$152+ 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 6/3. Fares are subject to change and may not be available on all flights or dates of travel.
STS — CHI
Jun 6 — Jun 131
Round-trip
1 adult, Economy
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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 May 7, 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 May 7, 2026.
This American Airlines deal was found by Cheapflights users on 5/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/264:20 pm
STS
- ORD
1 stop6h 10m
American Airlines
Wed 6/35:00 am
ORD
- STS
1 stop9h 03m
American Airlines
Deal found 5/3![American Airlines logo]()
$303
This American Airlines deal was found by Cheapflights users on 5/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/2712:43 pm
STS
- ORD
1 stop9h 59m
American Airlines
Sat 5/305:00 am
ORD
- STS
1 stop9h 33m
American Airlines
Deal found 5/3![American Airlines logo]()
$308
This Alaska Airlines deal was found by Cheapflights users on 5/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/237:06 am
STS
- ORD
1 stop9h 44m
Alaska Airlines
Wed 5/279:00 am
ORD
- STS
1 stop7h 13m
Alaska Airlines
Deal found 5/2![Alaska Airlines logo]()
$313
This Alaska Airlines deal was found by Cheapflights users on 5/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/268:26 pm
STS
- ORD
1 stop7h 54m
Alaska Airlines
Wed 5/279:00 am
ORD
- STS
1 stop7h 13m
Alaska Airlines
Deal found 5/2![Alaska Airlines logo]()
$329
This Alaska Airlines deal was found by Cheapflights users on 5/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/27:01 am
STS
- ORD
1 stop9h 49m
Alaska Airlines
Wed 6/36:00 am
ORD
- STS
1 stop8h 17m
Alaska Airlines
Deal found 5/4![Alaska Airlines logo]()
$330
This American Airlines deal was found by Cheapflights users on 5/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/44:20 pm
STS
- ORD
1 stop6h 08m
American Airlines
Tue 6/165:59 am
ORD
- STS
1 stop8h 06m
American Airlines
Deal found 5/4![American Airlines logo]()
$331
This American Airlines deal was found by Cheapflights users on 5/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/304:20 pm
STS
- ORD
1 stop6h 10m
American Airlines
Sat 6/65:59 am
ORD
- STS
1 stop8h 06m
American Airlines
Deal found 5/6![American Airlines logo]()
$335
This Expedia deal was found by Cheapflights users on 5/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/37:01 am
STS
- ORD
1 stop9h 49m
Alaska Airlines
Mon 6/87:59 pm
ORD
- STS
1 stop17h 26m
Alaska Airlines
Deal found 5/6![Alaska Airlines logo]()
$336
This Alaska Airlines deal was found by Cheapflights users on 5/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/47:01 am
STS
- ORD
1 stop9h 49m
Alaska Airlines
Tue 6/167:59 pm
ORD
- STS
1 stop16h 25m
Alaska Airlines
Deal found 5/6![Alaska Airlines logo]()
$341
This American Airlines deal was found by Cheapflights users on 5/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/51:09 pm
STS
- ORD
1 stop9h 19m
American Airlines
Tue 6/165:00 am
ORD
- STS
1 stop9h 39m
American Airlines
Deal found 5/4![American Airlines logo]()
$351
This Alaska Airlines deal was found by Cheapflights users on 5/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/237:06 am
STS
- ORD
1 stop9h 44m
Alaska Airlines
Thu 5/289:00 am
ORD
- STS
1 stop7h 13m
Alaska Airlines
Deal found 5/2![Alaska Airlines logo]()
$356
This Alaska Airlines deal was found by Cheapflights users on 5/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/12:52 pm
STS
- ORD
1 stop6h 49m
Alaska Airlines
Sat 9/56:00 am
ORD
- STS
1 stop8h 54m
Alaska Airlines
Deal found 5/6![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 May 7, 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 May 7, 2026.
This Alaska Airlines deal was found by Cheapflights users on 5/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/237:06 am
STS
- ORD
1 stop9h 44m
Alaska Airlines
Wed 5/279:00 am
ORD
- STS
1 stop7h 13m
Alaska Airlines
Deal found 5/2![Alaska Airlines logo]()
$313
This Alaska Airlines deal was found by Cheapflights users on 5/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/247:01 am
STS
- ORD
1 stop9h 49m
Alaska Airlines
Wed 5/279:00 am
ORD
- STS
1 stop7h 13m
Alaska Airlines
Deal found 5/2![Alaska Airlines logo]()
$356
This Alaska Airlines deal was found by Cheapflights users on 5/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/267:01 am
STS
- ORD
1 stop9h 49m
Alaska Airlines
Sat 5/309:00 am
ORD
- STS
1 stop7h 13m
Alaska Airlines
Deal found 5/4![Alaska Airlines logo]()
$356
This Alaska Airlines deal was found by Cheapflights users on 5/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/21:09 pm
STS
- ORD
1 stop8h 50m
Alaska Airlines
Wed 6/32:10 pm
ORD
- STS
1 stop11h 40m
Alaska Airlines
Deal found 5/6![Alaska Airlines logo]()
$368
This Alaska Airlines deal was found by Cheapflights users on 5/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/61:17 pm
STS
- ORD
1 stop8h 42m
Alaska Airlines
Sat 6/135:59 pm
ORD
- STS
1 stop6h 59m
Alaska Airlines
Deal found 5/6![Alaska Airlines logo]()
$423
This Alaska Airlines deal was found by Cheapflights users on 5/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/317:01 am
STS
- ORD
1 stop9h 49m
Alaska Airlines
Sat 6/135:59 pm
ORD
- STS
1 stop6h 59m
Alaska Airlines
Deal found 5/3![Alaska Airlines logo]()
$439
This Alaska Airlines deal was found by Cheapflights users on 5/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/76:13 am
STS
- ORD
1 stop10h 50m
Alaska Airlines
Wed 9/96:01 am
ORD
- STS
1 stop10h 11m
Alaska Airlines
Deal found 5/6![Alaska Airlines logo]()
$458
This Alaska Airlines deal was found by Cheapflights users on 5/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/68:26 pm
STS
- ORD
1 stop7h 54m
Alaska Airlines
Fri 6/126:00 am
ORD
- STS
1 stop7h 58m
Alaska Airlines
Deal found 5/6![Alaska Airlines logo]()
$459
This Alaska Airlines deal was found by Cheapflights users on 5/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/317:01 am
STS
- ORD
1 stop9h 49m
Alaska Airlines
Fri 6/126:00 am
ORD
- STS
1 stop7h 58m
Alaska Airlines
Deal found 5/3![Alaska Airlines logo]()
$475
Last-minute flights from Santa Rosa to ChicagoDiscover last-minute flight deals from Santa Rosa to Chicago. Data last updated May 7, 2026 and is based on user searches.
Discover last-minute flight deals from Santa Rosa to Chicago. Data last updated May 7, 2026 and is based on user searches.
This Alaska Airlines deal was found by Cheapflights users on 5/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/237:06 am
STS
- ORD
1 stop9h 44m
Alaska Airlines
Wed 5/279:00 am
ORD
- STS
1 stop7h 13m
Alaska Airlines
Deal found 5/2![Alaska Airlines logo]()
$313
This Alaska Airlines deal was found by Cheapflights users on 5/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/237:06 am
STS
- ORD
1 stop9h 44m
Alaska Airlines
Thu 5/289:00 am
ORD
- STS
1 stop7h 13m
Alaska Airlines
Deal found 5/2![Alaska Airlines logo]()
$356
This American Airlines deal was found by Cheapflights users on 5/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/264:20 pm
STS
- ORD
1 stop6h 10m
American Airlines
Wed 6/35:00 am
ORD
- STS
1 stop9h 03m
American Airlines
Deal found 5/3![American Airlines logo]()
$303
This Alaska Airlines deal was found by Cheapflights users on 5/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/268:26 pm
STS
- ORD
1 stop7h 54m
Alaska Airlines
Wed 5/279:00 am
ORD
- STS
1 stop7h 13m
Alaska Airlines
Deal found 5/2![Alaska Airlines logo]()
$329
This American Airlines deal was found by Cheapflights users on 5/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/2712:43 pm
STS
- ORD
1 stop9h 59m
American Airlines
Sat 5/305:00 am
ORD
- STS
1 stop9h 33m
American Airlines
Deal found 5/3![American Airlines logo]()
$308
This American Airlines deal was found by Cheapflights users on 5/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/304:20 pm
STS
- ORD
1 stop6h 10m
American Airlines
Sat 6/65:59 am
ORD
- STS
1 stop8h 06m
American Airlines
Deal found 5/6![American Airlines logo]()
$335
This Alaska Airlines deal was found by Cheapflights users on 5/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/27:01 am
STS
- ORD
1 stop9h 49m
Alaska Airlines
Wed 6/36:00 am
ORD
- STS
1 stop8h 17m
Alaska Airlines
Deal found 5/4![Alaska Airlines logo]()
$330
This Expedia deal was found by Cheapflights users on 5/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/37:01 am
STS
- ORD
1 stop9h 49m
Alaska Airlines
Mon 6/87:59 pm
ORD
- STS
1 stop17h 26m
Alaska Airlines
Deal found 5/6![Alaska Airlines logo]()
$336
This American Airlines deal was found by Cheapflights users on 5/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/44:20 pm
STS
- ORD
1 stop6h 08m
American Airlines
Tue 6/165:59 am
ORD
- STS
1 stop8h 06m
American Airlines
Deal found 5/4![American Airlines logo]()
$331
This Alaska Airlines deal was found by Cheapflights users on 5/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/47:01 am
STS
- ORD
1 stop9h 49m
Alaska Airlines
Tue 6/167:59 pm
ORD
- STS
1 stop16h 25m
Alaska Airlines
Deal found 5/6![Alaska Airlines logo]()
$341
This American Airlines deal was found by Cheapflights users on 5/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/51:09 pm
STS
- ORD
1 stop9h 19m
American Airlines
Tue 6/165:00 am
ORD
- STS
1 stop9h 39m
American Airlines
Deal found 5/4![American Airlines logo]()
$351
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 May 7, 2026.
Search for one-way flight options from Santa Rosa to Chicago. Find affordable one-way fares based on user searches. Data last updated May 7, 2026.
This Alaska Airlines deal was found by Cheapflights users on 5/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/31:09 pm
STS
- ORD
1 stop7h 50m
Alaska Airlines
Deal found 5/4![Alaska Airlines logo]()
$152
This Alaska Airlines deal was found by Cheapflights users on 5/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/271:09 pm
STS
- ORD
1 stop7h 50m
Alaska Airlines
Deal found 5/6![Alaska Airlines logo]()
$157
This Southwest deal was found by Cheapflights users on 5/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/26:00 am
STS
- ORD
2 stops14h 55m
Southwest
Deal found 5/6![Southwest logo]()
$168
This Alaska Airlines deal was found by Cheapflights users on 5/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/268:26 pm
STS
- ORD
1 stop7h 54m
Alaska Airlines
Deal found 5/2![Alaska Airlines logo]()
$179
This Alaska Airlines deal was found by Cheapflights users on 5/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/281:09 pm
STS
- ORD
1 stop8h 50m
Alaska Airlines
Deal found 5/6![Alaska Airlines logo]()
$180
This American Airlines deal was found by Cheapflights users on 5/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/164:20 pm
STS
- ORD
1 stop6h 08m
American Airlines
Deal found 5/3![American Airlines logo]()
$202
This American Airlines deal was found by Cheapflights users on 5/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/271:03 pm
STS
- ORD
2 stops9h 39m
American Airlines
Deal found 5/4![American Airlines logo]()
$207
This American Airlines deal was found by Cheapflights users on 5/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/301:03 pm
STS
- ORD
2 stops9h 39m
American Airlines
Deal found 5/6![American Airlines logo]()
$212
This Alaska Airlines deal was found by Cheapflights users on 5/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/157:00 am
STS
- ORD
1 stop7h 50m
Alaska Airlines
Deal found 5/6![Alaska Airlines logo]()
$230
This Alaska Airlines deal was found by Cheapflights users on 5/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/2011:04 am
STS
- ORD
1 stop6h 33m
Alaska Airlines
Deal found 5/3![Alaska Airlines logo]()
$240
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 May 7, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $303 (American Airlines) |
One-way from | $152 (American Airlines) |
Popular in | October |
Cheapest in | November |
Average price | $408 |
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 2,558,603 searches. Data last updated May 7, 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 - ORD
STSORD
Santa Rosa Sonoma County
Sat 5/23
7:06 am-6:50 pm
1 stop9h 44m
Chicago O'Hare Intl
Wed 5/27
9:00 am-2:13 pm
1 stop7h 13m
$313
Santa RosaChicago
STS - ORD
STSORD
Santa Rosa Sonoma County
Sun 5/24
7:01 am-6:50 pm
1 stop9h 49m
Chicago O'Hare Intl
Wed 5/27
9:00 am-2:13 pm
1 stop7h 13m
$356
Santa RosaChicago
STS - ORD
STSORD
Santa Rosa Sonoma County
Tue 5/26
7:01 am-6:50 pm
1 stop9h 49m
Chicago O'Hare Intl
Sat 5/30
9:00 am-2:13 pm
1 stop7h 13m
$356
Santa RosaChicago
STS - ORD
STSORD
Santa Rosa Sonoma County
Tue 6/2
1:09 pm-11:59 pm
1 stop8h 50m
Chicago O'Hare Intl
Wed 6/3
2:10 pm-11:50 pm
1 stop11h 40m
$368
Quickest round-trip
Santa RosaChicago
STS - ORD
STSORD
Santa Rosa Sonoma County
Sat 6/6
1:17 pm-11:59 pm
1 stop8h 42m
Chicago O'Hare Intl
Sat 6/13
5:59 pm-10:58 pm
1 stop6h 59m
$423
Santa RosaChicago
STS - ORD
STSORD
Santa Rosa Sonoma County
Sun 5/31
7:01 am-6:50 pm
1 stop9h 49m
Chicago O'Hare Intl
Sat 6/13
5:59 pm-10:58 pm
1 stop6h 59m
$439
Santa RosaChicago
STS - ORD
STSORD
Santa Rosa Sonoma County
Mon 9/7
6:13 am-7:03 pm
1 stop10h 50m
Chicago O'Hare Intl
Wed 9/9
6:01 am-2:12 pm
1 stop10h 11m
$458
Santa RosaChicago
STS - ORD
STSORD
Santa Rosa Sonoma County
Sat 6/6
8:26 pm-6:20 am
1 stop7h 54m
Chicago O'Hare Intl
Fri 6/12
6:00 am-11:58 am
1 stop7h 58m
$459
Santa RosaChicago
STS - ORD
STSORD
Santa Rosa Sonoma County
Sun 5/31
7:01 am-6:50 pm
1 stop9h 49m
Chicago O'Hare Intl
Fri 6/12
6:00 am-11:58 am
1 stop7h 58m
$475
Cheapest one-way
Quickest one-way
Santa RosaChicago
STS - ORD
STSORD
Santa Rosa Sonoma County
Tue 6/2
4:20 pm-12:30 am
1 stop6h 10m
$157
Showing 1-10 of 21 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?
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 May 7, 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.
Comfort
7.8
Overall
7.9
Boarding
8.1
Entertainment
7.0
Food
7.1
Crew
8.5
Reviews
1 / 20
10.0
ExcellentFranzi,Mar 2026
SFO - PDX
Comfort
7.8
Overall
7.9
Boarding
8.1
Entertainment
7.0
Food
7.1
Crew
8.5
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
Hammond
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 May 7, 2026.
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Santa Rosa and Chicago flights
Browse other Santa Rosa and Chicago flight options. Last updated on May 7, 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 May 7, 2026.
Popular flight searches
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 2,558,603 searches. Data last updated May 7, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$276 | Average$408 | FlexibilityNo cancel fee | On-time75% |