$180+ 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 10/15. Fares are subject to change and may not be available on all flights or dates of travel.
SBP — CHI
Sep 22 — Sep 291
Round-trip
1 adult, Economy
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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
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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
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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 August 23, 2026.
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 August 23, 2026.
This United Airlines deal was found by Cheapflights users on 8/18. 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.
Tue 9/152:10 pm -
1 stop6h 49m
Tue 9/223:48 pm -
1 stop8h 13m
Deal found 8/18![United Airlines logo]()
$359
This American Airlines deal was found by Cheapflights users on 8/18. 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.
Tue 9/151:00 pm -
2 stops8h 30m
Tue 10/65:00 am -
1 stop8h 48m
Deal found 8/18![American Airlines logo]()
$364
This American Airlines deal was found by Cheapflights users on 8/18. 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.
Tue 9/151:00 pm -
2 stops8h 30m
Tue 9/225:00 am -
2 stops9h 11m
Deal found 8/18![American Airlines logo]()
$369
This American Airlines deal was found by Cheapflights users on 8/18. 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 9/231:00 pm -
2 stops8h 30m
Sat 9/265:00 am -
2 stops9h 11m
Deal found 8/18![American Airlines logo]()
$388
This Expedia deal was found by Cheapflights users on 8/23. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/226:30 pm -
1 stop9h 10m
Fri 10/237:16 pm -
1 stop16h 13m
Deal found 8/23![Alaska Airlines logo]()
$394
This American Airlines deal was found by Cheapflights users on 8/21. 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 11/1112:42 pm -
2 stops9h 17m
Sun 11/155:00 am -
1 stop8h 52m
Deal found 8/21![American Airlines logo]()
$399
This Alaska Airlines deal was found by Cheapflights users on 8/20. 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 10/166:30 pm -
1 stop9h 10m
Mon 10/197:49 pm -
1 stop19h 57m
Deal found 8/20![Alaska Airlines logo]()
$411
This Alaska Airlines deal was found by Cheapflights users on 8/19. 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 9/110:11 am -
1 stop11h 48m
Sat 9/52:18 pm -
1 stop11h 32m
Deal found 8/19![Alaska Airlines logo]()
$413
This United Airlines deal was found by Cheapflights users on 8/21. 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.
Wed 10/72:15 pm -
1 stop6h 45m
Mon 10/126:00 am -
1 stop6h 07m
Deal found 8/21![United Airlines logo]()
$416
This United Airlines deal was found by Cheapflights users on 8/19. 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.
Sun 10/112:15 pm -
1 stop8h 40m
Sun 10/186:00 am -
1 stop6h 07m
Deal found 8/19![United Airlines logo]()
$419
This Alaska Airlines deal was found by Cheapflights users on 8/18. 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 9/296:03 am -
2 stops22h 17m
Fri 10/28:17 pm -
1 stop19h 29m
Deal found 8/18![Alaska Airlines logo]()
$426
This American Airlines deal was found by Cheapflights users on 8/20. 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 9/412:29 pm -
1 stop9h 01m
Tue 9/85:00 am -
1 stop9h 05m
Deal found 8/20![American Airlines logo]()
$429
Best flights from San Luis Obispo to ChicagoDiscover 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 August 23, 2026.
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 August 23, 2026.
This Alaska Airlines deal was found by Cheapflights users on 8/18. 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 9/296:43 pm -
1 stop9h 37m
Fri 10/28:17 pm -
1 stop19h 29m
Deal found 8/18![Alaska Airlines logo]()
$359
This United Airlines deal was found by Cheapflights users on 8/18. 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.
Wed 9/236:40 pm -
1 stop8h 21m
Sat 9/263:00 pm -
1 stop6h 52m
Deal found 8/18![United Airlines logo]()
$359
This American Airlines deal was found by Cheapflights users on 8/18. 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.
Tue 9/1512:31 pm -
1 stop8h 59m
Tue 10/65:00 am -
1 stop6h 14m
Deal found 8/18![American Airlines logo]()
$359
This Alaska Airlines deal was found by Cheapflights users on 8/22. 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 1/73:44 pm -
1 stop19h 31m
Thu 1/212:13 pm -
1 stop11h 21m
Deal found 8/22![Alaska Airlines logo]()
$359
This American Airlines deal was found by Cheapflights users on 8/23. 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 9/161:00 pm -
2 stops8h 30m
Wed 9/236:00 am -
1 stop7h 41m
Deal found 8/23![American Airlines logo]()
$364
This American Airlines deal was found by Cheapflights users on 8/18. 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 9/2312:31 pm -
1 stop9h 43m
Sat 9/265:00 am -
2 stops9h 11m
Deal found 8/18![American Airlines logo]()
$364
This Alaska Airlines deal was found by Cheapflights users on 8/22. 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.
Mon 11/26:00 am -
1 stop10h 59m
Fri 11/62:07 pm -
1 stop28h 55m
Deal found 8/22![Alaska Airlines logo]()
$394
This Expedia deal was found by Cheapflights users on 8/23. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/226:30 pm -
1 stop9h 10m
Fri 10/237:16 pm -
1 stop16h 13m
Deal found 8/23![Alaska Airlines logo]()
$394
This Alaska Airlines deal was found by Cheapflights users on 8/20. 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 10/166:30 pm -
1 stop9h 10m
Mon 10/197:49 pm -
1 stop19h 57m
Deal found 8/20![Alaska Airlines logo]()
$411
This Alaska Airlines deal was found by Cheapflights users on 8/20. 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.
Sat 2/66:00 am -
1 stop14h 08m
Tue 2/97:40 am -
1 stop9h 24m
Deal found 8/20![Alaska Airlines logo]()
$411
Last-minute flights from San Luis Obispo to ChicagoDiscover last-minute flight deals from San Luis Obispo to Chicago. Data last updated August 23, 2026 and is based on user searches.
Discover last-minute flight deals from San Luis Obispo to Chicago. Data last updated August 23, 2026 and is based on user searches.
This Alaska Airlines deal was found by Cheapflights users on 8/19. 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 9/110:11 am -
1 stop11h 48m
Sat 9/52:18 pm -
1 stop11h 32m
Deal found 8/19![Alaska Airlines logo]()
$413
This American Airlines deal was found by Cheapflights users on 8/19. 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.
Tue 9/112:51 pm -
2 stops9h 27m
Sat 9/56:00 am -
1 stop7h 39m
Deal found 8/19![American Airlines logo]()
$465
This United Airlines deal was found by Cheapflights users on 8/20. 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.
Thu 9/312:55 pm -
1 stop7h 05m
Tue 9/85:52 pm -
1 stop6h 09m
Deal found 8/20![United Airlines logo]()
$474
This American Airlines deal was found by Cheapflights users on 8/20. 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 9/412:29 pm -
1 stop9h 49m
Sun 9/66:00 am -
1 stop7h 39m
Deal found 8/20![American Airlines logo]()
$429
This American Airlines deal was found by Cheapflights users on 8/20. 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 9/412:51 pm -
2 stops9h 27m
Tue 9/85:00 am -
1 stop8h 39m
Deal found 8/20![American Airlines logo]()
$434
This United Airlines deal was found by Cheapflights users on 8/18. 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.
Tue 9/152:10 pm -
1 stop6h 49m
Tue 9/223:48 pm -
1 stop8h 13m
Deal found 8/18![United Airlines logo]()
$359
This American Airlines deal was found by Cheapflights users on 8/18. 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.
Tue 9/151:00 pm -
2 stops8h 30m
Tue 10/65:00 am -
1 stop8h 48m
Deal found 8/18![American Airlines logo]()
$364
This American Airlines deal was found by Cheapflights users on 8/18. 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.
Tue 9/151:00 pm -
2 stops8h 30m
Tue 9/225:00 am -
2 stops9h 11m
Deal found 8/18![American Airlines logo]()
$369
This American Airlines deal was found by Cheapflights users on 8/18. 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 9/231:00 pm -
2 stops8h 30m
Sat 9/265:00 am -
2 stops9h 11m
Deal found 8/18![American Airlines logo]()
$388
This Alaska Airlines deal was found by Cheapflights users on 8/18. 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 9/296:03 am -
2 stops22h 17m
Fri 10/28:17 pm -
1 stop19h 29m
Deal found 8/18![Alaska Airlines logo]()
$426
One-way flights from San Luis Obispo to ChicagoSearch for one-way flight options from San Luis Obispo to Chicago. Find affordable one-way fares based on user searches. Data last updated August 23, 2026.
Search for one-way flight options from San Luis Obispo to Chicago. Find affordable one-way fares based on user searches. Data last updated August 23, 2026.
This Alaska Airlines deal was found by Cheapflights users on 8/18. 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 10/152:26 pm -
1 stop7h 33m
Deal found 8/18![Alaska Airlines logo]()
$180
This Alaska Airlines deal was found by Cheapflights users on 8/18. 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 10/132:26 pm -
1 stop20h 59m
Deal found 8/18![Alaska Airlines logo]()
$185
This Alaska Airlines deal was found by Cheapflights users on 8/19. 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 11/53:16 pm -
1 stop6h 33m
Deal found 8/19![Alaska Airlines logo]()
$215
This Alaska Airlines deal was found by Cheapflights users on 8/19. 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.
Wed 10/146:08 am -
1 stop10h 45m
Deal found 8/19![Alaska Airlines logo]()
$220
This Expedia deal was found by Cheapflights users on 8/19. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/210:11 am -
1 stop11h 48m
Deal found 8/19![Alaska Airlines logo]()
$251
This Expedia deal was found by Cheapflights users on 8/18. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/267:33 am -
2 stops14h 26m
Deal found 8/18![Alaska Airlines logo]()
$288
This Expedia deal was found by Cheapflights users on 8/20. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/236:03 am -
2 stops22h 17m
Deal found 8/20![Alaska Airlines logo]()
$298
Find 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 August 23, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $359 (United Airlines) |
One-way from | $180 (Priceline) |
Popular in | October |
Cheapest in | March |
Average price | $470 |
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 7,457,451 searches. Data last updated August 23, 2026.
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
Cheapest round-trip
San Luis ObispoChicago
SBP San Luis Obispo County - ORD Chicago O'Hare Intl
SBPORD
San Luis Obispo County
Tue 9/29
6:43 pm-6:20 am
1 stop9h 37m
Chicago O'Hare Intl
Fri 10/2
8:17 pm-1:46 pm
1 stop19h 29m
$359
Quickest round-trip
San Luis ObispoChicago
SBP San Luis Obispo County - ORD Chicago O'Hare Intl
SBPORD
San Luis Obispo County
Wed 9/23
6:40 pm-5:01 am
1 stop8h 21m
Chicago O'Hare Intl
Sat 9/26
3:00 pm-7:52 pm
1 stop6h 52m
$359
San Luis ObispoChicago
SBP San Luis Obispo County - ORD Chicago O'Hare Intl
SBPORD
San Luis Obispo County
Tue 9/15
12:31 pm-11:30 pm
1 stop8h 59m
Chicago O'Hare Intl
Tue 10/6
5:00 am-9:14 am
1 stop6h 14m
$359
San Luis ObispoChicago
SBP San Luis Obispo County - ORD Chicago O'Hare Intl
SBPORD
San Luis Obispo County
Thu 1/7
3:44 pm-1:15 pm
1 stop19h 31m
Chicago O'Hare Intl
Thu 1/21
2:13 pm-11:34 pm
1 stop11h 21m
$359
San Luis ObispoChicago
SBP San Luis Obispo County - ORD Chicago O'Hare Intl
SBPORD
San Luis Obispo County
Wed 9/16
1:00 pm-11:30 pm
2 stops8h 30m
Chicago O'Hare Intl
Wed 9/23
6:00 am-11:41 am
1 stop7h 41m
$364
San Luis ObispoChicago
SBP San Luis Obispo County - ORD Chicago O'Hare Intl
SBPORD
San Luis Obispo County
Wed 9/23
12:31 pm-12:14 am
1 stop9h 43m
Chicago O'Hare Intl
Sat 9/26
5:00 am-12:11 pm
2 stops9h 11m
$364
San Luis ObispoChicago
SBP San Luis Obispo County - ORD Chicago O'Hare Intl
SBPORD
San Luis Obispo County
Mon 11/2
6:00 am-6:59 pm
1 stop10h 59m
Chicago O'Hare Intl
Fri 11/6
2:07 pm-5:02 pm
1 stop28h 55m
$394
San Luis ObispoChicago
SBP San Luis Obispo County - ORD Chicago O'Hare Intl
SBPORD
San Luis Obispo County
Thu 10/22
6:30 pm-5:40 am
1 stop9h 10m
Chicago O'Hare Intl
Fri 10/23
7:16 pm-9:29 am
1 stop16h 13m
$394
San Luis ObispoChicago
SBP San Luis Obispo County - ORD Chicago O'Hare Intl
SBPORD
San Luis Obispo County
Fri 10/16
6:30 pm-5:40 am
1 stop9h 10m
Chicago O'Hare Intl
Mon 10/19
7:49 pm-1:46 pm
1 stop19h 57m
$411
San Luis ObispoChicago
SBP San Luis Obispo County - ORD Chicago O'Hare Intl
SBPORD
San Luis Obispo County
Sat 2/6
6:00 am-10:08 pm
1 stop14h 08m
Chicago O'Hare Intl
Tue 2/9
7:40 am-3:04 pm
1 stop9h 24m
$411
Showing 1-10 of 14 resultsSorted by cheapest first
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 August.
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars |
- 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 FlightHub the most. FlightHub 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.
SBP-CHI
SBP-ORD
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
SBP-CHI
SBP-ORD
What is the cheapest month to book a flight from San Luis Obispo to Chicago?
Currently, January is the cheapest month in which you can book a flight from San Luis Obispo to Chicago (average of $378). Flying from San Luis Obispo to Chicago in July is currently the most expensive (average of $729). 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.
How much does it cost to fly round-trip from San Luis Obispo to Chicago?
Airfare is typical for this route at the moment.
San Luis Obispo to Chicago flights typically cost between $353 and $522 in September.The cheapest round-trip price found within the last 5 days was $359 on United Airlines (Sep 15-Sep 22).
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 August 23, 2026.
Read through reviews of airlines operating flights from San Luis Obispo to Chicago, such as Alaska Airlines,United Airlines, andAmerican Airlines. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Boarding
8.1
Overall
7.9
Crew
8.5
Entertainment
7.0
Comfort
7.8
Food
7.0
Reviews
1 / 20
10.0
ExcellentFranzi,Mar 2026
SFO - PDX
Boarding
8.1
Overall
7.9
Crew
8.5
Entertainment
7.0
Comfort
7.8
Food
7.0
Reviews
1 / 20
10.0
ExcellentFranzi,Mar 2026
SFO - PDX
Boarding
8.1
Overall
7.9
Crew
8.5
Entertainment
7.0
Comfort
7.8
Food
7.0
Reviews
1 / 20
10.0
ExcellentFranzi,Mar 2026
SFO - PDX
Boarding
8.1
Overall
7.9
Crew
8.5
Entertainment
7.0
Comfort
7.8
Food
7.0
Reviews
1 / 20
10.0
ExcellentFranzi,Mar 2026
SFO - PDX
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.
Traveling to a place near Chicago?
Book flights to Chicago if you plan to visit one of these locationsBenton Harbor
Lansing
Merrillville
Valparaiso
Hammond
Saint Joseph
Porter
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Alternative routes for San Luis Obispo to Chicago
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Other flights to Chicago
Explore flights to Chicago departing from other origins. Flights are based on user searches made on Cheapflights and were last updated on August 23, 2026.
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San Luis Obispo and Chicago flights
Browse other San Luis Obispo and Chicago flight options. Last updated on August 23, 2026.
Other flights from San Luis Obispo
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Top 3 airlines flying from San Luis Obispo to Chicago
Discover the top 3 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 7,457,451 searches. Data last updated August 23, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$279 | Average$445 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$290 | Average$620 | FlexibilityNo cancel fee | On-time75% | |
| Cheapest$348 | Average$550 | FlexibilityNo cancel fee | On-time69% |