$150+ Cheap flights from Santa Rosa (STS) to Chicago (CHI)
This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 10/28. Fares are subject to change and may not be available on all flights or dates of travel.
STS — CHI
Sep 23 — Sep 301
Round-trip
1 adult, Economy
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Find cheap flights from Santa Rosa to Chicago with Cheapflights
1. Tell us where you want to go
Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”2. Select your favorite providers
We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.3. Compare prices and book
Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.Cheap flight deals from Santa Rosa to Chicago
Cheapest
Best
Last-minute
One-way
Cheapest flights from Santa Rosa to ChicagoExplore the most affordable flight options available from Santa Rosa to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on August 24, 2026.
Explore the most affordable flight options available from Santa Rosa to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on August 24, 2026.
This Alaska Airlines deal was found by Cheapflights users on 8/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/66:16 am -
1 stop11h 05m
Thu 9/102:18 pm -
1 stop11h 36m
Deal found 8/22![Alaska Airlines logo]()
$299
This Alaska Airlines deal was found by Cheapflights users on 8/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/164:38 pm -
1 stop18h 39m
Wed 11/187:20 am -
1 stop17h 05m
Deal found 8/20![Alaska Airlines logo]()
$301
This Delta deal was found by Cheapflights users on 8/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/2811:21 am -
1 stop8h 44m
Sat 10/317:00 am -
2 stops11h 05m
Deal found 8/19![Delta logo]()
$304
This Alaska Airlines deal was found by Cheapflights users on 8/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/56:16 am -
1 stop11h 05m
Wed 9/92:18 pm -
1 stop11h 36m
Deal found 8/21![Alaska Airlines logo]()
$324
This American Airlines deal was found by Cheapflights users on 8/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/161:18 pm -
1 stop8h 20m
Mon 12/214:29 pm -
1 stop9h 09m
Deal found 8/20![American Airlines logo]()
$329
This Alaska Airlines deal was found by Cheapflights users on 8/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/2010:50 am -
1 stop24h 35m
Sat 10/242:21 pm -
1 stop7h 29m
Deal found 8/19![Alaska Airlines logo]()
$331
This Alaska Airlines deal was found by Cheapflights users on 8/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/126:16 am -
1 stop11h 05m
Mon 9/148:17 pm -
1 stop29h 37m
Deal found 8/22![Alaska Airlines logo]()
$333
This Alaska Airlines deal was found by Cheapflights users on 8/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/186:47 pm -
1 stop22h 34m
Mon 9/218:17 pm -
1 stop15h 37m
Deal found 8/19![Alaska Airlines logo]()
$343
This Travelocity deal was found by Cheapflights users on 8/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Travelocity is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/306:16 am -
2 stops15h 43m
Tue 10/67:20 am -
1 stop9h 32m
Deal found 8/20![Alaska Airlines logo]()
$346
This Alaska Airlines deal was found by Cheapflights users on 8/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/186:47 pm -
1 stop16h 35m
Sat 9/194:08 pm -
1 stop7h 51m
Deal found 8/19![Alaska Airlines logo]()
$352
This Alaska Airlines deal was found by Cheapflights users on 8/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/108:40 am -
1 stop8h 19m
Thu 11/122:15 pm -
1 stop10h 10m
Deal found 8/20![Alaska Airlines logo]()
$359
Best flights from Santa Rosa to ChicagoDiscover carefully curated flight deals from Santa Rosa to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated August 24, 2026.
Discover carefully curated flight deals from Santa Rosa to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated August 24, 2026.
This Alaska Airlines deal was found by Cheapflights users on 8/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/66:16 am -
1 stop11h 05m
Thu 9/102:18 pm -
1 stop11h 36m
Deal found 8/22![Alaska Airlines logo]()
$299
This American Airlines deal was found by Cheapflights users on 8/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/181:18 pm -
1 stop8h 15m
Thu 11/265:00 am -
1 stop9h 54m
Deal found 8/19![American Airlines logo]()
$399
This Alaska Airlines deal was found by Cheapflights users on 8/23. 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 9/226:47 pm -
1 stop16h 35m
Mon 9/288:17 pm -
1 stop15h 37m
Deal found 8/23![Alaska Airlines logo]()
$299
This Alaska Airlines deal was found by Cheapflights users on 8/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/56:16 am -
1 stop11h 05m
Wed 9/92:18 pm -
1 stop11h 36m
Deal found 8/21![Alaska Airlines logo]()
$324
This Alaska Airlines deal was found by Cheapflights users on 8/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/2010:50 am -
1 stop24h 35m
Sat 10/242:21 pm -
1 stop7h 29m
Deal found 8/19![Alaska Airlines logo]()
$331
This Alaska Airlines deal was found by Cheapflights users on 8/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/126:16 am -
1 stop11h 05m
Mon 9/148:17 pm -
1 stop29h 37m
Deal found 8/22![Alaska Airlines logo]()
$333
This Alaska Airlines deal was found by Cheapflights users on 8/23. 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 1/267:00 am -
1 stop8h 59m
Sat 1/302:11 pm -
1 stop7h 04m
Deal found 8/23![Alaska Airlines logo]()
$359
This Alaska Airlines deal was found by Cheapflights users on 8/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/117:00 am -
1 stop8h 37m
Thu 11/122:15 pm -
1 stop10h 10m
Deal found 8/20![Alaska Airlines logo]()
$370
This Alaska Airlines deal was found by Cheapflights users on 8/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/176:16 am -
1 stop15h 43m
Sun 9/207:20 am -
1 stop28h 34m
Deal found 8/21![Alaska Airlines logo]()
$403
This Alaska Airlines deal was found by Cheapflights users on 8/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/86:19 am -
1 stop15h 40m
Tue 10/132:21 pm -
1 stop7h 29m
Deal found 8/21![Alaska Airlines logo]()
$412
Last-minute flights from Santa Rosa to ChicagoDiscover last-minute flight deals from Santa Rosa to Chicago. Data last updated August 24, 2026 and is based on user searches.
Discover last-minute flight deals from Santa Rosa to Chicago. Data last updated August 24, 2026 and is based on user searches.
This Alaska Airlines deal was found by Cheapflights users on 8/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/56:16 am -
1 stop11h 05m
Wed 9/92:18 pm -
1 stop11h 36m
Deal found 8/21![Alaska Airlines logo]()
$324
This American Airlines deal was found by Cheapflights users on 8/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/512:39 pm -
1 stop7h 34m
Sat 9/126:59 am -
1 stop7h 39m
Deal found 8/22![American Airlines logo]()
$399
This Alaska Airlines deal was found by Cheapflights users on 8/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/66:16 am -
1 stop11h 05m
Thu 9/102:18 pm -
1 stop11h 36m
Deal found 8/22![Alaska Airlines logo]()
$299
This Alaska Airlines deal was found by Cheapflights users on 8/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/126:16 am -
1 stop11h 05m
Mon 9/148:17 pm -
1 stop29h 37m
Deal found 8/22![Alaska Airlines logo]()
$333
This Alaska Airlines deal was found by Cheapflights users on 8/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/176:16 am -
1 stop15h 43m
Mon 9/218:17 pm -
1 stop29h 37m
Deal found 8/24![Alaska Airlines logo]()
$373
This Alaska Airlines deal was found by Cheapflights users on 8/23. 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 9/176:16 am -
1 stop15h 43m
Sun 9/207:20 am -
1 stop18h 34m
Deal found 8/23![Alaska Airlines logo]()
$403
This Alaska Airlines deal was found by Cheapflights users on 8/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/186:16 am -
1 stop15h 43m
Mon 9/218:17 pm -
1 stop29h 37m
Deal found 8/24![Alaska Airlines logo]()
$385
This Alaska Airlines deal was found by Cheapflights users on 8/23. 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 9/226:16 am -
1 stop11h 05m
Mon 9/287:20 am -
2 stops11h 19m
Deal found 8/23![Alaska Airlines logo]()
$366
This Orbitz deal was found by Cheapflights users on 8/23. 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 9/246:16 am -
1 stop11h 05m
Sat 9/262:18 pm -
1 stop21h 36m
Deal found 8/23![Alaska Airlines logo]()
$359
This Travelocity deal was found by Cheapflights users on 8/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Travelocity is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/306:16 am -
2 stops15h 43m
Tue 10/67:20 am -
1 stop9h 32m
Deal found 8/20![Alaska Airlines logo]()
$346
One-way flights from Santa Rosa to ChicagoSearch for one-way flight options from Santa Rosa to Chicago. Find affordable one-way fares based on user searches. Data last updated August 24, 2026.
Search for one-way flight options from Santa Rosa to Chicago. Find affordable one-way fares based on user searches. Data last updated August 24, 2026.
This Delta deal was found by Cheapflights users on 8/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/2811:21 am -
1 stop8h 44m
Deal found 8/19![Delta logo]()
$150
This Expedia deal was found by Cheapflights users on 8/23. 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 9/116:47 pm -
1 stop16h 35m
Deal found 8/23![Alaska Airlines logo]()
$155
This Alaska Airlines deal was found by Cheapflights users on 8/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/276:19 am -
1 stop29h 06m
Deal found 8/24![Alaska Airlines logo]()
$157
This Delta deal was found by Cheapflights users on 8/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/711:21 am -
1 stop8h 44m
Deal found 8/21![Delta logo]()
$180
This Alaska Airlines deal was found by Cheapflights users on 8/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/16:47 pm -
1 stop16h 35m
Deal found 8/20![Alaska Airlines logo]()
$185
This American Airlines deal was found by Cheapflights users on 8/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/181:08 pm -
1 stop8h 35m
Deal found 8/20![American Airlines logo]()
$191
This Alaska Airlines deal was found by Cheapflights users on 8/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/211:40 pm -
2 stops27h 41m
Deal found 8/22![Alaska Airlines logo]()
$195
This Alaska Airlines deal was found by Cheapflights users on 8/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/86:19 am -
1 stop15h 40m
Deal found 8/21![Alaska Airlines logo]()
$197
This American Airlines deal was found by Cheapflights users on 8/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/271:10 pm -
2 stops8h 49m
Deal found 8/24![American Airlines logo]()
$205
This Alaska Airlines deal was found by Cheapflights users on 8/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/96:19 am -
1 stop15h 40m
Deal found 8/21![Alaska Airlines logo]()
$209
This Delta deal was found by Cheapflights users on 8/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/2711:29 am -
1 stop8h 18m
Deal found 8/20![Delta logo]()
$230
This Travelocity deal was found by Cheapflights users on 8/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Travelocity is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/236:16 am -
2 stops15h 43m
Deal found 8/24![Alaska Airlines logo]()
$232
Find flight deals from Santa Rosa to Chicago
Discover tips and strategies to find the most affordable flight options for your journey from Santa Rosa (STS) to Chicago (CHI). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated August 24, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $299 (Alaska Airlines) |
One-way from | $150 (Delta) |
Popular in | October |
Cheapest in | November |
Average price | $458 |
Cheapflights Fare Finder
Customize your flight search to find flights from Santa Rosa to Chicago that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 7,457,451 searches. Data last updated August 24, 2026.
Use the filters below to find and compare flights from Santa Rosa to Chicago that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
Santa RosaChicago
STS Santa Rosa Sonoma County - ORD Chicago O'Hare Intl
STSORD
Santa Rosa Sonoma County
Sun 9/6
6:16 am-7:21 pm
1 stop11h 05m
Chicago O'Hare Intl
Thu 9/10
2:18 pm-11:54 pm
1 stop11h 36m
$299
Santa RosaChicago
STS Santa Rosa Sonoma County - ORD Chicago O'Hare Intl
STSORD
Santa Rosa Sonoma County
Tue 9/22
6:47 pm-1:22 pm
1 stop16h 35m
Chicago O'Hare Intl
Mon 9/28
8:17 pm-9:54 am
1 stop15h 37m
$299
Santa RosaChicago
STS Santa Rosa Sonoma County - ORD Chicago O'Hare Intl
STSORD
Santa Rosa Sonoma County
Sat 9/5
6:16 am-7:21 pm
1 stop11h 05m
Chicago O'Hare Intl
Wed 9/9
2:18 pm-11:54 pm
1 stop11h 36m
$324
Santa RosaChicago
STS Santa Rosa Sonoma County - ORD Chicago O'Hare Intl
STSORD
Santa Rosa Sonoma County
Tue 10/20
10:50 am-1:25 pm
1 stop24h 35m
Chicago O'Hare Intl
Sat 10/24
2:21 pm-7:50 pm
1 stop7h 29m
$331
Santa RosaChicago
STS Santa Rosa Sonoma County - ORD Chicago O'Hare Intl
STSORD
Santa Rosa Sonoma County
Sat 9/12
6:16 am-7:21 pm
1 stop11h 05m
Chicago O'Hare Intl
Mon 9/14
8:17 pm-11:54 pm
1 stop29h 37m
$333
Quickest round-trip
Santa RosaChicago
STS Santa Rosa Sonoma County - ORD Chicago O'Hare Intl
STSORD
Santa Rosa Sonoma County
Tue 1/26
7:00 am-5:59 pm
1 stop8h 59m
Chicago O'Hare Intl
Sat 1/30
2:11 pm-7:15 pm
1 stop7h 04m
$359
Santa RosaChicago
STS Santa Rosa Sonoma County - ORD Chicago O'Hare Intl
STSORD
Santa Rosa Sonoma County
Wed 11/11
7:00 am-5:37 pm
1 stop8h 37m
Chicago O'Hare Intl
Thu 11/12
2:15 pm-10:25 pm
1 stop10h 10m
$370
Santa RosaChicago
STS Santa Rosa Sonoma County - ORD Chicago O'Hare Intl
STSORD
Santa Rosa Sonoma County
Wed 11/18
1:18 pm-11:33 pm
1 stop8h 15m
Chicago O'Hare Intl
Thu 11/26
5:00 am-12:54 pm
1 stop9h 54m
$399
Santa RosaChicago
STS Santa Rosa Sonoma County - ORD Chicago O'Hare Intl
STSORD
Santa Rosa Sonoma County
Thu 9/17
6:16 am-11:59 pm
1 stop15h 43m
Chicago O'Hare Intl
Sun 9/20
7:20 am-9:54 am
1 stop28h 34m
$403
Santa RosaChicago
STS Santa Rosa Sonoma County - ORD Chicago O'Hare Intl
STSORD
Santa Rosa Sonoma County
Thu 10/8
6:19 am-11:59 pm
1 stop15h 40m
Chicago O'Hare Intl
Tue 10/13
2:21 pm-7:50 pm
1 stop7h 29m
$412
Showing 1-10 of 20 resultsSorted by cheapest first
- Most accurate provider: When it comes to deals on Santa Rosa-Chicago flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Santa Rosa-Chicago flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Santa Rosa-Chicago flight searches over the past month and is updated monthly.
- Most trusted provider: When it comes to deals on Santa Rosa-Chicago 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 Santa Rosa-Chicago 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 Santa Rosa to Chicago
Have a flexible travel schedule? Discover the best time to fly to Chicago from Santa Rosa with our price prediction graph.
STS-CHI
STS-ORD
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.
Cheapflights Insights
Everything you need to know about your flight from Santa Rosa to Chicago
STS-CHI
STS-ORD
How much does it cost to fly round-trip from Santa Rosa to Chicago?
Airfare is below average for this route at the moment.
Santa Rosa to Chicago flights typically cost between $424 and $606 in September.The cheapest round-trip price found within the last 5 days was $299 on Alaska Airlines (Sep 6-Sep 10).
Reviews of airlines servicing Chicago
Get insights into the airlines that provide service to Chicago. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Chicago. Reviews last updated August 24, 2026.
See what other customers who have flown with Alaska Airlines from Santa Rosa to Chicago have to say. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
Boarding
8.1
Food
7.0
Entertainment
7.0
Crew
8.5
Comfort
7.8
Overall
7.9
Reviews
1 / 20
10.0
ExcellentFranzi,Mar 2026
SFO - PDX
Boarding
8.1
Food
7.0
Entertainment
7.0
Crew
8.5
Comfort
7.8
Overall
7.9
Reviews
1 / 20
10.0
ExcellentFranzi,Mar 2026
SFO - PDX
Related info for your journey
Find useful and relevant information for your journey from Santa Rosa to Chicago. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
Traveling to a place near Chicago?
Book flights to Chicago if you plan to visit one of these locationsBenton Harbor
Lansing
Merrillville
Valparaiso
Hammond
Saint Joseph
Porter
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Alternative routes for Santa Rosa to Chicago
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Other flights to Chicago
Explore flights to Chicago departing from other origins. Flights are based on user searches made on Cheapflights and were last updated on August 24, 2026.
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Santa Rosa and Chicago flights
Browse other Santa Rosa and Chicago flight options. Last updated on August 24, 2026.
Other flights from Santa Rosa
Browse through other flights departing from Santa Rosa. Flights are based on user searches made on Cheapflights and were last updated on August 24, 2026.
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Check out other popular destinations found by fellow travelers in 2026
Top airline flying from Santa Rosa to Chicago
Discover the top airline that operate flights from Santa Rosa to Chicago. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 7,457,451 searches. Data last updated August 24, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$276 | Average$398 | FlexibilityNo cancel fee | On-time75% |