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$163+ 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 3/9. Fares are subject to change and may not be available on all flights or dates of travel.
SBP — CHI
Mar 5 — Mar 121
Thu 3/5
Thu 3/12
1 adult, Economy
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Cheap 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 February 3, 2026.

This Alaska Airlines deal was found by Cheapflights users on 2/2. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/36:00 am
SBP
-
ORD
1 stop6h 58m
Alaska Airlines
Tue 3/108:20 am
ORD
-
SBP
1 stop16h 57m
Alaska Airlines
Deal found 2/2$210
This Alaska Airlines deal was found by Cheapflights users on 2/2. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/223:39 pm
SBP
-
ORD
1 stop19h 34m
Alaska Airlines
Wed 5/63:52 pm
ORD
-
SBP
1 stop9h 23m
Alaska Airlines
Deal found 2/2$223
This Alaska Airlines deal was found by Cheapflights users on 2/1. 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.
Sat 5/25:36 pm
SBP
-
ORD
1 stop18h 32m
Alaska Airlines
Sat 5/98:50 am
ORD
-
SBP
1 stop8h 09m
Alaska Airlines
Deal found 2/1$253
This Alaska Airlines deal was found by Cheapflights users on 2/1. 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.
Mon 2/235:34 pm
SBP
-
ORD
1 stop17h 37m
Alaska Airlines
Thu 2/268:20 am
ORD
-
SBP
1 stop16h 57m
Alaska Airlines
Deal found 2/1$291
This Alaska Airlines deal was found by Cheapflights users on 1/31. 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.
Mon 3/23:47 pm
SBP
-
ORD
2 stops21h 11m
Alaska Airlines
Mon 3/93:07 pm
ORD
-
SBP
1 stop22h 32m
Alaska Airlines
Deal found 1/31$295
This United Airlines deal was found by Cheapflights users on 2/2. 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.
Thu 3/52:13 pm
SBP
-
ORD
1 stop8h 46m
United Airlines
Mon 3/92:45 pm
ORD
-
SBP
1 stop8h 19m
United Airlines
Deal found 2/2$309
This Alaska Airlines deal was found by Cheapflights users on 2/2. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 3/65:34 pm
SBP
-
ORD
1 stop17h 37m
Alaska Airlines
Sun 3/88:20 am
ORD
-
SBP
1 stop29h 19m
Alaska Airlines
Deal found 2/2$333
This United Airlines deal was found by Cheapflights users on 2/2. 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.
Fri 3/62:15 pm
SBP
-
ORD
1 stop7h 23m
United Airlines
Mon 3/96:20 pm
ORD
-
SBP
1 stop7h 24m
United Airlines
Deal found 2/2$334

Find 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 February 3, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$210
(Alaska Airlines)

One-way from

$163
(Expedia)

Popular in

November

Cheapest in

August

Average price

$446
Provider with most accurate pricing for San Luis Obispo County-Chicago (CHI) flight deals.
Search Deals
Provider most trusted by Cheapflights users for San Luis Obispo County-Chicago (CHI) flights.
Search Deals
From San Luis Obispo County to Chicago (CHI)
Search Deals
One-way flight from San Luis Obispo County to Chicago (CHI)
Search Deals
Highest demand for flights based on searches. 8% potential increase in price ($44 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($10 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in February 2026
Search Deals

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 February 3, 2026.
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 4/22

3:39 pm-1:13 pm

1 stop19h 34m

Chicago O'Hare Intl

Wed 5/6

3:52 pm-11:15 pm

1 stop9h 23m

$223

San Luis ObispoChicago

SBP - ORD

SBPORD

San Luis Obispo County

Sat 5/2

5:36 pm-2:08 pm

1 stop18h 32m

Chicago O'Hare Intl

Sat 5/9

8:50 am-2:59 pm

1 stop8h 09m

$253

San Luis ObispoChicago

SBP - ORD

SBPORD

San Luis Obispo County

Tue 3/3

12:19 pm-11:59 pm

1 stop9h 40m

Chicago O'Hare Intl

Tue 3/10

7:00 am-11:17 pm

2 stops18h 17m

$278

San Luis ObispoChicago

SBP - ORD

SBPORD

San Luis Obispo County

Mon 2/23

5:34 pm-1:11 pm

1 stop17h 37m

Chicago O'Hare Intl

Thu 2/26

8:20 am-11:17 pm

1 stop16h 57m

$291

San Luis ObispoChicago

SBP - ORD

SBPORD

San Luis Obispo County

Mon 3/2

3:47 pm-2:58 pm

2 stops21h 11m

Chicago O'Hare Intl

Mon 3/9

3:07 pm-11:39 am

1 stop22h 32m

$295

San Luis ObispoChicago

SBP - ORD

SBPORD

San Luis Obispo County

Thu 3/5

2:13 pm-12:59 am

1 stop8h 46m

Chicago O'Hare Intl

Sun 3/8

6:20 pm-11:44 pm

1 stop7h 24m

$309

San Luis ObispoChicago

SBP - ORD

SBPORD

San Luis Obispo County

Sat 5/2

12:55 pm-10:00 pm

1 stop7h 05m

Chicago O'Hare Intl

Sat 5/9

6:05 am-12:10 pm

1 stop8h 05m

$309

San Luis ObispoChicago

SBP - ORD

SBPORD

San Luis Obispo County

Thu 3/5

2:13 pm-12:59 am

1 stop8h 46m

Chicago O'Hare Intl

Mon 3/9

2:45 pm-9:04 pm

1 stop8h 19m

$309

San Luis ObispoChicago

SBP - ORD

SBPORD

San Luis Obispo County

Mon 3/2

5:56 pm-5:01 am

1 stop9h 05m

Chicago O'Hare Intl

Mon 3/9

6:20 pm-11:44 pm

1 stop7h 24m

$309

San Luis ObispoChicago

SBP - ORD

SBPORD

San Luis Obispo County

Mon 3/9

3:47 pm-2:58 pm

2 stops21h 11m

$163

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/31

Showing 1-10 of 20 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 February.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice 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 FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on San Luis Obispo-Chicago flight deals on Cheapflights vs. FlightHub >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 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 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.

How much does it cost to fly round-trip from San Luis Obispo to Chicago?

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 February 3, 2026.
Read through reviews of airlines operating flights from San Luis Obispo to Chicago, such as Alaska Airlines, United Airlines, and American Airlines. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Alaska Airlines
8.0
Very good
11,833 reviews

Food

7.1

Overall

8.0

Boarding

8.1

Comfort

7.8

Entertainment

7.0

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Anonymous,Jan 2026

STS - LAX

Enjoyed staff assistance from ticking thru tsa , boarding and in the plane Couldn’t pick a seat except upgrading
Alaska Airlines
8.0
Very good
11,833 reviews
Alaska Airlines
8.0
Very good
11,833 reviews

Food

7.1

Overall

8.0

Boarding

8.1

Comfort

7.8

Entertainment

7.0

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Anonymous,Jan 2026

STS - LAX

Enjoyed staff assistance from ticking thru tsa , boarding and in the plane Couldn’t pick a seat except upgrading
United Airlines
7.4
Good
9,236 reviews
Alaska Airlines
8.0
Very good
11,833 reviews

Food

7.1

Overall

8.0

Boarding

8.1

Comfort

7.8

Entertainment

7.0

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Anonymous,Jan 2026

STS - LAX

Enjoyed staff assistance from ticking thru tsa , boarding and in the plane Couldn’t pick a seat except upgrading
American Airlines
7.2
Good
11,218 reviews
Alaska Airlines
8.0
Very good
11,833 reviews

Food

7.1

Overall

8.0

Boarding

8.1

Comfort

7.8

Entertainment

7.0

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Anonymous,Jan 2026

STS - LAX

Enjoyed staff assistance from ticking thru tsa , boarding and in the plane Couldn’t pick a seat except upgrading

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 19h 34m. There are 1814 mi between San Luis Obispo and Chicago.

  • 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 45% below the average price you’ll pay for this route.

  • 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
Merrillville
Hammond
Porter
Benton Harbor

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Alternative routes for San Luis Obispo to Chicago

See prices for flight routes from nearby airports that may be better suited for you.
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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 February 3, 2026.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$274Average$488FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$362Average$627FlexibilityNo cancel feeOn-time69%

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