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

Alaska Airlines, at $344, was found to be the cheapest airline from San Luis Obispo to Chicago.Alternate airlines to your destination round-trip include United Airlines and American Airlines. Alaska Airlines is currently priced 43% 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 $177. Alaska Airlines flights start at $183 while deals on American Airlines start at $185 one-way.

What is the cheapest day to fly from San Luis Obispo to Chicago?

Travelers seeking maximum savings on their San Luis Obispo to Chicago flight should consider departing on Monday evenings when fares are most often at their lowest. Friday afternoons flights should be avoided if possible as fares are typically the most expensive at this time.

What is the cheapest day to fly round-trip from San Luis Obispo to Chicago?

Departing on a Wednesday is a good option for securing a great price. You can expect to save up to 38% when planning your travel around this day of the week.

What is the cheapest month to fly from San Luis Obispo to Chicago?

Flights from San Luis Obispo to Chicago lean towards being more expensive in March. Prices are generally better when you fly from San Luis Obispo to Chicago in February, with the cheapest ticket starting at $375.

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 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.

$177+ Flights from San Luis Obispo to Chicago

Home Search by date Vacation packages Hotels Flight deals Car rental Travel tips & news

Find cheap flights from San Luis Obispo to Chicago with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

Cheap flight deals from San Luis Obispo to Chicago

Most accurate provider	FlightHub 3 stars
Most trusted provider	eDreams 3 stars
Round-trip from	$344 (Alaska Airlines)
One-way from	$177 (Hawaiian Airlines)
Popular in	March
Cheapest in	February
Average price	$425

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

High demand for flights, 7% potential price rise

Search Deals

Cheapest flight prices on average. 4% potential price decrease ($26 potential savings vs. average RT price).

Search Deals

Average for round-trip flights in April 2025

Search Deals

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 April 17, 2025.

Fri 5/237:35 pmSBP - ORD

1 stop24h 48mAlaska Airlines

Tue 5/277:51 pmORD - SBP

2 stops19h 34mAlaska Airlines

Deal found 4/17

$344

Wed 5/142:21 pmSBP - ORD

1 stop6h 39mUnited Airlines

Sat 5/175:55 pmORD - SBP

1 stop8h 04mUnited Airlines

Deal found 4/16

$359

Wed 5/147:09 pmSBP - ORD

1 stop8h 04mAmerican Airlines

Sat 5/175:00 amORD - SBP

2 stops9h 00mAmerican Airlines

Deal found 4/16

$364

Mon 4/287:14 pmSBP - ORD

1 stop8h 51mHawaiian Airlines

Wed 4/3012:00 pmORD - SBP

1 stop8h 22mHawaiian Airlines

Deal found 4/17

$858

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 April 17, 2025.

Fri 5/237:35 pmSBP - ORD

1 stop24h 48mAlaska Airlines

Tue 5/277:51 pmORD - SBP

2 stops19h 34mAlaska Airlines

Deal found 4/17

$344

Wed 5/142:21 pmSBP - ORD

1 stop6h 39mUnited Airlines

Sat 5/175:55 pmORD - SBP

1 stop8h 04mUnited Airlines

Deal found 4/16

$359

Wed 5/147:09 pmSBP - ORD

1 stop8h 04mAmerican Airlines

Sat 5/175:00 amORD - SBP

2 stops9h 00mAmerican Airlines

Deal found 4/16

$364

Mon 4/287:14 pmSBP - ORD

1 stop8h 51mHawaiian Airlines

Wed 4/3012:00 pmORD - SBP

1 stop8h 22mHawaiian Airlines

Deal found 4/17

$858

Last-minute flights from San Luis Obispo to Chicago
Discover last-minute flight deals from San Luis Obispo to Chicago. Data last updated April 17, 2025 and is based on user searches.

Sun 4/2010:40 amSBP - ORD

1 stop6h 59mUnited Airlines

Sat 4/267:50 pmORD - SBP

1 stop27h 28mUnited Airlines

Deal found 4/16

$842

Sun 4/2012:26 pmSBP - ORD

1 stop9h 23mAmerican Airlines

Sat 4/263:18 pmORD - SBP

2 stops8h 59mAmerican Airlines

Deal found 4/17

$904

Mon 4/286:05 amSBP - ORD

2 stops34h 15mAlaska Airlines

Wed 4/306:58 pmORD - SBP

2 stops20h 54mAlaska Airlines

Deal found 4/16

$637

Mon 4/287:14 pmSBP - ORD

1 stop8h 51mHawaiian Airlines

Wed 4/3012:00 pmORD - SBP

1 stop8h 22mHawaiian Airlines

Deal found 4/17

$858

Wed 5/142:21 pmSBP - ORD

1 stop6h 39mUnited Airlines

Sat 5/175:55 pmORD - SBP

1 stop8h 04mUnited Airlines

Deal found 4/16

$359

Wed 5/147:09 pmSBP - ORD

1 stop8h 04mAmerican Airlines

Sat 5/175:00 amORD - SBP

2 stops9h 00mAmerican Airlines

Deal found 4/16

$364

Fri 5/237:35 pmSBP - ORD

1 stop24h 48mAlaska Airlines

Tue 5/277:51 pmORD - SBP

2 stops19h 34mAlaska Airlines

Deal found 4/17

$344

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 April 17, 2025.

Wed 5/77:14 pmSBP - ORD

1 stop8h 51mHawaiian Airlines

Deal found 4/16

$177

Fri 5/97:14 pmSBP - ORD

1 stop17h 34mAlaska Airlines

Deal found 4/16

$183

Wed 5/712:43 pmSBP - ORD

2 stops9h 13mAmerican Airlines

Deal found 4/16

$185

Sat 4/265:00 amSBP - ORD

2 stops10h 10mUnited Airlines

Deal found 4/17

$415

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 5/23

7:35 pm-10:23 pm

1 stop24h 48m

Chicago O'Hare Intl

Tue 5/27

7:51 pm-1:25 pm

2 stops19h 34m

$344

San Luis ObispoChicago

SBP - ORD

SBPORD

San Luis Obispo County

Wed 5/14

2:21 pm-11:00 pm

1 stop6h 39m

Chicago O'Hare Intl

Sat 5/17

5:55 pm-11:59 pm

1 stop8h 04m

$359

San Luis ObispoChicago

SBP - ORD

SBPORD

San Luis Obispo County

Wed 5/14

7:09 pm-5:13 am

1 stop8h 04m

Chicago O'Hare Intl

Sat 5/17

5:00 am-12:00 pm

2 stops9h 00m

$364

San Luis ObispoChicago

SBP - ORD

SBPORD

San Luis Obispo County

Mon 4/28

7:14 pm-6:05 am

1 stop8h 51m

Chicago O'Hare Intl

Wed 4/30

12:00 pm-6:22 pm

1 stop8h 22m

$858

San Luis ObispoChicago

SBP - ORD

SBPORD

San Luis Obispo County

Wed 5/7

7:14 pm-6:05 am

1 stop8h 51m

$177

San Luis ObispoChicago

SBP - ORD

SBPORD

San Luis Obispo County

Fri 5/9

7:14 pm-2:48 pm

1 stop17h 34m

$183

San Luis ObispoChicago

SBP - ORD

SBPORD

San Luis Obispo County

Wed 5/7

12:43 pm-11:56 pm

2 stops9h 13m

$185

San Luis ObispoChicago

SBP - ORD

SBPORD

San Luis Obispo County

Sat 4/26

5:00 am-5:10 pm

2 stops10h 10m

$415

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/16

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 April.

Provider	Price Accuracy	Trust Score*
Expedia	Price Accuracy1 star	Trust Score*3 stars
FlightHub	Price Accuracy3 stars	Trust Score*2 stars
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 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 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, 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?

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.

Rainfall in Chicago by month

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.

Temperature in Chicago by month

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).

Reviews of airlines servicing Chicago

To help decide which airline to fly from San Luis Obispo to Chicago, see what other customers have to say about Alaska Airlines, Hawaiian Airlines and United Airlines. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.

Alaska Airlines

8.0

Very good

9,882 reviews

Reviews

1 / 20

10.0

Excellent

Cheri,Jan 2025

FAT - SEA

Very friendly. I really liked that they had water for us in cartons not plastic. Impressed with Alaska Airlines, First time I had flown them

Alaska Airlines

8.0

Very good

9,882 reviews

Alaska Airlines

8.0

Very good

9,882 reviews

Reviews

1 / 20

10.0

Excellent

Cheri,Jan 2025

FAT - SEA

Very friendly. I really liked that they had water for us in cartons not plastic. Impressed with Alaska Airlines, First time I had flown them

Hawaiian Airlines

7.9

Good

2,382 reviews

Alaska Airlines

8.0

Very good

9,882 reviews

Reviews

1 / 20

10.0

Excellent

Cheri,Jan 2025

FAT - SEA

Very friendly. I really liked that they had water for us in cartons not plastic. Impressed with Alaska Airlines, First time I had flown them

United Airlines

7.4

Good

8,667 reviews

Alaska Airlines

8.0

Very good

9,882 reviews

Reviews

1 / 20

10.0

Excellent

Cheri,Jan 2025

FAT - SEA

Very friendly. I really liked that they had water for us in cartons not plastic. Impressed with Alaska Airlines, First time I had flown them

American Airlines

7.2

Good

10,000 reviews

Alaska Airlines

8.0

Very good

9,882 reviews

Reviews

1 / 20

10.0

Excellent

Cheri,Jan 2025

FAT - SEA

Very friendly. I really liked that they had water for us in cartons not plastic. Impressed with Alaska Airlines, First time I had flown them

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.
What are the cheapest airlines flying from San Luis Obispo to Chicago round-trip?
Alaska Airlines, at $344, was found to be the cheapest airline from San Luis Obispo to Chicago.Alternate airlines to your destination round-trip include United Airlines and American Airlines. Alaska Airlines is currently priced 43% 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 $177. Alaska Airlines flights start at $183 while deals on American Airlines start at $185 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

Merrillville

Hammond

Benton Harbor

Porter

Lansing

Valparaiso

Chesterton

Browse thousands of different options on Cheapflights for your next trip

Top 2 airlines flying from San Luis Obispo to Chicago

Airline	Cheapest	Average	Flexibility	On-time
United Airlines	Cheapest$362	Average$646	FlexibilityNo cancel fee	On-time69%
American Airlines	Cheapest$362	Average$539	FlexibilityNo cancel fee	On-time71%

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.

$177+ 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 5/7. 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

Most accurate provider

Most trusted provider

Round-trip from

One-way from

Popular in

Cheapest in

Average price

Find 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 April 17, 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 April 17, 2025.

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 April.

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 April 17, 2025.

Rainfall in Chicago by month

Plan your trip to Chicago by taking into account the average rainfall totals by month.

Temperature in Chicago by month

Plan your trip to Chicago by taking into account the average temperature totals by month.

Reviews of airlines servicing Chicago

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?

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

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

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 San Luis Obispo?

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for San Luis Obispo to Chicago

See prices for flight routes from nearby airports that may be better suited for you.

Top 2 airlines flying from San Luis Obispo to Chicago

100% Free

Book with Flexibility

Travel Smart

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 April 17, 2025.