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

Departing from San Luis Obispo to Chicago will take you 6h 29m. 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 47% below the average price you’ll pay for this route.

In terms of precipitation, rainfall in Chicago ranges from 1.7 - 4.9 inches per month. August is typically the wettest month, when rainfall can reach 4.9 in. January is typically the driest time to visit Chicago when rainfall is around 1.7 in.

If weather is an important factor for your trip to Chicago, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 73.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 23.0 F).

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.

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.

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.

$139+ Flights from San Luis Obispo to Chicago

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

Airfare is below average for this route at the moment. San Luis Obispo to Chicago flights typically cost between $515 and $568 in January. The cheapest round-trip price found within the last 3 days was $289 on Alaska Airlines (Jan 9-Jan 13).

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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 December 18, 2025.

Tue 12/3012:36 pmSBP - ORD

1 stop7h 44mAmerican Airlines

Fri 1/210:40 amORD - SBP

1 stop7h 20mAmerican Airlines

Deal found 12/16

$575

Tue 12/306:23 pmSBP - ORD

2 stops13h 21mUnited Airlines

Fri 1/26:15 amORD - SBP

1 stop7h 48mUnited Airlines

Deal found 12/16

$620

Sat 12/205:20 pmSBP - ORD

1 stop19h 17mAlaska Airlines

Mon 12/228:39 amORD - SBP

1 stop10h 01mAlaska Airlines

Deal found 12/16

$1,010

Sat 12/2012:54 pmSBP - ORD

2 stops8h 21mAmerican Airlines

Mon 12/221:40 pmORD - SBP

1 stop6h 44mAmerican Airlines

Deal found 12/16

$1,016

Tue 12/307:45 pmSBP - ORD

2 stops19h 27mAlaska Airlines

Fri 1/28:39 amORD - SBP

2 stops12h 26mAlaska Airlines

Deal found 12/17

$1,979

Best flights from San Luis Obispo to Chicago
Discover carefully curated flight deals from San Luis Obispo to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated December 18, 2025.

Fri 1/96:00 amSBP - ORD

1 stop6h 29mAlaska Airlines

Tue 1/139:00 amORD - SBP

1 stop9h 34mAlaska Airlines

Deal found 12/15

$289

Tue 2/245:00 amSBP - ORD

1 stop6h 14mUnited Airlines

Sun 3/16:20 pmORD - SBP

1 stop7h 39mUnited Airlines

Deal found 12/15

$365

Tue 2/176:00 amSBP - ORD

1 stop6h 58mAlaska Airlines

Sun 2/223:07 pmORD - SBP

1 stop10h 10mAlaska Airlines

Deal found 12/15

$289

Wed 2/2512:19 pmSBP - ORD

1 stop9h 40mAlaska Airlines

Mon 3/23:07 pmORD - SBP

1 stop22h 32mAlaska Airlines

Deal found 12/15

$300

Fri 1/303:12 pmSBP - ORD

1 stop21h 17mAlaska Airlines

Sun 2/13:44 pmORD - SBP

1 stop9h 36mAlaska Airlines

Deal found 12/16

$310

Tue 2/246:00 amSBP - ORD

2 stops15h 56mAlaska Airlines

Sun 3/18:20 amORD - SBP

1 stop29h 19mAlaska Airlines

Deal found 12/15

$328

Last-minute flights from San Luis Obispo to Chicago
Discover last-minute flight deals from San Luis Obispo to Chicago. Data last updated December 18, 2025 and is based on user searches.

Tue 12/3012:36 pmSBP - ORD

1 stop7h 44mAmerican Airlines

Fri 1/210:40 amORD - SBP

1 stop7h 20mAmerican Airlines

Deal found 12/16

$575

Tue 12/306:23 pmSBP - ORD

2 stops13h 21mUnited Airlines

Fri 1/26:15 amORD - SBP

1 stop7h 48mUnited Airlines

Deal found 12/16

$620

Thu 1/15:00 amSBP - ORD

1 stop6h 19mUnited Airlines

Mon 1/51:55 pmORD - SBP

1 stop9h 10mUnited Airlines

Deal found 12/17

$476

Thu 1/13:55 pmSBP - ORD

1 stop12h 34mAlaska Airlines

Mon 1/58:58 pmORD - SBP

2 stops24h 07mAlaska Airlines

Deal found 12/17

$615

Fri 1/96:00 amSBP - ORD

1 stop6h 29mAlaska Airlines

Tue 1/139:00 amORD - SBP

1 stop9h 34mAlaska Airlines

Deal found 12/15

$289

Fri 1/303:12 pmSBP - ORD

1 stop6h 25mAlaska Airlines

Sun 2/13:44 pmORD - SBP

1 stop9h 36mAlaska Airlines

Deal found 12/17

$298

Fri 1/306:00 amSBP - ORD

2 stops9h 09mAmerican Airlines

Sun 2/13:23 pmORD - SBP

2 stops8h 53mAmerican Airlines

Deal found 12/16

$442

One-way flights from San Luis Obispo to Chicago
Search for one-way flight options from San Luis Obispo to Chicago. Find affordable one-way fares based on user searches. Data last updated December 18, 2025.

Wed 2/116:00 amSBP - ORD

1 stop6h 29mAlaska Airlines

Deal found 12/17

$139

Fri 2/66:00 amSBP - ORD

1 stop6h 29mAlaska Airlines

Deal found 12/16

$149

Thu 1/153:12 pmSBP - ORD

1 stop6h 25mAlaska Airlines

Deal found 12/16

$191

Fri 3/206:00 pmSBP - ORD

1 stop9h 18mUnited Airlines

Deal found 12/16

$248

Thu 1/157:09 amSBP - ORD

2 stops19h 57mUnited Airlines

Deal found 12/16

$273

Wed 2/116:17 pmSBP - ORD

3 stops41h 18mMultiple Airlines

Deal found 12/17

$312

Fri 2/66:17 pmSBP - ORD

3 stops50h 25mMultiple Airlines

Deal found 12/16

$386

Fri 3/202:51 pmSBP - ORD

2 stops12h 09mAlaska Airlines

Deal found 12/16

$445

Thu 1/156:17 pmSBP - ORD

3 stops44h 35mMultiple Airlines

Deal found 12/16

$450

Find flight deals from San Luis Obispo to Chicago

Most accurate provider	eDreams 3 stars
Most trusted provider	eDreams 3 stars
Round-trip from	$289 (Alaska Airlines)
One-way from	$139 (Alaska Airlines)
Popular in	March
Cheapest in	August
Average price	$530

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. 7% potential increase in price ($41 potential increase over avg. RT price).

Search Deals

Cheapest flight prices on average. 6% potential price decrease ($34 potential savings vs. average RT price).

Search Deals

Average for round-trip flights in December 2025

Search Deals

Cheapflights Fare Finder

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

Fly from

Fly to

Route

Depart

Return

Price

San Luis ObispoChicago

SBP - ORD

SBPORD

San Luis Obispo County

Fri 1/9

6:00 am-2:29 pm

1 stop6h 29m

Chicago O'Hare Intl

Tue 1/13

9:00 am-4:34 pm

1 stop9h 34m

$289

San Luis ObispoChicago

SBP - ORD

SBPORD

San Luis Obispo County

Tue 2/17

6:00 am-2:58 pm

1 stop6h 58m

Chicago O'Hare Intl

Sun 2/22

3:07 pm-11:17 pm

1 stop10h 10m

$289

San Luis ObispoChicago

SBP - ORD

SBPORD

San Luis Obispo County

Wed 2/25

12:19 pm-11:59 pm

1 stop9h 40m

Chicago O'Hare Intl

Mon 3/2

3:07 pm-11:39 am

1 stop22h 32m

$300

San Luis ObispoChicago

SBP - ORD

SBPORD

San Luis Obispo County

Fri 1/30

3:12 pm-2:29 pm

1 stop21h 17m

Chicago O'Hare Intl

Sun 2/1

3:44 pm-11:20 pm

1 stop9h 36m

$310

San Luis ObispoChicago

SBP - ORD

SBPORD

San Luis Obispo County

Tue 2/24

6:00 am-11:56 pm

2 stops15h 56m

Chicago O'Hare Intl

Sun 3/1

8:20 am-11:39 am

1 stop29h 19m

$328

San Luis ObispoChicago

SBP - ORD

SBPORD

San Luis Obispo County

Tue 2/24

5:00 am-1:14 pm

1 stop6h 14m

Chicago O'Hare Intl

Sun 3/1

6:20 pm-11:59 pm

1 stop7h 39m

$365

San Luis ObispoChicago

SBP - ORD

SBPORD

San Luis Obispo County

Wed 2/11

6:00 am-2:29 pm

1 stop6h 29m

$139

San Luis ObispoChicago

SBP - ORD

SBPORD

San Luis Obispo County

Fri 2/6

6:00 am-2:29 pm

1 stop6h 29m

$149

San Luis ObispoChicago

SBP - ORD

SBPORD

San Luis Obispo County

Thu 1/15

3:12 pm-11:37 pm

1 stop6h 25m

$191

San Luis ObispoChicago

SBP - ORD

SBPORD

San Luis Obispo County

Fri 3/20

6:00 pm-5:18 am

1 stop9h 18m

$248

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/17

Showing 1-10 of 14 results

Compare providers for flights from San Luis Obispo to Chicago

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 December.

Provider	Price Accuracy	Trust Score*
Expedia	Price Accuracy2 stars	Trust Score*3 stars
FlightHub	Price Accuracy3 stars	Trust Score*1 star
eDreams	Price Accuracy3 stars	Trust 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?

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.

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

Reviews of airlines servicing Chicago

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

9,091 reviews

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

9,091 reviews

United Airlines

7.4

Good

9,091 reviews

Reviews

1 / 20

8.0

Excellent

Anonymous,Oct 2025

YUL - ORD

American Airlines

7.2

Good

11,054 reviews

United Airlines

7.4

Good

9,091 reviews

Reviews

1 / 20

8.0

Excellent

Anonymous,Oct 2025

YUL - ORD

Related info for your journey

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 29m. 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 47% 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

Lansing

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Hammond

Porter

Benton Harbor

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Top 2 airlines flying from San Luis Obispo to Chicago

Airline	Cheapest	Average	Flexibility	On-time
American Airlines	Cheapest$274	Average$497	FlexibilityNo cancel fee	On-time71%
United Airlines	Cheapest$362	Average$587	FlexibilityNo cancel fee	On-time69%

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$139+ 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 2/11. Fares are subject to change and may not be available on all flights or dates of travel.

Find cheap flights from San Luis Obispo to Chicago with Cheapflights

1. Tell us where you want to go

2. Select your favorite providers

3. Compare prices and book

Cheap flight deals from San Luis Obispo to Chicago

Cheapest flights from San Luis Obispo to ChicagoExplore 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 December 18, 2025.

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 December 18, 2025.

Find flight deals from San Luis Obispo to Chicago

Most accurate provider

Most trusted provider

Round-trip from

One-way from

Popular in

Cheapest in

Average price

Cheapflights Fare Finder

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

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 December.

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.

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?

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 December 18, 2025.

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

Reviews of airlines servicing Chicago

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.

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?

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

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

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

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

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

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

Traveling to a place near Chicago?

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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

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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 December 18, 2025.