$190+ Cheap flights from Chicago (CHI) to Santa Rosa (STS)
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 10/24. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — STS
Aug 4 — Aug 111
Round-trip
1 adult, Economy
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Find cheap flights from Chicago to Santa Rosa with Cheapflights
1. Tell us where you want to go
Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”2. Select your favorite providers
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Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.Cheap flight deals from Chicago to Santa Rosa
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Cheapest flights from Chicago to Santa RosaExplore the most affordable flight options available from Chicago to Santa Rosa. Find the lowest fares from popular airlines and budget airlines, with prices last updated on July 5, 2026.
Explore the most affordable flight options available from Chicago to Santa Rosa. Find the lowest fares from popular airlines and budget airlines, with prices last updated on July 5, 2026.
This Alaska Airlines deal was found by Cheapflights users on 7/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/262:18 pm
ORD
- STS
1 stop21h 36m
Alaska Airlines
Sat 10/34:35 pm
STS
- ORD
1 stop18h 50m
Alaska Airlines
Deal found 7/1![Alaska Airlines logo]()
$379
This Alaska Airlines deal was found by Cheapflights users on 7/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/23:43 pm
ORD
- STS
1 stop8h 16m
Alaska Airlines
Mon 9/76:13 am
STS
- ORD
1 stop29h 09m
Alaska Airlines
Deal found 7/1![Alaska Airlines logo]()
$381
This Delta deal was found by Cheapflights users on 7/2. Clicking the “Pick Dates” 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 10/209:59 am
ORD
- STS
2 stops8h 09m
Delta
Sat 10/2411:29 am
STS
- ORD
1 stop8h 31m
Delta
Deal found 7/2![Delta logo]()
$384
This Delta deal was found by Cheapflights users on 7/4. Clicking the “Pick Dates” 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 11/78:05 am
ORD
- STS
2 stops10h 03m
Delta
Sat 11/1411:25 am
STS
- ORD
2 stops10h 25m
Delta
Deal found 7/4![Delta logo]()
$389
This Alaska Airlines deal was found by Cheapflights users on 7/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/172:17 pm
ORD
- STS
1 stop7h 30m
Alaska Airlines
Mon 10/267:00 am
STS
- ORD
1 stop9h 20m
Alaska Airlines
Deal found 7/2![Alaska Airlines logo]()
$390
This Alaska Airlines deal was found by Cheapflights users on 7/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/173:52 pm
ORD
- STS
1 stop8h 07m
Alaska Airlines
Mon 9/216:13 am
STS
- ORD
1 stop29h 09m
Alaska Airlines
Deal found 7/1![Alaska Airlines logo]()
$392
This Alaska Airlines deal was found by Cheapflights users on 7/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/146:00 am
ORD
- STS
1 stop8h 46m
Alaska Airlines
Wed 9/2310:34 am
STS
- ORD
1 stop6h 47m
Alaska Airlines
Deal found 7/3![Alaska Airlines logo]()
$394
This Delta deal was found by Cheapflights users on 7/2. Clicking the “Pick Dates” 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 10/209:59 am
ORD
- STS
2 stops8h 09m
Delta
Fri 10/2311:29 am
STS
- ORD
1 stop8h 31m
Delta
Deal found 7/2![Delta logo]()
$395
This Alaska Airlines deal was found by Cheapflights users on 7/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/36:01 am
ORD
- STS
1 stop10h 11m
Alaska Airlines
Mon 9/76:13 am
STS
- ORD
1 stop29h 09m
Alaska Airlines
Deal found 7/1![Alaska Airlines logo]()
$396
This Alaska Airlines deal was found by Cheapflights users on 7/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/183:52 pm
ORD
- STS
1 stop8h 07m
Alaska Airlines
Wed 9/2310:34 am
STS
- ORD
1 stop6h 47m
Alaska Airlines
Deal found 7/3![Alaska Airlines logo]()
$399
This Alaska Airlines deal was found by Cheapflights users on 6/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/216:00 am
ORD
- STS
1 stop7h 58m
Alaska Airlines
Fri 7/317:03 pm
STS
- ORD
1 stop7h 57m
Alaska Airlines
Deal found 6/30![Alaska Airlines logo]()
$401
This Expedia deal was found by Cheapflights users on 7/1. Clicking the “Pick Dates” 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 8/196:01 am
ORD
- STS
2 stops12h 38m
Alaska Airlines
Sat 8/226:13 am
STS
- ORD
1 stop11h 08m
Alaska Airlines
Deal found 7/1![Alaska Airlines logo]()
$406
Best flights from Chicago to Santa RosaDiscover carefully curated flight deals from Chicago to Santa Rosa that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated July 5, 2026.
Discover carefully curated flight deals from Chicago to Santa Rosa that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated July 5, 2026.
This Alaska Airlines deal was found by Cheapflights users on 7/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/222:18 pm
ORD
- STS
1 stop21h 36m
Alaska Airlines
Sat 8/296:13 am
STS
- ORD
1 stop11h 08m
Alaska Airlines
Deal found 7/1![Alaska Airlines logo]()
$379
This Delta deal was found by Cheapflights users on 7/2. Clicking the “Pick Dates” 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 10/209:59 am
ORD
- STS
2 stops8h 09m
Delta
Sat 10/2411:29 am
STS
- ORD
1 stop8h 31m
Delta
Deal found 7/2![Delta logo]()
$384
This Alaska Airlines deal was found by Cheapflights users on 7/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/142:25 pm
ORD
- STS
1 stop10h 08m
Alaska Airlines
Tue 11/177:00 am
STS
- ORD
1 stop8h 37m
Alaska Airlines
Deal found 7/1![Alaska Airlines logo]()
$379
This Alaska Airlines deal was found by Cheapflights users on 7/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/103:52 pm
ORD
- STS
1 stop8h 07m
Alaska Airlines
Thu 9/246:47 pm
STS
- ORD
1 stop16h 35m
Alaska Airlines
Deal found 7/5![Alaska Airlines logo]()
$419
This Alaska Airlines deal was found by Cheapflights users on 7/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/216:00 am
ORD
- STS
1 stop7h 58m
Alaska Airlines
Tue 7/286:26 am
STS
- ORD
1 stop10h 31m
Alaska Airlines
Deal found 7/2![Alaska Airlines logo]()
$421
This Alaska Airlines deal was found by Cheapflights users on 7/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/166:00 am
ORD
- STS
1 stop7h 58m
Alaska Airlines
Sun 8/2310:34 am
STS
- ORD
1 stop6h 47m
Alaska Airlines
Deal found 7/4![Alaska Airlines logo]()
$469
This Expedia deal was found by Cheapflights users on 6/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/158:02 am
ORD
- STS
2 stops11h 14m
Alaska Airlines
Sat 8/226:13 am
STS
- ORD
1 stop11h 08m
Alaska Airlines
Deal found 6/30![Alaska Airlines logo]()
$471
This Alaska Airlines deal was found by Cheapflights users on 7/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/219:00 am
ORD
- STS
2 stops13h 20m
Alaska Airlines
Thu 10/227:00 am
STS
- ORD
1 stop9h 20m
Alaska Airlines
Deal found 7/2![Alaska Airlines logo]()
$487
This Alaska Airlines deal was found by Cheapflights users on 6/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/142:20 pm
ORD
- STS
2 stops28h 56m
Alaska Airlines
Fri 8/211:40 pm
STS
- ORD
2 stops27h 41m
Alaska Airlines
Deal found 6/30![Alaska Airlines logo]()
$490
Last-minute flights from Chicago to Santa RosaDiscover last-minute flight deals from Chicago to Santa Rosa. Data last updated July 5, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to Santa Rosa. Data last updated July 5, 2026 and is based on user searches.
This Alaska Airlines deal was found by Cheapflights users on 6/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/216:00 am
ORD
- STS
1 stop7h 58m
Alaska Airlines
Fri 7/317:03 pm
STS
- ORD
1 stop7h 57m
Alaska Airlines
Deal found 6/30![Alaska Airlines logo]()
$401
This Alaska Airlines deal was found by Cheapflights users on 7/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/216:00 am
ORD
- STS
1 stop7h 58m
Alaska Airlines
Tue 7/286:26 am
STS
- ORD
1 stop10h 31m
Alaska Airlines
Deal found 7/2![Alaska Airlines logo]()
$421
This Expedia deal was found by Cheapflights users on 7/2. Clicking the “Pick Dates” 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.
Tue 8/116:00 am
ORD
- STS
2 stops12h 55m
Alaska Airlines
Sat 8/155:56 pm
STS
- ORD
1 stop17h 25m
Alaska Airlines
Deal found 7/2![Alaska Airlines logo]()
$413
This Alaska Airlines deal was found by Cheapflights users on 7/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/156:00 am
ORD
- STS
1 stop7h 58m
Alaska Airlines
Sat 8/2210:34 am
STS
- ORD
1 stop6h 47m
Alaska Airlines
Deal found 7/3![Alaska Airlines logo]()
$394
This Alaska Airlines deal was found by Cheapflights users on 7/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/156:00 am
ORD
- STS
1 stop7h 58m
Alaska Airlines
Thu 8/2010:34 am
STS
- ORD
1 stop6h 47m
Alaska Airlines
Deal found 7/3![Alaska Airlines logo]()
$409
This Alaska Airlines deal was found by Cheapflights users on 7/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/156:00 am
ORD
- STS
1 stop7h 58m
Alaska Airlines
Sun 8/2310:34 am
STS
- ORD
1 stop6h 47m
Alaska Airlines
Deal found 7/3![Alaska Airlines logo]()
$414
This Expedia deal was found by Cheapflights users on 7/1. Clicking the “Pick Dates” 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.
Sun 8/168:20 pm
ORD
- STS
1 stop17h 38m
Alaska Airlines
Sat 8/226:13 am
STS
- ORD
1 stop11h 08m
Alaska Airlines
Deal found 7/1![Alaska Airlines logo]()
$390
This Expedia deal was found by Cheapflights users on 7/1. Clicking the “Pick Dates” 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 8/196:01 am
ORD
- STS
2 stops12h 38m
Alaska Airlines
Sat 8/226:13 am
STS
- ORD
1 stop11h 08m
Alaska Airlines
Deal found 7/1![Alaska Airlines logo]()
$406
This Alaska Airlines deal was found by Cheapflights users on 7/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/222:18 pm
ORD
- STS
1 stop21h 36m
Alaska Airlines
Sat 8/296:13 am
STS
- ORD
1 stop11h 08m
Alaska Airlines
Deal found 7/1![Alaska Airlines logo]()
$379
This Alaska Airlines deal was found by Cheapflights users on 7/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/276:01 am
ORD
- STS
1 stop10h 11m
Alaska Airlines
Tue 9/110:34 am
STS
- ORD
1 stop6h 47m
Alaska Airlines
Deal found 7/5![Alaska Airlines logo]()
$399
This Alaska Airlines deal was found by Cheapflights users on 7/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/276:01 am
ORD
- STS
1 stop10h 11m
Alaska Airlines
Mon 8/3110:34 am
STS
- ORD
1 stop6h 47m
Alaska Airlines
Deal found 7/5![Alaska Airlines logo]()
$419
This Alaska Airlines deal was found by Cheapflights users on 7/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/282:22 pm
ORD
- STS
1 stop8h 36m
Alaska Airlines
Wed 9/210:34 am
STS
- ORD
1 stop6h 47m
Alaska Airlines
Deal found 7/5![Alaska Airlines logo]()
$429
One-way flights from Chicago to Santa RosaSearch for one-way flight options from Chicago to Santa Rosa. Find affordable one-way fares based on user searches. Data last updated July 5, 2026.
Search for one-way flight options from Chicago to Santa Rosa. Find affordable one-way fares based on user searches. Data last updated July 5, 2026.
This Alaska Airlines deal was found by Cheapflights users on 7/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/242:17 pm
ORD
- STS
1 stop7h 30m
Alaska Airlines
Deal found 7/3![Alaska Airlines logo]()
$190
This Alaska Airlines deal was found by Cheapflights users on 7/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/287:20 am
ORD
- STS
1 stop7h 06m
Alaska Airlines
Deal found 7/2![Alaska Airlines logo]()
$201
This American Airlines deal was found by Cheapflights users on 7/3. Clicking the “Pick Dates” 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 9/105:00 am
ORD
- STS
1 stop9h 26m
American Airlines
Deal found 7/3![American Airlines logo]()
$205
This Alaska Airlines deal was found by Cheapflights users on 7/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/253:52 pm
ORD
- STS
1 stop8h 07m
Alaska Airlines
Deal found 7/3![Alaska Airlines logo]()
$210
This Expedia deal was found by Cheapflights users on 7/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/181:03 pm
ORD
- STS
1 stop10h 56m
Alaska Airlines
Deal found 7/4![Alaska Airlines logo]()
$215
This Alaska Airlines deal was found by Cheapflights users on 7/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/157:20 am
ORD
- STS
2 stops11h 19m
Alaska Airlines
Deal found 7/1![Alaska Airlines logo]()
$217
This American Airlines deal was found by Cheapflights users on 7/4. Clicking the “Pick Dates” 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 9/185:00 am
ORD
- STS
1 stop9h 26m
American Airlines
Deal found 7/4![American Airlines logo]()
$218
This Alaska Airlines deal was found by Cheapflights users on 7/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/46:20 am
ORD
- STS
1 stop18h 38m
Alaska Airlines
Deal found 7/2![Alaska Airlines logo]()
$220
This Alaska Airlines deal was found by Cheapflights users on 7/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/292:20 pm
ORD
- STS
1 stop10h 38m
Alaska Airlines
Deal found 7/2![Alaska Airlines logo]()
$226
This Alaska Airlines deal was found by Cheapflights users on 7/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/15:59 pm
ORD
- STS
1 stop6h 59m
Alaska Airlines
Deal found 7/1![Alaska Airlines logo]()
$240
This Travelocity deal was found by Cheapflights users on 7/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Travelocity is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/227:20 am
ORD
- STS
2 stops11h 35m
Alaska Airlines
Deal found 7/1![Alaska Airlines logo]()
$242
This American Airlines deal was found by Cheapflights users on 7/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/195:00 am
ORD
- STS
2 stops9h 28m
American Airlines
Deal found 7/5![American Airlines logo]()
$245
Find flight deals from Chicago to Santa Rosa
Discover tips and strategies to find the most affordable flight options for your journey from Chicago (CHI) to Santa Rosa (STS). 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 5, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $379 (Alaska Airlines) |
One-way from | $190 (Alaska Airlines) |
Popular in | February |
Cheapest in | March |
Average price | $532 |
Cheapflights Fare Finder
Customize your flight search to find flights from Chicago to Santa Rosa 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 5, 2026.
Use the filters below to find and compare flights from Chicago to Santa Rosa that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
ChicagoSanta Rosa
ORD - STS
ORDSTS
Chicago O'Hare Intl
Sat 8/22
2:18 pm-9:54 am
1 stop21h 36m
Santa Rosa Sonoma County
Sat 8/29
6:13 am-7:21 pm
1 stop11h 08m
$379
ChicagoSanta Rosa
ORD - STS
ORDSTS
Chicago O'Hare Intl
Sat 11/14
2:25 pm-10:33 pm
1 stop10h 08m
Santa Rosa Sonoma County
Tue 11/17
7:00 am-5:37 pm
1 stop8h 37m
$379
ChicagoSanta Rosa
ORD - STS
ORDSTS
Chicago O'Hare Intl
Tue 10/20
9:59 am-4:08 pm
2 stops8h 09m
Santa Rosa Sonoma County
Sat 10/24
11:29 am-10:00 pm
1 stop8h 31m
$384
ChicagoSanta Rosa
ORD - STS
ORDSTS
Chicago O'Hare Intl
Thu 9/10
3:52 pm-9:59 pm
1 stop8h 07m
Santa Rosa Sonoma County
Thu 9/24
6:47 pm-1:22 pm
1 stop16h 35m
$419
ChicagoSanta Rosa
ORD - STS
ORDSTS
Chicago O'Hare Intl
Tue 7/21
6:00 am-11:58 am
1 stop7h 58m
Santa Rosa Sonoma County
Tue 7/28
6:26 am-6:57 pm
1 stop10h 31m
$421
Quickest round-trip
ChicagoSanta Rosa
ORD - STS
ORDSTS
Chicago O'Hare Intl
Sun 8/16
6:00 am-11:58 am
1 stop7h 58m
Santa Rosa Sonoma County
Sun 8/23
10:34 am-7:21 pm
1 stop6h 47m
$469
ChicagoSanta Rosa
ORD - STS
ORDSTS
Chicago O'Hare Intl
Sat 8/15
8:02 am-5:16 pm
2 stops11h 14m
Santa Rosa Sonoma County
Sat 8/22
6:13 am-7:21 pm
1 stop11h 08m
$471
ChicagoSanta Rosa
ORD - STS
ORDSTS
Chicago O'Hare Intl
Wed 10/21
9:00 am-8:20 pm
2 stops13h 20m
Santa Rosa Sonoma County
Thu 10/22
7:00 am-6:20 pm
1 stop9h 20m
$487
ChicagoSanta Rosa
ORD - STS
ORDSTS
Chicago O'Hare Intl
Fri 8/14
2:20 pm-5:16 pm
2 stops28h 56m
Santa Rosa Sonoma County
Fri 8/21
1:40 pm-7:21 pm
2 stops27h 41m
$490
Cheapest one-way
ChicagoSanta Rosa
ORD - STS
ORDSTS
Chicago O'Hare Intl
Fri 9/18
1:03 pm-9:59 pm
1 stop10h 56m
$215
Showing 1-10 of 17 resultsSorted by cheapest first
Compare providers for flights from Chicago to Santa Rosa
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 Chicago to Santa Rosa in July.
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars |
- Most accurate provider: When it comes to deals on Chicago-Santa Rosa flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Chicago-Santa Rosa flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Chicago-Santa Rosa flight searches over the past month and is updated monthly.
- Most trusted provider: When it comes to deals on Chicago-Santa Rosa 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 Chicago-Santa Rosa 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 Chicago to Santa Rosa
Have a flexible travel schedule? Discover the best time to fly to Santa Rosa from Chicago with our price prediction graph.
CHI-STS
ORD-STS
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 Chicago to Santa Rosa
CHI-STS
ORD-STS
What is the cheapest month to book a flight from Chicago to Santa Rosa?
Currently, August is the cheapest month in which you can book a flight from Chicago to Santa Rosa (average of $236). Flying from Chicago to Santa Rosa in February is currently the most expensive (average of $545). 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.
Reviews of airlines servicing Santa Rosa
Get insights into the airlines that provide service to Santa Rosa. 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 Santa Rosa. Reviews last updated July 5, 2026.
Peruse reviews from past customers who have flown with Alaska Airlines and American Airlines from Chicago to Santa Rosa to help guide your decision. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Entertainment
7.0
Boarding
8.1
Comfort
7.8
Overall
7.9
Crew
8.5
Food
7.1
Reviews
1 / 20
10.0
Excellentrobert,Feb 2026
LAS - SAN
Entertainment
7.0
Boarding
8.1
Comfort
7.8
Overall
7.9
Crew
8.5
Food
7.1
Reviews
1 / 20
10.0
Excellentrobert,Feb 2026
LAS - SAN
Entertainment
7.0
Boarding
8.1
Comfort
7.8
Overall
7.9
Crew
8.5
Food
7.1
Reviews
1 / 20
10.0
Excellentrobert,Feb 2026
LAS - SAN
Related info for your journey
Find useful and relevant information for your journey from Chicago to Santa Rosa. 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 Santa Rosa?
Book flights to Santa Rosa if you plan to visit one of these locationsFort Bragg
Ukiah
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Chicago and Santa Rosa flights
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Chicago to Santa Rosa flights
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Top 2 airlines flying from Chicago to Santa Rosa
Discover the top 2 airlines that operate flights from Chicago to Santa Rosa. 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 5, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$285 | Average$478 | FlexibilityNo cancel fee | On-time75% | |
| Cheapest$412 | Average$563 | FlexibilityNo cancel fee | On-time71% |