$152+ 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 6/9. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — STS
Jun 5 — Jun 121
Round-trip
1 adult, Economy
We work with more than 300 partners to bring you better travel deals
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
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.Cheap flight deals from Chicago to Santa Rosa
Cheapest
Best
Last-minute
One-way
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 May 6, 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 May 6, 2026.
This American Airlines deal was found by Cheapflights users on 5/1. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/95:00 am
ORD
- STS
1 stop9h 05m
American Airlines
Tue 6/164:20 pm
STS
- ORD
1 stop6h 08m
American Airlines
Deal found 5/1![American Airlines logo]()
$303
This American Airlines deal was found by Cheapflights users on 5/5. 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 6/35:00 am
ORD
- STS
1 stop9h 03m
American Airlines
Tue 6/94:20 pm
STS
- ORD
1 stop6h 08m
American Airlines
Deal found 5/5![American Airlines logo]()
$313
This American Airlines deal was found by Cheapflights users on 5/1. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/15:00 am
ORD
- STS
1 stop9h 33m
American Airlines
Wed 6/312:43 pm
STS
- ORD
1 stop9h 59m
American Airlines
Deal found 5/1![American Airlines logo]()
$331
This Alaska Airlines deal was found by Cheapflights users on 5/5. 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.
Mon 6/17:59 pm
ORD
- STS
1 stop17h 26m
Alaska Airlines
Sat 6/67:40 pm
STS
- ORD
1 stop15h 34m
Alaska Airlines
Deal found 5/5![Alaska Airlines logo]()
$336
This Alaska Airlines deal was found by Cheapflights users on 5/5. 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.
Tue 9/226:01 am
ORD
- STS
1 stop10h 11m
Alaska Airlines
Wed 9/232:52 pm
STS
- ORD
1 stop6h 49m
Alaska Airlines
Deal found 5/5![Alaska Airlines logo]()
$341
This Travelocity deal was found by Cheapflights users on 5/1. 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.
Sun 5/317:59 pm
ORD
- STS
1 stop17h 26m
Alaska Airlines
Wed 6/1711:04 am
STS
- ORD
1 stop10h 32m
Alaska Airlines
Deal found 5/1![Alaska Airlines logo]()
$351
This Expedia deal was found by Cheapflights users on 5/5. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/172:18 pm
ORD
- STS
1 stop11h 36m
Alaska Airlines
Mon 9/216:53 pm
STS
- ORD
1 stop16h 33m
Alaska Airlines
Deal found 5/5![Alaska Airlines logo]()
$359
This Alaska Airlines deal was found by Cheapflights users on 5/5. 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.
Tue 6/27:49 pm
ORD
- STS
1 stop18h 28m
Alaska Airlines
Tue 6/97:00 am
STS
- ORD
2 stops13h 59m
Alaska Airlines
Deal found 5/5![Alaska Airlines logo]()
$368
This Alaska Airlines deal was found by Cheapflights users on 5/5. 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.
Wed 6/32:10 pm
ORD
- STS
2 stops30h 09m
Alaska Airlines
Tue 6/97:01 am
STS
- ORD
1 stop9h 49m
Alaska Airlines
Deal found 5/5![Alaska Airlines logo]()
$391
This Alaska Airlines deal was found by Cheapflights users on 5/1. 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 6/99:00 am
ORD
- STS
1 stop7h 13m
Alaska Airlines
Tue 6/161:06 pm
STS
- ORD
2 stops32h 30m
Alaska Airlines
Deal found 5/1![Alaska Airlines logo]()
$392
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 May 6, 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 May 6, 2026.
This Alaska Airlines deal was found by Cheapflights users on 5/1. 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.
Mon 6/19:00 am
ORD
- STS
2 stops35h 19m
Alaska Airlines
Sat 6/67:06 am
STS
- ORD
1 stop9h 44m
Alaska Airlines
Deal found 5/1![Alaska Airlines logo]()
$402
This Alaska Airlines deal was found by Cheapflights users on 5/3. 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.
Sun 5/249:00 am
ORD
- STS
1 stop7h 13m
Alaska Airlines
Tue 5/267:40 pm
STS
- ORD
1 stop15h 34m
Alaska Airlines
Deal found 5/3![Alaska Airlines logo]()
$411
This Alaska Airlines deal was found by Cheapflights users on 5/5. 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 9/182:18 pm
ORD
- STS
1 stop11h 36m
Alaska Airlines
Thu 9/248:07 am
STS
- ORD
1 stop13h 34m
Alaska Airlines
Deal found 5/5![Alaska Airlines logo]()
$419
This Alaska Airlines deal was found by Cheapflights users on 5/5. 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 9/42:18 pm
ORD
- STS
1 stop11h 36m
Alaska Airlines
Fri 9/116:29 pm
STS
- ORD
1 stop16h 53m
Alaska Airlines
Deal found 5/5![Alaska Airlines logo]()
$479
This Alaska Airlines deal was found by Cheapflights users on 5/3. 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 8/15:59 pm
ORD
- STS
1 stop6h 59m
Alaska Airlines
Sat 8/87:03 pm
STS
- ORD
1 stop7h 57m
Alaska Airlines
Deal found 5/3![Alaska Airlines logo]()
$499
This Alaska Airlines deal was found by Cheapflights users on 5/3. 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.
Sun 7/127:59 pm
ORD
- STS
1 stop16h 25m
Alaska Airlines
Fri 7/175:56 pm
STS
- ORD
1 stop17h 25m
Alaska Airlines
Deal found 5/3![Alaska Airlines logo]()
$499
This Alaska Airlines deal was found by Cheapflights users on 5/5. 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.
Sat 6/69:00 am
ORD
- STS
1 stop16h 28m
Alaska Airlines
Sun 6/146:26 am
STS
- ORD
1 stop15h 10m
Alaska Airlines
Deal found 5/5![Alaska Airlines logo]()
$518
This Alaska Airlines deal was found by Cheapflights users on 5/2. 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.
Sun 10/42:54 pm
ORD
- STS
1 stop9h 59m
Alaska Airlines
Fri 10/98:01 pm
STS
- ORD
1 stop8h 19m
Alaska Airlines
Deal found 5/2![Alaska Airlines logo]()
$519
This Alaska Airlines deal was found by Cheapflights users on 5/1. 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 6/106:00 am
ORD
- STS
2 stops16h 14m
Alaska Airlines
Fri 6/197:03 pm
STS
- ORD
1 stop7h 57m
Alaska Airlines
Deal found 5/1![Alaska Airlines logo]()
$541
Last-minute flights from Chicago to Santa RosaDiscover last-minute flight deals from Chicago to Santa Rosa. Data last updated May 6, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to Santa Rosa. Data last updated May 6, 2026 and is based on user searches.
This Alaska Airlines deal was found by Cheapflights users on 5/3. 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.
Sun 5/249:00 am
ORD
- STS
1 stop7h 13m
Alaska Airlines
Thu 5/287:01 am
STS
- ORD
1 stop9h 49m
Alaska Airlines
Deal found 5/3![Alaska Airlines logo]()
$399
This Travelocity deal was found by Cheapflights users on 5/1. 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.
Sun 5/317:59 pm
ORD
- STS
1 stop17h 26m
Alaska Airlines
Wed 6/1711:04 am
STS
- ORD
1 stop10h 32m
Alaska Airlines
Deal found 5/1![Alaska Airlines logo]()
$351
This American Airlines deal was found by Cheapflights users on 5/2. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/315:00 am
ORD
- STS
1 stop9h 33m
American Airlines
Wed 6/174:20 pm
STS
- ORD
1 stop6h 08m
American Airlines
Deal found 5/2![American Airlines logo]()
$401
This American Airlines deal was found by Cheapflights users on 5/1. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/15:00 am
ORD
- STS
1 stop9h 33m
American Airlines
Wed 6/312:43 pm
STS
- ORD
1 stop9h 59m
American Airlines
Deal found 5/1![American Airlines logo]()
$331
This Alaska Airlines deal was found by Cheapflights users on 5/5. 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.
Mon 6/17:59 pm
ORD
- STS
1 stop17h 26m
Alaska Airlines
Sat 6/67:40 pm
STS
- ORD
1 stop15h 34m
Alaska Airlines
Deal found 5/5![Alaska Airlines logo]()
$336
This Alaska Airlines deal was found by Cheapflights users on 5/5. 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.
Tue 6/27:49 pm
ORD
- STS
1 stop18h 28m
Alaska Airlines
Tue 6/97:00 am
STS
- ORD
2 stops13h 59m
Alaska Airlines
Deal found 5/5![Alaska Airlines logo]()
$368
This American Airlines deal was found by Cheapflights users on 5/5. 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 6/35:00 am
ORD
- STS
1 stop9h 03m
American Airlines
Tue 6/94:20 pm
STS
- ORD
1 stop6h 08m
American Airlines
Deal found 5/5![American Airlines logo]()
$313
This Alaska Airlines deal was found by Cheapflights users on 5/5. 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.
Wed 6/32:10 pm
ORD
- STS
2 stops30h 09m
Alaska Airlines
Tue 6/97:01 am
STS
- ORD
1 stop9h 49m
Alaska Airlines
Deal found 5/5![Alaska Airlines logo]()
$391
This American Airlines deal was found by Cheapflights users on 5/1. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/95:00 am
ORD
- STS
1 stop9h 05m
American Airlines
Tue 6/164:20 pm
STS
- ORD
1 stop6h 08m
American Airlines
Deal found 5/1![American Airlines logo]()
$303
This Alaska Airlines deal was found by Cheapflights users on 5/1. 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 6/99:00 am
ORD
- STS
1 stop7h 13m
Alaska Airlines
Tue 6/161:06 pm
STS
- ORD
2 stops32h 30m
Alaska Airlines
Deal found 5/1![Alaska Airlines logo]()
$392
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 May 6, 2026.
Search for one-way flight options from Chicago to Santa Rosa. Find affordable one-way fares based on user searches. Data last updated May 6, 2026.
This Alaska Airlines deal was found by Cheapflights users on 5/4. 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.
Tue 6/99:00 am
ORD
- STS
1 stop7h 13m
Alaska Airlines
Deal found 5/4![Alaska Airlines logo]()
$152
This Alaska Airlines deal was found by Cheapflights users on 5/1. 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 5/279:00 am
ORD
- STS
1 stop7h 13m
Alaska Airlines
Deal found 5/1![Alaska Airlines logo]()
$157
This Southwest deal was found by Cheapflights users on 5/4. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/2710:30 am
ORD
- STS
2 stops13h 40m
Southwest
Deal found 5/4![Southwest logo]()
$163
This American Airlines deal was found by Cheapflights users on 5/2. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/65:00 am
ORD
- STS
1 stop9h 05m
American Airlines
Deal found 5/2![American Airlines logo]()
$179
This American Airlines deal was found by Cheapflights users on 5/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/15:00 am
ORD
- STS
1 stop9h 33m
American Airlines
Deal found 5/6![American Airlines logo]()
$180
This Southwest deal was found by Cheapflights users on 5/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/11:35 pm
ORD
- STS
2 stops11h 05m
Southwest
Deal found 5/6![Southwest logo]()
$185
This Alaska Airlines deal was found by Cheapflights users on 5/1. 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 5/289:00 am
ORD
- STS
1 stop7h 13m
Alaska Airlines
Deal found 5/1![Alaska Airlines logo]()
$200
This American Airlines deal was found by Cheapflights users on 5/1. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/266:00 am
ORD
- STS
1 stop8h 03m
American Airlines
Deal found 5/1![American Airlines logo]()
$202
This American Airlines deal was found by Cheapflights users on 5/1. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/105:59 am
ORD
- STS
2 stops11h 51m
American Airlines
Deal found 5/1![American Airlines logo]()
$207
This Alaska Airlines deal was found by Cheapflights users on 5/5. 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.
Tue 8/46:00 am
ORD
- STS
1 stop7h 58m
Alaska Airlines
Deal found 5/5![Alaska Airlines logo]()
$212
This American Airlines deal was found by Cheapflights users on 5/2. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 6/75:00 am
ORD
- STS
1 stop9h 39m
American Airlines
Deal found 5/2![American Airlines logo]()
$236
This SmartFares deal was found by Cheapflights users on 5/3. 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 SmartFares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/66:01 am
ORD
- STS
1 stop10h 11m
Alaska Airlines
Deal found 5/3![Alaska Airlines logo]()
$237
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 May 6, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $303 (American Airlines) |
One-way from | $152 (Alaska Airlines) |
Popular in | February |
Cheapest in | March |
Average price | $747 |
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 May 6, 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
Mon 6/1
9:00 am-6:19 pm
2 stops35h 19m
Santa Rosa Sonoma County
Sat 6/6
7:06 am-6:50 pm
1 stop9h 44m
$402
ChicagoSanta Rosa
ORD - STS
ORDSTS
Chicago O'Hare Intl
Sun 5/24
9:00 am-2:13 pm
1 stop7h 13m
Santa Rosa Sonoma County
Tue 5/26
7:40 pm-1:14 pm
1 stop15h 34m
$411
ChicagoSanta Rosa
ORD - STS
ORDSTS
Chicago O'Hare Intl
Fri 9/18
2:18 pm-11:54 pm
1 stop11h 36m
Santa Rosa Sonoma County
Thu 9/24
8:07 am-11:41 pm
1 stop13h 34m
$419
ChicagoSanta Rosa
ORD - STS
ORDSTS
Chicago O'Hare Intl
Fri 9/4
2:18 pm-11:54 pm
1 stop11h 36m
Santa Rosa Sonoma County
Fri 9/11
6:29 pm-1:22 pm
1 stop16h 53m
$479
Quickest round-trip
ChicagoSanta Rosa
ORD - STS
ORDSTS
Chicago O'Hare Intl
Sat 8/1
5:59 pm-10:58 pm
1 stop6h 59m
Santa Rosa Sonoma County
Sat 8/8
7:03 pm-5:00 am
1 stop7h 57m
$499
ChicagoSanta Rosa
ORD - STS
ORDSTS
Chicago O'Hare Intl
Sun 7/12
7:59 pm-10:24 am
1 stop16h 25m
Santa Rosa Sonoma County
Fri 7/17
5:56 pm-1:21 pm
1 stop17h 25m
$499
ChicagoSanta Rosa
ORD - STS
ORDSTS
Chicago O'Hare Intl
Sat 6/6
9:00 am-11:28 pm
1 stop16h 28m
Santa Rosa Sonoma County
Sun 6/14
6:26 am-11:36 pm
1 stop15h 10m
$518
ChicagoSanta Rosa
ORD - STS
ORDSTS
Chicago O'Hare Intl
Sun 10/4
2:54 pm-10:53 pm
1 stop9h 59m
Santa Rosa Sonoma County
Fri 10/9
8:01 pm-6:20 am
1 stop8h 19m
$519
ChicagoSanta Rosa
ORD - STS
ORDSTS
Chicago O'Hare Intl
Wed 6/10
6:00 am-8:14 pm
2 stops16h 14m
Santa Rosa Sonoma County
Fri 6/19
7:03 pm-5:00 am
1 stop7h 57m
$541
Cheapest one-way
ChicagoSanta Rosa
ORD - STS
ORDSTS
Chicago O'Hare Intl
Sat 5/30
9:00 am-2:13 pm
1 stop7h 13m
$157
Showing 1-10 of 20 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 May.
| 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.
How much does it cost to fly round-trip from Chicago to Santa Rosa?
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 May 6, 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.
Boarding
8.1
Entertainment
7.0
Food
7.1
Comfort
7.8
Crew
8.5
Overall
7.9
Reviews
1 / 20
10.0
Excellentrobert,Feb 2026
LAS - SAN
Boarding
8.1
Entertainment
7.0
Food
7.1
Comfort
7.8
Crew
8.5
Overall
7.9
Reviews
1 / 20
10.0
Excellentrobert,Feb 2026
LAS - SAN
Boarding
8.1
Entertainment
7.0
Food
7.1
Comfort
7.8
Crew
8.5
Overall
7.9
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
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
Complete your trip
Flights by cabin class
Other flight options
Other flights from Chicago
Popular flights
Santa Rosa flight routes
Top destinations
Alternative routes for Chicago to Santa Rosa
See prices for flight routes from nearby airports that may be better suited for you.
Complete your trip
Complete your trip to Santa Rosa by adding a car rental and/or hotel reservation to your travel itinerary.
Search flights from Chicago to Santa Rosa by cabin class
Find flights from Chicago to Santa Rosa, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Chicago and Santa Rosa flights
Browse other Chicago and Santa Rosa flight options. Last updated on May 6, 2026.
Other flights from Chicago
Browse through other flights departing from Chicago. Flights are based on user searches made on Cheapflights and were last updated on May 6, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Other flights to Santa Rosa
Explore flights to Santa Rosa departing from other origins. Flights are based on user searches made on Cheapflights and were last updated on May 6, 2026.
Chicago to Santa Rosa flights
Consider these flights traveling from Chicago to Santa Rosa.
Top airline flying from Chicago to Santa Rosa
Discover the top airline 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 May 6, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$478 | Average$783 | FlexibilityNo cancel fee | On-time71% |