$150+ 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 1/30. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — STS
Oct 2 — Oct 91
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
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 September 2, 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 September 2, 2026.
This Alaska Airlines deal was found by Cheapflights users on 8/28. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/12:18 pm -
1 stop11h 36m
Mon 10/54:35 pm -
1 stop18h 50m
Deal found 8/28![Alaska Airlines logo]()
$299
This Delta deal was found by Cheapflights users on 8/31. Clicking the “Pick Dates” 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 10/69:59 am -
2 stops8h 06m
Tue 10/1311:21 am -
1 stop8h 44m
Deal found 8/31![Delta logo]()
$304
This Alaska Airlines deal was found by Cheapflights users on 8/30. 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.
Thu 9/242:18 pm -
1 stop11h 36m
Tue 9/296:16 am -
1 stop11h 05m
Deal found 8/30![Alaska Airlines logo]()
$329
This Alaska Airlines deal was found by Cheapflights users on 9/1. 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 10/242:21 pm -
1 stop7h 29m
Wed 10/287:00 am -
1 stop7h 50m
Deal found 9/1![Alaska Airlines logo]()
$340
This Alaska Airlines deal was found by Cheapflights users on 9/1. 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 11/162:15 pm -
1 stop10h 10m
Mon 11/236:08 am -
1 stop15h 41m
Deal found 9/1![Alaska Airlines logo]()
$341
This Expedia deal was found by Cheapflights users on 8/30. 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.
Thu 9/102:18 pm -
1 stop11h 36m
Sat 9/126:16 am -
1 stop11h 05m
Deal found 8/30![Alaska Airlines logo]()
$349
This Alaska Airlines deal was found by Cheapflights users on 9/1. 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 11/122:15 pm -
1 stop10h 10m
Sun 11/156:00 am -
1 stop29h 17m
Deal found 9/1![Alaska Airlines logo]()
$351
This Alaska Airlines deal was found by Cheapflights users on 8/28. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/242:18 pm -
1 stop11h 36m
Mon 9/286:16 am -
1 stop11h 05m
Deal found 8/28![Alaska Airlines logo]()
$359
This Orbitz deal was found by Cheapflights users on 8/30. 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 Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/247:20 am -
2 stops11h 19m
Wed 9/306:47 pm -
1 stop16h 35m
Deal found 8/30![Alaska Airlines logo]()
$362
This Alaska Airlines deal was found by Cheapflights users on 8/30. 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.
Sat 9/267:20 am -
1 stop8h 52m
Mon 9/281:40 pm -
2 stops27h 41m
Deal found 8/30![Alaska Airlines logo]()
$363
This Alaska Airlines deal was found by Cheapflights users on 8/31. Clicking the “Pick Dates” 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 9/102:18 pm -
1 stop11h 36m
Thu 9/245:34 pm -
1 stop10h 46m
Deal found 8/31![Alaska Airlines logo]()
$365
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 September 2, 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 September 2, 2026.
This Alaska Airlines deal was found by Cheapflights users on 8/31. Clicking the “Pick Dates” 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 10/12:18 pm -
1 stop11h 36m
Tue 10/64:35 pm -
1 stop18h 50m
Deal found 8/31![Alaska Airlines logo]()
$299
This Delta deal was found by Cheapflights users on 8/28. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 1/199:30 am -
2 stops14h 18m
Tue 1/2612:39 pm -
1 stop7h 14m
Deal found 8/28![Delta logo]()
$382
This Alaska Airlines deal was found by Cheapflights users on 8/29. Clicking the “Pick Dates” 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 11/117:20 am -
1 stop7h 42m
Wed 12/23:18 pm -
1 stop6h 41m
Deal found 8/29![Alaska Airlines logo]()
$299
This Alaska Airlines deal was found by Cheapflights users on 8/29. Clicking the “Pick Dates” 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 11/122:15 pm -
1 stop10h 10m
Wed 12/23:18 pm -
1 stop6h 41m
Deal found 8/29![Alaska Airlines logo]()
$299
This Alaska Airlines deal was found by Cheapflights users on 8/28. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/12:18 pm -
1 stop11h 36m
Mon 10/54:35 pm -
1 stop18h 50m
Deal found 8/28![Alaska Airlines logo]()
$299
This Alaska Airlines deal was found by Cheapflights users on 9/1. 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 10/242:21 pm -
1 stop7h 29m
Wed 10/287:00 am -
1 stop7h 50m
Deal found 9/1![Alaska Airlines logo]()
$340
This Alaska Airlines deal was found by Cheapflights users on 8/28. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 1/197:40 am -
1 stop8h 53m
Sat 1/237:00 am -
1 stop8h 59m
Deal found 8/28![Alaska Airlines logo]()
$359
This Alaska Airlines deal was found by Cheapflights users on 8/28. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/248:17 pm -
1 stop29h 37m
Mon 9/281:40 pm -
2 stops27h 41m
Deal found 8/28![Alaska Airlines logo]()
$385
Last-minute flights from Chicago to Santa RosaDiscover last-minute flight deals from Chicago to Santa Rosa. Data last updated September 2, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to Santa Rosa. Data last updated September 2, 2026 and is based on user searches.
This Expedia deal was found by Cheapflights users on 8/30. 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.
Thu 9/102:18 pm -
1 stop11h 36m
Sat 9/126:16 am -
1 stop11h 05m
Deal found 8/30![Alaska Airlines logo]()
$349
This Alaska Airlines deal was found by Cheapflights users on 8/31. Clicking the “Pick Dates” 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 9/102:18 pm -
1 stop11h 36m
Thu 9/245:34 pm -
1 stop10h 46m
Deal found 8/31![Alaska Airlines logo]()
$365
This Expedia deal was found by Cheapflights users on 8/31. Clicking the “Pick Dates” 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 9/227:20 am -
2 stops11h 19m
Wed 9/236:16 am -
1 stop11h 05m
Deal found 8/31![Alaska Airlines logo]()
$372
This Alaska Airlines deal was found by Cheapflights users on 8/30. 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.
Thu 9/242:18 pm -
1 stop11h 36m
Tue 9/296:16 am -
1 stop11h 05m
Deal found 8/30![Alaska Airlines logo]()
$329
This Alaska Airlines deal was found by Cheapflights users on 8/28. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/242:18 pm -
1 stop11h 36m
Mon 9/286:16 am -
1 stop11h 05m
Deal found 8/28![Alaska Airlines logo]()
$359
This Orbitz deal was found by Cheapflights users on 8/30. 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 Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/247:20 am -
2 stops11h 19m
Wed 9/306:47 pm -
1 stop16h 35m
Deal found 8/30![Alaska Airlines logo]()
$362
This Alaska Airlines deal was found by Cheapflights users on 8/30. 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.
Sat 9/267:20 am -
1 stop8h 52m
Mon 9/281:40 pm -
2 stops27h 41m
Deal found 8/30![Alaska Airlines logo]()
$363
This Alaska Airlines deal was found by Cheapflights users on 8/28. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/12:18 pm -
1 stop11h 36m
Mon 10/54:35 pm -
1 stop18h 50m
Deal found 8/28![Alaska Airlines logo]()
$299
This Alaska Airlines deal was found by Cheapflights users on 8/28. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/12:18 pm -
1 stop11h 36m
Sun 10/46:19 am -
1 stop15h 40m
Deal found 8/28![Alaska Airlines logo]()
$381
This Delta deal was found by Cheapflights users on 8/31. Clicking the “Pick Dates” 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 10/69:59 am -
2 stops8h 06m
Tue 10/1311:21 am -
1 stop8h 44m
Deal found 8/31![Delta logo]()
$304
This Alaska Airlines deal was found by Cheapflights users on 9/1. 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 10/242:21 pm -
1 stop7h 29m
Wed 10/287:00 am -
1 stop7h 50m
Deal found 9/1![Alaska Airlines logo]()
$340
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 September 2, 2026.
Search for one-way flight options from Chicago to Santa Rosa. Find affordable one-way fares based on user searches. Data last updated September 2, 2026.
This Priceline deal was found by Cheapflights users on 9/1. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/32:21 pm -
1 stop7h 29m
Deal found 9/1![Alaska Airlines logo]()
$150
This Delta deal was found by Cheapflights users on 8/31. Clicking the “Pick Dates” 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 11/79:59 am -
2 stops8h 06m
Deal found 8/31![Delta logo]()
$155
This Alaska Airlines deal was found by Cheapflights users on 9/1. 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.
Fri 9/113:52 pm -
1 stop8h 07m
Deal found 9/1![Alaska Airlines logo]()
$175
This Alaska Airlines deal was found by Cheapflights users on 9/2. 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 10/137:20 am -
1 stop9h 32m
Deal found 9/2![Alaska Airlines logo]()
$180
This Alaska Airlines deal was found by Cheapflights users on 8/30. 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.
Mon 10/196:00 am -
1 stop9h 06m
Deal found 8/30![Alaska Airlines logo]()
$191
This Alaska Airlines deal was found by Cheapflights users on 9/1. 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 9/103:52 pm -
1 stop8h 07m
Deal found 9/1![Alaska Airlines logo]()
$200
This Alaska Airlines deal was found by Cheapflights users on 8/30. 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.
Thu 9/248:17 pm -
1 stop29h 37m
Deal found 8/30![Alaska Airlines logo]()
$207
This American Airlines deal was found by Cheapflights users on 8/30. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/276:50 am -
1 stop8h 01m
Deal found 8/30![American Airlines logo]()
$219
This Alaska Airlines deal was found by Cheapflights users on 8/30. 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.
Sun 10/47:49 pm -
1 stop16h 10m
Deal found 8/30![Alaska Airlines logo]()
$227
This Booking.com deal was found by Cheapflights users on 8/30. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/47:00 am -
2 stops11h 29m
Deal found 8/30![Alaska Airlines logo]()
$233
This Expedia deal was found by Cheapflights users on 9/1. 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 10/217:00 am -
2 stops14h 50m
Deal found 9/1![Alaska Airlines logo]()
$237
This Alaska Airlines deal was found by Cheapflights users on 9/2. 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.
Mon 10/127:49 pm -
1 stop16h 10m
Deal found 9/2![Alaska Airlines logo]()
$242
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 September 2, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $299 (Alaska Airlines) |
One-way from | $150 (Priceline) |
Popular in | February |
Cheapest in | March |
Average price | $481 |
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 7,457,451 searches. Data last updated September 2, 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 Chicago O'Hare Intl - STS Santa Rosa Sonoma County
ORDSTS
Chicago O'Hare Intl
Thu 10/1
2:18 pm-11:54 pm
1 stop11h 36m
Santa Rosa Sonoma County
Tue 10/6
4:35 pm-1:25 pm
1 stop18h 50m
$299
Quickest round-trip
ChicagoSanta Rosa
ORD Chicago O'Hare Intl - STS Santa Rosa Sonoma County
ORDSTS
Chicago O'Hare Intl
Wed 11/11
7:20 am-1:02 pm
1 stop7h 42m
Santa Rosa Sonoma County
Wed 12/2
3:18 pm-11:59 pm
1 stop6h 41m
$299
ChicagoSanta Rosa
ORD Chicago O'Hare Intl - STS Santa Rosa Sonoma County
ORDSTS
Chicago O'Hare Intl
Thu 11/12
2:15 pm-10:25 pm
1 stop10h 10m
Santa Rosa Sonoma County
Wed 12/2
3:18 pm-11:59 pm
1 stop6h 41m
$299
ChicagoSanta Rosa
ORD Chicago O'Hare Intl - STS Santa Rosa Sonoma County
ORDSTS
Chicago O'Hare Intl
Thu 10/1
2:18 pm-11:54 pm
1 stop11h 36m
Santa Rosa Sonoma County
Mon 10/5
4:35 pm-1:25 pm
1 stop18h 50m
$299
ChicagoSanta Rosa
ORD Chicago O'Hare Intl - STS Santa Rosa Sonoma County
ORDSTS
Chicago O'Hare Intl
Sat 10/24
2:21 pm-7:50 pm
1 stop7h 29m
Santa Rosa Sonoma County
Wed 10/28
7:00 am-4:50 pm
1 stop7h 50m
$340
ChicagoSanta Rosa
ORD Chicago O'Hare Intl - STS Santa Rosa Sonoma County
ORDSTS
Chicago O'Hare Intl
Tue 1/19
7:40 am-2:33 pm
1 stop8h 53m
Santa Rosa Sonoma County
Sat 1/23
7:00 am-5:59 pm
1 stop8h 59m
$359
ChicagoSanta Rosa
ORD Chicago O'Hare Intl - STS Santa Rosa Sonoma County
ORDSTS
Chicago O'Hare Intl
Tue 1/19
9:30 am-9:48 pm
2 stops14h 18m
Santa Rosa Sonoma County
Tue 1/26
12:39 pm-9:53 pm
1 stop7h 14m
$382
ChicagoSanta Rosa
ORD Chicago O'Hare Intl - STS Santa Rosa Sonoma County
ORDSTS
Chicago O'Hare Intl
Thu 9/24
8:17 pm-11:54 pm
1 stop29h 37m
Santa Rosa Sonoma County
Mon 9/28
1:40 pm-7:21 pm
2 stops27h 41m
$385
Cheapest one-way
Quickest one-way
ChicagoSanta Rosa
ORD Chicago O'Hare Intl - STS Santa Rosa Sonoma County
ORDSTS
Chicago O'Hare Intl
Sat 1/30
7:30 am-11:54 am
1 stop6h 24m
$150
ChicagoSanta Rosa
ORD Chicago O'Hare Intl - STS Santa Rosa Sonoma County
ORDSTS
Chicago O'Hare Intl
Thu 10/8
7:49 pm-11:00 pm
1 stop29h 11m
$207
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 September.
| 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, December is the cheapest month in which you can book a flight from Chicago to Santa Rosa (average of $239). Flying from Chicago to Santa Rosa in November is currently the most expensive (average of $885). 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 September 2, 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.
Food
7.0
Entertainment
7.0
Overall
7.9
Boarding
8.1
Comfort
7.8
Crew
8.5
Reviews
1 / 20
2.0
MediocreChris,Aug 2026
GEG - SFO
Food
7.0
Entertainment
7.0
Overall
7.9
Boarding
8.1
Comfort
7.8
Crew
8.5
Reviews
1 / 20
2.0
MediocreChris,Aug 2026
GEG - SFO
Food
7.0
Entertainment
7.0
Overall
7.9
Boarding
8.1
Comfort
7.8
Crew
8.5
Reviews
1 / 20
2.0
MediocreChris,Aug 2026
GEG - SFO
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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Alternative routes for Chicago to Santa Rosa
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Complete your trip
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Chicago and Santa Rosa flights
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Other flights to Santa Rosa
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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 7,457,451 searches. Data last updated September 2, 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% |