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$138+ 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 10/21. Fares are subject to change and may not be available on all flights or dates of travel.
SBP — CHI
Oct 15 — Oct 221
Wed 10/15
Wed 10/22
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 September 15, 2025.

Round-trip from

$276
(Hawaiian Airlines)

One-way from

$138
(Hawaiian Airlines)

Popular in

March

Cheapest in

August

Average price

$448
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. 13% potential increase in price ($80 potential increase over avg. RT price).
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Cheapest flight prices on average. 6% potential price decrease ($32 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 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 September 15, 2025.

This Hawaiian 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 Hawaiian Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/247:50 pmSBP - ORD
1 stop8h 34mHawaiian Airlines
Tue 10/289:20 amORD - SBP
1 stop6h 45mHawaiian Airlines
Deal found 9/14$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.
Tue 11/182:59 pmSBP - ORD
1 stop7h 00mAlaska Airlines
Sat 11/223:51 pmORD - SBP
1 stop9h 42mAlaska 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.
Fri 10/247:16 pmSBP - ORD
1 stop8h 24mAmerican Airlines
Tue 10/2810:32 amORD - SBP
2 stops9h 55mAmerican Airlines
Deal found 9/14$282
This United 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/102:19 pmSBP - ORD
1 stop8h 35mUnited Airlines
Tue 10/146:15 amORD - SBP
1 stop8h 01mUnited Airlines
Deal found 9/13$334
This Alaska 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/57:51 pmSBP - ORD
1 stop16h 48mAlaska Airlines
Sun 12/76:00 amORD - SBP
2 stops19h 13mAlaska Airlines
Deal found 9/15$355
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 12/233:55 pmSBP - ORD
1 stop12h 34mAlaska Airlines
Tue 12/303:37 pmORD - SBP
1 stop9h 58mAlaska Airlines
Deal found 9/14$363
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.
Thu 10/167:16 pmSBP - ORD
1 stop8h 24mAmerican Airlines
Sun 10/195:00 amORD - SBP
1 stop8h 37mAmerican Airlines
Deal found 9/14$383
This American 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/264:18 pmSBP - ORD
1 stop5h 54mAmerican Airlines
Fri 11/285:00 amORD - SBP
1 stop6h 22mAmerican Airlines
Deal found 9/13$388
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.
Mon 12/226:54 pmSBP - ORD
1 stop8h 40mAmerican Airlines
Mon 12/295:00 amORD - SBP
1 stop6h 27mAmerican Airlines
Deal found 9/14$392
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.
Fri 10/245:38 pmSBP - ORD
2 stops10h 46mAlaska Airlines
Tue 10/289:20 amORD - SBP
2 stops9h 35mAlaska Airlines
Deal found 9/14$400

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 September 15, 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

Fri 10/24

7:50 pm-6:24 am

1 stop8h 34m

Chicago O'Hare Intl

Tue 10/28

9:20 am-2:05 pm

1 stop6h 45m

$276

San Luis ObispoChicago

SBP - ORD

SBPORD

San Luis Obispo County

Fri 12/5

7:51 pm-2:39 pm

1 stop16h 48m

Chicago O'Hare Intl

Sun 12/7

6:00 am-6:59 pm

1 stop14h 59m

$277

San Luis ObispoChicago

SBP - ORD

SBPORD

San Luis Obispo County

Tue 11/18

2:59 pm-11:59 pm

1 stop7h 00m

Chicago O'Hare Intl

Sat 11/22

3:51 pm-11:33 pm

1 stop9h 42m

$277

San Luis ObispoChicago

SBP - ORD

SBPORD

San Luis Obispo County

Fri 10/10

2:19 pm-12:54 am

1 stop8h 35m

Chicago O'Hare Intl

Tue 10/14

6:15 am-12:16 pm

1 stop8h 01m

$334

San Luis ObispoChicago

SBP - ORD

SBPORD

San Luis Obispo County

Wed 11/26

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

$388

San Luis ObispoChicago

SBP - ORD

SBPORD

San Luis Obispo County

Thu 10/2

6:29 pm-12:03 am

1 stop27h 34m

Chicago O'Hare Intl

Mon 10/6

3:50 pm-11:24 pm

1 stop9h 34m

$426

San Luis ObispoChicago

SBP - ORD

SBPORD

San Luis Obispo County

Fri 12/26

3:55 pm-6:29 am

1 stop12h 34m

Chicago O'Hare Intl

Fri 1/2

3:37 pm-11:35 pm

1 stop9h 58m

$436

San Luis ObispoChicago

SBP - ORD

SBPORD

San Luis Obispo County

Tue 10/21

7:50 pm-6:24 am

1 stop8h 34m

$138

San Luis ObispoChicago

SBP - ORD

SBPORD

San Luis Obispo County

Thu 10/23

8:00 am-6:52 pm

1 stop8h 52m

$139

San Luis ObispoChicago

SBP - ORD

SBPORD

San Luis Obispo County

Tue 10/21

12:47 pm-11:42 pm

2 stops8h 55m

$144

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/14

Showing 1-10 of 14 results
1
2

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, August is the cheapest month in which you can book a flight from San Luis Obispo to Chicago (average of $245). Flying from San Luis Obispo to Chicago in March is currently the most expensive (average of $321). 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 September 15, 2025.

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

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 September 15, 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
8,929 reviews

Crew

8.1

Boarding

7.7

Comfort

7.3

Entertainment

7.1

Food

6.6

Overall

7.4

Reviews

1 / 20
2.0
Mediocre

Deb,Jan 2025

MKE - ORD

It was terrible! So much to say, but in a nutshell we used vouchers from United because our last trip with them was awful with many mishaps and errors made. Unfortunately, this trip was even worse!
United Airlines
7.4
Good
8,929 reviews
United Airlines
7.4
Good
8,929 reviews

Crew

8.1

Boarding

7.7

Comfort

7.3

Entertainment

7.1

Food

6.6

Overall

7.4

Reviews

1 / 20
2.0
Mediocre

Deb,Jan 2025

MKE - ORD

It was terrible! So much to say, but in a nutshell we used vouchers from United because our last trip with them was awful with many mishaps and errors made. Unfortunately, this trip was even worse!
American Airlines
7.2
Good
10,000 reviews
United Airlines
7.4
Good
8,929 reviews

Crew

8.1

Boarding

7.7

Comfort

7.3

Entertainment

7.1

Food

6.6

Overall

7.4

Reviews

1 / 20
2.0
Mediocre

Deb,Jan 2025

MKE - ORD

It was terrible! So much to say, but in a nutshell we used vouchers from United because our last trip with them was awful with many mishaps and errors made. Unfortunately, this trip was even worse!

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 8h 34m. 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 48% 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 Hawaiian Airlines, which is currently one of the cheapest options available, starting at $138. United Airlines flights start at $139 while deals on American Airlines start at $144 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, August is the cheapest month in which you can book a flight from San Luis Obispo to Chicago (average of $245). Flying from San Luis Obispo to Chicago in March is currently the most expensive (average of $321). 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
Merrillville
Lansing
Hammond
Benton Harbor
Porter
Chesterton

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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 September 15, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$274Average$512FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$362Average$647FlexibilityNo cancel feeOn-time69%

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