$99+ Cheap flights from Hobby (HOU) to O'Hare Intl (ORD)
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 4/15. Fares are subject to change and may not be available on all flights or dates of travel.
HOU — ORD
Mar 30 — Apr 61
1 adult, Economy
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Cheapest flights from Hobby to O'Hare IntlExplore the most affordable flight options available from Hobby to O'Hare Intl. Find the lowest fares from popular airlines and budget airlines, with prices last updated on February 28, 2026.
Explore the most affordable flight options available from Hobby to O'Hare Intl. Find the lowest fares from popular airlines and budget airlines, with prices last updated on February 28, 2026.
This Delta deal was found by Cheapflights users on 2/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/65:23 pm
HOU
- ORD
1 stop6h 36m
Delta
Wed 5/137:07 am
ORD
- HOU
1 stop5h 04m
Delta
Deal found 2/27![Delta logo]()
$197
This Delta deal was found by Cheapflights users on 2/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/15:23 pm
HOU
- ORD
1 stop6h 36m
Delta
Mon 5/49:48 am
ORD
- HOU
1 stop6h 40m
Delta
Deal found 2/26![Delta logo]()
$198
This Southwest deal was found by Cheapflights users on 2/25. 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 4/185:35 am
HOU
- ORD
1 stop5h 55m
Southwest
Tue 4/2111:55 am
ORD
- HOU
1 stop5h 55m
Southwest
Deal found 2/25![Southwest logo]()
$205
This Delta deal was found by Cheapflights users on 2/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/25:23 pm
HOU
- ORD
1 stop6h 36m
Delta
Mon 5/411:19 am
ORD
- HOU
1 stop5h 09m
Delta
Deal found 2/27![Delta logo]()
$207
This Delta deal was found by Cheapflights users on 2/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/175:23 pm
HOU
- ORD
1 stop6h 36m
Delta
Sun 4/197:10 am
ORD
- HOU
1 stop5h 30m
Delta
Deal found 2/24![Delta logo]()
$208
This Southwest deal was found by Cheapflights users on 2/24. 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 4/76:00 am
HOU
- ORD
1 stop5h 10m
Southwest
Wed 4/811:55 am
ORD
- HOU
1 stop4h 55m
Southwest
Deal found 2/24![Southwest logo]()
$210
This Southwest deal was found by Cheapflights users on 2/28. Clicking the “Pick Dates” 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 4/206:55 am
HOU
- ORD
1 stop5h 55m
Southwest
Sat 4/257:00 am
ORD
- HOU
1 stop8h 10m
Southwest
Deal found 2/28![Southwest logo]()
$217
This Southwest deal was found by Cheapflights users on 2/24. 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.
Wed 5/66:00 am
HOU
- ORD
1 stop5h 10m
Southwest
Mon 5/116:15 pm
ORD
- HOU
1 stop6h 10m
Southwest
Deal found 2/24![Southwest logo]()
$222
This Southwest deal was found by Cheapflights users on 2/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/76:00 am
HOU
- ORD
1 stop5h 10m
Southwest
Thu 4/92:40 pm
ORD
- HOU
2 stops6h 30m
Southwest
Deal found 2/25![Southwest logo]()
$227
This Southwest deal was found by Cheapflights users on 2/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/176:00 am
HOU
- ORD
1 stop10h 05m
Southwest
Sun 4/197:35 pm
ORD
- HOU
1 stop13h 00m
Southwest
Deal found 2/27![Southwest logo]()
$228
Best flights from Hobby to O'Hare IntlDiscover carefully curated flight deals from Hobby to O'Hare Intl that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated February 28, 2026.
Discover carefully curated flight deals from Hobby to O'Hare Intl that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated February 28, 2026.
This Delta deal was found by Cheapflights users on 2/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/315:27 pm
HOU
- ORD
1 stop6h 27m
Delta
Sat 4/42:59 pm
ORD
- HOU
1 stop7h 52m
Delta
Deal found 2/25![Delta logo]()
$237
This Southwest deal was found by Cheapflights users on 2/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/88:05 am
HOU
- ORD
2 stops10h 45m
Southwest
Mon 5/116:15 pm
ORD
- HOU
1 stop6h 10m
Southwest
Deal found 2/24![Southwest logo]()
$276
This Delta deal was found by Cheapflights users on 2/24. 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 3/246:00 am
HOU
- ORD
1 stop7h 38m
Delta
Tue 3/319:40 am
ORD
- HOU
1 stop6h 52m
Delta
Deal found 2/24![Delta logo]()
$237
This Southwest deal was found by Cheapflights users on 2/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/258:15 am
HOU
- ORD
2 stops14h 05m
Southwest
Mon 4/274:15 pm
ORD
- HOU
1 stop5h 00m
Southwest
Deal found 2/27![Southwest logo]()
$290
This Delta deal was found by Cheapflights users on 2/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/265:02 pm
HOU
- ORD
1 stop5h 25m
Delta
Tue 6/911:10 am
ORD
- HOU
1 stop5h 16m
Delta
Deal found 2/27![Delta logo]()
$279
This Southwest deal was found by Cheapflights users on 2/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/25:30 am
HOU
- ORD
1 stop10h 40m
Southwest
Mon 4/64:15 pm
ORD
- HOU
1 stop6h 55m
Southwest
Deal found 2/24![Southwest logo]()
$306
This Delta deal was found by Cheapflights users on 2/24. 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 6/110:27 am
HOU
- ORD
1 stop6h 28m
Delta
Tue 6/307:10 am
ORD
- HOU
1 stop5h 00m
Delta
Deal found 2/24![Delta logo]()
$279
This Southwest deal was found by Cheapflights users on 2/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/197:55 am
HOU
- ORD
1 stop4h 55m
Southwest
Thu 4/22:40 pm
ORD
- HOU
2 stops7h 05m
Southwest
Deal found 2/24![Southwest logo]()
$316
This Delta deal was found by Cheapflights users on 2/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/1011:33 am
HOU
- ORD
1 stop5h 16m
Delta
Tue 3/245:30 am
ORD
- HOU
1 stop7h 58m
Delta
Deal found 2/27![Delta logo]()
$302
This Southwest deal was found by Cheapflights users on 2/25. 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.
Fri 6/53:00 pm
HOU
- ORD
1 stop4h 20m
Southwest
Wed 6/102:40 pm
ORD
- HOU
1 stop5h 50m
Southwest
Deal found 2/25![Southwest logo]()
$325
This Southwest deal was found by Cheapflights users on 2/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 3/218:15 am
HOU
- ORD
1 stop6h 05m
Southwest
Mon 3/232:40 pm
ORD
- HOU
2 stops7h 05m
Southwest
Deal found 2/27![Southwest logo]()
$338
This Southwest deal was found by Cheapflights users on 2/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/25:30 am
HOU
- ORD
1 stop10h 40m
Southwest
Sun 4/127:35 pm
ORD
- HOU
1 stop13h 00m
Southwest
Deal found 2/25![Southwest logo]()
$341
Last-minute flights from Hobby to O'Hare IntlDiscover last-minute flight deals from Hobby to O'Hare Intl. Data last updated February 28, 2026 and is based on user searches.
Discover last-minute flight deals from Hobby to O'Hare Intl. Data last updated February 28, 2026 and is based on user searches.
This Delta deal was found by Cheapflights users on 2/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/175:22 pm
HOU
- ORD
1 stop6h 32m
Delta
Tue 3/3111:10 am
ORD
- HOU
1 stop5h 22m
Delta
Deal found 2/27![Delta logo]()
$263
This American Airlines deal was found by Cheapflights users on 2/24. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/2412:18 pm
HOU
- ORD
1 stop6h 12m
American Airlines
Mon 3/304:49 pm
ORD
- HOU
1 stop7h 09m
American Airlines
Deal found 2/24![American Airlines logo]()
$257
This Southwest deal was found by Cheapflights users on 2/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/256:10 am
HOU
- ORD
1 stop7h 45m
Southwest
Wed 4/12:40 pm
ORD
- HOU
1 stop5h 25m
Southwest
Deal found 2/25![Southwest logo]()
$268
This Southwest deal was found by Cheapflights users on 2/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/256:10 am
HOU
- ORD
1 stop7h 45m
Southwest
Thu 4/94:15 pm
ORD
- HOU
1 stop5h 00m
Southwest
Deal found 2/25![Southwest logo]()
$271
This American Airlines deal was found by Cheapflights users on 2/24. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 3/276:00 am
HOU
- ORD
1 stop7h 04m
American Airlines
Mon 3/304:49 pm
ORD
- HOU
1 stop7h 09m
American Airlines
Deal found 2/24![American Airlines logo]()
$277
This Southwest deal was found by Cheapflights users on 2/28. Clicking the “Pick Dates” 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 3/288:15 am
HOU
- ORD
1 stop6h 05m
Southwest
Sat 4/41:35 pm
ORD
- HOU
1 stop8h 20m
Southwest
Deal found 2/28![Southwest logo]()
$245
This Southwest deal was found by Cheapflights users on 2/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/308:55 pm
HOU
- ORD
1 stop12h 50m
Southwest
Tue 3/314:15 pm
ORD
- HOU
1 stop6h 25m
Southwest
Deal found 2/25![Southwest logo]()
$274
This Delta deal was found by Cheapflights users on 2/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/315:27 pm
HOU
- ORD
1 stop6h 27m
Delta
Sat 4/42:59 pm
ORD
- HOU
1 stop7h 52m
Delta
Deal found 2/27![Delta logo]()
$237
This Southwest deal was found by Cheapflights users on 2/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/316:00 am
HOU
- ORD
1 stop5h 10m
Southwest
Fri 4/32:40 pm
ORD
- HOU
2 stops7h 05m
Southwest
Deal found 2/27![Southwest logo]()
$273
One-way flights from Hobby to O'Hare IntlSearch for one-way flight options from Hobby to O'Hare Intl. Find affordable one-way fares based on user searches. Data last updated February 28, 2026.
Search for one-way flight options from Hobby to O'Hare Intl. Find affordable one-way fares based on user searches. Data last updated February 28, 2026.
This Delta deal was found by Cheapflights users on 2/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/155:23 pm
HOU
- ORD
1 stop6h 36m
Delta
Deal found 2/24![Delta logo]()
$99
This Delta deal was found by Cheapflights users on 2/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/175:23 pm
HOU
- ORD
1 stop6h 36m
Delta
Deal found 2/24![Delta logo]()
$100
This Southwest deal was found by Cheapflights users on 2/24. 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.
Wed 4/88:45 am
HOU
- ORD
1 stop10h 05m
Southwest
Deal found 2/24![Southwest logo]()
$105
This Delta deal was found by Cheapflights users on 2/24. 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 3/315:27 pm
HOU
- ORD
1 stop6h 27m
Delta
Deal found 2/24![Delta logo]()
$109
This Southwest deal was found by Cheapflights users on 2/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/156:00 am
HOU
- ORD
2 stops6h 50m
Southwest
Deal found 2/27![Southwest logo]()
$114
This Southwest deal was found by Cheapflights users on 2/24. 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 5/126:00 am
HOU
- ORD
2 stops9h 00m
Southwest
Deal found 2/24![Southwest logo]()
$118
This Southwest deal was found by Cheapflights users on 2/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/316:00 am
HOU
- ORD
1 stop5h 10m
Southwest
Deal found 2/25![Southwest logo]()
$120
This Southwest deal was found by Cheapflights users on 2/25. 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 4/116:50 am
HOU
- ORD
1 stop8h 40m
Southwest
Deal found 2/25![Southwest logo]()
$122
This Delta deal was found by Cheapflights users on 2/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/245:22 pm
HOU
- ORD
1 stop6h 32m
Delta
Deal found 2/27![Delta logo]()
$129
This Southwest deal was found by Cheapflights users on 2/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/146:00 am
HOU
- ORD
2 stops6h 50m
Southwest
Deal found 2/26![Southwest logo]()
$131
This American Airlines deal was found by Cheapflights users on 2/25. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/276:00 am
HOU
- ORD
1 stop4h 43m
American Airlines
Deal found 2/25![American Airlines logo]()
$140
This Southwest deal was found by Cheapflights users on 2/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/308:55 pm
HOU
- ORD
1 stop12h 50m
Southwest
Deal found 2/27![Southwest logo]()
$145
Find flight deals from Hobby to O'Hare Intl
Discover tips and strategies to find the most affordable flight options for your journey from Hobby (HOU) to O'Hare Intl (ORD). 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 February 28, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $197 (Delta) |
One-way from | $99 (Delta) |
Popular in | April |
Cheapest in | January |
Average price | $180 |
Cheapflights Fare Finder
Customize your flight search to find flights from Hobby to O'Hare Intl 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 February 28, 2026.
Use the filters below to find and compare flights from Houston Hobby Airport to Chicago O'Hare Intl Airport that are best for you.
Fly from
Fly to
Route
Depart
Return
HoustonChicago
HOU - ORD
HOUORD
Houston Hobby
Tue 3/31
5:27 pm-11:54 pm
1 stop6h 27m
Chicago O'Hare Intl
Sat 4/4
2:59 pm-10:51 pm
1 stop7h 52m
$237
HoustonChicago
HOU - ORD
HOUORD
Houston Hobby
Tue 3/24
6:00 am-1:38 pm
1 stop7h 38m
Chicago O'Hare Intl
Tue 3/31
9:40 am-4:32 pm
1 stop6h 52m
$237
HoustonChicago
HOU - ORD
HOUORD
Houston Hobby
Fri 5/8
8:05 am-6:50 pm
2 stops10h 45m
Chicago O'Hare Intl
Mon 5/11
6:15 pm-12:25 am
1 stop6h 10m
$276
HoustonChicago
HOU - ORD
HOUORD
Houston Hobby
Tue 5/26
5:02 pm-10:27 pm
1 stop5h 25m
Chicago O'Hare Intl
Tue 6/9
11:10 am-4:26 pm
1 stop5h 16m
$279
HoustonChicago
HOU - ORD
HOUORD
Houston Hobby
Mon 6/1
10:27 am-4:55 pm
1 stop6h 28m
Chicago O'Hare Intl
Tue 6/30
7:10 am-12:10 pm
1 stop5h 00m
$279
HoustonChicago
HOU - ORD
HOUORD
Houston Hobby
Sat 4/25
8:15 am-10:20 pm
2 stops14h 05m
Chicago O'Hare Intl
Mon 4/27
4:15 pm-9:15 pm
1 stop5h 00m
$290
HoustonChicago
HOU - ORD
HOUORD
Houston Hobby
Tue 3/10
11:33 am-4:49 pm
1 stop5h 16m
Chicago O'Hare Intl
Tue 3/24
5:30 am-1:28 pm
1 stop7h 58m
$302
HoustonChicago
HOU - ORD
HOUORD
Houston Hobby
Thu 4/2
5:30 am-4:10 pm
1 stop10h 40m
Chicago O'Hare Intl
Mon 4/6
4:15 pm-11:10 pm
1 stop6h 55m
$306
HoustonChicago
HOU - ORD
HOUORD
Houston Hobby
Thu 3/19
7:55 am-12:50 pm
1 stop4h 55m
Chicago O'Hare Intl
Thu 4/2
2:40 pm-9:45 pm
2 stops7h 05m
$316
HoustonChicago
HOU - ORD
HOUORD
Houston Hobby
Fri 6/5
3:00 pm-7:20 pm
1 stop4h 20m
Chicago O'Hare Intl
Wed 6/10
2:40 pm-8:30 pm
1 stop5h 50m
$325
Showing 1-10 of 23 resultsSorted by cheapest first
Compare providers for flights from Hobby to O'Hare Intl
Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Hobby to O'Hare Intl in February.
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy2 stars | Trust Score*2 stars | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy- | Trust Score*1 star | |
| Price Accuracy- | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars |
- Most accurate provider: When it comes to deals on Houston Hobby Airport-Chicago O'Hare Intl Airport flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Houston Hobby Airport-Chicago O'Hare Intl Airport flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Houston Hobby Airport-Chicago O'Hare Intl Airport flight searches over the past month and is updated monthly.
- Most trusted provider: When it comes to deals on Houston Hobby Airport-Chicago O'Hare Intl Airport flights, Cheapflights users trust FlightHub the most. FlightHub has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Houston Hobby Airport-Chicago O'Hare Intl Airport flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.
Best time to book a flight from Hobby to O'Hare Intl
Have a flexible travel schedule? Discover the best time to fly to O'Hare Intl from Hobby with our price prediction graph.
HOU-ORD
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.
Cheapflights Insights
Everything you need to know about your flight from Houston Hobby Airport to Chicago O'Hare Intl Airport
Prices
Delays
How far ahead should I book a flight from Houston Hobby Airport to Chicago O'Hare Intl Airport?
Use this chart to determine the optimal time to book a round-trip flight from Hobby to O'Hare Intl. Price data was last updated on February 20, 2026.
To ensure you get the cheapest price possible for a flight from Houston Hobby Airport to Chicago O'Hare Intl Airport, you should look to book at least 69 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 Hobby Airport to Chicago O'Hare Intl Airport?
Currently, March is the cheapest month in which you can book a flight from Houston Hobby Airport to Chicago O'Hare Intl Airport (average of $57). Flying from Houston Hobby Airport to Chicago O'Hare Intl Airport in June is currently the most expensive (average of $130). 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.
How often are flights from Houston to Chicago delayed?
About 33% of weekly flights between Houston and Chicago have experienced delays in the past year, with the average delay time being 26 minutes.
What is the most punctual flight time for Houston to Chicago flights?
Historically, flights departing at night are less likely to be delayed, whereas flights leaving in the morning tend to experience delays more often.
Reviews of airlines servicing O'Hare Intl
Get insights into the airlines that provide service to O'Hare Intl. 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 O'Hare Intl. Reviews last updated February 28, 2026.
Read reviews from past customers who have flown United Airlines, American Airlines, and Spirit Airlines from Houston Hobby Airport to Chicago O'Hare Intl Airport. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
Food
6.6
Comfort
7.3
Crew
8.1
Entertainment
7.1
Overall
7.4
Boarding
7.7
Reviews
1 / 20
2.0
MediocreSebrena,Oct 2025
IAH - RSW
Food
6.6
Comfort
7.3
Crew
8.1
Entertainment
7.1
Overall
7.4
Boarding
7.7
Reviews
1 / 20
2.0
MediocreSebrena,Oct 2025
IAH - RSW
Food
6.6
Comfort
7.3
Crew
8.1
Entertainment
7.1
Overall
7.4
Boarding
7.7
Reviews
1 / 20
2.0
MediocreSebrena,Oct 2025
IAH - RSW
Food
6.6
Comfort
7.3
Crew
8.1
Entertainment
7.1
Overall
7.4
Boarding
7.7
Reviews
1 / 20
2.0
MediocreSebrena,Oct 2025
IAH - RSW
Food
6.6
Comfort
7.3
Crew
8.1
Entertainment
7.1
Overall
7.4
Boarding
7.7
Reviews
1 / 20
2.0
MediocreSebrena,Oct 2025
IAH - RSW
Related info for your journey
Find useful and relevant information for your journey from Hobby to O'Hare Intl. 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 O'Hare Intl Airport?
Book flights to Chicago O'Hare Intl Airport if you plan to visit one of these locationsSchaumburg
Rosemont
Gurnee
Naperville
Hoffman Estates
Beloit
Delavan
Des Plaines
Elgin
Downers Grove
Elk Grove Village
Skokie
Oak Brook
South Holland
Libertyville
Oakbrook Terrace
Lake Geneva
Waukegan
Bridgeview
Kenosha
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Other flights to O'Hare Intl
Explore flights to O'Hare Intl departing from other origins. Flights are based on user searches made on Cheapflights and were last updated on February 28, 2026.
Hobby and O'Hare Intl flights
Browse other Hobby and O'Hare Intl flight options. Last updated on February 28, 2026.
Other flights from Hobby
Browse through other flights departing from Hobby. Flights are based on user searches made on Cheapflights and were last updated on February 28, 2026.
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Top 4 airlines flying from Hobby to O'Hare Intl
Discover the top 4 airlines that operate flights from Hobby to O'Hare Intl. 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 February 28, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$62 | Average$176 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$71 | Average$154 | FlexibilityNo cancel fee | On-time65% | |
| Cheapest$141 | Average$305 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$177 | Average$253 | FlexibilityNo cancel fee | On-time71% |