$175+ Cheap flights from Chicago (CHI) to San Luis Obispo (SBP)
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 8/17. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — SBP
Jun 4 — Jun 111
Round-trip
1 adult, Economy
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Cheapest flights from Chicago to San Luis ObispoExplore the most affordable flight options available from Chicago to San Luis Obispo. Find the lowest fares from popular airlines and budget airlines, with prices last updated on May 5, 2026.
Explore the most affordable flight options available from Chicago to San Luis Obispo. Find the lowest fares from popular airlines and budget airlines, with prices last updated on May 5, 2026.
This American Airlines deal was found by Cheapflights users on 4/30. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/283:22 pm
ORD
- SBP
1 stop8h 40m
American Airlines
Sat 10/3112:34 pm
SBP
- ORD
1 stop8h 38m
American Airlines
Deal found 4/30![American Airlines logo]()
$275
This United 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/210:53 am
ORD
- SBP
1 stop8h 31m
United Airlines
Tue 6/98:34 pm
SBP
- ORD
1 stop6h 24m
United Airlines
Deal found 5/2![United Airlines logo]()
$294
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.
Tue 9/12:22 pm
ORD
- SBP
1 stop7h 39m
Alaska Airlines
Sat 9/53:24 pm
SBP
- ORD
1 stop6h 33m
Alaska Airlines
Deal found 5/3![Alaska Airlines logo]()
$312
This American Airlines deal was found by Cheapflights users on 5/1. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/23:50 pm
ORD
- SBP
2 stops8h 55m
American Airlines
Sat 6/612:28 pm
SBP
- ORD
1 stop8h 32m
American Airlines
Deal found 5/1![American Airlines logo]()
$317
This Alaska Airlines deal was found by Cheapflights users on 5/1. 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 5/242:10 pm
ORD
- SBP
1 stop11h 43m
Alaska Airlines
Tue 5/262:59 pm
SBP
- ORD
1 stop20h 15m
Alaska Airlines
Deal found 5/1![Alaska Airlines logo]()
$341
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.
Thu 5/287:02 am
ORD
- SBP
1 stop6h 59m
American Airlines
Sat 5/3012:28 pm
SBP
- ORD
2 stops9h 09m
American Airlines
Deal found 5/3![American Airlines logo]()
$346
This Expedia 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/66:20 am
ORD
- SBP
1 stop12h 57m
Alaska Airlines
Wed 8/125:57 pm
SBP
- ORD
1 stop17h 24m
Alaska Airlines
Deal found 5/3![Alaska Airlines logo]()
$347
This Expedia 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/172:20 pm
ORD
- SBP
1 stop11h 20m
Alaska Airlines
Mon 7/205:50 pm
SBP
- ORD
1 stop9h 10m
Alaska Airlines
Deal found 5/4![Alaska Airlines logo]()
$349
This American 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/155:00 am
ORD
- SBP
1 stop8h 51m
American Airlines
Sun 7/197:02 pm
SBP
- ORD
1 stop9h 23m
American Airlines
Deal found 5/2![American Airlines logo]()
$358
This Alaska Airlines deal was found by Cheapflights users on 4/30. 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 5/282:10 pm
ORD
- SBP
1 stop11h 43m
Alaska Airlines
Thu 6/42:59 pm
SBP
- ORD
1 stop6h 56m
Alaska Airlines
Deal found 4/30![Alaska Airlines logo]()
$359
This Alaska Airlines deal was found by Cheapflights users on 5/1. 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 5/123:52 pm
ORD
- SBP
1 stop9h 29m
Alaska Airlines
Sat 5/162:59 pm
SBP
- ORD
1 stop6h 56m
Alaska Airlines
Deal found 5/1![Alaska Airlines logo]()
$367
Best flights from Chicago to San Luis ObispoDiscover carefully curated flight deals from Chicago to San Luis Obispo that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated May 5, 2026.
Discover carefully curated flight deals from Chicago to San Luis Obispo that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated May 5, 2026.
This United 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/26:10 pm
ORD
- SBP
1 stop7h 34m
United Airlines
Tue 6/98:34 pm
SBP
- ORD
1 stop7h 23m
United Airlines
Deal found 5/3![United Airlines logo]()
$275
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 9/12:22 pm
ORD
- SBP
1 stop7h 39m
Alaska Airlines
Sat 9/53:24 pm
SBP
- ORD
1 stop6h 33m
Alaska Airlines
Deal found 5/4![Alaska Airlines logo]()
$312
This United 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/26:02 am
ORD
- SBP
1 stop7h 51m
United Airlines
Tue 10/62:20 pm
SBP
- ORD
1 stop6h 35m
United Airlines
Deal found 5/3![United Airlines logo]()
$312
This United Airlines deal was found by Cheapflights users on 5/1. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/254:30 pm
ORD
- SBP
1 stop7h 42m
United Airlines
Mon 8/38:28 pm
SBP
- ORD
1 stop6h 33m
United Airlines
Deal found 5/1![United Airlines logo]()
$312
This Alaska Airlines deal was found by Cheapflights users on 4/30. 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.
Fri 8/287:59 pm
ORD
- SBP
1 stop20h 45m
Alaska Airlines
Sun 8/306:00 am
SBP
- ORD
1 stop11h 03m
Alaska Airlines
Deal found 4/30![Alaska Airlines logo]()
$349
This Alaska Airlines deal was found by Cheapflights users on 4/30. 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 5/282:10 pm
ORD
- SBP
1 stop11h 43m
Alaska Airlines
Thu 6/42:59 pm
SBP
- ORD
1 stop6h 56m
Alaska Airlines
Deal found 4/30![Alaska Airlines logo]()
$359
This Expedia deal was found by Cheapflights users on 4/30. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/92:54 pm
ORD
- SBP
1 stop10h 20m
Alaska Airlines
Mon 10/126:07 am
SBP
- ORD
1 stop5h 47m
Alaska Airlines
Deal found 4/30![Alaska Airlines logo]()
$384
This United 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/286:00 am
ORD
- SBP
2 stops13h 56m
United Airlines
Sat 10/312:12 pm
SBP
- ORD
1 stop7h 17m
United Airlines
Deal found 5/4![United Airlines logo]()
$417
Last-minute flights from Chicago to San Luis ObispoDiscover last-minute flight deals from Chicago to San Luis Obispo. Data last updated May 5, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to San Luis Obispo. Data last updated May 5, 2026 and is based on user searches.
This Alaska Airlines deal was found by Cheapflights users on 5/1. 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 5/123:52 pm
ORD
- SBP
1 stop9h 29m
Alaska Airlines
Sat 5/162:59 pm
SBP
- ORD
1 stop6h 56m
Alaska Airlines
Deal found 5/1![Alaska Airlines logo]()
$367
This American Airlines deal was found by Cheapflights users on 5/1. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/1311:43 am
ORD
- SBP
2 stops8h 49m
American Airlines
Sat 5/1612:55 pm
SBP
- ORD
1 stop6h 50m
American Airlines
Deal found 5/1![American Airlines logo]()
$372
This Alaska Airlines deal was found by Cheapflights users on 5/1. 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 5/242:10 pm
ORD
- SBP
1 stop11h 43m
Alaska Airlines
Tue 5/262:59 pm
SBP
- ORD
1 stop20h 15m
Alaska Airlines
Deal found 5/1![Alaska Airlines logo]()
$341
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.
Sun 5/243:50 pm
ORD
- SBP
2 stops8h 55m
American Airlines
Tue 5/2612:51 pm
SBP
- ORD
1 stop9h 51m
American Airlines
Deal found 5/3![American Airlines logo]()
$373
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.
Thu 5/287:02 am
ORD
- SBP
1 stop6h 59m
American Airlines
Sat 5/3012:28 pm
SBP
- ORD
2 stops9h 09m
American Airlines
Deal found 5/3![American Airlines logo]()
$346
This Alaska Airlines deal was found by Cheapflights users on 4/30. 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 5/282:10 pm
ORD
- SBP
1 stop11h 43m
Alaska Airlines
Thu 6/42:59 pm
SBP
- ORD
1 stop6h 56m
Alaska Airlines
Deal found 4/30![Alaska Airlines logo]()
$359
This Expedia deal was found by Cheapflights users on 5/1. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/17:59 pm
ORD
- SBP
1 stop20h 20m
Alaska Airlines
Sat 6/62:59 pm
SBP
- ORD
1 stop6h 56m
Alaska Airlines
Deal found 5/1![Alaska Airlines logo]()
$312
This American Airlines deal was found by Cheapflights users on 5/1. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/15:00 am
ORD
- SBP
1 stop8h 47m
American Airlines
Sat 6/612:28 pm
SBP
- ORD
1 stop8h 32m
American Airlines
Deal found 5/1![American Airlines logo]()
$349
This United 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/26:10 pm
ORD
- SBP
1 stop7h 34m
United Airlines
Tue 6/98:34 pm
SBP
- ORD
1 stop7h 23m
United Airlines
Deal found 5/3![United Airlines logo]()
$275
This American Airlines deal was found by Cheapflights users on 5/1. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/23:50 pm
ORD
- SBP
2 stops8h 55m
American Airlines
Sat 6/612:28 pm
SBP
- ORD
1 stop8h 32m
American Airlines
Deal found 5/1![American Airlines logo]()
$317
This American 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/23:50 pm
ORD
- SBP
2 stops8h 55m
American Airlines
Tue 6/912:52 pm
SBP
- ORD
1 stop8h 40m
American Airlines
Deal found 5/2![American Airlines logo]()
$383
One-way flights from Chicago to San Luis ObispoSearch for one-way flight options from Chicago to San Luis Obispo. Find affordable one-way fares based on user searches. Data last updated May 5, 2026.
Search for one-way flight options from Chicago to San Luis Obispo. Find affordable one-way fares based on user searches. Data last updated May 5, 2026.
This American Airlines deal was found by Cheapflights users on 4/30. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/175:00 am
ORD
- SBP
1 stop8h 58m
American Airlines
Deal found 4/30![American Airlines logo]()
$175
This United 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/233:26 pm
ORD
- SBP
1 stop8h 47m
United Airlines
Deal found 5/4![United Airlines logo]()
$179
This United Airlines deal was found by Cheapflights users on 4/30. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/283:26 pm
ORD
- SBP
1 stop8h 46m
United Airlines
Deal found 4/30![United Airlines logo]()
$180
This American Airlines deal was found by Cheapflights users on 4/30. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/247:02 am
ORD
- SBP
1 stop6h 59m
American Airlines
Deal found 4/30![American Airlines logo]()
$185
This Alaska Airlines deal was found by Cheapflights users on 4/30. 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.
Fri 5/227:59 pm
ORD
- SBP
1 stop20h 20m
Alaska Airlines
Deal found 4/30![Alaska Airlines logo]()
$190
This American Airlines deal was found by Cheapflights users on 5/1. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/155:25 pm
ORD
- SBP
1 stop6h 45m
American Airlines
Deal found 5/1![American Airlines logo]()
$210
This Alaska Airlines deal was found by Cheapflights users on 4/30. 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.
Sun 6/147:59 pm
ORD
- SBP
1 stop23h 18m
Alaska Airlines
Deal found 4/30![Alaska Airlines logo]()
$263
This American Airlines deal was found by Cheapflights users on 4/30. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/116:48 pm
ORD
- SBP
1 stop5h 57m
American Airlines
Deal found 4/30![American Airlines logo]()
$265
This American Airlines deal was found by Cheapflights users on 4/30. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/285:00 am
ORD
- SBP
2 stops8h 47m
American Airlines
Deal found 4/30![American Airlines logo]()
$270
This American Airlines deal was found by Cheapflights users on 4/30. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/25:00 am
ORD
- SBP
1 stop8h 51m
American Airlines
Deal found 4/30![American Airlines logo]()
$280
This Expedia 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/87:49 pm
ORD
- SBP
2 stops20h 30m
Alaska Airlines
Deal found 5/3![Alaska Airlines logo]()
$313
Find flight deals from Chicago to San Luis Obispo
Discover tips and strategies to find the most affordable flight options for your journey from Chicago (CHI) to San Luis Obispo (SBP). 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 5, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $275 (American Airlines) |
One-way from | $175 (American Airlines) |
Popular in | June |
Cheapest in | January |
Average price | $406 |
Cheapflights Fare Finder
Customize your flight search to find flights from Chicago to San Luis Obispo 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 5, 2026.
Use the filters below to find and compare flights from Chicago to San Luis Obispo that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
ChicagoSan Luis Obispo
ORD - SBP
ORDSBP
Chicago O'Hare Intl
Tue 6/2
6:10 pm-11:44 pm
1 stop7h 34m
San Luis Obispo County
Tue 6/9
8:34 pm-5:57 am
1 stop7h 23m
$275
Quickest round-trip
ChicagoSan Luis Obispo
ORD - SBP
ORDSBP
Chicago O'Hare Intl
Tue 9/1
2:22 pm-8:01 pm
1 stop7h 39m
San Luis Obispo County
Sat 9/5
3:24 pm-11:57 pm
1 stop6h 33m
$312
ChicagoSan Luis Obispo
ORD - SBP
ORDSBP
Chicago O'Hare Intl
Fri 10/2
6:02 am-11:53 am
1 stop7h 51m
San Luis Obispo County
Tue 10/6
2:20 pm-10:55 pm
1 stop6h 35m
$312
ChicagoSan Luis Obispo
ORD - SBP
ORDSBP
Chicago O'Hare Intl
Sat 7/25
4:30 pm-10:12 pm
1 stop7h 42m
San Luis Obispo County
Mon 8/3
8:28 pm-5:01 am
1 stop6h 33m
$312
ChicagoSan Luis Obispo
ORD - SBP
ORDSBP
Chicago O'Hare Intl
Fri 8/28
7:59 pm-2:44 pm
1 stop20h 45m
San Luis Obispo County
Sun 8/30
6:00 am-7:03 pm
1 stop11h 03m
$349
ChicagoSan Luis Obispo
ORD - SBP
ORDSBP
Chicago O'Hare Intl
Thu 5/28
2:10 pm-11:53 pm
1 stop11h 43m
San Luis Obispo County
Thu 6/4
2:59 pm-11:55 pm
1 stop6h 56m
$359
ChicagoSan Luis Obispo
ORD - SBP
ORDSBP
Chicago O'Hare Intl
Fri 10/9
2:54 pm-11:14 pm
1 stop10h 20m
San Luis Obispo County
Mon 10/12
6:07 am-1:54 pm
1 stop5h 47m
$384
ChicagoSan Luis Obispo
ORD - SBP
ORDSBP
Chicago O'Hare Intl
Wed 10/28
6:00 am-5:56 pm
2 stops13h 56m
San Luis Obispo County
Sat 10/31
2:12 pm-11:29 pm
1 stop7h 17m
$417
Cheapest one-way
Quickest one-way
ChicagoSan Luis Obispo
ORD - SBP
ORDSBP
Chicago O'Hare Intl
Mon 8/17
6:00 am-11:39 am
1 stop7h 39m
$175
ChicagoSan Luis Obispo
ORD - SBP
ORDSBP
Chicago O'Hare Intl
Sun 6/21
5:00 am-11:47 am
1 stop8h 47m
$175
Showing 1-10 of 14 resultsSorted by cheapest first
Compare providers for flights from Chicago to San Luis Obispo
Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Chicago to San Luis Obispo in May.
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars |
- Most accurate provider: When it comes to deals on Chicago-San Luis Obispo flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Chicago-San Luis Obispo flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Chicago-San Luis Obispo flight searches over the past month and is updated monthly.
- Most trusted provider: When it comes to deals on Chicago-San Luis Obispo flights, Cheapflights users trust FlightHub the most. FlightHub has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Chicago-San Luis Obispo flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.
Best time to book a flight from Chicago to San Luis Obispo
Have a flexible travel schedule? Discover the best time to fly to San Luis Obispo from Chicago with our price prediction graph.
CHI-SBP
ORD-SBP
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.
Cheapflights Insights
Everything you need to know about your flight from Chicago to San Luis Obispo
CHI-SBP
ORD-SBP
What is the cheapest month to book a flight from Chicago to San Luis Obispo?
Currently, September is the cheapest month in which you can book a flight from Chicago to San Luis Obispo (average of $230). Flying from Chicago to San Luis Obispo in December is currently the most expensive (average of $436). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.
How much does it cost to fly round-trip from Chicago to San Luis Obispo?
Reviews of airlines servicing San Luis Obispo
Get insights into the airlines that provide service to San Luis Obispo. 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 San Luis Obispo. Reviews last updated May 5, 2026.
Get a feel of what it's like to fly with United Airlines and American Airlines from Chicago to San Luis Obispo by reading reviews from past customers. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Boarding
7.7
Crew
8.1
Entertainment
7.1
Overall
7.4
Comfort
7.3
Food
6.6
Reviews
1 / 20
8.0
ExcellentRuth,Dec 2024
ORD - AMS
Boarding
7.7
Crew
8.1
Entertainment
7.1
Overall
7.4
Comfort
7.3
Food
6.6
Reviews
1 / 20
8.0
ExcellentRuth,Dec 2024
ORD - AMS
Boarding
7.7
Crew
8.1
Entertainment
7.1
Overall
7.4
Comfort
7.3
Food
6.6
Reviews
1 / 20
8.0
ExcellentRuth,Dec 2024
ORD - AMS
Related info for your journey
Find useful and relevant information for your journey from Chicago to San Luis Obispo. 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 San Luis Obispo?
Book flights to San Luis Obispo if you plan to visit one of these locationsMorro Bay
Cambria
Arroyo Grande
San Simeon
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Chicago and San Luis Obispo flights
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Top 2 airlines flying from Chicago to San Luis Obispo
Discover the top 2 airlines that operate flights from Chicago to San Luis Obispo. 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 5, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$247 | Average$436 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$309 | Average$390 | FlexibilityNo cancel fee | On-time69% |