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San Luis Obispo

$139+ 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 10/24. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — SBP
Oct 15 — Oct 221
Wed 10/15
Wed 10/22
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 September 15, 2025.

Round-trip from

$276
(Hawaiian Airlines)

One-way from

$139
(United Airlines)

Popular in

February

Cheapest in

December

Average price

$423
From Chicago (CHI) to San Luis Obispo County
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One-way flight from Chicago (CHI) to San Luis Obispo County
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Highest demand for flights based on searches. 13% potential increase in price ($84 potential increase over avg. RT price).
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Cheapest flight prices on average. 7% potential price decrease ($37 potential savings vs. average RT price).
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Average for round-trip flights in September 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 September 15, 2025.

This Hawaiian Airlines deal was found by Cheapflights users on 9/15. 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 Hawaiian Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/59:20 amORD - SBP
1 stop6h 45mHawaiian Airlines
Mon 11/107:56 pmSBP - ORD
1 stop8h 26mHawaiian Airlines
Deal found 9/15$276
This Alaska Airlines deal was found by Cheapflights users on 9/14. 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 11/510:00 amORD - SBP
1 stop11h 01mAlaska Airlines
Sat 11/85:27 pmSBP - ORD
1 stop9h 34mAlaska Airlines
Deal found 9/14$277
This American Airlines deal was found by Cheapflights users on 9/14. 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 10/295:00 amORD - SBP
1 stop8h 37mAmerican Airlines
Sat 11/112:38 pmSBP - ORD
2 stops9h 04mAmerican Airlines
Deal found 9/14$282
This United Airlines deal was found by Cheapflights users on 9/14. 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 11/57:10 amORD - SBP
1 stop7h 09mUnited Airlines
Mon 11/106:25 pmSBP - ORD
1 stop8h 35mUnited Airlines
Deal found 9/14$296
This KAYAK deal was found by Cheapflights users on 9/14. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/313:37 pmORD - SBP
1 stop9h 58mAlaska Airlines
Sun 1/186:00 amSBP - ORD
1 stop5h 59mAlaska Airlines
Deal found 9/14$302
This Alaska Airlines deal was found by Cheapflights users on 9/14. 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 11/49:20 amORD - SBP
2 stops9h 35mAlaska Airlines
Sat 11/85:27 pmSBP - ORD
1 stop9h 34mAlaska Airlines
Deal found 9/14$306
This Alaska Airlines deal was found by Cheapflights users on 9/14. 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 11/69:20 amORD - SBP
1 stop16h 06mAlaska Airlines
Wed 11/125:27 pmSBP - ORD
1 stop9h 34mAlaska Airlines
Deal found 9/14$309
This Alaska Airlines deal was found by Cheapflights users on 9/14. 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 10/143:50 pmORD - SBP
1 stop8h 51mAlaska Airlines
Tue 10/212:19 pmSBP - ORD
2 stops14h 05mAlaska Airlines
Deal found 9/14$321
This American Airlines deal was found by Cheapflights users on 9/15. 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 10/295:00 amORD - SBP
2 stops8h 57mAmerican Airlines
Wed 11/59:53 amSBP - ORD
1 stop9h 15mAmerican Airlines
Deal found 9/15$323
This Alaska Airlines deal was found by Cheapflights users on 9/13. 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 11/72:54 pmORD - SBP
1 stop10h 32mAlaska Airlines
Sat 11/85:27 pmSBP - ORD
1 stop9h 34mAlaska Airlines
Deal found 9/13$325
This Alaska Airlines deal was found by Cheapflights users on 9/14. 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 11/88:00 amORD - SBP
1 stop13h 01mAlaska Airlines
Wed 11/125:27 pmSBP - ORD
1 stop9h 34mAlaska Airlines
Deal found 9/14$335

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 September 15, 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

Tue 11/4

9:20 am-2:05 pm

1 stop6h 45m

San Luis Obispo County

Sat 11/8

5:27 pm-5:01 am

1 stop9h 34m

$277

ChicagoSan Luis Obispo

ORD - SBP

ORDSBP

Chicago O'Hare Intl

Thu 11/13

4:40 pm-9:34 pm

1 stop6h 54m

San Luis Obispo County

Sun 11/16

2:16 pm-12:59 am

1 stop8h 43m

$277

ChicagoSan Luis Obispo

ORD - SBP

ORDSBP

Chicago O'Hare Intl

Tue 10/14

3:50 pm-10:41 pm

1 stop8h 51m

San Luis Obispo County

Tue 10/21

7:50 pm-6:24 am

1 stop8h 34m

$277

ChicagoSan Luis Obispo

ORD - SBP

ORDSBP

Chicago O'Hare Intl

Wed 11/5

7:10 am-12:19 pm

1 stop7h 09m

San Luis Obispo County

Mon 11/10

6:25 pm-5:00 am

1 stop8h 35m

$277

ChicagoSan Luis Obispo

ORD - SBP

ORDSBP

Chicago O'Hare Intl

Wed 11/5

10:00 am-7:01 pm

1 stop11h 01m

San Luis Obispo County

Wed 11/12

2:59 pm-11:59 pm

1 stop7h 00m

$277

ChicagoSan Luis Obispo

ORD - SBP

ORDSBP

Chicago O'Hare Intl

Tue 11/4

9:20 am-2:05 pm

1 stop6h 45m

San Luis Obispo County

Fri 11/7

7:56 pm-6:22 am

1 stop8h 26m

$277

ChicagoSan Luis Obispo

ORD - SBP

ORDSBP

Chicago O'Hare Intl

Wed 11/5

10:00 am-7:01 pm

1 stop11h 01m

San Luis Obispo County

Sat 11/8

5:27 pm-5:01 am

1 stop9h 34m

$277

ChicagoSan Luis Obispo

ORD - SBP

ORDSBP

Chicago O'Hare Intl

Wed 11/5

9:20 am-2:05 pm

1 stop6h 45m

San Luis Obispo County

Thu 11/13

5:27 pm-5:01 am

1 stop9h 34m

$277

ChicagoSan Luis Obispo

ORD - SBP

ORDSBP

Chicago O'Hare Intl

Tue 11/4

9:20 am-2:05 pm

1 stop6h 45m

San Luis Obispo County

Wed 11/12

2:59 pm-11:59 pm

1 stop7h 00m

$277

ChicagoSan Luis Obispo

ORD - SBP

ORDSBP

Chicago O'Hare Intl

Fri 10/31

5:00 am-11:37 am

1 stop8h 37m

$139

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/14

Showing 1-10 of 15 results
1
2

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, January is the cheapest month in which you can book a flight from Chicago to San Luis Obispo (average of $374). Flying from Chicago to San Luis Obispo in June is currently the most expensive (average of $511). 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 September 15, 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 19% 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 September 15, 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
8,929 reviews

Overall

7.4

Food

6.6

Comfort

7.3

Boarding

7.7

Entertainment

7.1

Crew

8.1

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
8,929 reviews
United Airlines
7.4
Good
8,929 reviews

Overall

7.4

Food

6.6

Comfort

7.3

Boarding

7.7

Entertainment

7.1

Crew

8.1

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
10,000 reviews
United Airlines
7.4
Good
8,929 reviews

Overall

7.4

Food

6.6

Comfort

7.3

Boarding

7.7

Entertainment

7.1

Crew

8.1

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 6h 45m. Fly via Alaska Airlines to get the fastest option. The distance from Chicago to San Luis Obispo is about 1814 mi.

  • 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 50% 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 $139 on American Airlines. Other airlines that offer cheap prices include United Airlines from $139 and Alaska Airlines from $177 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, January is the cheapest month in which you can book a flight from Chicago to San Luis Obispo (average of $374). Flying from Chicago to San Luis Obispo in June is currently the most expensive (average of $511). 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
Avila Beach
Arroyo Grande
San Simeon

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Alternative routes for Chicago to San Luis Obispo

See prices for flight routes from nearby airports that may be better suited for you.
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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 September 15, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$268Average$564FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$518Average$617FlexibilityNo cancel feeOn-time69%

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