$155+ Cheap flights from Chicago (CHI) to Santa Rosa (STS)
This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 11/21. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — STS
Nov 30 — Dec 71
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
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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 October 31, 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 October 31, 2026.
This Alaska Airlines deal was found by Cheapflights users on 10/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/147:27 am -
1 stop18h 02m
Tue 1/197:20 pm -
1 stop15h 55m
Deal found 10/27![Alaska Airlines logo]()
$323
This Expedia deal was found by Cheapflights users on 10/28. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/172:15 pm -
1 stop26h 49m
Thu 11/196:00 am -
1 stop15h 49m
Deal found 10/28![Alaska Airlines logo]()
$353
This Alaska Airlines deal was found by Cheapflights users on 10/29. 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 11/267:26 am -
2 stops15h 43m
Thu 12/37:13 pm -
1 stop21h 47m
Deal found 10/29![Alaska Airlines logo]()
$365
This Alaska Airlines deal was found by Cheapflights users on 10/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/277:26 am -
2 stops34h 23m
Sat 12/127:13 pm -
1 stop16h 02m
Deal found 10/26![Alaska Airlines logo]()
$391
This Alaska Airlines deal was found by Cheapflights users on 10/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/147:20 am -
1 stop28h 28m
Sat 11/217:52 pm -
1 stop15h 26m
Deal found 10/27![Alaska Airlines logo]()
$403
This Delta deal was found by Cheapflights users on 10/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/149:59 am -
2 stops8h 06m
Tue 1/1912:44 pm -
1 stop7h 24m
Deal found 10/27![Delta logo]()
$405
This Alaska Airlines deal was found by Cheapflights users on 10/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/237:58 pm -
1 stop16h 15m
Wed 12/306:26 am -
1 stop15h 33m
Deal found 10/26![Alaska Airlines logo]()
$415
This Alaska Airlines deal was found by Cheapflights users on 10/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/142:13 pm -
1 stop11h 16m
Sun 1/177:00 am -
1 stop8h 59m
Deal found 10/27![Alaska Airlines logo]()
$424
This Southwest deal was found by Cheapflights users on 10/29. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/267:55 am -
2 stops10h 50m
Thu 12/36:45 am -
1 stop13h 15m
Deal found 10/29![Southwest logo]()
$440
This Southwest deal was found by Cheapflights users on 10/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/243:45 pm -
1 stop7h 45m
Wed 12/305:00 pm -
1 stop9h 25m
Deal found 10/26![Southwest logo]()
$505
This Southwest deal was found by Cheapflights users on 10/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/173:45 pm -
1 stop7h 45m
Thu 11/193:00 pm -
1 stop12h 40m
Deal found 10/28![Southwest logo]()
$580
This Southwest deal was found by Cheapflights users on 10/29. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/175:50 am -
1 stop8h 25m
Fri 11/203:10 pm -
1 stop7h 05m
Deal found 10/29![Southwest logo]()
$614
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 October 31, 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 October 31, 2026.
This Alaska Airlines deal was found by Cheapflights users on 10/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/157:27 am -
1 stop9h 38m
Tue 1/197:20 pm -
1 stop15h 55m
Deal found 10/27![Alaska Airlines logo]()
$323
This Delta deal was found by Cheapflights users on 10/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/149:59 am -
2 stops8h 06m
Tue 1/1912:44 pm -
1 stop7h 24m
Deal found 10/27![Delta logo]()
$405
This Southwest deal was found by Cheapflights users on 10/29. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/267:55 am -
2 stops10h 50m
Thu 12/36:45 am -
1 stop13h 15m
Deal found 10/29![Southwest logo]()
$440
This Alaska Airlines deal was found by Cheapflights users on 10/28. 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.
Fri 1/16:00 am -
1 stop9h 16m
Mon 1/47:13 pm -
1 stop16h 02m
Deal found 10/28![Alaska Airlines logo]()
$381
This Delta deal was found by Cheapflights users on 10/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 1/47:15 am -
1 stop6h 49m
Fri 1/812:44 pm -
1 stop7h 24m
Deal found 10/26![Delta logo]()
$439
This Alaska Airlines deal was found by Cheapflights users on 10/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/237:58 pm -
1 stop16h 15m
Wed 12/306:26 am -
1 stop15h 33m
Deal found 10/26![Alaska Airlines logo]()
$415
This Delta deal was found by Cheapflights users on 10/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/159:59 am -
2 stops8h 06m
Sun 1/1712:44 pm -
1 stop7h 24m
Deal found 10/27![Delta logo]()
$448
This Alaska Airlines deal was found by Cheapflights users on 10/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/237:58 pm -
1 stop16h 15m
Tue 12/296:26 am -
1 stop15h 33m
Deal found 10/26![Alaska Airlines logo]()
$415
This Southwest deal was found by Cheapflights users on 10/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/243:45 pm -
1 stop7h 45m
Wed 12/305:00 pm -
1 stop9h 25m
Deal found 10/26![Southwest logo]()
$505
This Alaska Airlines deal was found by Cheapflights users on 10/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/142:13 pm -
1 stop11h 16m
Sun 1/177:00 am -
1 stop8h 59m
Deal found 10/27![Alaska Airlines logo]()
$424
This Southwest deal was found by Cheapflights users on 10/30. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 1/611:45 am -
2 stops11h 40m
Tue 2/27:35 am -
1 stop6h 50m
Deal found 10/30![Southwest logo]()
$536
This Alaska Airlines deal was found by Cheapflights users on 10/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/277:26 am -
2 stops34h 23m
Sat 12/128:50 am -
2 stops18h 47m
Deal found 10/26![Alaska Airlines logo]()
$436
This Southwest deal was found by Cheapflights users on 10/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 3/206:00 am -
1 stop6h 30m
Tue 3/236:00 am -
2 stops12h 05m
Deal found 10/28![Southwest logo]()
$571
This Southwest deal was found by Cheapflights users on 10/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/173:45 pm -
1 stop7h 45m
Thu 11/193:00 pm -
1 stop12h 40m
Deal found 10/28![Southwest logo]()
$580
This Southwest deal was found by Cheapflights users on 10/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/277:20 am -
2 stops9h 15m
Sat 12/126:30 am -
2 stops9h 25m
Deal found 10/26![Southwest logo]()
$580
Last-minute flights from Chicago to Santa RosaDiscover last-minute flight deals from Chicago to Santa Rosa. Data last updated October 31, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to Santa Rosa. Data last updated October 31, 2026 and is based on user searches.
This Southwest deal was found by Cheapflights users on 10/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/115:50 am -
1 stop8h 25m
Sun 11/154:10 pm -
1 stop10h 15m
Deal found 10/27![Southwest logo]()
$674
This Alaska Airlines deal was found by Cheapflights users on 10/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/147:20 am -
1 stop28h 28m
Sat 11/217:52 pm -
1 stop15h 26m
Deal found 10/27![Alaska Airlines logo]()
$403
This Southwest deal was found by Cheapflights users on 10/30. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/146:05 am -
1 stop7h 10m
Wed 11/183:00 pm -
1 stop7h 15m
Deal found 10/30![Southwest logo]()
$669
This Expedia deal was found by Cheapflights users on 10/28. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/172:15 pm -
1 stop26h 49m
Thu 11/196:00 am -
1 stop15h 49m
Deal found 10/28![Alaska Airlines logo]()
$353
This Expedia deal was found by Cheapflights users on 10/29. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/177:20 am -
1 stop9h 44m
Fri 11/204:43 pm -
1 stop11h 13m
Deal found 10/29![Alaska Airlines logo]()
$442
This Southwest deal was found by Cheapflights users on 10/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/173:45 pm -
1 stop7h 45m
Thu 11/193:00 pm -
1 stop12h 40m
Deal found 10/28![Southwest logo]()
$580
This Southwest deal was found by Cheapflights users on 10/29. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/175:50 am -
1 stop8h 25m
Fri 11/203:10 pm -
1 stop7h 05m
Deal found 10/29![Southwest logo]()
$614
This American Airlines deal was found by Cheapflights users on 10/28. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/196:05 pm -
1 stop7h 54m
Wed 11/2512:49 pm -
1 stop8h 19m
Deal found 10/28![American Airlines logo]()
$460
This Alaska Airlines deal was found by Cheapflights users on 10/29. 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 11/267:26 am -
2 stops15h 43m
Thu 12/37:13 pm -
1 stop21h 47m
Deal found 10/29![Alaska Airlines logo]()
$365
This Southwest deal was found by Cheapflights users on 10/29. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/267:55 am -
2 stops10h 50m
Thu 12/36:45 am -
1 stop13h 15m
Deal found 10/29![Southwest logo]()
$440
This Alaska Airlines deal was found by Cheapflights users on 10/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/277:26 am -
2 stops34h 23m
Sat 12/127:13 pm -
1 stop16h 02m
Deal found 10/26![Alaska Airlines logo]()
$391
This Southwest deal was found by Cheapflights users on 10/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/275:55 am -
1 stop9h 45m
Sat 12/126:30 am -
2 stops12h 20m
Deal found 10/26![Southwest logo]()
$636
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 October 31, 2026.
Search for one-way flight options from Chicago to Santa Rosa. Find affordable one-way fares based on user searches. Data last updated October 31, 2026.
This Delta deal was found by Cheapflights users on 10/30. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/219:59 am -
2 stops8h 07m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/30![Delta logo]()
$155
This Expedia deal was found by Cheapflights users on 10/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 1/197:40 am -
1 stop17h 17m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/27![Alaska Airlines logo]()
$167
This Priceline deal was found by Cheapflights users on 10/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 1/212:13 pm -
1 stop10h 44m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/27![Alaska Airlines logo]()
$202
This Delta deal was found by Cheapflights users on 10/29. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 1/94:00 pm -
1 stop8h 08m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/29![Delta logo]()
$220
This Delta deal was found by Cheapflights users on 10/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 1/111:59 pm -
2 stops10h 04m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/26![Delta logo]()
$225
This Alaska Airlines deal was found by Cheapflights users on 10/30. 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 4/67:20 am -
1 stop15h 30m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/30![Alaska Airlines logo]()
$227
This Alaska Airlines deal was found by Cheapflights users on 10/30. 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 11/147:20 am -
1 stop9h 13m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/30![Alaska Airlines logo]()
$242
This Southwest deal was found by Cheapflights users on 10/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 1/2111:55 am -
2 stops11h 30m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/27![Southwest logo]()
$246
This Delta deal was found by Cheapflights users on 10/30. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 2/287:30 am -
1 stop6h 24m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/30![Delta logo]()
$248
This Delta deal was found by Cheapflights users on 10/29. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/97:30 am -
1 stop6h 24m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/29![Delta logo]()
$253
This Delta deal was found by Cheapflights users on 10/29. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 2/171:35 pm -
2 stops10h 13m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/29![Delta logo]()
$255
This Delta deal was found by Cheapflights users on 10/28. 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.
Wed 12/29:37 am -
2 stops8h 28m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/28![Delta logo]()
$255
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 October 31, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $323 (Alaska Airlines) |
One-way from | $155 (Delta) |
Popular in | February |
Cheapest in | March |
Average price | $605 |
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 October 31, 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
Sat 11/21
9:59 am-4:06 pm
2 stops8h 07m
Santa Rosa Sonoma County
Wed 12/31
12:00 am-2:00 am
Nonstop0h 00m
$155
ChicagoSanta Rosa
ORD Chicago O'Hare Intl - STS Santa Rosa Sonoma County
ORDSTS
Chicago O'Hare Intl
Sat 1/9
4:00 pm-10:08 pm
1 stop8h 08m
Santa Rosa Sonoma County
Wed 12/31
12:00 am-2:00 am
Nonstop0h 00m
$220
ChicagoSanta Rosa
ORD Chicago O'Hare Intl - STS Santa Rosa Sonoma County
ORDSTS
Chicago O'Hare Intl
Fri 1/22
7:15 am-12:04 pm
1 stop6h 49m
Santa Rosa Sonoma County
Wed 12/31
12:00 am-2:00 am
Nonstop0h 00m
$220
ChicagoSanta Rosa
ORD Chicago O'Hare Intl - STS Santa Rosa Sonoma County
ORDSTS
Chicago O'Hare Intl
Sat 1/23
4:00 pm-10:08 pm
1 stop8h 08m
Santa Rosa Sonoma County
Wed 12/31
12:00 am-2:00 am
Nonstop0h 00m
$220
ChicagoSanta Rosa
ORD Chicago O'Hare Intl - STS Santa Rosa Sonoma County
ORDSTS
Chicago O'Hare Intl
Mon 1/11
1:45 pm-10:03 pm
2 stops10h 18m
Santa Rosa Sonoma County
Wed 12/31
12:00 am-2:00 am
Nonstop0h 00m
$225
ChicagoSanta Rosa
ORD Chicago O'Hare Intl - STS Santa Rosa Sonoma County
ORDSTS
Chicago O'Hare Intl
Sat 2/20
1:35 pm-10:08 pm
2 stops10h 33m
Santa Rosa Sonoma County
Wed 12/31
12:00 am-2:00 am
Nonstop0h 00m
$225
ChicagoSanta Rosa
MDW Chicago Midway - STS Santa Rosa Sonoma County
MDWSTS
Chicago Midway
Tue 1/19
12:44 pm-10:03 pm
2 stops11h 19m
Santa Rosa Sonoma County
Wed 12/31
12:00 am-2:00 am
Nonstop0h 00m
$225
ChicagoSanta Rosa
MDW Chicago Midway - STS Santa Rosa Sonoma County
MDWSTS
Chicago Midway
Mon 1/11
1:59 pm-10:03 pm
2 stops10h 04m
Santa Rosa Sonoma County
Wed 12/31
12:00 am-2:00 am
Nonstop0h 00m
$225
ChicagoSanta Rosa
MDW Chicago Midway - STS Santa Rosa Sonoma County
MDWSTS
Chicago Midway
Thu 1/21
11:55 am-9:25 pm
2 stops11h 30m
Santa Rosa Sonoma County
Wed 12/31
12:00 am-2:00 am
Nonstop0h 00m
$246
Quickest round-trip
ChicagoSanta Rosa
ORD Chicago O'Hare Intl - STS Santa Rosa Sonoma County
ORDSTS
Chicago O'Hare Intl
Sun 2/28
7:30 am-11:54 am
1 stop6h 24m
Santa Rosa Sonoma County
Wed 12/31
12:00 am-2:00 am
Nonstop0h 00m
$248
Showing 1-10 of 35 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 October.
| 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
MDW-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
MDW-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 February is currently the most expensive (average of $749). 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 October 31, 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
Boarding
8.1
Comfort
7.8
Crew
8.5
Overall
7.9
Entertainment
7.0
Reviews
1 / 20
2.0
MediocreChris,Aug 2026
GEG - SFO
Food
7.0
Boarding
8.1
Comfort
7.8
Crew
8.5
Overall
7.9
Entertainment
7.0
Reviews
1 / 20
2.0
MediocreChris,Aug 2026
GEG - SFO
Food
7.0
Boarding
8.1
Comfort
7.8
Crew
8.5
Overall
7.9
Entertainment
7.0
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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Chicago and Santa Rosa flights
Browse other Chicago and Santa Rosa flight options. Last updated on October 31, 2026.
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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 October 31, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$285 | Average$439 | FlexibilityNo cancel fee | On-time75% | |
| Cheapest$412 | Average$541 | FlexibilityNo cancel fee | On-time71% |