$57+ 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 7/21. Fares are subject to change and may not be available on all flights or dates of travel.
HOU — CHI
May 22 — May 291
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 63 days in advance, depart on a Wednesday or Saturday 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 April 22, 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 April 22, 2026.
This Frontier deal was found by Cheapflights users on 4/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/308:12 pm
IAH
- ORD
Nonstop2h 49m
Frontier
Thu 6/44:05 pm
ORD
- IAH
Nonstop3h 12m
Frontier
Deal found 4/17![Frontier logo]()
$111
This Cheapflightsfares deal was found by Cheapflights users on 4/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/117:15 am
IAH
- ORD
Nonstop2h 39m
Spirit Airlines
Wed 5/134:06 pm
ORD
- IAH
Nonstop2h 54m
Spirit Airlines
Deal found 4/20![Spirit Airlines logo]()
$112
This Super.com deal was found by Cheapflights users on 4/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/208:12 pm
IAH
- ORD
Nonstop2h 49m
Frontier
Fri 5/224:05 pm
ORD
- IAH
Nonstop3h 12m
Frontier
Deal found 4/17![Frontier logo]()
$113
This Priceline deal was found by Cheapflights users on 4/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/58:12 pm
IAH
- ORD
Nonstop2h 49m
Multiple Airlines
Sat 5/94:50 pm
ORD
- IAH
Nonstop2h 54m
Multiple Airlines
Deal found 4/20![Multiple Airlines logo]()
$114
This Frontier deal was found by Cheapflights users on 4/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/138:50 pm
IAH
- ORD
1 stop11h 05m
Frontier
Wed 5/204:05 pm
ORD
- IAH
Nonstop3h 12m
Frontier
Deal found 4/19![Frontier logo]()
$115
This Cheapflightsfares deal was found by Cheapflights users on 4/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/67:15 am
IAH
- ORD
Nonstop2h 39m
Spirit Airlines
Tue 5/124:06 pm
ORD
- IAH
Nonstop2h 54m
Spirit Airlines
Deal found 4/19![Spirit Airlines logo]()
$116
This Frontier deal was found by Cheapflights users on 4/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/98:12 pm
IAH
- ORD
Nonstop2h 49m
Frontier
Fri 5/157:30 am
ORD
- IAH
1 stop12h 25m
Frontier
Deal found 4/19![Frontier logo]()
$117
This Expedia deal was found by Cheapflights users on 4/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/68:50 pm
IAH
- ORD
1 stop11h 05m
Frontier
Wed 5/204:05 pm
ORD
- IAH
Nonstop3h 12m
Frontier
Deal found 4/17![Frontier logo]()
$118
This Frontier deal was found by Cheapflights users on 4/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/58:12 pm
IAH
- ORD
Nonstop2h 49m
Frontier
Mon 6/84:05 pm
ORD
- IAH
Nonstop3h 12m
Frontier
Deal found 4/20![Frontier logo]()
$119
This Kiwi.com deal was found by Cheapflights users on 4/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/117:15 am
IAH
- ORD
Nonstop2h 39m
Multiple Airlines
Fri 5/158:30 am
ORD
- IAH
Nonstop3h 20m
Multiple Airlines
Deal found 4/18![Multiple Airlines logo]()
$120
This Super.com deal was found by Cheapflights users on 4/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/2212:27 pm
IAH
- ORD
Nonstop2h 50m
Frontier
Tue 5/54:05 pm
ORD
- IAH
Nonstop3h 12m
Frontier
Deal found 4/17![Frontier logo]()
$121
This Frontier deal was found by Cheapflights users on 4/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/38:12 pm
IAH
- ORD
Nonstop2h 49m
Frontier
Mon 6/84:05 pm
ORD
- IAH
Nonstop3h 12m
Frontier
Deal found 4/17![Frontier logo]()
$122
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 April 22, 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 April 22, 2026.
This Spirit deal was found by Cheapflights users on 4/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Spirit is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/177:15 am
IAH
- ORD
Nonstop2h 39m
Spirit Airlines
Sun 5/247:33 pm
ORD
- IAH
1 stop13h 30m
Spirit Airlines
Deal found 4/18![Spirit Airlines logo]()
$187
This Delta deal was found by Cheapflights users on 4/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/2011:34 am
IAH
- ORD
1 stop6h 31m
Delta
Wed 5/277:07 am
ORD
- IAH
1 stop6h 07m
Delta
Deal found 4/17![Delta logo]()
$197
This Southwest deal was found by Cheapflights users on 4/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/208:40 pm
HOU
- MDW
Nonstop2h 25m
Southwest
Wed 5/278:40 pm
MDW
- HOU
Nonstop2h 40m
Southwest
Deal found 4/21![Southwest logo]()
$199
This United Airlines deal was found by Cheapflights users on 4/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/28:25 pm
IAH
- ORD
Nonstop2h 49m
United Airlines
Thu 6/49:21 pm
ORD
- IAH
Nonstop2h 54m
United Airlines
Deal found 4/17![United Airlines logo]()
$260
This Delta deal was found by Cheapflights users on 4/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/195:55 am
IAH
- ORD
1 stop7h 52m
Delta
Wed 5/272:59 pm
ORD
- IAH
1 stop6h 26m
Delta
Deal found 4/17![Delta logo]()
$197
This Kiwi.com deal was found by Cheapflights users on 4/22. 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.
Thu 7/3010:08 pm
IAH
- RFD
2 stops22h 15m
Multiple Airlines
Mon 8/37:50 pm
RFD
- IAH
1 stop12h 57m
Multiple Airlines
Deal found 4/22![Multiple Airlines logo]()
$398
This Delta deal was found by Cheapflights users on 4/22. 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 5/116:35 pm
IAH
- ORD
1 stop5h 24m
Delta
Wed 5/139:25 am
ORD
- IAH
1 stop5h 05m
Delta
Deal found 4/22![Delta logo]()
$217
This Southwest deal was found by Cheapflights users on 4/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/98:10 am
HOU
- MDW
1 stop4h 00m
Southwest
Wed 5/138:40 pm
MDW
- HOU
Nonstop2h 40m
Southwest
Deal found 4/21![Southwest logo]()
$254
This Delta deal was found by Cheapflights users on 4/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/99:44 am
IAH
- ORD
1 stop7h 12m
Delta
Sat 5/167:00 am
ORD
- IAH
1 stop7h 30m
Delta
Deal found 4/18![Delta logo]()
$219
This United Airlines deal was found by Cheapflights users on 4/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/42:37 pm
IAH
- ORD
Nonstop2h 56m
United Airlines
Sat 7/48:03 pm
ORD
- IAH
Nonstop2h 56m
United Airlines
Deal found 4/17![United Airlines logo]()
$276
This Southwest deal was found by Cheapflights users on 4/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/206:00 am
HOU
- ORD
2 stops6h 50m
Southwest
Wed 5/2710:30 am
ORD
- HOU
2 stops11h 40m
Southwest
Deal found 4/21![Southwest logo]()
$257
This Delta deal was found by Cheapflights users on 4/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/245:20 am
IAH
- MDW
1 stop7h 16m
Delta
Mon 6/295:41 pm
MDW
- IAH
1 stop6h 18m
Delta
Deal found 4/17![Delta logo]()
$248
This Southwest deal was found by Cheapflights users on 4/21. 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.
Mon 6/110:25 am
HOU
- MDW
1 stop5h 25m
Southwest
Fri 6/55:00 am
MDW
- HOU
Nonstop2h 35m
Southwest
Deal found 4/21![Southwest logo]()
$276
This Delta deal was found by Cheapflights users on 4/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/255:20 am
IAH
- ORD
1 stop7h 29m
Delta
Sat 4/255:04 pm
ORD
- IAH
1 stop5h 50m
Delta
Deal found 4/20![Delta logo]()
$251
This Southwest deal was found by Cheapflights users on 4/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/68:40 pm
HOU
- MDW
Nonstop2h 25m
Southwest
Wed 5/138:40 pm
MDW
- HOU
Nonstop2h 40m
Southwest
Deal found 4/17![Southwest logo]()
$287
This Southwest deal was found by Cheapflights users on 4/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/26:10 pm
HOU
- MDW
Nonstop2h 25m
Southwest
Tue 6/93:10 pm
MDW
- HOU
2 stops5h 30m
Southwest
Deal found 4/18![Southwest logo]()
$290
This Delta deal was found by Cheapflights users on 4/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/910:27 am
HOU
- ORD
1 stop8h 14m
Delta
Wed 5/137:07 am
ORD
- HOU
1 stop5h 04m
Delta
Deal found 4/21![Delta logo]()
$268
This Kiwi.com deal was found by Cheapflights users on 4/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/226:00 am
IAH
- RFD
1 stop13h 13m
Multiple Airlines
Mon 5/258:03 pm
RFD
- IAH
1 stop12h 47m
Multiple Airlines
Deal found 4/20![Multiple Airlines logo]()
$436
This Kiwi.com deal was found by Cheapflights users on 4/21. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/1911:54 am
IAH
- RFD
1 stop24h 20m
Multiple Airlines
Mon 6/227:53 pm
RFD
- IAH
1 stop22h 36m
Multiple Airlines
Deal found 4/21![Multiple Airlines logo]()
$439
This Southwest deal was found by Cheapflights users on 4/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/295:05 am
HOU
- MDW
Nonstop2h 25m
Southwest
Mon 6/19:40 pm
MDW
- HOU
Nonstop2h 40m
Southwest
Deal found 4/18![Southwest logo]()
$308
This Delta deal was found by Cheapflights users on 4/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/225:20 am
IAH
- ORD
1 stop7h 41m
Delta
Tue 5/266:06 pm
ORD
- IAH
1 stop5h 48m
Delta
Deal found 4/21![Delta logo]()
$289
This Southwest deal was found by Cheapflights users on 4/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/125:40 pm
HOU
- MDW
1 stop4h 15m
Southwest
Sun 6/149:40 pm
MDW
- HOU
Nonstop2h 30m
Southwest
Deal found 4/21![Southwest logo]()
$317
This Delta deal was found by Cheapflights users on 4/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/175:20 am
IAH
- MDW
1 stop7h 22m
Delta
Sun 5/246:23 am
MDW
- IAH
1 stop6h 51m
Delta
Deal found 4/18![Delta logo]()
$289
This Delta deal was found by Cheapflights users on 4/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/25:23 pm
HOU
- MDW
1 stop5h 05m
Delta
Tue 5/510:41 am
MDW
- HOU
1 stop5h 47m
Delta
Deal found 4/19![Delta logo]()
$294
This Southwest deal was found by Cheapflights users on 4/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/73:20 pm
HOU
- MDW
Nonstop2h 25m
Southwest
Mon 5/119:25 am
MDW
- HOU
1 stop4h 55m
Southwest
Deal found 4/19![Southwest logo]()
$324
This Delta deal was found by Cheapflights users on 4/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/25:20 am
IAH
- ORD
1 stop4h 59m
Delta
Tue 5/511:19 am
ORD
- IAH
1 stop6h 32m
Delta
Deal found 4/19![Delta logo]()
$294
This Southwest deal was found by Cheapflights users on 4/21. 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 5/214:25 pm
HOU
- MDW
1 stop4h 00m
Southwest
Thu 5/289:40 pm
MDW
- HOU
Nonstop2h 40m
Southwest
Deal found 4/21![Southwest logo]()
$342
This Delta deal was found by Cheapflights users on 4/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 7/66:37 pm
IAH
- ORD
1 stop5h 22m
Delta
Mon 7/208:03 am
ORD
- IAH
1 stop5h 30m
Delta
Deal found 4/20![Delta logo]()
$299
This Southwest deal was found by Cheapflights users on 4/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/263:50 pm
HOU
- MDW
1 stop4h 50m
Southwest
Sun 6/287:25 am
MDW
- HOU
1 stop5h 20m
Southwest
Deal found 4/18![Southwest logo]()
$353
This Delta deal was found by Cheapflights users on 4/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/302:43 pm
IAH
- MDW
1 stop7h 34m
Delta
Wed 7/2212:41 pm
MDW
- IAH
1 stop5h 01m
Delta
Deal found 4/20![Delta logo]()
$299
Last-minute flights from Houston to ChicagoDiscover last-minute flight deals from Houston to Chicago. Data last updated April 22, 2026 and is based on user searches.
Discover last-minute flight deals from Houston to Chicago. Data last updated April 22, 2026 and is based on user searches.
This Super.com deal was found by Cheapflights users on 4/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/2212:27 pm
IAH
- ORD
Nonstop2h 50m
Frontier
Tue 5/54:05 pm
ORD
- IAH
Nonstop3h 12m
Frontier
Deal found 4/17![Frontier logo]()
$121
This Priceline deal was found by Cheapflights users on 4/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/58:12 pm
IAH
- ORD
Nonstop2h 49m
Multiple Airlines
Sat 5/94:50 pm
ORD
- IAH
Nonstop2h 54m
Multiple Airlines
Deal found 4/20![Multiple Airlines logo]()
$114
This Frontier deal was found by Cheapflights users on 4/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/58:12 pm
IAH
- ORD
Nonstop2h 49m
Frontier
Mon 6/84:05 pm
ORD
- IAH
Nonstop3h 12m
Frontier
Deal found 4/20![Frontier logo]()
$119
This Cheapflightsfares deal was found by Cheapflights users on 4/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/67:15 am
IAH
- ORD
Nonstop2h 39m
Spirit Airlines
Tue 5/124:06 pm
ORD
- IAH
Nonstop2h 54m
Spirit Airlines
Deal found 4/19![Spirit Airlines logo]()
$116
This Expedia deal was found by Cheapflights users on 4/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/68:50 pm
IAH
- ORD
1 stop11h 05m
Frontier
Wed 5/204:05 pm
ORD
- IAH
Nonstop3h 12m
Frontier
Deal found 4/17![Frontier logo]()
$118
This Frontier deal was found by Cheapflights users on 4/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/98:12 pm
IAH
- ORD
Nonstop2h 49m
Frontier
Fri 5/157:30 am
ORD
- IAH
1 stop12h 25m
Frontier
Deal found 4/19![Frontier logo]()
$117
This Frontier deal was found by Cheapflights users on 4/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/98:12 pm
IAH
- ORD
Nonstop2h 49m
Frontier
Mon 6/84:05 pm
ORD
- IAH
Nonstop3h 12m
Frontier
Deal found 4/17![Frontier logo]()
$122
This Cheapflightsfares deal was found by Cheapflights users on 4/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/117:15 am
IAH
- ORD
Nonstop2h 39m
Spirit Airlines
Wed 5/134:06 pm
ORD
- IAH
Nonstop2h 54m
Spirit Airlines
Deal found 4/20![Spirit Airlines logo]()
$112
This Kiwi.com deal was found by Cheapflights users on 4/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/117:15 am
IAH
- ORD
Nonstop2h 39m
Multiple Airlines
Fri 5/158:30 am
ORD
- IAH
Nonstop3h 20m
Multiple Airlines
Deal found 4/18![Multiple Airlines logo]()
$120
This Frontier deal was found by Cheapflights users on 4/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/138:50 pm
IAH
- ORD
1 stop11h 05m
Frontier
Wed 5/204:05 pm
ORD
- IAH
Nonstop3h 12m
Frontier
Deal found 4/19![Frontier logo]()
$115
This Super.com deal was found by Cheapflights users on 4/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/208:12 pm
IAH
- ORD
Nonstop2h 49m
Frontier
Fri 5/224:05 pm
ORD
- IAH
Nonstop3h 12m
Frontier
Deal found 4/17![Frontier logo]()
$113
This Frontier deal was found by Cheapflights users on 4/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/308:12 pm
IAH
- ORD
Nonstop2h 49m
Frontier
Thu 6/44:05 pm
ORD
- IAH
Nonstop3h 12m
Frontier
Deal found 4/17![Frontier logo]()
$111
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 April 22, 2026.
Search for one-way flight options from Houston to Chicago. Find affordable one-way fares based on user searches. Data last updated April 22, 2026.
This Kiwi.com deal was found by Cheapflights users on 4/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/219:52 pm
IAH
- ORD
Nonstop2h 50m
Frontier
Deal found 4/19![Frontier logo]()
$57
This Kiwi.com deal was found by Cheapflights users on 4/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/259:58 pm
IAH
- ORD
Nonstop2h 50m
Frontier
Deal found 4/17![Frontier logo]()
$63
This Cheapflightsfares deal was found by Cheapflights users on 4/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/247:15 am
IAH
- ORD
Nonstop2h 39m
Spirit Airlines
Deal found 4/20![Spirit Airlines logo]()
$64
This Kiwi.com deal was found by Cheapflights users on 4/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/1110:05 pm
IAH
- ORD
1 stop22h 27m
Frontier
Deal found 4/17![Frontier logo]()
$65
This Super.com deal was found by Cheapflights users on 4/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/68:12 pm
IAH
- ORD
Nonstop2h 49m
Frontier
Deal found 4/20![Frontier logo]()
$68
This Cheapflightsfares deal was found by Cheapflights users on 4/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/117:15 am
IAH
- ORD
Nonstop2h 39m
Spirit Airlines
Deal found 4/17![Spirit Airlines logo]()
$69
This Spirit deal was found by Cheapflights users on 4/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Spirit is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/117:15 am
IAH
- ORD
Nonstop2h 39m
Spirit Airlines
Deal found 4/20![Spirit Airlines logo]()
$70
This CheapOair deal was found by Cheapflights users on 4/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/135:45 am
IAH
- MDW
1 stop5h 24m
Frontier
Deal found 4/20![Frontier logo]()
$70
This Kiwi.com deal was found by Cheapflights users on 4/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/137:44 pm
IAH
- ORD
1 stop27h 29m
Frontier
Deal found 4/18![Frontier logo]()
$71
This Kiwi.com deal was found by Cheapflights users on 4/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/175:45 am
IAH
- MDW
1 stop16h 26m
Frontier
Deal found 4/18![Frontier logo]()
$73
This Cheapflightsfares deal was found by Cheapflights users on 4/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/77:15 am
IAH
- ORD
Nonstop2h 39m
Spirit Airlines
Deal found 4/20![Spirit Airlines logo]()
$74
This Frontier deal was found by Cheapflights users on 4/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/1812:45 pm
IAH
- ORD
Nonstop2h 58m
Frontier
Deal found 4/17![Frontier logo]()
$75
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 April 22, 2026.
Round-trip from | $111 (Frontier) |
|---|---|
One-way from | $57 (Kiwi.com) |
Popular in | March |
Cheapest in | January |
Average price | $206 |
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 April 22, 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 - ORD
IAHORD
Houston George Bush Intcntl
Sun 5/17
7:15 am-9:54 am
Nonstop2h 39m
Chicago O'Hare Intl
Sun 5/24
7:33 pm-9:03 am
1 stop13h 30m
$187
HoustonChicago
IAH - ORD
IAHORD
Houston George Bush Intcntl
Wed 5/20
11:34 am-6:05 pm
1 stop6h 31m
Chicago O'Hare Intl
Wed 5/27
7:07 am-1:14 pm
1 stop6h 07m
$197
HoustonChicago
IAH - ORD
IAHORD
Houston George Bush Intcntl
Tue 5/19
5:55 am-1:47 pm
1 stop7h 52m
Chicago O'Hare Intl
Wed 5/27
2:59 pm-9:25 pm
1 stop6h 26m
$197
Quickest round-trip
HoustonChicago
HOU - MDW
HOUMDW
Houston Hobby
Wed 5/20
8:40 pm-11:05 pm
Nonstop2h 25m
Chicago Midway
Wed 5/27
8:40 pm-11:20 pm
Nonstop2h 40m
$199
HoustonChicago
IAH - ORD
IAHORD
Houston George Bush Intcntl
Mon 5/11
6:35 pm-11:59 pm
1 stop5h 24m
Chicago O'Hare Intl
Wed 5/13
9:25 am-2:30 pm
1 stop5h 05m
$217
HoustonChicago
IAH - ORD
IAHORD
Houston George Bush Intcntl
Sat 5/9
9:44 am-4:56 pm
1 stop7h 12m
Chicago O'Hare Intl
Sat 5/16
7:00 am-2:30 pm
1 stop7h 30m
$219
HoustonChicago
IAH - MDW
IAHMDW
Houston George Bush Intcntl
Wed 6/24
5:20 am-12:36 pm
1 stop7h 16m
Chicago Midway
Mon 6/29
5:41 pm-11:59 pm
1 stop6h 18m
$248
HoustonChicago
IAH - ORD
IAHORD
Houston George Bush Intcntl
Sat 4/25
5:20 am-12:49 pm
1 stop7h 29m
Chicago O'Hare Intl
Sat 4/25
5:04 pm-10:54 pm
1 stop5h 50m
$251
HoustonChicago
HOU - MDW
HOUMDW
Houston Hobby
Sat 5/9
8:10 am-12:10 pm
1 stop4h 00m
Chicago Midway
Wed 5/13
8:40 pm-11:20 pm
Nonstop2h 40m
$254
HoustonChicago
HOU - ORD
HOUORD
Houston Hobby
Wed 5/20
6:00 am-12:50 pm
2 stops6h 50m
Chicago O'Hare Intl
Wed 5/27
10:30 am-10:10 pm
2 stops11h 40m
$257
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-MDW
IAH-ORD
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-MDW
IAH-ORD
HOU-MDW
IAH-RFD
How far ahead should I book a flight from Houston to Chicago?
Use this chart to determine the optimal time to book a round-trip flight from Houston to Chicago. Price data was last updated on April 17, 2026.
To ensure you get the cheapest price possible for a flight from Houston to Chicago, you should look to book at least 63 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 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 $183). 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 April 22, 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 49% on your trip compared to booking a flight at noon.
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.
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 146 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?
Tuesday tends to have the lowest number of delays on this route, whereas Sunday has historically faced a higher average of delays compared to other days of the week.
Which airline has the best punctuality record on Houston to Chicago flights?
Over the last year, United Airlines have had the lowest number of delays on this route, with just 10% of flights being delayed.
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 April 22, 2026.
Get a feel of what it's like to fly with Southwest,United Airlines, andAmerican 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.
Entertainment
7.5
Boarding
8.1
Overall
8.0
Food
7.0
Comfort
8.0
Crew
8.6
Reviews
1 / 20
6.0
GoodScott,Feb 2026
HOU - FLL
Entertainment
7.5
Boarding
8.1
Overall
8.0
Food
7.0
Comfort
8.0
Crew
8.6
Reviews
1 / 20
6.0
GoodScott,Feb 2026
HOU - FLL
Entertainment
7.5
Boarding
8.1
Overall
8.0
Food
7.0
Comfort
8.0
Crew
8.6
Reviews
1 / 20
6.0
GoodScott,Feb 2026
HOU - FLL
Entertainment
7.5
Boarding
8.1
Overall
8.0
Food
7.0
Comfort
8.0
Crew
8.6
Reviews
1 / 20
6.0
GoodScott,Feb 2026
HOU - FLL
Entertainment
7.5
Boarding
8.1
Overall
8.0
Food
7.0
Comfort
8.0
Crew
8.6
Reviews
1 / 20
6.0
GoodScott,Feb 2026
HOU - FLL
Entertainment
7.5
Boarding
8.1
Overall
8.0
Food
7.0
Comfort
8.0
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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Complete your trip
Flights by cabin class
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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 April 22, 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 April 22, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Top 6 airlines flying from Houston to Chicago
Discover the top 6 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 April 22, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$58 | Average$175 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$71 | Average$160 | FlexibilityNo cancel fee | On-time65% | |
| Cheapest$148 | Average$348 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$159 | Average$395 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$162 | Average$302 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$216 | Average$358 | 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.