$90+ 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 8/31. Fares are subject to change and may not be available on all flights or dates of travel.
HOU — CHI
Aug 25 — Sep 11
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 85 days in advance, depart on a Saturday or Wednesday and return on a Wednesday
Cheap flight deals from Houston to Chicago
Cheapest
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 July 26, 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 July 26, 2026.
This Frontier deal was found by Cheapflights users on 7/22. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/138:02 pm
IAH
- ORD
1 stop12h 00m
Frontier
Tue 8/188:45 am
ORD
- IAH
Nonstop3h 11m
Frontier
Deal found 7/22![Frontier logo]()
$171
This Frontier deal was found by Cheapflights users on 7/22. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/2710:14 pm
IAH
- ORD
1 stop15h 22m
Frontier
Mon 8/315:46 pm
ORD
- IAH
Nonstop3h 17m
Frontier
Deal found 7/22![Frontier logo]()
$172
This Southwest deal was found by Cheapflights users on 7/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/186:50 am
HOU
- MDW
Nonstop2h 25m
Southwest
Tue 8/255:15 pm
MDW
- HOU
Nonstop2h 30m
Southwest
Deal found 7/21![Southwest logo]()
$173
This Frontier deal was found by Cheapflights users on 7/23. 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 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
Fri 8/215:46 pm
ORD
- IAH
Nonstop3h 17m
Frontier
Deal found 7/23![Frontier logo]()
$173
This American Airlines deal was found by Cheapflights users on 7/21. 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 8/134:40 pm
IAH
- ORD
Nonstop3h 04m
American Airlines
Mon 8/178:00 am
ORD
- IAH
Nonstop2h 44m
American Airlines
Deal found 7/21![American Airlines logo]()
$174
This Frontier deal was found by Cheapflights users on 7/23. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/89:42 pm
IAH
- ORD
Nonstop2h 51m
Frontier
Sat 8/228:45 am
ORD
- IAH
Nonstop3h 11m
Frontier
Deal found 7/23![Frontier logo]()
$175
This Frontier deal was found by Cheapflights users on 7/22. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/209:58 pm
IAH
- ORD
Nonstop2h 51m
Frontier
Sat 8/291:59 pm
ORD
- IAH
1 stop8h 15m
Frontier
Deal found 7/22![Frontier logo]()
$176
This Kiwi.com deal was found by Cheapflights users on 7/23. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/109:42 pm
IAH
- ORD
Nonstop2h 51m
Frontier
Tue 8/252:41 pm
ORD
- IAH
1 stop9h 59m
Frontier
Deal found 7/23![Frontier logo]()
$177
This Kiwi.com deal was found by Cheapflights users on 7/23. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/109:42 pm
IAH
- ORD
Nonstop2h 51m
Frontier
Sat 8/222:41 pm
ORD
- IAH
1 stop9h 59m
Frontier
Deal found 7/23![Frontier logo]()
$178
This Super.com deal was found by Cheapflights users on 7/24. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/119:42 pm
IAH
- ORD
Nonstop2h 51m
Frontier
Thu 8/205:46 pm
ORD
- IAH
Nonstop3h 17m
Frontier
Deal found 7/24![Frontier logo]()
$179
This Frontier deal was found by Cheapflights users on 7/23. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/89:42 pm
IAH
- ORD
Nonstop2h 51m
Frontier
Tue 8/258:45 am
ORD
- IAH
Nonstop3h 11m
Frontier
Deal found 7/23![Frontier logo]()
$180
This Frontier deal was found by Cheapflights users on 7/22. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/2011:32 am
IAH
- ORD
1 stop8h 27m
Frontier
Tue 8/258:45 am
ORD
- IAH
Nonstop3h 11m
Frontier
Deal found 7/22![Frontier logo]()
$181
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 July 26, 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 July 26, 2026.
This Southwest deal was found by Cheapflights users on 7/22. 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 8/177:55 pm
HOU
- MDW
Nonstop2h 20m
Southwest
Wed 8/2610:30 am
MDW
- HOU
Nonstop2h 30m
Southwest
Deal found 7/22![Southwest logo]()
$183
This Delta deal was found by Cheapflights users on 7/23. 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 8/225:20 pm
HOU
- ORD
1 stop6h 37m
Delta
Tue 8/251:50 pm
ORD
- HOU
1 stop8h 15m
Delta
Deal found 7/23![Delta logo]()
$203
This Kiwi.com deal was found by Cheapflights users on 7/24. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/108:25 pm
IAH
- RFD
1 stop12h 27m
Multiple Airlines
Sun 9/139:29 pm
RFD
- IAH
1 stop17h 21m
Multiple Airlines
Deal found 7/24![Multiple Airlines logo]()
$239
This Southwest deal was found by Cheapflights users on 7/21. 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 10/225:00 am
HOU
- MDW
Nonstop2h 25m
Southwest
Sat 10/242:20 pm
MDW
- HOU
2 stops6h 35m
Southwest
Deal found 7/21![Southwest logo]()
$188
This Delta deal was found by Cheapflights users on 7/22. 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 9/222:44 pm
IAH
- ORD
1 stop6h 12m
Delta
Tue 9/295:30 am
ORD
- IAH
1 stop8h 00m
Delta
Deal found 7/22![Delta logo]()
$207
This Southwest deal was found by Cheapflights users on 7/22. 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 8/275:00 am
HOU
- MDW
Nonstop2h 25m
Southwest
Mon 8/311:05 pm
MDW
- HOU
1 stop5h 20m
Southwest
Deal found 7/22![Southwest logo]()
$189
This Delta deal was found by Cheapflights users on 7/22. 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.
Mon 8/175:20 am
IAH
- MDW
1 stop7h 19m
Delta
Thu 8/2012:46 pm
MDW
- IAH
1 stop7h 08m
Delta
Deal found 7/22![Delta logo]()
$207
This Southwest deal was found by Cheapflights users on 7/24. 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 9/88:30 am
HOU
- MDW
1 stop5h 00m
Southwest
Sat 9/121:45 pm
MDW
- HOU
Nonstop2h 30m
Southwest
Deal found 7/24![Southwest logo]()
$193
This Delta deal was found by Cheapflights users on 7/22. 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 10/16:10 am
IAH
- MDW
1 stop7h 10m
Delta
Mon 10/56:05 am
MDW
- IAH
1 stop7h 25m
Delta
Deal found 7/22![Delta logo]()
$207
This Southwest deal was found by Cheapflights users on 7/24. 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.
Mon 9/211:45 pm
HOU
- MDW
2 stops5h 35m
Southwest
Mon 9/287:25 am
MDW
- HOU
Nonstop2h 30m
Southwest
Deal found 7/24![Southwest logo]()
$198
This Delta deal was found by Cheapflights users on 7/21. 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 10/225:28 pm
HOU
- ORD
1 stop6h 23m
Delta
Sat 10/245:39 pm
ORD
- HOU
1 stop5h 30m
Delta
Deal found 7/21![Delta logo]()
$207
This Kiwi.com deal was found by Cheapflights users on 7/25. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/108:25 pm
IAH
- RFD
1 stop12h 27m
Multiple Airlines
Mon 9/148:44 pm
RFD
- IAH
1 stop17h 13m
Multiple Airlines
Deal found 7/25![Multiple Airlines logo]()
$279
This Southwest deal was found by Cheapflights users on 7/23. 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.
Tue 8/1811:20 am
HOU
- MDW
1 stop4h 40m
Southwest
Tue 8/2510:10 am
MDW
- HOU
1 stop3h 50m
Southwest
Deal found 7/23![Southwest logo]()
$198
This Delta deal was found by Cheapflights users on 7/23. 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 8/205:20 pm
HOU
- ORD
1 stop6h 37m
Delta
Sat 8/2211:22 am
ORD
- HOU
2 stops10h 01m
Delta
Deal found 7/23![Delta logo]()
$208
This Southwest deal was found by Cheapflights users on 7/23. 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 9/115:00 am
HOU
- MDW
Nonstop2h 25m
Southwest
Tue 9/1510:30 am
MDW
- HOU
Nonstop2h 30m
Southwest
Deal found 7/23![Southwest logo]()
$201
This Delta deal was found by Cheapflights users on 7/23. 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 10/132:59 pm
HOU
- ORD
1 stop6h 01m
Delta
Sat 10/172:00 pm
ORD
- HOU
2 stops9h 09m
Delta
Deal found 7/23![Delta logo]()
$208
This Delta deal was found by Cheapflights users on 7/21. 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 10/225:28 pm
HOU
- MDW
1 stop4h 57m
Delta
Sat 10/241:28 pm
MDW
- HOU
2 stops9h 41m
Delta
Deal found 7/21![Delta logo]()
$212
This Southwest deal was found by Cheapflights users on 7/25. 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 9/51:20 pm
HOU
- MDW
1 stop5h 55m
Southwest
Tue 9/88:25 pm
MDW
- HOU
Nonstop2h 30m
Southwest
Deal found 7/25![Southwest logo]()
$219
This Delta deal was found by Cheapflights users on 7/21. 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 8/135:20 am
IAH
- ORD
1 stop5h 22m
Delta
Thu 8/201:44 pm
ORD
- IAH
2 stops10h 08m
Delta
Deal found 7/21![Delta logo]()
$212
This Kiwi.com deal was found by Cheapflights users on 7/24. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/276:30 am
IAH
- RFD
2 stops14h 15m
Multiple Airlines
Sun 8/309:35 pm
RFD
- IAH
1 stop15h 23m
Multiple Airlines
Deal found 7/24![Multiple Airlines logo]()
$409
This Delta deal was found by Cheapflights users on 7/22. 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 9/125:40 am
IAH
- MDW
2 stops11h 17m
Delta
Mon 9/149:24 am
MDW
- IAH
1 stop5h 00m
Delta
Deal found 7/22![Delta logo]()
$212
This Delta deal was found by Cheapflights users on 7/22. 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.
Mon 8/175:20 am
IAH
- MDW
1 stop7h 19m
Delta
Wed 8/269:24 am
MDW
- IAH
2 stops8h 16m
Delta
Deal found 7/22![Delta logo]()
$212
This Southwest deal was found by Cheapflights users on 7/23. 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.
Thu 9/36:05 am
HOU
- MDW
1 stop4h 00m
Southwest
Tue 9/88:25 pm
MDW
- HOU
Nonstop2h 30m
Southwest
Deal found 7/23![Southwest logo]()
$269
This Delta deal was found by Cheapflights users on 7/24. 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 9/2110:44 am
IAH
- MDW
1 stop7h 35m
Delta
Mon 9/286:05 am
MDW
- IAH
1 stop7h 25m
Delta
Deal found 7/24![Delta logo]()
$213
This Kiwi.com deal was found by Cheapflights users on 7/25. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/910:09 pm
IAH
- RFD
2 stops22h 30m
Multiple Airlines
Sun 9/139:29 pm
RFD
- IAH
1 stop8h 33m
Multiple Airlines
Deal found 7/25![Multiple Airlines logo]()
$458
This Delta deal was found by Cheapflights users on 7/24. 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 9/811:01 am
HOU
- ORD
1 stop7h 40m
Delta
Sat 9/125:00 pm
ORD
- HOU
1 stop5h 39m
Delta
Deal found 7/24![Delta logo]()
$213
This Kiwi.com deal was found by Cheapflights users on 7/23. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/206:10 am
IAH
- RFD
2 stops14h 35m
Multiple Airlines
Sun 8/239:35 pm
RFD
- IAH
1 stop15h 23m
Multiple Airlines
Deal found 7/23![Multiple Airlines logo]()
$486
This Delta deal was found by Cheapflights users on 7/23. 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 8/225:20 am
IAH
- ORD
2 stops11h 31m
Delta
Sat 8/296:59 am
ORD
- IAH
2 stops8h 56m
Delta
Deal found 7/23![Delta logo]()
$214
This Delta deal was found by Cheapflights users on 7/22. 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 8/2511:28 am
IAH
- ORD
2 stops9h 27m
Delta
Mon 8/311:59 pm
ORD
- IAH
2 stops8h 41m
Delta
Deal found 7/22![Delta logo]()
$217
This Delta deal was found by Cheapflights users on 7/24. 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.
Thu 8/206:36 pm
IAH
- ORD
1 stop5h 21m
Delta
Sat 8/222:30 pm
ORD
- IAH
2 stops9h 22m
Delta
Deal found 7/24![Delta logo]()
$218
Last-minute flights from Houston to ChicagoDiscover last-minute flight deals from Houston to Chicago. Data last updated July 26, 2026 and is based on user searches.
Discover last-minute flight deals from Houston to Chicago. Data last updated July 26, 2026 and is based on user searches.
This Frontier deal was found by Cheapflights users on 7/23. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/89:42 pm
IAH
- ORD
Nonstop2h 51m
Frontier
Sat 8/228:45 am
ORD
- IAH
Nonstop3h 11m
Frontier
Deal found 7/23![Frontier logo]()
$175
This Frontier deal was found by Cheapflights users on 7/23. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/89:42 pm
IAH
- ORD
Nonstop2h 51m
Frontier
Tue 8/258:45 am
ORD
- IAH
Nonstop3h 11m
Frontier
Deal found 7/23![Frontier logo]()
$180
This Kiwi.com deal was found by Cheapflights users on 7/23. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/109:42 pm
IAH
- ORD
Nonstop2h 51m
Frontier
Tue 8/252:41 pm
ORD
- IAH
1 stop9h 59m
Frontier
Deal found 7/23![Frontier logo]()
$177
This Kiwi.com deal was found by Cheapflights users on 7/23. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/109:42 pm
IAH
- ORD
Nonstop2h 51m
Frontier
Sat 8/222:41 pm
ORD
- IAH
1 stop9h 59m
Frontier
Deal found 7/23![Frontier logo]()
$178
This Super.com deal was found by Cheapflights users on 7/24. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/119:42 pm
IAH
- ORD
Nonstop2h 51m
Frontier
Thu 8/205:46 pm
ORD
- IAH
Nonstop3h 17m
Frontier
Deal found 7/24![Frontier logo]()
$179
This Frontier deal was found by Cheapflights users on 7/22. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/138:02 pm
IAH
- ORD
1 stop12h 00m
Frontier
Tue 8/188:45 am
ORD
- IAH
Nonstop3h 11m
Frontier
Deal found 7/22![Frontier logo]()
$171
This Frontier deal was found by Cheapflights users on 7/23. 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 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
Fri 8/215:46 pm
ORD
- IAH
Nonstop3h 17m
Frontier
Deal found 7/23![Frontier logo]()
$173
This American Airlines deal was found by Cheapflights users on 7/21. 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 8/134:40 pm
IAH
- ORD
Nonstop3h 04m
American Airlines
Mon 8/178:00 am
ORD
- IAH
Nonstop2h 44m
American Airlines
Deal found 7/21![American Airlines logo]()
$174
This Southwest deal was found by Cheapflights users on 7/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/186:50 am
HOU
- MDW
Nonstop2h 25m
Southwest
Tue 8/255:15 pm
MDW
- HOU
Nonstop2h 30m
Southwest
Deal found 7/21![Southwest logo]()
$173
This Frontier deal was found by Cheapflights users on 7/22. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/209:58 pm
IAH
- ORD
Nonstop2h 51m
Frontier
Sat 8/291:59 pm
ORD
- IAH
1 stop8h 15m
Frontier
Deal found 7/22![Frontier logo]()
$176
This Frontier deal was found by Cheapflights users on 7/22. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/2011:32 am
IAH
- ORD
1 stop8h 27m
Frontier
Tue 8/258:45 am
ORD
- IAH
Nonstop3h 11m
Frontier
Deal found 7/22![Frontier logo]()
$181
This Frontier deal was found by Cheapflights users on 7/22. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/2710:14 pm
IAH
- ORD
1 stop15h 22m
Frontier
Mon 8/315:46 pm
ORD
- IAH
Nonstop3h 17m
Frontier
Deal found 7/22![Frontier logo]()
$172
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 July 26, 2026.
Search for one-way flight options from Houston to Chicago. Find affordable one-way fares based on user searches. Data last updated July 26, 2026.
This Kiwi.com deal was found by Cheapflights users on 7/25. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/318:35 am
IAH
- ORD
1 stop28h 15m
Frontier
Deal found 7/25![Frontier logo]()
$90
This Kiwi.com deal was found by Cheapflights users on 7/25. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/248:35 am
IAH
- ORD
1 stop28h 15m
Frontier
Deal found 7/25![Frontier logo]()
$91
This Kiwi.com deal was found by Cheapflights users on 7/25. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/277:00 am
IAH
- MDW
1 stop14h 53m
Frontier
Deal found 7/25![Frontier logo]()
$91
This Southwest deal was found by Cheapflights users on 7/22. 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 9/236:50 am
HOU
- MDW
Nonstop2h 25m
Southwest
Deal found 7/22![Southwest logo]()
$92
This Frontier deal was found by Cheapflights users on 7/22. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/246:42 pm
IAH
- ORD
Nonstop2h 52m
Frontier
Deal found 7/22![Frontier logo]()
$92
This Super.com deal was found by Cheapflights users on 7/22. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/206:42 pm
IAH
- ORD
Nonstop2h 52m
Frontier
Deal found 7/22![Frontier logo]()
$93
This Southwest deal was found by Cheapflights users on 7/22. 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 8/2511:25 am
HOU
- MDW
1 stop4h 05m
Southwest
Deal found 7/22![Southwest logo]()
$97
This Super.com deal was found by Cheapflights users on 7/23. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/149:42 pm
IAH
- ORD
Nonstop2h 51m
Frontier
Deal found 7/23![Frontier logo]()
$98
This Kiwi.com deal was found by Cheapflights users on 7/22. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/226:50 am
IAH
- ORD
1 stop27h 11m
Frontier
Deal found 7/22![Frontier logo]()
$100
This Kiwi.com deal was found by Cheapflights users on 7/22. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/2010:15 pm
IAH
- ORD
1 stop11h 46m
Frontier
Deal found 7/22![Frontier logo]()
$101
This Kiwi.com deal was found by Cheapflights users on 7/22. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/158:16 am
IAH
- RFD
1 stop26h 31m
Multiple Airlines
Deal found 7/22![Multiple Airlines logo]()
$101
This Delta deal was found by Cheapflights users on 7/23. 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 8/176:36 pm
IAH
- ORD
1 stop5h 21m
Delta
Deal found 7/23![Delta logo]()
$102
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 July 26, 2026.
Round-trip from | $171 (Frontier) |
|---|---|
One-way from | $90 (Kiwi.com) |
Popular in | July |
Cheapest in | January |
Average price | $302 |
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 July 26, 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
Quickest round-trip
HoustonChicago
HOU - MDW
HOUMDW
Houston Hobby
Mon 8/17
7:55 pm-10:15 pm
Nonstop2h 20m
Chicago Midway
Wed 8/26
10:30 am-1:00 pm
Nonstop2h 30m
$183
HoustonChicago
HOU - MDW
HOUMDW
Houston Hobby
Thu 10/22
5:00 am-7:25 am
Nonstop2h 25m
Chicago Midway
Sat 10/24
2:20 pm-8:55 pm
2 stops6h 35m
$188
HoustonChicago
HOU - MDW
HOUMDW
Houston Hobby
Thu 8/27
5:00 am-7:25 am
Nonstop2h 25m
Chicago Midway
Mon 8/31
1:05 pm-6:25 pm
1 stop5h 20m
$189
HoustonChicago
HOU - MDW
HOUMDW
Houston Hobby
Tue 9/8
8:30 am-1:30 pm
1 stop5h 00m
Chicago Midway
Sat 9/12
1:45 pm-4:15 pm
Nonstop2h 30m
$193
HoustonChicago
HOU - MDW
HOUMDW
Houston Hobby
Mon 9/21
1:45 pm-7:20 pm
2 stops5h 35m
Chicago Midway
Mon 9/28
7:25 am-9:55 am
Nonstop2h 30m
$198
HoustonChicago
HOU - MDW
HOUMDW
Houston Hobby
Tue 8/18
11:20 am-4:00 pm
1 stop4h 40m
Chicago Midway
Tue 8/25
10:10 am-2:00 pm
1 stop3h 50m
$198
HoustonChicago
HOU - MDW
HOUMDW
Houston Hobby
Fri 9/11
5:00 am-7:25 am
Nonstop2h 25m
Chicago Midway
Tue 9/15
10:30 am-1:00 pm
Nonstop2h 30m
$201
HoustonChicago
HOU - ORD
HOUORD
Houston Hobby
Sat 8/22
5:20 pm-11:57 pm
1 stop6h 37m
Chicago O'Hare Intl
Tue 8/25
1:50 pm-10:05 pm
1 stop8h 15m
$203
HoustonChicago
IAH - ORD
IAHORD
Houston George Bush Intcntl
Tue 9/22
2:44 pm-8:56 pm
1 stop6h 12m
Chicago O'Hare Intl
Tue 9/29
5:30 am-1:30 pm
1 stop8h 00m
$207
HoustonChicago
IAH - MDW
IAHMDW
Houston George Bush Intcntl
Mon 8/17
5:20 am-12:39 pm
1 stop7h 19m
Chicago Midway
Thu 8/20
12:46 pm-7:54 pm
1 stop7h 08m
$207
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, October is the cheapest month in which you can book a flight from Houston to Chicago (average of $197). Flying from Houston to Chicago in June is currently the most expensive (average of $346). 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 July 26, 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 46% on your trip compared to booking a flight at noon.
How much does it cost to fly round-trip from Houston to Chicago?
Airfare is below average for this route at the moment.
Houston to Chicago flights typically cost between $194 and $346 in August.The cheapest round-trip price found within the last 5 days was $171 on Frontier (Aug 13-Aug 18).
How often are flights from Houston to Chicago delayed?
About 16% of weekly flights between Houston and Chicago have experienced delays in the past year, with the average delay time being 142 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 9% 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. Monday at noon 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 July 26, 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.
Crew
8.6
Entertainment
7.5
Comfort
8.0
Food
7.0
Boarding
8.1
Overall
8.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Crew
8.6
Entertainment
7.5
Comfort
8.0
Food
7.0
Boarding
8.1
Overall
8.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Crew
8.6
Entertainment
7.5
Comfort
8.0
Food
7.0
Boarding
8.1
Overall
8.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Crew
8.6
Entertainment
7.5
Comfort
8.0
Food
7.0
Boarding
8.1
Overall
8.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Crew
8.6
Entertainment
7.5
Comfort
8.0
Food
7.0
Boarding
8.1
Overall
8.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Crew
8.6
Entertainment
7.5
Comfort
8.0
Food
7.0
Boarding
8.1
Overall
8.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
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
Valparaiso
Hammond
Saint Joseph
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.
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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 July 26, 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 July 26, 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 July 26, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$61 | Average$182 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$158 | Average$398 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$176 | Average$397 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$181 | Average$375 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$216 | Average$328 | 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.