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$185+ Cheap flights from San Luis Obispo (SBP) to Chicago (CHI)

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 12/31. Fares are subject to change and may not be available on all flights or dates of travel.
SBP — CHI
Dec 13 — Dec 201
Sat 12/13
Sat 12/20
1 adult, Economy
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Cheap flight deals from San Luis Obispo to Chicago

Discover tips and strategies to find the most affordable flight options for your journey from San Luis Obispo (SBP) 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 November 13, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$258
(Alaska Airlines)

One-way from

$185
(United Airlines)

Popular in

March

Cheapest in

August

Average price

$613
Provider with most accurate pricing for San Luis Obispo County-Chicago (CHI) flight deals.
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Provider most trusted by Cheapflights users for San Luis Obispo County-Chicago (CHI) flights.
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From San Luis Obispo County to Chicago (CHI)
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One-way flight from San Luis Obispo County to Chicago (CHI)
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Highest demand for flights based on searches. 8% potential increase in price ($47 potential increase over avg. RT price).
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Cheapest flight prices on average. 7% 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 San Luis Obispo to Chicago

Cheapest flights from San Luis Obispo to Chicago
Explore the most affordable flight options available from San Luis Obispo to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on November 13, 2025.

This Alaska Airlines deal was found by Cheapflights users on 11/10. 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 12/36:00 amSBP - ORD
1 stop6h 09mAlaska Airlines
Wed 12/108:55 amORD - SBP
1 stop6h 57mAlaska Airlines
Deal found 11/10$258
This American Airlines deal was found by Cheapflights users on 11/11. 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 12/41:08 pmSBP - ORD
1 stop5h 53mAmerican Airlines
Sun 12/712:10 pmORD - SBP
1 stop8h 19mAmerican Airlines
Deal found 11/11$298
This American Airlines deal was found by Cheapflights users on 11/12. 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 12/267:07 pmSBP - ORD
1 stop8h 27mAmerican Airlines
Tue 12/305:00 amORD - SBP
1 stop6h 23mAmerican Airlines
Deal found 11/12$358
This American Airlines deal was found by Cheapflights users on 11/13. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/244:18 pmSBP - ORD
1 stop5h 54mAmerican Airlines
Fri 11/285:00 amORD - SBP
1 stop6h 22mAmerican Airlines
Deal found 11/13$379
This Alaska Airlines deal was found by Cheapflights users on 11/11. 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 12/43:12 pmSBP - ORD
2 stops13h 09mAlaska Airlines
Sun 12/78:59 pmORD - SBP
1 stop21h 08mAlaska Airlines
Deal found 11/11$396
This Alaska Airlines deal was found by Cheapflights users on 11/12. 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 12/206:00 amSBP - ORD
1 stop15h 59mAlaska Airlines
Mon 12/298:58 pmORD - SBP
1 stop28h 37mAlaska Airlines
Deal found 11/12$467
This Alaska Airlines deal was found by Cheapflights users on 11/12. 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 12/216:00 amSBP - ORD
1 stop6h 37mAlaska Airlines
Mon 12/298:58 pmORD - SBP
1 stop28h 37mAlaska Airlines
Deal found 11/12$476
This Alaska Airlines deal was found by Cheapflights users on 11/12. 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 12/196:00 amSBP - ORD
1 stop12h 02mAlaska Airlines
Mon 12/298:58 pmORD - SBP
1 stop28h 37mAlaska Airlines
Deal found 11/12$477

Cheapflights Fare Finder

 
Customize your flight search to find flights from San Luis Obispo to Chicago that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated November 13, 2025.
Use the filters below to find and compare flights from San Luis Obispo to Chicago that are best for you.

Fly from

San Luis Obispo

Fly to

Chicago

Route

Depart

Return

Price

San Luis ObispoChicago

SBP - ORD

SBPORD

San Luis Obispo County

Wed 12/3

6:00 am-2:09 pm

1 stop6h 09m

Chicago O'Hare Intl

Wed 12/10

8:55 am-1:52 pm

1 stop6h 57m

$258

San Luis ObispoChicago

SBP - ORD

SBPORD

San Luis Obispo County

Fri 1/16

1:03 pm-10:18 pm

1 stop7h 15m

Chicago O'Hare Intl

Mon 1/19

10:57 am-5:00 pm

1 stop8h 03m

$298

San Luis ObispoChicago

SBP - ORD

SBPORD

San Luis Obispo County

Thu 12/4

1:08 pm-9:01 pm

1 stop5h 53m

Chicago O'Hare Intl

Sun 12/7

12:10 pm-6:29 pm

1 stop8h 19m

$298

San Luis ObispoChicago

SBP - ORD

SBPORD

San Luis Obispo County

Fri 12/26

7:07 pm-5:34 am

1 stop8h 27m

Chicago O'Hare Intl

Tue 12/30

5:00 am-9:23 am

1 stop6h 23m

$358

San Luis ObispoChicago

SBP - ORD

SBPORD

San Luis Obispo County

Mon 11/24

4:18 pm-12:12 am

1 stop5h 54m

Chicago O'Hare Intl

Fri 11/28

5:00 am-9:22 am

1 stop6h 22m

$379

San Luis ObispoChicago

SBP - ORD

SBPORD

San Luis Obispo County

Thu 12/4

3:12 pm-6:21 am

2 stops13h 09m

Chicago O'Hare Intl

Sun 12/7

8:59 pm-4:07 pm

1 stop21h 08m

$396

San Luis ObispoChicago

SBP - ORD

SBPORD

San Luis Obispo County

Tue 4/7

2:30 pm-11:10 pm

1 stop6h 40m

Chicago O'Hare Intl

Wed 4/8

9:00 am-1:47 pm

1 stop6h 47m

$404

San Luis ObispoChicago

SBP - ORD

SBPORD

San Luis Obispo County

Sat 4/25

2:30 pm-11:10 pm

1 stop6h 40m

Chicago O'Hare Intl

Fri 5/1

2:59 pm-11:18 pm

1 stop10h 19m

$404

San Luis ObispoChicago

SBP - ORD

SBPORD

San Luis Obispo County

Tue 4/7

6:00 am-1:59 pm

1 stop5h 59m

Chicago O'Hare Intl

Wed 4/8

9:00 am-1:47 pm

1 stop6h 47m

$404

San Luis ObispoChicago

SBP - ORD

SBPORD

San Luis Obispo County

Wed 12/31

6:23 pm-5:58 am

1 stop9h 35m

$185

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/11

Showing 1-10 of 14 results
1
2

Compare providers for flights from San Luis Obispo to Chicago

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 San Luis Obispo to Chicago 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 San Luis Obispo-Chicago flights, users find the pricing of eDreams to be most consistent on Cheapflights vs. eDreams Users can find the same prices on San Luis Obispo-Chicago flight deals on Cheapflights vs. eDreams >95% of the time. Price accuracy is based on data collected from San Luis Obispo-Chicago flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on San Luis Obispo-Chicago 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 San Luis Obispo-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 San Luis Obispo to Chicago

Have a flexible travel schedule? Discover the best time to fly to Chicago from San Luis Obispo 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 San Luis Obispo to Chicago

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

Currently, February is the cheapest month in which you can book a flight from San Luis Obispo to Chicago (average of $218). Flying from San Luis Obispo to Chicago in November 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 SBP to CHI?

Find hourly flight availability from San Luis Obispo to Chicago. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated November 13, 2025.

It’s optimal to fly from San Luis Obispo to Chicago in the afternoon. By choosing this option you can save up to 28% on the cost of your flight, compared to a flight in the morning.

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 November 13, 2025.
Read through reviews of airlines operating flights from San Luis Obispo to Chicago, such as United Airlines and American Airlines. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
United Airlines
7.4
Good
9,017 reviews

Entertainment

7.1

Crew

8.1

Overall

7.4

Comfort

7.3

Boarding

7.7

Food

6.6

Reviews

1 / 20
8.0
Excellent

Anonymous,Oct 2025

YUL - ORD

Crew and customer service are 5 stars. I had a lot of luggage for a very long trip and they were nothing but helpful and found solutions to every problem. It was my first time flying with United, and they really are the friendly skies. Leg room however, on 2/3 flights was terrible. Same for entertainment: There was only a seat-mounted screen on 1/3 flights. It would have been nice to have on the longest leg of the journey.
United Airlines
7.4
Good
9,017 reviews
United Airlines
7.4
Good
9,017 reviews

Entertainment

7.1

Crew

8.1

Overall

7.4

Comfort

7.3

Boarding

7.7

Food

6.6

Reviews

1 / 20
8.0
Excellent

Anonymous,Oct 2025

YUL - ORD

Crew and customer service are 5 stars. I had a lot of luggage for a very long trip and they were nothing but helpful and found solutions to every problem. It was my first time flying with United, and they really are the friendly skies. Leg room however, on 2/3 flights was terrible. Same for entertainment: There was only a seat-mounted screen on 1/3 flights. It would have been nice to have on the longest leg of the journey.
American Airlines
7.2
Good
11,051 reviews
United Airlines
7.4
Good
9,017 reviews

Entertainment

7.1

Crew

8.1

Overall

7.4

Comfort

7.3

Boarding

7.7

Food

6.6

Reviews

1 / 20
8.0
Excellent

Anonymous,Oct 2025

YUL - ORD

Crew and customer service are 5 stars. I had a lot of luggage for a very long trip and they were nothing but helpful and found solutions to every problem. It was my first time flying with United, and they really are the friendly skies. Leg room however, on 2/3 flights was terrible. Same for entertainment: There was only a seat-mounted screen on 1/3 flights. It would have been nice to have on the longest leg of the journey.

Related info for your journey

Find useful and relevant information for your journey from San Luis Obispo to Chicago. 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 from for flights from San Luis Obispo to Chicago?

    If you book a flight to Chicago from San Luis Obispo, you will be flying from County, which is the city’s only airport. San Luis Obispo County (SBP) is located 3.3 mi from the center of San Luis Obispo. There are 0 flights from County to Chicago per day from 2 different airlines.

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

    Departing from San Luis Obispo to Chicago will take you 6h 09m. There are 1814 mi between San Luis Obispo and Chicago. Both multi-stop and nonstop flights can be found to your destination and back.

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

    American Airlines, at $274, was found to be the cheapest airline from San Luis Obispo to Chicago. An alternate airline flying to your destination would be United Airlines. American Airlines is currently priced 46% below the average price you’ll pay for this route.

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

    To fly one-way, consider booking your trip with United Airlines, which is currently one of the cheapest options available, starting at $185. American Airlines flights start at $225 while deals on Alaska Airlines start at $257 one-way.

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

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

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

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

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

    Yes. Cheapflights offers flight deals from San Luis Obispo to Chicago 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 San Luis Obispo to Chicago?

    Currently, February is the cheapest month in which you can book a flight from San Luis Obispo to Chicago (average of $218). Flying from San Luis Obispo to Chicago in November 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 Chicago?

Book flights to Chicago if you plan to visit one of these locations
Lansing
Hammond
Porter
Benton Harbor
Merrillville

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Alternative routes for San Luis Obispo to Chicago

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Top 2 airlines flying from San Luis Obispo to Chicago

Discover the top 2 airlines that operate flights from San Luis Obispo to Chicago. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated November 13, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$274Average$559FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$362Average$620FlexibilityNo cancel feeOn-time69%

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