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

American Airlines, at $359, was found to be the cheapest airline from San Luis Obispo to Chicago.Alternate airlines to your destination round-trip include Alaska Airlines and United Airlines. American Airlines is currently priced 39% 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 Alaska Airlines, which is currently one of the cheapest options available, starting at $178. American Airlines flights start at $188 while deals on Hawaiian Airlines start at $233 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.

$178+ Flights from San Luis Obispo to Chicago - Compare & Save Big

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1. Tell us where you want to go

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Cheap flight deals from San Luis Obispo to Chicago

Most accurate provider	FlightHub 3 stars
Most trusted provider	eDreams 3 stars
Round-trip from	$359 (American Airlines)
One-way from	$178 (Alaska Airlines)
Popular in	March
Cheapest in	February
Average price	$542

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.

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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)

Search Deals

High demand for flights, 6% potential price rise

Search Deals

Cheapest flight prices on average. 4% potential price decrease ($27 potential savings vs. average RT price).

Search Deals

Average for round-trip flights in May 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 mayo 1, 2025.

mié. 5/217:09 pmSBP - ORD

1 stop8h 04mAmerican Airlines

mar. 5/276:00 amORD - SBP

1 stop8h 00mAmerican Airlines

Deal found 4/30

$359

vie. 5/237:35 pmSBP - ORD

1 stop26h 24mAlaska Airlines

mar. 5/275:58 pmORD - SBP

1 stop26h 42mAlaska Airlines

Deal found 4/29

$365

jue. 5/226:00 amSBP - ORD

1 stop6h 39mUnited Airlines

sáb. 5/242:33 pmORD - SBP

1 stop8h 32mUnited Airlines

Deal found 4/28

$517

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 mayo 1, 2025.

mié. 5/217:09 pmSBP - ORD

1 stop8h 04mAmerican Airlines

mar. 5/276:00 amORD - SBP

1 stop8h 00mAmerican Airlines

Deal found 4/30

$359

lun. 7/217:35 pmSBP - ORD

1 stop8h 05mAlaska Airlines

mié. 7/236:00 amORD - SBP

1 stop14h 43mAlaska Airlines

Deal found 4/30

$375

jue. 5/152:21 pmSBP - ORD

1 stop7h 38mUnited Airlines

lun. 5/197:00 amORD - SBP

1 stop6h 45mUnited Airlines

Deal found 4/30

$557

Last-minute flights from San Luis Obispo to Chicago
Discover last-minute flight deals from San Luis Obispo to Chicago. Data last updated mayo 1, 2025 and is based on user searches.

vie. 5/912:43 pmSBP - ORD

1 stop6h 04mAmerican Airlines

dom. 5/115:00 amORD - SBP

1 stop8h 32mAmerican Airlines

Deal found 4/29

$467

mié. 5/217:09 pmSBP - ORD

1 stop8h 04mAmerican Airlines

mar. 5/276:00 amORD - SBP

1 stop8h 00mAmerican Airlines

Deal found 4/30

$359

jue. 5/226:00 amSBP - ORD

1 stop8h 56mUnited Airlines

mar. 5/277:40 pmORD - SBP

1 stop6h 19mUnited Airlines

Deal found 4/28

$517

vie. 5/237:35 pmSBP - ORD

1 stop26h 24mAlaska Airlines

mar. 5/275:58 pmORD - SBP

1 stop26h 42mAlaska Airlines

Deal found 4/29

$365

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 mayo 1, 2025.

mar. 6/107:35 pmSBP - ORD

1 stop8h 05mAlaska Airlines

Deal found 4/30

$178

lun. 6/304:35 pmSBP - ORD

1 stop5h 57mAmerican Airlines

Deal found 4/30

$188

mié. 5/77:14 pmSBP - ORD

1 stop8h 51mHawaiian Airlines

Deal found 4/30

$233

mar. 6/104:50 pmSBP - ORD

3 stops23h 55mUnited Airlines

Deal found 4/30

$334

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

mié. 5/21

7:09 pm-5:13 am

1 stop8h 04m

Chicago O'Hare Intl

mar. 5/27

6:00 am-12:00 pm

1 stop8h 00m

$359

San Luis ObispoChicago

SBP - ORD

SBPORD

San Luis Obispo County

vie. 5/23

7:35 pm-11:59 pm

1 stop26h 24m

Chicago O'Hare Intl

mar. 5/27

5:58 pm-6:40 pm

1 stop26h 42m

$365

San Luis ObispoChicago

SBP - ORD

SBPORD

San Luis Obispo County

jue. 5/22

6:00 am-4:56 pm

1 stop8h 56m

Chicago O'Hare Intl

mar. 5/27

7:40 pm-11:59 pm

1 stop6h 19m

$517

San Luis ObispoChicago

SBP - ORD

SBPORD

San Luis Obispo County

lun. 6/30

4:35 pm-12:32 am

1 stop5h 57m

$188

San Luis ObispoChicago

SBP - ORD

SBPORD

San Luis Obispo County

mié. 5/7

6:05 am-6:20 pm

2 stops10h 15m

$218

San Luis ObispoChicago

SBP - ORD

SBPORD

San Luis Obispo County

mié. 5/7

7:14 pm-6:05 am

1 stop8h 51m

$233

San Luis ObispoChicago

SBP - ORD

SBPORD

San Luis Obispo County

vie. 10/10

2:19 pm-12:47 am

1 stop8h 28m

$283

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/30

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 May.

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

Alaska Airlines

8.0

Very good

9,968 reviews

Reviews

1 / 20

10.0

Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.

Alaska Airlines

8.0

Very good

9,968 reviews

Alaska Airlines

8.0

Very good

9,968 reviews

Reviews

1 / 20

10.0

Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.

Hawaiian Airlines

7.9

Good

2,409 reviews

Alaska Airlines

8.0

Very good

9,968 reviews

Reviews

1 / 20

10.0

Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.

United Airlines

7.4

Good

8,696 reviews

Alaska Airlines

8.0

Very good

9,968 reviews

Reviews

1 / 20

10.0

Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.

American Airlines

7.2

Good

10,000 reviews

Alaska Airlines

8.0

Very good

9,968 reviews

Reviews

1 / 20

10.0

Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.

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?
American Airlines, at $359, was found to be the cheapest airline from San Luis Obispo to Chicago.Alternate airlines to your destination round-trip include Alaska Airlines and United Airlines. American Airlines is currently priced 39% 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 Alaska Airlines, which is currently one of the cheapest options available, starting at $178. American Airlines flights start at $188 while deals on Hawaiian Airlines start at $233 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

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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$533	FlexibilityNo cancel fee	On-time71%

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$178+ 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 6/10. 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 mayo 1, 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 mayo 1, 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 May.

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 mayo 1, 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?

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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.

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 mayo 1, 2025.