$190+ 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 8/29. Fares are subject to change and may not be available on all flights or dates of travel.
STS — CHI
Aug 1 — Aug 81
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
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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
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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 July 2, 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 July 2, 2026.
This Alaska Airlines deal was found by Cheapflights users on 6/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/2910:34 am
STS
- ORD
1 stop6h 47m
Alaska Airlines
Wed 9/307:20 am
ORD
- STS
1 stop8h 52m
Alaska Airlines
Deal found 6/28![Alaska Airlines logo]()
$379
This Alaska Airlines deal was found by Cheapflights users on 7/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/510:34 am
STS
- ORD
1 stop6h 47m
Alaska Airlines
Tue 9/87:20 am
ORD
- STS
1 stop18h 34m
Alaska Airlines
Deal found 7/1![Alaska Airlines logo]()
$381
This Alaska Airlines deal was found by Cheapflights users on 7/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/316:47 pm
STS
- ORD
1 stop16h 35m
Alaska Airlines
Tue 9/82:18 pm
ORD
- STS
1 stop11h 36m
Alaska Airlines
Deal found 7/1![Alaska Airlines logo]()
$383
This Delta deal was found by Cheapflights users on 6/29. 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 10/2011:29 am
STS
- ORD
1 stop8h 31m
Delta
Sat 10/245:30 am
ORD
- STS
2 stops12h 38m
Delta
Deal found 6/29![Delta logo]()
$384
This Alaska Airlines deal was found by Cheapflights users on 6/28. 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.
Sat 8/157:03 pm
STS
- ORD
1 stop7h 57m
Alaska Airlines
Wed 8/266:01 am
ORD
- STS
1 stop10h 11m
Alaska Airlines
Deal found 6/28![Alaska Airlines logo]()
$390
This Alaska Airlines deal was found by Cheapflights users on 7/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/177:03 pm
STS
- ORD
1 stop7h 57m
Alaska Airlines
Tue 8/256:01 am
ORD
- STS
1 stop19h 53m
Alaska Airlines
Deal found 7/1![Alaska Airlines logo]()
$392
This Alaska Airlines deal was found by Cheapflights users on 6/28. 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.
Mon 9/2810:34 am
STS
- ORD
1 stop6h 47m
Alaska Airlines
Tue 9/293:52 pm
ORD
- STS
1 stop8h 07m
Alaska Airlines
Deal found 6/28![Alaska Airlines logo]()
$394
This Priceline deal was found by Cheapflights users on 7/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/37:03 pm
STS
- ORD
1 stop7h 57m
Alaska Airlines
Tue 8/47:20 am
ORD
- STS
1 stop7h 06m
Alaska Airlines
Deal found 7/1![Alaska Airlines logo]()
$395
This Alaska Airlines deal was found by Cheapflights users on 7/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/310:34 am
STS
- ORD
1 stop6h 47m
Alaska Airlines
Tue 9/87:20 am
ORD
- STS
1 stop18h 34m
Alaska Airlines
Deal found 7/1![Alaska Airlines logo]()
$396
This Alaska Airlines deal was found by Cheapflights users on 6/29. 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.
Fri 10/237:00 am
STS
- ORD
1 stop9h 20m
Alaska Airlines
Sat 10/242:17 pm
ORD
- STS
1 stop7h 30m
Alaska Airlines
Deal found 6/29![Alaska Airlines logo]()
$399
This Alaska Airlines deal was found by Cheapflights users on 7/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/247:03 pm
STS
- ORD
1 stop7h 57m
Alaska Airlines
Tue 7/287:20 am
ORD
- STS
1 stop7h 06m
Alaska Airlines
Deal found 7/1![Alaska Airlines logo]()
$401
This Delta deal was found by Cheapflights users on 6/29. 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.
Sun 10/1811:29 am
STS
- ORD
1 stop8h 31m
Delta
Wed 10/289:59 am
ORD
- STS
2 stops8h 09m
Delta
Deal found 6/29![Delta logo]()
$404
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 July 2, 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 July 2, 2026.
This Alaska Airlines deal was found by Cheapflights users on 7/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/2210:34 am
STS
- ORD
1 stop6h 47m
Alaska Airlines
Thu 8/276:01 am
ORD
- STS
1 stop10h 11m
Alaska Airlines
Deal found 7/1![Alaska Airlines logo]()
$394
This Alaska Airlines deal was found by Cheapflights users on 6/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/110:34 am
STS
- ORD
1 stop6h 47m
Alaska Airlines
Sat 10/33:49 pm
ORD
- STS
1 stop8h 07m
Alaska Airlines
Deal found 6/28![Alaska Airlines logo]()
$394
This Alaska Airlines deal was found by Cheapflights users on 7/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/247:03 pm
STS
- ORD
1 stop7h 57m
Alaska Airlines
Tue 7/287:20 am
ORD
- STS
1 stop7h 06m
Alaska Airlines
Deal found 7/1![Alaska Airlines logo]()
$401
This Alaska Airlines deal was found by Cheapflights users on 6/27. 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.
Wed 8/57:03 pm
STS
- ORD
1 stop7h 57m
Alaska Airlines
Sat 8/85:59 pm
ORD
- STS
1 stop6h 59m
Alaska Airlines
Deal found 6/27![Alaska Airlines logo]()
$405
This Alaska Airlines deal was found by Cheapflights users on 7/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/2410:34 am
STS
- ORD
1 stop6h 47m
Alaska Airlines
Sat 8/296:01 am
ORD
- STS
1 stop10h 11m
Alaska Airlines
Deal found 7/1![Alaska Airlines logo]()
$405
This Alaska Airlines deal was found by Cheapflights users on 6/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/137:03 pm
STS
- ORD
1 stop7h 57m
Alaska Airlines
Sat 8/155:59 pm
ORD
- STS
1 stop6h 59m
Alaska Airlines
Deal found 6/30![Alaska Airlines logo]()
$405
This Alaska Airlines deal was found by Cheapflights users on 6/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/297:03 am
STS
- ORD
1 stop8h 58m
Alaska Airlines
Sun 10/46:00 am
ORD
- STS
1 stop9h 06m
Alaska Airlines
Deal found 6/28![Alaska Airlines logo]()
$429
This Alaska Airlines deal was found by Cheapflights users on 7/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/283:40 pm
STS
- ORD
2 stops12h 40m
Alaska Airlines
Sat 10/316:00 am
ORD
- STS
1 stop9h 06m
Alaska Airlines
Deal found 7/1![Alaska Airlines logo]()
$437
This Alaska Airlines deal was found by Cheapflights users on 7/2. 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.
Fri 7/247:03 pm
STS
- ORD
1 stop7h 57m
Alaska Airlines
Sat 7/255:59 pm
ORD
- STS
1 stop6h 59m
Alaska Airlines
Deal found 7/2![Alaska Airlines logo]()
$450
This Alaska Airlines deal was found by Cheapflights users on 7/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/57:03 pm
STS
- ORD
1 stop7h 57m
Alaska Airlines
Tue 8/116:00 am
ORD
- STS
2 stops11h 55m
Alaska Airlines
Deal found 7/1![Alaska Airlines logo]()
$461
This Alaska Airlines deal was found by Cheapflights users on 6/28. 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 8/147:03 pm
STS
- ORD
1 stop7h 57m
Alaska Airlines
Mon 8/176:00 am
ORD
- STS
1 stop7h 58m
Alaska Airlines
Deal found 6/28![Alaska Airlines logo]()
$464
Last-minute flights from Santa Rosa to ChicagoDiscover last-minute flight deals from Santa Rosa to Chicago. Data last updated July 2, 2026 and is based on user searches.
Discover last-minute flight deals from Santa Rosa to Chicago. Data last updated July 2, 2026 and is based on user searches.
This Alaska Airlines deal was found by Cheapflights users on 7/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/247:03 pm
STS
- ORD
1 stop7h 57m
Alaska Airlines
Tue 7/287:20 am
ORD
- STS
1 stop7h 06m
Alaska Airlines
Deal found 7/1![Alaska Airlines logo]()
$401
This Priceline deal was found by Cheapflights users on 7/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/37:03 pm
STS
- ORD
1 stop7h 57m
Alaska Airlines
Tue 8/47:20 am
ORD
- STS
1 stop7h 06m
Alaska Airlines
Deal found 7/1![Alaska Airlines logo]()
$395
This Alaska Airlines deal was found by Cheapflights users on 6/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/137:03 pm
STS
- ORD
1 stop7h 57m
Alaska Airlines
Tue 8/187:20 am
ORD
- STS
1 stop7h 06m
Alaska Airlines
Deal found 6/30![Alaska Airlines logo]()
$405
This Alaska Airlines deal was found by Cheapflights users on 6/28. 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.
Sat 8/157:03 pm
STS
- ORD
1 stop7h 57m
Alaska Airlines
Tue 8/256:01 am
ORD
- STS
1 stop10h 11m
Alaska Airlines
Deal found 6/28![Alaska Airlines logo]()
$390
This Alaska Airlines deal was found by Cheapflights users on 7/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/177:03 pm
STS
- ORD
1 stop7h 57m
Alaska Airlines
Tue 8/256:01 am
ORD
- STS
1 stop19h 53m
Alaska Airlines
Deal found 7/1![Alaska Airlines logo]()
$392
This Alaska Airlines deal was found by Cheapflights users on 6/28. 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.
Wed 8/1910:34 am
STS
- ORD
1 stop6h 47m
Alaska Airlines
Wed 8/262:22 pm
ORD
- STS
1 stop8h 36m
Alaska Airlines
Deal found 6/28![Alaska Airlines logo]()
$379
This Alaska Airlines deal was found by Cheapflights users on 6/29. 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.
Sat 8/2210:34 am
STS
- ORD
1 stop6h 47m
Alaska Airlines
Mon 8/246:01 am
ORD
- STS
1 stop19h 53m
Alaska Airlines
Deal found 6/29![Alaska Airlines logo]()
$406
This Alaska Airlines deal was found by Cheapflights users on 7/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/3010:34 am
STS
- ORD
1 stop6h 47m
Alaska Airlines
Wed 9/97:20 am
ORD
- STS
1 stop8h 52m
Alaska Airlines
Deal found 7/1![Alaska Airlines logo]()
$399
This Alaska Airlines deal was found by Cheapflights users on 7/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/316:47 pm
STS
- ORD
1 stop16h 35m
Alaska Airlines
Wed 9/97:20 am
ORD
- STS
1 stop8h 52m
Alaska Airlines
Deal found 7/1![Alaska Airlines logo]()
$381
This Alaska Airlines deal was found by Cheapflights users on 7/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/316:47 pm
STS
- ORD
1 stop16h 35m
Alaska Airlines
Tue 9/82:18 pm
ORD
- STS
1 stop11h 36m
Alaska Airlines
Deal found 7/1![Alaska Airlines logo]()
$383
This Alaska Airlines deal was found by Cheapflights users on 7/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/316:47 pm
STS
- ORD
1 stop16h 35m
Alaska Airlines
Thu 9/36:01 am
ORD
- STS
1 stop10h 11m
Alaska Airlines
Deal found 7/1![Alaska Airlines logo]()
$396
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 July 2, 2026.
Search for one-way flight options from Santa Rosa to Chicago. Find affordable one-way fares based on user searches. Data last updated July 2, 2026.
This Alaska Airlines deal was found by Cheapflights users on 7/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/2910:34 am
STS
- ORD
1 stop6h 47m
Alaska Airlines
Deal found 7/1![Alaska Airlines logo]()
$190
This Alaska Airlines deal was found by Cheapflights users on 7/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/246:13 am
STS
- ORD
1 stop29h 09m
Alaska Airlines
Deal found 7/1![Alaska Airlines logo]()
$197
This Alaska Airlines deal was found by Cheapflights users on 7/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/117:03 pm
STS
- ORD
1 stop7h 57m
Alaska Airlines
Deal found 7/1![Alaska Airlines logo]()
$201
This Alaska Airlines deal was found by Cheapflights users on 6/28. 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.
Mon 8/3110:34 am
STS
- ORD
1 stop6h 47m
Alaska Airlines
Deal found 6/28![Alaska Airlines logo]()
$205
This Alaska Airlines deal was found by Cheapflights users on 7/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/216:47 pm
STS
- ORD
1 stop16h 22m
Alaska Airlines
Deal found 7/1![Alaska Airlines logo]()
$206
This Delta deal was found by Cheapflights users on 6/27. 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.
Fri 11/611:29 am
STS
- ORD
1 stop8h 31m
Delta
Deal found 6/27![Delta logo]()
$210
This Alaska Airlines deal was found by Cheapflights users on 7/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/196:47 pm
STS
- ORD
1 stop16h 35m
Alaska Airlines
Deal found 7/1![Alaska Airlines logo]()
$217
This Alaska Airlines deal was found by Cheapflights users on 7/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/66:26 am
STS
- ORD
1 stop15h 10m
Alaska Airlines
Deal found 7/1![Alaska Airlines logo]()
$220
This Alaska Airlines deal was found by Cheapflights users on 6/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/291:40 pm
STS
- ORD
2 stops27h 41m
Alaska Airlines
Deal found 6/28![Alaska Airlines logo]()
$223
This Alaska Airlines deal was found by Cheapflights users on 6/29. 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.
Tue 7/281:06 pm
STS
- ORD
2 stops32h 30m
Alaska Airlines
Deal found 6/29![Alaska Airlines logo]()
$231
This Alaska Airlines deal was found by Cheapflights users on 6/29. 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.
Fri 8/216:47 pm
STS
- ORD
1 stop16h 35m
Alaska Airlines
Deal found 6/29![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 July 2, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $379 (Alaska Airlines) |
One-way from | $190 (Alaska Airlines) |
Popular in | October |
Cheapest in | November |
Average price | $569 |
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 July 2, 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 8/22
10:34 am-7:21 pm
1 stop6h 47m
Chicago O'Hare Intl
Thu 8/27
6:01 am-2:12 pm
1 stop10h 11m
$394
Quickest round-trip
Santa RosaChicago
STS - ORD
STSORD
Santa Rosa Sonoma County
Thu 10/1
10:34 am-7:21 pm
1 stop6h 47m
Chicago O'Hare Intl
Sat 10/3
3:49 pm-9:56 pm
1 stop8h 07m
$394
Santa RosaChicago
STS - ORD
STSORD
Santa Rosa Sonoma County
Fri 7/24
7:03 pm-5:00 am
1 stop7h 57m
Chicago O'Hare Intl
Tue 7/28
7:20 am-12:26 pm
1 stop7h 06m
$401
Santa RosaChicago
STS - ORD
STSORD
Santa Rosa Sonoma County
Wed 8/5
7:03 pm-5:00 am
1 stop7h 57m
Chicago O'Hare Intl
Sat 8/8
5:59 pm-10:58 pm
1 stop6h 59m
$405
Santa RosaChicago
STS - ORD
STSORD
Santa Rosa Sonoma County
Mon 8/24
10:34 am-7:21 pm
1 stop6h 47m
Chicago O'Hare Intl
Sat 8/29
6:01 am-2:12 pm
1 stop10h 11m
$405
Santa RosaChicago
STS - ORD
STSORD
Santa Rosa Sonoma County
Thu 8/13
7:03 pm-5:00 am
1 stop7h 57m
Chicago O'Hare Intl
Sat 8/15
5:59 pm-10:58 pm
1 stop6h 59m
$405
Santa RosaChicago
STS - ORD
STSORD
Santa Rosa Sonoma County
Tue 9/29
7:03 am-6:01 pm
1 stop8h 58m
Chicago O'Hare Intl
Sun 10/4
6:00 am-1:06 pm
1 stop9h 06m
$429
Santa RosaChicago
STS - ORD
STSORD
Santa Rosa Sonoma County
Wed 10/28
3:40 pm-6:20 am
2 stops12h 40m
Chicago O'Hare Intl
Sat 10/31
6:00 am-1:06 pm
1 stop9h 06m
$437
Santa RosaChicago
STS - ORD
STSORD
Santa Rosa Sonoma County
Fri 7/24
7:03 pm-5:00 am
1 stop7h 57m
Chicago O'Hare Intl
Sat 7/25
5:59 pm-10:58 pm
1 stop6h 59m
$450
Santa RosaChicago
STS - ORD
STSORD
Santa Rosa Sonoma County
Wed 8/5
7:03 pm-5:00 am
1 stop7h 57m
Chicago O'Hare Intl
Tue 8/11
6:00 am-3:55 pm
2 stops11h 55m
$461
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
No data available for this route at this time. Please check back soon.
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 July 2, 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.
Food
7.1
Boarding
8.1
Entertainment
7.0
Crew
8.5
Comfort
7.8
Overall
7.9
Reviews
1 / 20
10.0
ExcellentFranzi,Mar 2026
SFO - PDX
Food
7.1
Boarding
8.1
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
Hammond
Lansing
Merrillville
Valparaiso
Porter
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Santa Rosa and Chicago flights
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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 July 2, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$276 | Average$350 | FlexibilityNo cancel fee | On-time75% |