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San Luis Obispo

$284+ Cheap flights from Chicago (CHI) to San Luis Obispo (SBP)

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 12/3. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — SBP
Dec 2 — Dec 91
Tue 12/2
Tue 12/9
1 adult, Economy
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Cheap 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 November 2, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$284
(Alaska Airlines)

Popular in

February

Cheapest in

December

Average price

$552
Provider with most accurate pricing for Chicago (CHI)-San Luis Obispo County flight deals.
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Provider most trusted by Cheapflights users for Chicago (CHI)-San Luis Obispo County flights.
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From Chicago (CHI) to San Luis Obispo County
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Highest demand for flights based on searches. 10% potential increase in price ($66 potential increase over avg. RT price).
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Cheapest flight prices on average. 6% potential price decrease ($34 potential savings vs. average RT price).
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Average for round-trip flights in November 2025
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Find flight deals from Chicago to San Luis Obispo

Cheapest flights from Chicago to San Luis Obispo
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 November 2, 2025.

This Alaska Airlines deal was found by Cheapflights users on 10/31. 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 12/33:05 pmORD - SBP
2 stops25h 27mAlaska Airlines
Sat 12/67:51 pmSBP - ORD
1 stop8h 30mAlaska Airlines
Deal found 10/31$284
This American Airlines deal was found by Cheapflights users on 10/31. 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 12/98:50 amORD - SBP
2 stops8h 46mAmerican Airlines
Sat 12/134:18 pmSBP - ORD
1 stop6h 13mAmerican Airlines
Deal found 10/31$304
This Alaska Airlines deal was found by Cheapflights users on 10/31. 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 12/148:59 pmORD - SBP
1 stop28h 19mAlaska Airlines
Wed 12/174:47 pmSBP - ORD
2 stops19h 50mAlaska Airlines
Deal found 10/31$308
This Alaska Airlines deal was found by Cheapflights users on 10/31. 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 12/118:55 amORD - SBP
1 stop16h 23mAlaska Airlines
Mon 12/154:47 pmSBP - ORD
2 stops19h 22mAlaska Airlines
Deal found 10/31$316
This Alaska Airlines deal was found by Cheapflights users on 10/31. 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 12/193:37 pmORD - SBP
1 stop9h 58mAlaska Airlines
Sun 1/45:25 pmSBP - ORD
1 stop17h 51mAlaska Airlines
Deal found 10/31$372
This Alaska Airlines deal was found by Cheapflights users on 10/31. 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 11/288:20 amORD - SBP
1 stop17h 13mAlaska Airlines
Tue 12/24:47 pmSBP - ORD
2 stops19h 22mAlaska Airlines
Deal found 10/31$391
This American Airlines deal was found by Cheapflights users on 10/31. 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 12/38:50 amORD - SBP
2 stops8h 46mAmerican Airlines
Sat 12/69:55 amSBP - ORD
2 stops9h 29mAmerican Airlines
Deal found 10/31$404

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 November 2, 2025.
Use the filters below to find and compare flights from Chicago to San Luis Obispo that are best for you.

Fly from

Chicago

Fly to

San Luis Obispo

Route

Depart

Return

Price

ChicagoSan Luis Obispo

ORD - SBP

ORDSBP

Chicago O'Hare Intl

Wed 12/3

8:59 pm-4:07 pm

1 stop21h 08m

San Luis Obispo County

Sat 12/6

2:52 pm-11:50 pm

1 stop6h 58m

$298

ChicagoSan Luis Obispo

ORD - SBP

ORDSBP

Chicago O'Hare Intl

Tue 1/27

3:49 pm-11:20 pm

1 stop9h 31m

San Luis Obispo County

Sat 1/31

6:00 am-2:29 pm

1 stop6h 29m

$298

ChicagoSan Luis Obispo

ORD - SBP

ORDSBP

Chicago O'Hare Intl

Mon 1/26

6:06 pm-11:20 pm

2 stops31h 14m

San Luis Obispo County

Sat 1/31

5:14 pm-2:29 pm

2 stops19h 15m

$303

ChicagoSan Luis Obispo

ORD - SBP

ORDSBP

Chicago O'Hare Intl

Fri 1/16

3:49 pm-11:20 pm

1 stop9h 31m

San Luis Obispo County

Sun 1/18

3:12 pm-11:37 pm

1 stop6h 25m

$310

ChicagoSan Luis Obispo

ORD - SBP

ORDSBP

Chicago O'Hare Intl

Fri 1/16

3:49 pm-4:34 pm

1 stop26h 45m

San Luis Obispo County

Sun 1/18

6:00 am-2:29 pm

1 stop6h 29m

$310

ChicagoSan Luis Obispo

ORD - SBP

ORDSBP

Chicago O'Hare Intl

Tue 1/27

9:00 am-4:34 pm

1 stop9h 34m

San Luis Obispo County

Thu 1/29

6:00 am-2:29 pm

1 stop6h 29m

$310

ChicagoSan Luis Obispo

ORD - SBP

ORDSBP

Chicago O'Hare Intl

Sun 1/25

9:00 am-11:20 pm

1 stop16h 20m

San Luis Obispo County

Sat 1/31

6:00 am-2:29 pm

1 stop6h 29m

$310

ChicagoSan Luis Obispo

ORD - SBP

ORDSBP

Chicago O'Hare Intl

Tue 1/27

3:49 pm-11:20 pm

1 stop9h 31m

San Luis Obispo County

Sun 2/1

6:00 am-2:29 pm

1 stop6h 29m

$310

ChicagoSan Luis Obispo

ORD - SBP

ORDSBP

Chicago O'Hare Intl

Sun 12/14

3:05 pm-2:32 pm

2 stops25h 27m

San Luis Obispo County

Wed 12/17

4:47 pm-2:37 pm

2 stops19h 50m

$313

ChicagoSan Luis Obispo

ORD - SBP

ORDSBP

Chicago O'Hare Intl

Thu 12/11

8:55 am-11:18 pm

1 stop16h 23m

San Luis Obispo County

Mon 12/15

4:47 pm-2:09 pm

2 stops19h 22m

$316

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/31

Showing 1-10 of 15 results
1
2

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 November.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy2 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*1 star
eDreamsPrice Accuracy3 starsTrust Score*3 stars

*The Trust Score is based on feedback from users after their booking experience. It measures overall satisfaction, helping us identify issues like hidden fees, problems during the ticketing process, and the quality of customer service. This score is our best indicator of the provider's quality and reliability.

  • Most accurate provider: When it comes to deals on Chicago-San Luis Obispo flights, users find the pricing of eDreams to be most consistent on Cheapflights vs. eDreams Users can find the same prices on Chicago-San Luis Obispo flight deals on Cheapflights vs. eDreams >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 eDreams the most. eDreams 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.
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

What is the cheapest month to book a flight from Chicago to San Luis Obispo?

Currently, February is the cheapest month in which you can book a flight from Chicago to San Luis Obispo (average of $229). Flying from Chicago to San Luis Obispo in July is currently the most expensive (average of $388). 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.

What is the cheapest time of day to fly from CHI to SBP?

Find hourly flight availability from Chicago to San Luis Obispo. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated November 2, 2025.

When flying from Chicago to San Luis Obispo, the time of day you fly usually plays a role in the price. Save by searching for a flight in the morning, which can drop the price by up to 20% versus a flight in the evening.

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 November 2, 2025.
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.
United Airlines
7.4
Good
8,997 reviews

Crew

8.1

Boarding

7.7

Food

6.6

Entertainment

7.1

Overall

7.4

Comfort

7.3

Reviews

1 / 20
8.0
Excellent

Ruth,Dec 2024

ORD - AMS

United Airlines flights seem to always use a bus to/from the boarding gate to the plane. Can they not get their own gate? This time there was no lift when leaving the plane and people in wheelchairs somehow had to climb down the steps to the ground to get to the bus. I udon’t know how some managed that!
United Airlines
7.4
Good
8,997 reviews
United Airlines
7.4
Good
8,997 reviews

Crew

8.1

Boarding

7.7

Food

6.6

Entertainment

7.1

Overall

7.4

Comfort

7.3

Reviews

1 / 20
8.0
Excellent

Ruth,Dec 2024

ORD - AMS

United Airlines flights seem to always use a bus to/from the boarding gate to the plane. Can they not get their own gate? This time there was no lift when leaving the plane and people in wheelchairs somehow had to climb down the steps to the ground to get to the bus. I udon’t know how some managed that!
American Airlines
7.2
Good
11,034 reviews
United Airlines
7.4
Good
8,997 reviews

Crew

8.1

Boarding

7.7

Food

6.6

Entertainment

7.1

Overall

7.4

Comfort

7.3

Reviews

1 / 20
8.0
Excellent

Ruth,Dec 2024

ORD - AMS

United Airlines flights seem to always use a bus to/from the boarding gate to the plane. Can they not get their own gate? This time there was no lift when leaving the plane and people in wheelchairs somehow had to climb down the steps to the ground to get to the bus. I udon’t know how some managed that!

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.

  • What airport do you fly into for flights to San Luis Obispo from Chicago?

    San Luis Obispo County (SBP), located 3.3 mi from the city center, is the airport you fly into when you book flights from Chicago to San Luis Obispo. 2 airlines have flights to County from Chicago on a regular basis. Booking flights from Chicago to San Luis Obispo County should not be difficult; the airport handles an average of 0 inbound flights from Chicago per day.

  • How long is the flight from Chicago to San Luis Obispo?

    There are many flights that can get you from Chicago to San Luis Obispo in 9h 31m. Fly via Alaska Airlines or Hawaiian Airlines to get the fastest option. The distance from Chicago to San Luis Obispo is about 1814 mi. Both multi-stop and nonstop flights can be found to your destination and back.

  • What are the cheapest airlines flying from Chicago to San Luis Obispo round-trip?

    Cheapflights users have booked flights from Chicago to San Luis Obispo round-trip from $268. Another airline that can offer you cheap pricing is United Airlines. American Airlines is 51% cheaper than the average price of flights available within the next 90 days to this destination.

  • What are the cheapest airlines to fly from Chicago to San Luis Obispo one-way?

    One-way options have recently been found by users for as low as $475 on United Airlines. Other airlines that offer cheap prices include Alaska Airlines from $580 and American Airlines from $812 one-way.

  • Can I find deals for flights from Chicago to San Luis Obispo that include hotel bookings?

    Yes. In addition to deals on Chicago to San Luis Obispo flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Chicago to San Luis Obispo?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Chicago to San Luis Obispo.

  • Can I find deals for business class flights from Chicago to San Luis Obispo?

    Yes. Cheapflights offers flight deals from Chicago to San Luis Obispo by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Chicago to San Luis Obispo?

    Currently, February is the cheapest month in which you can book a flight from Chicago to San Luis Obispo (average of $229). Flying from Chicago to San Luis Obispo in July is currently the most expensive (average of $388). 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.

See more FAQs

Traveling to a place near San Luis Obispo?

Book flights to San Luis Obispo if you plan to visit one of these locations
Morro Bay
Arroyo Grande
Avila Beach
San Simeon

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Alternative routes for Chicago to San Luis Obispo

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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 November 2, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$268Average$572FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$276Average$544FlexibilityNo cancel feeOn-time69%

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