$156+ Cheap flights from Santa Rosa (STS) to Chicago (CHI)
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 11/2. Fares are subject to change and may not be available on all flights or dates of travel.
STS — CHI
Nov 7 — Nov 141
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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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 October 8, 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 October 8, 2026.
This Southwest deal was found by Cheapflights users on 10/5. 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 10/271:30 pm -
1 stop6h 45m
Wed 10/286:05 am -
1 stop7h 00m
Deal found 10/5![Southwest logo]()
$311
This Alaska Airlines deal was found by Cheapflights users on 10/7. 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 12/26:40 am -
1 stop9h 09m
Sat 12/59:00 am -
1 stop10h 56m
Deal found 10/7![Alaska Airlines logo]()
$311
This Delta deal was found by Cheapflights users on 10/7. 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 12/211:27 am -
1 stop8h 29m
Sat 12/59:59 am -
2 stops8h 06m
Deal found 10/7![Delta logo]()
$316
This Southwest deal was found by Cheapflights users on 10/7. 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 11/103:00 pm -
1 stop12h 40m
Wed 11/185:50 am -
1 stop8h 25m
Deal found 10/7![Southwest logo]()
$317
This Delta deal was found by Cheapflights users on 10/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/284:49 pm -
2 stops14h 36m
Wed 11/49:59 am -
2 stops8h 06m
Deal found 10/5![Delta logo]()
$321
This Expedia deal was found by Cheapflights users on 10/5. 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 10/2710:00 am -
2 stops17h 40m
Wed 10/287:20 am -
1 stop9h 32m
Deal found 10/5![Alaska Airlines logo]()
$323
This Alaska Airlines deal was found by Cheapflights users on 10/7. 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 12/27:48 am -
2 stops14h 11m
Mon 12/76:00 am -
1 stop8h 16m
Deal found 10/7![Alaska Airlines logo]()
$332
This Alaska Airlines deal was found by Cheapflights users on 10/7. 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 12/47:48 am -
2 stops14h 11m
Sat 12/56:00 am -
1 stop8h 16m
Deal found 10/7![Alaska Airlines logo]()
$342
This Alaska Airlines deal was found by Cheapflights users on 10/7. 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 12/46:28 am -
1 stop10h 32m
Mon 12/76:00 am -
1 stop8h 16m
Deal found 10/7![Alaska Airlines logo]()
$344
This Alaska Airlines deal was found by Cheapflights users on 10/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/31:12 pm -
2 stops27h 47m
Wed 11/117:20 am -
1 stop9h 44m
Deal found 10/8![Alaska Airlines logo]()
$348
This Delta deal was found by Cheapflights users on 10/7. 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.
Thu 12/311:27 am -
2 stops10h 30m
Tue 12/89:59 am -
2 stops8h 06m
Deal found 10/7![Delta logo]()
$357
This Delta deal was found by Cheapflights users on 10/7. 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 12/211:27 am -
1 stop8h 29m
Fri 12/49:59 am -
2 stops8h 06m
Deal found 10/7![Delta 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 October 8, 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 October 8, 2026.
This Delta deal was found by Cheapflights users on 10/7. 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.
Thu 10/2911:21 am -
1 stop8h 44m
Sat 10/319:59 am -
2 stops8h 06m
Deal found 10/7![Delta logo]()
$316
This Southwest deal was found by Cheapflights users on 10/7. 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 12/26:45 am -
2 stops8h 25m
Mon 12/75:50 am -
1 stop8h 25m
Deal found 10/7![Southwest logo]()
$400
This Alaska Airlines deal was found by Cheapflights users on 10/5. 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 12/128:50 am -
2 stops18h 47m
Tue 12/157:27 am -
1 stop18h 02m
Deal found 10/5![Alaska Airlines logo]()
$417
This Delta deal was found by Cheapflights users on 10/7. 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 2/197:00 am -
2 stops14h 46m
Mon 2/227:30 am -
1 stop6h 24m
Deal found 10/7![Delta logo]()
$352
This Southwest deal was found by Cheapflights users on 10/5. 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 12/126:30 am -
2 stops12h 20m
Tue 12/155:50 am -
1 stop8h 25m
Deal found 10/5![Southwest logo]()
$403
This Alaska Airlines deal was found by Cheapflights users on 10/3. 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.
Tue 1/262:12 pm -
1 stop21h 03m
Sat 1/302:13 pm -
1 stop10h 44m
Deal found 10/3![Alaska Airlines logo]()
$442
This Southwest deal was found by Cheapflights users on 10/7. 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 10/293:10 pm -
1 stop7h 50m
Sun 11/18:45 am -
1 stop6h 55m
Deal found 10/7![Southwest logo]()
$429
This Alaska Airlines deal was found by Cheapflights users on 10/4. 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.
Thu 12/38:50 am -
2 stops13h 09m
Sun 12/67:27 am -
1 stop28h 48m
Deal found 10/4![Alaska Airlines logo]()
$457
This Alaska Airlines deal was found by Cheapflights users on 10/8. 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 11/136:00 am -
1 stop15h 49m
Mon 11/307:26 am -
1 stop16h 06m
Deal found 10/8![Alaska Airlines logo]()
$469
This Southwest deal was found by Cheapflights users on 10/7. 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 2/192:35 pm -
1 stop7h 30m
Mon 2/225:55 am -
2 stops11h 10m
Deal found 10/7![Southwest logo]()
$473
This Southwest deal was found by Cheapflights users on 10/7. 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 10/304:50 pm -
2 stops10h 10m
Sun 11/18:45 am -
1 stop6h 55m
Deal found 10/7![Southwest logo]()
$477
This Alaska Airlines deal was found by Cheapflights users on 10/7. 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 12/46:28 am -
1 stop10h 32m
Sun 12/66:00 am -
2 stops15h 35m
Deal found 10/7![Alaska Airlines logo]()
$485
This Alaska Airlines deal was found by Cheapflights users on 10/6. 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.
Fri 12/256:37 pm -
1 stop10h 03m
Tue 12/297:00 am -
1 stop17h 45m
Deal found 10/6![Alaska Airlines logo]()
$485
This Southwest deal was found by Cheapflights users on 10/4. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/264:50 pm -
2 stops10h 50m
Thu 10/295:25 am -
1 stop7h 00m
Deal found 10/4![Southwest logo]()
$490
This Alaska Airlines deal was found by Cheapflights users on 10/6. 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 12/287:48 pm -
1 stop15h 31m
Wed 12/307:58 pm -
1 stop16h 13m
Deal found 10/6![Alaska Airlines logo]()
$490
This Southwest deal was found by Cheapflights users on 10/4. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/33:00 pm -
1 stop7h 15m
Sun 12/68:55 am -
1 stop6h 45m
Deal found 10/4![Southwest logo]()
$516
This Alaska Airlines deal was found by Cheapflights users on 10/6. 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 12/246:37 pm -
1 stop10h 03m
Sat 1/27:00 am -
1 stop9h 49m
Deal found 10/6![Alaska Airlines logo]()
$503
Last-minute flights from Santa Rosa to ChicagoDiscover last-minute flight deals from Santa Rosa to Chicago. Data last updated October 8, 2026 and is based on user searches.
Discover last-minute flight deals from Santa Rosa to Chicago. Data last updated October 8, 2026 and is based on user searches.
This American Airlines deal was found by Cheapflights users on 10/5. 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.
Mon 10/264:11 pm -
1 stop6h 24m
Wed 10/285:00 am -
1 stop9h 40m
Deal found 10/5![American Airlines logo]()
$311
This Expedia deal was found by Cheapflights users on 10/5. 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.
Mon 10/2611:57 am -
2 stops15h 43m
Wed 10/287:20 am -
1 stop9h 32m
Deal found 10/5![Alaska Airlines logo]()
$365
This Southwest deal was found by Cheapflights users on 10/5. 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 10/271:30 pm -
1 stop6h 45m
Wed 10/286:05 am -
1 stop7h 00m
Deal found 10/5![Southwest logo]()
$311
This Expedia deal was found by Cheapflights users on 10/5. 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 10/2710:00 am -
2 stops17h 40m
Wed 10/287:20 am -
1 stop9h 32m
Deal found 10/5![Alaska Airlines logo]()
$323
This Alaska Airlines deal was found by Cheapflights users on 10/4. 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 10/276:19 am -
1 stop29h 06m
Tue 11/32:15 pm -
1 stop10h 23m
Deal found 10/4![Alaska Airlines logo]()
$401
This Delta deal was found by Cheapflights users on 10/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/2811:21 am -
1 stop8h 44m
Wed 11/49:59 am -
2 stops8h 06m
Deal found 10/5![Delta logo]()
$316
This Southwest deal was found by Cheapflights users on 10/7. 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 10/293:10 pm -
1 stop7h 50m
Sun 11/18:45 am -
1 stop6h 55m
Deal found 10/7![Southwest logo]()
$429
This Southwest deal was found by Cheapflights users on 10/7. 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 10/303:10 pm -
1 stop7h 50m
Sun 11/18:45 am -
1 stop6h 55m
Deal found 10/7![Southwest logo]()
$472
This Alaska Airlines deal was found by Cheapflights users on 10/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/31:12 pm -
2 stops27h 47m
Wed 11/117:20 am -
1 stop9h 44m
Deal found 10/8![Alaska Airlines logo]()
$348
This Alaska Airlines deal was found by Cheapflights users on 10/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/48:40 am -
1 stop8h 19m
Thu 11/127:57 pm -
1 stop28h 41m
Deal found 10/7![Alaska Airlines logo]()
$344
This Southwest deal was found by Cheapflights users on 10/7. 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 11/103:00 pm -
1 stop12h 40m
Wed 11/185:50 am -
1 stop8h 25m
Deal found 10/7![Southwest logo]()
$317
This American Airlines deal was found by Cheapflights users on 10/6. 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.
Fri 11/201:29 pm -
1 stop8h 05m
Thu 11/265:00 am -
1 stop9h 59m
Deal found 10/6![American Airlines logo]()
$398
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 October 8, 2026.
Search for one-way flight options from Santa Rosa to Chicago. Find affordable one-way fares based on user searches. Data last updated October 8, 2026.
This Delta deal was found by Cheapflights users on 10/8. 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 11/211:21 am -
1 stop8h 44m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/8![Delta logo]()
$156
This Delta deal was found by Cheapflights users on 10/5. 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 11/74:49 pm -
2 stops15h 14m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/5![Delta logo]()
$161
This Delta deal was found by Cheapflights users on 10/5. 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 11/711:21 am -
2 stops10h 36m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/5![Delta logo]()
$161
This Orbitz deal was found by Cheapflights users on 10/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/216:08 am -
1 stop15h 41m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/8![Alaska Airlines logo]()
$189
This Alaska Airlines deal was found by Cheapflights users on 10/8. 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 11/136:00 am -
1 stop10h 59m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/8![Alaska Airlines logo]()
$194
This Alaska Airlines deal was found by Cheapflights users on 10/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/246:08 am -
1 stop29h 10m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/7![Alaska Airlines logo]()
$196
This Southwest deal was found by Cheapflights users on 10/5. 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 11/63:10 pm -
1 stop7h 00m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/5![Southwest logo]()
$199
This Delta deal was found by Cheapflights users on 10/6. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/611:21 am -
1 stop8h 44m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/6![Delta logo]()
$199
This Delta deal was found by Cheapflights users on 10/8. 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 10/2711:21 am -
1 stop8h 44m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/8![Delta logo]()
$205
This Alaska Airlines deal was found by Cheapflights users on 10/4. 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.
Sat 11/146:00 am -
1 stop10h 59m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/4![Alaska Airlines logo]()
$207
This Southwest deal was found by Cheapflights users on 10/8. 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 11/215:10 pm -
1 stop9h 15m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/8![Southwest logo]()
$211
This Delta deal was found by Cheapflights users on 10/4. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/2111:28 am -
1 stop8h 41m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/4![Delta logo]()
$211
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 October 8, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $311 (Southwest) |
One-way from | $156 (Delta) |
Popular in | April |
Cheapest in | November |
Average price | $635 |
Cheapflights Fare Finder
Customize your flight search to find flights from Santa Rosa to Chicago that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 7,457,451 searches. Data last updated October 8, 2026.
Use the filters below to find and compare flights from Santa Rosa to Chicago that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
Santa RosaChicago
STS Santa Rosa Sonoma County - ORD Chicago O'Hare Intl
STSORD
Santa Rosa Sonoma County
Mon 11/2
11:21 am-10:05 pm
1 stop8h 44m
Chicago O'Hare Intl
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$156
Santa RosaChicago
STS Santa Rosa Sonoma County - ORD Chicago O'Hare Intl
STSORD
Santa Rosa Sonoma County
Sat 11/14
11:29 am-9:33 pm
2 stops8h 04m
Chicago O'Hare Intl
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$161
Santa RosaChicago
STS Santa Rosa Sonoma County - ORD Chicago O'Hare Intl
STSORD
Santa Rosa Sonoma County
Sat 11/7
11:21 am-11:57 pm
2 stops10h 36m
Chicago O'Hare Intl
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$161
Santa RosaChicago
STS Santa Rosa Sonoma County - ORD Chicago O'Hare Intl
STSORD
Santa Rosa Sonoma County
Thu 11/26
11:29 am-11:20 pm
2 stops9h 51m
Chicago O'Hare Intl
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$161
Santa RosaChicago
STS Santa Rosa Sonoma County - MDW Chicago Midway
STSMDW
Santa Rosa Sonoma County
Fri 11/6
3:10 pm-12:10 am
1 stop7h 00m
Chicago Midway
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$199
Santa RosaChicago
STS Santa Rosa Sonoma County - ORD Chicago O'Hare Intl
STSORD
Santa Rosa Sonoma County
Fri 11/13
11:29 am-9:47 pm
1 stop8h 18m
Chicago O'Hare Intl
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$199
Santa RosaChicago
STS Santa Rosa Sonoma County - ORD Chicago O'Hare Intl
STSORD
Santa Rosa Sonoma County
Tue 1/5
7:20 pm-10:08 pm
1 stop24h 48m
Chicago O'Hare Intl
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$226
Santa RosaChicago
STS Santa Rosa Sonoma County - ORD Chicago O'Hare Intl
STSORD
Santa Rosa Sonoma County
Wed 10/21
6:19 am-6:53 pm
1 stop10h 34m
Chicago O'Hare Intl
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$230
Santa RosaChicago
STS Santa Rosa Sonoma County - MDW Chicago Midway
STSMDW
Santa Rosa Sonoma County
Fri 11/20
3:10 pm-12:15 am
1 stop7h 05m
Chicago Midway
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$243
Santa RosaChicago
STS Santa Rosa Sonoma County - ORD Chicago O'Hare Intl
STSORD
Santa Rosa Sonoma County
Tue 12/1
11:27 am-9:56 pm
1 stop8h 29m
Chicago O'Hare Intl
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$243
Showing 1-10 of 36 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
STS-MDW
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
STS-MDW
How much does it cost to fly round-trip from Santa Rosa to Chicago?
Airfare is below average for this route at the moment.
Santa Rosa to Chicago flights typically cost between $635 and $678 in October.The cheapest round-trip price found within the last 5 days was $311 on Southwest (Oct 27-Oct 28).
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 October 8, 2026.
See what other customers who have flown with Alaska Airlines from Santa Rosa to Chicago have to say. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
Boarding
8.1
Crew
8.5
Comfort
7.8
Entertainment
7.0
Food
7.0
Overall
7.9
Reviews
1 / 20
10.0
ExcellentFranzi,Mar 2026
SFO - PDX
Boarding
8.1
Crew
8.5
Comfort
7.8
Entertainment
7.0
Food
7.0
Overall
7.9
Reviews
1 / 20
10.0
ExcellentFranzi,Mar 2026
SFO - PDX
Related info for your journey
Find useful and relevant information for your journey from Santa Rosa to Chicago. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
Traveling to a place near Chicago?
Book flights to Chicago if you plan to visit one of these locationsBenton Harbor
Lansing
Merrillville
Valparaiso
Hammond
Saint Joseph
Porter
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Other flights to Chicago
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Santa Rosa and Chicago flights
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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 October 8, 2026.
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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 7,457,451 searches. Data last updated October 8, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$298 | Average$429 | FlexibilityNo cancel fee | On-time75% |