$148+ 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 7/15. Fares are subject to change and may not be available on all flights or dates of travel.
SBP — CHI
Jul 16 — Jul 231
Round-trip
1 adult, Economy
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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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Best
Last-minute
One-way
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 June 16, 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 June 16, 2026.
This Alaska Airlines deal was found by Cheapflights users on 6/15. 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 9/13:24 pm
SBP
- ORD
1 stop19h 58m
Alaska Airlines
Sat 9/56:01 am
ORD
- SBP
1 stop10h 43m
Alaska Airlines
Deal found 6/15![Alaska Airlines logo]()
$295
This American Airlines deal was found by Cheapflights users on 6/11. 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 9/112:45 pm
SBP
- ORD
2 stops9h 33m
American Airlines
Sat 9/56:00 am
ORD
- SBP
1 stop7h 39m
American Airlines
Deal found 6/11![American Airlines logo]()
$300
This Expedia deal was found by Cheapflights users on 6/12. 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.
Fri 7/35:57 pm
SBP
- ORD
1 stop17h 24m
Alaska Airlines
Sat 7/185:59 pm
ORD
- SBP
1 stop7h 41m
Alaska Airlines
Deal found 6/12![Alaska Airlines logo]()
$311
This Alaska Airlines deal was found by Cheapflights users on 6/11. 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 9/173:24 pm
SBP
- ORD
1 stop6h 35m
Alaska Airlines
Tue 9/222:18 pm
ORD
- SBP
1 stop11h 32m
Alaska Airlines
Deal found 6/11![Alaska Airlines logo]()
$322
This American Airlines deal was found by Cheapflights users on 6/12. 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.
Thu 9/176:51 pm
SBP
- ORD
1 stop8h 12m
American Airlines
Tue 9/2211:00 am
ORD
- SBP
2 stops9h 34m
American Airlines
Deal found 6/12![American Airlines logo]()
$327
This Alaska Airlines deal was found by Cheapflights users on 6/11. 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 7/35:20 pm
SBP
- ORD
1 stop9h 40m
Alaska Airlines
Wed 7/86:20 am
ORD
- SBP
1 stop12h 57m
Alaska Airlines
Deal found 6/11![Alaska Airlines logo]()
$338
This American Airlines deal was found by Cheapflights users on 6/12. 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.
Thu 7/912:29 pm
SBP
- ORD
1 stop9h 01m
American Airlines
Mon 7/135:00 am
ORD
- SBP
1 stop8h 49m
American Airlines
Deal found 6/12![American Airlines logo]()
$349
This American Airlines deal was found by Cheapflights users on 6/11. 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
SBP
- ORD
2 stops8h 30m
American Airlines
Tue 10/65:00 am
ORD
- SBP
1 stop8h 45m
American Airlines
Deal found 6/11![American Airlines logo]()
$354
This United Airlines deal was found by Cheapflights users on 6/12. 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 8/272:20 pm
SBP
- ORD
1 stop8h 39m
United Airlines
Sun 8/305:55 am
ORD
- SBP
1 stop6h 16m
United Airlines
Deal found 6/12![United Airlines logo]()
$374
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 June 16, 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 June 16, 2026.
This Alaska Airlines deal was found by Cheapflights users on 6/15. 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 9/13:24 pm
SBP
- ORD
1 stop19h 58m
Alaska Airlines
Sat 9/56:01 am
ORD
- SBP
1 stop10h 43m
Alaska Airlines
Deal found 6/15![Alaska Airlines logo]()
$295
This Alaska Airlines deal was found by Cheapflights users on 6/13. 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 9/153:24 pm
SBP
- ORD
1 stop19h 58m
Alaska Airlines
Tue 10/67:49 pm
ORD
- SBP
1 stop21h 07m
Alaska Airlines
Deal found 6/13![Alaska Airlines logo]()
$295
This Alaska Airlines deal was found by Cheapflights users on 6/14. 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 9/173:24 pm
SBP
- ORD
1 stop6h 35m
Alaska Airlines
Tue 9/222:18 pm
ORD
- SBP
1 stop11h 32m
Alaska Airlines
Deal found 6/14![Alaska Airlines logo]()
$322
This Travelocity deal was found by Cheapflights users on 6/13. 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 Travelocity is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/33:36 pm
SBP
- ORD
1 stop6h 23m
Alaska Airlines
Mon 10/57:20 am
ORD
- SBP
1 stop9h 36m
Alaska Airlines
Deal found 6/13![Alaska Airlines logo]()
$322
This Alaska Airlines deal was found by Cheapflights users on 6/15. 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 7/35:57 pm
SBP
- ORD
1 stop17h 24m
Alaska Airlines
Tue 7/76:20 am
ORD
- SBP
1 stop12h 57m
Alaska Airlines
Deal found 6/15![Alaska Airlines logo]()
$338
This Alaska Airlines deal was found by Cheapflights users on 6/11. 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 7/35:20 pm
SBP
- ORD
1 stop9h 40m
Alaska Airlines
Wed 7/86:20 am
ORD
- SBP
1 stop12h 57m
Alaska Airlines
Deal found 6/11![Alaska Airlines logo]()
$338
Last-minute flights from San Luis Obispo to ChicagoDiscover last-minute flight deals from San Luis Obispo to Chicago. Data last updated June 16, 2026 and is based on user searches.
Discover last-minute flight deals from San Luis Obispo to Chicago. Data last updated June 16, 2026 and is based on user searches.
This United Airlines deal was found by Cheapflights users on 6/11. 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 6/176:00 am
SBP
- ORD
1 stop6h 35m
United Airlines
Tue 6/233:26 pm
ORD
- SBP
1 stop8h 46m
United Airlines
Deal found 6/11![United Airlines logo]()
$439
This Expedia deal was found by Cheapflights users on 6/11. 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 6/206:04 am
SBP
- ORD
1 stop11h 33m
Alaska Airlines
Mon 7/207:59 pm
ORD
- SBP
1 stop23h 18m
Alaska Airlines
Deal found 6/11![Alaska Airlines logo]()
$429
This Alaska Airlines deal was found by Cheapflights users on 6/11. 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.
Sun 6/285:20 pm
SBP
- ORD
1 stop9h 40m
Alaska Airlines
Thu 7/27:59 pm
ORD
- SBP
1 stop23h 18m
Alaska Airlines
Deal found 6/11![Alaska Airlines logo]()
$384
This Expedia deal was found by Cheapflights users on 6/12. 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.
Fri 7/35:57 pm
SBP
- ORD
1 stop17h 24m
Alaska Airlines
Sat 7/185:59 pm
ORD
- SBP
1 stop7h 41m
Alaska Airlines
Deal found 6/12![Alaska Airlines logo]()
$311
This Alaska Airlines deal was found by Cheapflights users on 6/11. 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 7/35:20 pm
SBP
- ORD
1 stop9h 40m
Alaska Airlines
Wed 7/86:20 am
ORD
- SBP
1 stop12h 57m
Alaska Airlines
Deal found 6/11![Alaska Airlines logo]()
$338
This American Airlines deal was found by Cheapflights users on 6/12. 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 7/34:05 pm
SBP
- ORD
1 stop6h 46m
American Airlines
Sat 7/185:00 am
ORD
- SBP
2 stops8h 49m
American Airlines
Deal found 6/12![American Airlines logo]()
$431
This American Airlines deal was found by Cheapflights users on 6/15. 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.
Sun 7/57:02 pm
SBP
- ORD
1 stop9h 23m
American Airlines
Sat 7/115:00 am
ORD
- SBP
2 stops8h 49m
American Airlines
Deal found 6/15![American Airlines logo]()
$389
This American Airlines deal was found by Cheapflights users on 6/15. 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.
Mon 7/612:29 pm
SBP
- ORD
1 stop9h 01m
American Airlines
Sat 7/115:00 am
ORD
- SBP
2 stops8h 49m
American Airlines
Deal found 6/15![American Airlines logo]()
$354
This Expedia deal was found by Cheapflights users on 6/12. 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.
Tue 7/75:57 pm
SBP
- ORD
1 stop17h 24m
Alaska Airlines
Sat 7/185:59 pm
ORD
- SBP
1 stop7h 41m
Alaska Airlines
Deal found 6/12![Alaska Airlines logo]()
$322
This American Airlines deal was found by Cheapflights users on 6/12. 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 7/74:07 pm
SBP
- ORD
1 stop6h 44m
American Airlines
Sat 7/185:00 am
ORD
- SBP
2 stops8h 49m
American Airlines
Deal found 6/12![American Airlines logo]()
$442
This American Airlines deal was found by Cheapflights users on 6/12. 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.
Thu 7/912:29 pm
SBP
- ORD
1 stop9h 01m
American Airlines
Mon 7/135:00 am
ORD
- SBP
1 stop8h 49m
American Airlines
Deal found 6/12![American Airlines logo]()
$349
This Alaska Airlines deal was found by Cheapflights users on 6/15. 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 7/135:50 pm
SBP
- ORD
1 stop9h 10m
Alaska Airlines
Tue 8/42:20 pm
ORD
- SBP
1 stop11h 20m
Alaska Airlines
Deal found 6/15![Alaska Airlines logo]()
$450
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 June 16, 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 June 16, 2026.
This United Airlines deal was found by Cheapflights users on 6/11. 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 7/152:06 pm
SBP
- ORD
1 stop6h 53m
United Airlines
Deal found 6/11![United Airlines logo]()
$148
This Alaska Airlines deal was found by Cheapflights users on 6/11. 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 11/52:27 pm
SBP
- ORD
1 stop7h 22m
Alaska Airlines
Deal found 6/11![Alaska Airlines logo]()
$175
This Expedia deal was found by Cheapflights users on 6/12. 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.
Mon 8/246:00 am
SBP
- ORD
1 stop11h 21m
Alaska Airlines
Deal found 6/12![Alaska Airlines logo]()
$180
This American Airlines deal was found by Cheapflights users on 6/10. 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.
Thu 7/1612:40 pm
SBP
- ORD
1 stop10h 10m
American Airlines
Deal found 6/10![American Airlines logo]()
$185
This American Airlines deal was found by Cheapflights users on 6/11. 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 7/144:07 pm
SBP
- ORD
1 stop6h 44m
American Airlines
Deal found 6/11![American Airlines logo]()
$198
This Alaska Airlines deal was found by Cheapflights users on 6/11. 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.
Sun 6/285:20 pm
SBP
- ORD
1 stop9h 40m
Alaska Airlines
Deal found 6/11![Alaska Airlines logo]()
$210
This Travelocity deal was found by Cheapflights users on 6/13. 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 Travelocity is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 7/136:04 am
SBP
- ORD
1 stop10h 53m
Alaska Airlines
Deal found 6/13![Alaska Airlines logo]()
$215
This American Airlines deal was found by Cheapflights users on 6/12. 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.
Mon 8/2412:45 pm
SBP
- ORD
2 stops9h 33m
American Airlines
Deal found 6/12![American Airlines logo]()
$240
This American Airlines deal was found by Cheapflights users on 6/12. 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 11/1112:57 pm
SBP
- ORD
2 stops9h 31m
American Airlines
Deal found 6/12![American Airlines logo]()
$256
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 June 16, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $295 (Alaska Airlines) |
One-way from | $148 (United Airlines) |
Popular in | July |
Cheapest in | August |
Average price | $609 |
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 June 16, 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 - ORD
SBPORD
San Luis Obispo County
Tue 9/1
3:24 pm-1:22 pm
1 stop19h 58m
Chicago O'Hare Intl
Sat 9/5
6:01 am-2:44 pm
1 stop10h 43m
$295
San Luis ObispoChicago
SBP - ORD
SBPORD
San Luis Obispo County
Tue 9/15
3:24 pm-1:22 pm
1 stop19h 58m
Chicago O'Hare Intl
Tue 10/6
7:49 pm-2:56 pm
1 stop21h 07m
$295
San Luis ObispoChicago
SBP - ORD
SBPORD
San Luis Obispo County
Thu 9/17
3:24 pm-11:59 pm
1 stop6h 35m
Chicago O'Hare Intl
Tue 9/22
2:18 pm-11:50 pm
1 stop11h 32m
$322
Quickest round-trip
San Luis ObispoChicago
SBP - ORD
SBPORD
San Luis Obispo County
Sat 10/3
3:36 pm-11:59 pm
1 stop6h 23m
Chicago O'Hare Intl
Mon 10/5
7:20 am-2:56 pm
1 stop9h 36m
$322
San Luis ObispoChicago
SBP - ORD
SBPORD
San Luis Obispo County
Fri 7/3
5:57 pm-1:21 pm
1 stop17h 24m
Chicago O'Hare Intl
Tue 7/7
6:20 am-5:17 pm
1 stop12h 57m
$338
San Luis ObispoChicago
SBP - ORD
SBPORD
San Luis Obispo County
Fri 7/3
5:20 pm-5:00 am
1 stop9h 40m
Chicago O'Hare Intl
Wed 7/8
6:20 am-5:17 pm
1 stop12h 57m
$338
Cheapest one-way
San Luis ObispoChicago
SBP - ORD
SBPORD
San Luis Obispo County
Wed 11/11
6:55 pm-5:27 am
1 stop8h 32m
$148
San Luis ObispoChicago
SBP - ORD
SBPORD
San Luis Obispo County
Wed 7/15
2:06 pm-10:59 pm
1 stop6h 53m
$148
San Luis ObispoChicago
SBP - ORD
SBPORD
San Luis Obispo County
Thu 7/16
5:50 pm-5:00 am
1 stop9h 10m
$175
San Luis ObispoChicago
SBP - ORD
SBPORD
San Luis Obispo County
Thu 11/5
2:27 pm-11:49 pm
1 stop7h 22m
$175
Showing 1-10 of 13 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 June.
| 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, August is the cheapest month in which you can book a flight from San Luis Obispo to Chicago (average of $230). Flying from San Luis Obispo to Chicago in November is currently the most expensive (average of $364). 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 June 16, 2026.
When flying from San Luis Obispo to Chicago, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.
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 June 16, 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.
Comfort
7.8
Food
7.1
Boarding
8.1
Entertainment
7.0
Overall
7.9
Crew
8.5
Reviews
1 / 20
10.0
ExcellentFranzi,Mar 2026
SFO - PDX
Comfort
7.8
Food
7.1
Boarding
8.1
Entertainment
7.0
Overall
7.9
Crew
8.5
Reviews
1 / 20
10.0
ExcellentFranzi,Mar 2026
SFO - PDX
Comfort
7.8
Food
7.1
Boarding
8.1
Entertainment
7.0
Overall
7.9
Crew
8.5
Reviews
1 / 20
10.0
ExcellentFranzi,Mar 2026
SFO - PDX
Comfort
7.8
Food
7.1
Boarding
8.1
Entertainment
7.0
Overall
7.9
Crew
8.5
Reviews
1 / 20
10.0
ExcellentFranzi,Mar 2026
SFO - PDX
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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.
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Top 2 airlines flying from San Luis Obispo to Chicago
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| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$274 | Average$432 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$373 | Average$565 | FlexibilityNo cancel fee | On-time69% |