / 20
6.0
GoodScott,Feb 2026
HOU - FLL
Comfort
8.0
Overall
7.9
Boarding
8.1
Entertainment
7.5
Food
7.0
Crew
8.6
Reviews
1 / 20
6.0
GoodScott,Feb 2026
HOU - FLL
Comfort
8.0
Overall
7.9
Boarding
8.1
Entertainment
7.5
Food
7.0
Crew
8.6
Reviews
1 / 20
6.0
GoodScott,Feb 2026
HOU - FLL
Comfort
8.0
Overall
7.9
Boarding
8.1
Entertainment
7.5
Food
7.0
Crew
8.6
Reviews
1 / 20
6.0
GoodScott,Feb 2026
HOU - FLL
Comfort
8.0
Overall
7.9
Boarding
8.1
Entertainment
7.5
Food
7.0
Crew
8.6
Reviews
1 / 20
6.0
GoodScott,Feb 2026
HOU - FLL
Comfort
8.0
Overall
7.9
Boarding
8.1
Entertainment
7.5
Food
7.0
Crew
8.6
Reviews
1 / 20
6.0
GoodScott,Feb 2026
HOU - FLL
Houston to Chicago Travel Guide
You can land at Chicago O’Hare that’s on the northwest side of the city. It’s 14 miles from the busy Loop business sector. This is Chicago’s busiest airport. It serves flights that go to Europe, Africa, Asia, and North and South America. It’s the sixth busiest airport in the world.
Your other option is to land at Chicago Midway. This was once the city’s main airport until O’Hare came on the scene. The airport is still quite busy, serving more than 22 million passengers in 2018. The majority of the traffic coming through this airport is provided by Southwest Airlines.
Southwest has some other options between Hobby and Midway. They make stops in St. Louis, New Orleans, Orlando, Dallas, Oklahoma City, Nashville, Jacksonville, Austin, and a few others. Most of their stopovers are under an hour.
Related info for your journey
Find useful and relevant information for your journey from Houston 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
Lansing
Merrillville
Hammond
Porter
Browse thousands of different options on Cheapflights for your next trip
Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.
Alternative routes
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Alternative routes for Houston to Chicago
See prices for flight routes from nearby airports that may be better suited for you.
Other flights to Chicago
Explore flights to Chicago departing from other origins. Flights are based on user searches made on Cheapflights and were last updated on June 11, 2026.
Complete your trip
Complete your trip to Chicago by adding a car rental and/or hotel reservation to your travel itinerary.
Search flights from Houston to Chicago by cabin class
Find flights from Houston to Chicago, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Houston and Chicago flights
Browse other Houston and Chicago flight options. Last updated on June 11, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Top 5 airlines flying from Houston to Chicago
Discover the top 5 airlines that operate flights from Houston 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 June 11, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$58 | Average$179 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$157 | Average$379 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$167 | Average$346 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$172 | Average$390 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$216 | Average$349 | FlexibilityNo cancel fee | On-timeN/A |
Helpful tips for your next trip to Chicago
Get useful tips and recommendations to enhance your travel experience on your next trip to Chicago. Learn about must-visit attractions, local customs, transportation options, weather conditions, and other valuable tips to make your trip more enjoyable and hassle-free.
- Passengers traveling from Houston to Chicago through George Bush International Airport (IAH) can get to the airport using a town car, taxi, or drive. However, the most sustainable means is by boarding a bus. Line 102 bus is located at Milan St. and Mc Kinney St.
- Travelers moving from Houston to Chicago can use airports like Houston Southwest Airport, West Houston Airport, or William P. Hobby Airport. However, George Bush International Airport (IAH) has been vocal about its sustainability commitment. The airport seeks to achieve trash-free travel.
- When traveling to Chicago from Houston, consider booking economy class flights since they don't spend much fuel, producing less carbon. Economy class flights are available at IAH.