HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Chicago

$234+ 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 11/15. Fares are subject to change and may not be available on all flights or dates of travel.
SBP — CHI
Nov 29 — Dec 61
Sat 11/29
Sat 12/6
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

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

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 October 30, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$310
(Alaska Airlines)

One-way from

$234
(KAYAK)

Popular in

March

Cheapest in

August

Average price

$498
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. 19% potential increase in price ($128 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 7% potential price decrease ($36 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in October 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 October 30, 2025.

This Alaska Airlines deal was found by Cheapflights users on 10/29. 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.
Thu 12/43:12 pmSBP - ORD
1 stop6h 38mAlaska Airlines
Sat 1/109:00 amORD - SBP
1 stop9h 34mAlaska Airlines
Deal found 10/29$331
This Kiwi.com deal was found by Cheapflights users on 10/30. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/215:25 pmSBP - ORD
1 stop9h 37mAlaska Airlines
Wed 12/313:37 pmORD - SBP
1 stop9h 58mAlaska Airlines
Deal found 10/30$357
This Alaska Airlines deal was found by Cheapflights users on 10/30. 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.
Thu 12/43:12 pmSBP - ORD
1 stop6h 38mAlaska Airlines
Sun 12/78:55 amORD - SBP
1 stop16h 23mAlaska Airlines
Deal found 10/30$358
This Orbitz deal was found by Cheapflights users on 10/30. 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 Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/217:45 pmSBP - ORD
2 stops22h 17mAlaska Airlines
Tue 12/308:58 pmORD - SBP
2 stops24h 07mAlaska Airlines
Deal found 10/30$363
This Alaska Airlines deal was found by Cheapflights users on 10/29. 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 stop26h 56mAlaska Airlines
Sat 11/226:00 amORD - SBP
1 stop14h 40mAlaska Airlines
Deal found 10/29$392
This Orbitz deal was found by Cheapflights users on 10/30. 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 Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/237:45 pmSBP - ORD
2 stops22h 17mAlaska Airlines
Tue 12/308:58 pmORD - SBP
1 stop21h 46mAlaska Airlines
Deal found 10/30$402

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 October 30, 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

Tue 1/13

5:14 pm-2:29 pm

1 stop19h 15m

Chicago O'Hare Intl

Fri 1/16

3:49 pm-11:25 pm

1 stop9h 36m

$310

San Luis ObispoChicago

SBP - ORD

SBPORD

San Luis Obispo County

Thu 12/4

3:12 pm-11:50 pm

1 stop6h 38m

Chicago O'Hare Intl

Sat 1/10

9:00 am-4:34 pm

1 stop9h 34m

$331

San Luis ObispoChicago

SBP - ORD

SBPORD

San Luis Obispo County

Sun 12/21

5:25 pm-5:02 am

1 stop9h 37m

Chicago O'Hare Intl

Wed 12/31

3:37 pm-11:35 pm

1 stop9h 58m

$357

San Luis ObispoChicago

SBP - ORD

SBPORD

San Luis Obispo County

Sun 12/21

7:45 pm-8:02 pm

2 stops22h 17m

Chicago O'Hare Intl

Tue 12/30

8:58 pm-7:05 pm

2 stops24h 07m

$363

San Luis ObispoChicago

SBP - ORD

SBPORD

San Luis Obispo County

Thu 12/4

3:12 pm-11:50 pm

1 stop6h 38m

Chicago O'Hare Intl

Sun 12/7

8:00 am-4:38 pm

2 stops10h 38m

$398

San Luis ObispoChicago

SBP - ORD

SBPORD

San Luis Obispo County

Tue 12/23

7:45 pm-8:02 pm

2 stops22h 17m

Chicago O'Hare Intl

Tue 12/30

8:58 pm-4:44 pm

1 stop21h 46m

$402

San Luis ObispoChicago

SBP - ORD

SBPORD

San Luis Obispo County

Fri 11/28

5:15 am-1:15 pm

1 stop6h 00m

Chicago O'Hare Intl

Wed 12/3

2:40 pm-9:12 pm

1 stop8h 32m

$407

San Luis ObispoChicago

SBP - ORD

SBPORD

San Luis Obispo County

Sat 11/15

7:15 am-5:33 am

2 stops20h 18m

$384

San Luis ObispoChicago

SBP - ORD

SBPORD

San Luis Obispo County

Sun 11/9

6:00 am-1:54 pm

1 stop5h 54m

$411

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/29

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 October.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy2 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*1 star
eDreamsPrice 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 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 December is currently the most expensive (average of $338). 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 October 30, 2025.

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

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 October 30, 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
8,998 reviews

Overall

7.4

Entertainment

7.1

Boarding

7.7

Food

6.6

Crew

8.1

Comfort

7.3

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
8,998 reviews
United Airlines
7.4
Good
8,998 reviews

Overall

7.4

Entertainment

7.1

Boarding

7.7

Food

6.6

Crew

8.1

Comfort

7.3

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.
American Airlines
7.2
Good
11,035 reviews
United Airlines
7.4
Good
8,998 reviews

Overall

7.4

Entertainment

7.1

Boarding

7.7

Food

6.6

Crew

8.1

Comfort

7.3

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.

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 15m. 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 December is currently the most expensive (average of $338). 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
Porter
Benton Harbor

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.
Los Angeles to O'Hare Intl flights
San Francisco to O'Hare Intl flights
Ontario to O'Hare Intl flights
Los Angeles to Midway flights
San Francisco to Midway flights
Santa Ana to O'Hare Intl flights
San Diego to O'Hare Intl flights
Sacramento to O'Hare Intl flights
San Jose to O'Hare Intl flights
Burbank to O'Hare Intl flights
Oakland to O'Hare Intl flights
Los Angeles to St. Louis flights
Las Vegas to O'Hare Intl flights
San Francisco to St. Louis flights
San Diego to Midway flights
Sacramento to Midway flights
Ontario to St. Louis flights
Oakland to Midway flights
Reno to O'Hare Intl flights
Santa Ana to Midway flights
Las Vegas to Midway flights
Fresno to O'Hare Intl flights
San Diego to St. Louis flights
Palm Springs to O'Hare Intl flights
Burbank to Midway flights
Las Vegas to St. Louis flights
Ontario to Midway flights
Long Beach to O'Hare Intl flights
Burbank to St. Louis flights
Fresno to Midway flights
San Jose to Midway flights
Oakland to St. Louis flights
Santa Ana to St. Louis flights
San Jose to St. Louis flights
Monterey to O'Hare Intl flights
Santa Barbara to O'Hare Intl flights
Sacramento to St. Louis flights
Los Angeles to Moline flights
Reno to Midway flights
Los Angeles to Rockford flights
Long Beach to St. Louis flights
Santa Ana to Moline flights
San Luis Obispo to O'Hare Intl flights
Los Angeles to Peoria flights
Long Beach to Midway flights
Santa Ana to Bloomington flights
Palm Springs to Midway flights
San Francisco to Rockford flights
Las Vegas to Moline flights
San Diego to Peoria flights

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 October 30, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$274Average$559FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$362Average$633FlexibilityNo cancel feeOn-time69%

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.