$138+ 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 8/19. Fares are subject to change and may not be available on all flights or dates of travel.
SBP — CHI
Jun 3 — Jun 101
Round-trip
1 adult, Economy
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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 May 4, 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 May 4, 2026.
This Alaska Airlines deal was found by Cheapflights users on 5/3. 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 stop6h 33m
Alaska Airlines
Sat 9/56:01 am
ORD
- SBP
1 stop10h 43m
Alaska Airlines
Deal found 5/3![Alaska Airlines logo]()
$275
This American Airlines deal was found by Cheapflights users on 4/30. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/112:29 pm
SBP
- ORD
1 stop8h 41m
American Airlines
Sat 9/55:00 am
ORD
- SBP
2 stops8h 58m
American Airlines
Deal found 4/30![American Airlines logo]()
$280
This Alaska Airlines deal was found by Cheapflights users on 5/1. 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 6/27:27 pm
SBP
- ORD
1 stop8h 53m
Alaska Airlines
Tue 6/99:00 am
ORD
- SBP
1 stop7h 19m
Alaska Airlines
Deal found 5/1![Alaska Airlines logo]()
$294
This American Airlines deal was found by Cheapflights users on 5/1. 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 9/111:07 pm
SBP
- ORD
1 stop7h 11m
American Airlines
Tue 9/156:00 am
ORD
- SBP
1 stop7h 45m
American Airlines
Deal found 5/1![American Airlines logo]()
$312
This American Airlines deal was found by Cheapflights users on 5/1. 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 8/1112:45 pm
SBP
- ORD
1 stop8h 14m
American Airlines
Tue 9/15:00 am
ORD
- SBP
2 stops8h 58m
American Airlines
Deal found 5/1![American Airlines logo]()
$326
This Alaska Airlines deal was found by Cheapflights users on 4/30. 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 7/165:57 pm
SBP
- ORD
1 stop17h 24m
Alaska Airlines
Mon 7/207:59 pm
ORD
- SBP
1 stop23h 18m
Alaska Airlines
Deal found 4/30![Alaska Airlines logo]()
$349
This American Airlines deal was found by Cheapflights users on 5/4. 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 7/112:52 pm
SBP
- ORD
1 stop9h 47m
American Airlines
Sat 7/116:04 am
ORD
- SBP
1 stop7h 40m
American Airlines
Deal found 5/4![American Airlines logo]()
$358
This American Airlines deal was found by Cheapflights users on 5/1. 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 7/164:07 pm
SBP
- ORD
1 stop6h 44m
American Airlines
Mon 7/205:00 am
ORD
- SBP
1 stop8h 51m
American Airlines
Deal found 5/1![American Airlines logo]()
$359
This United Airlines deal was found by Cheapflights users on 5/1. 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.
Sat 5/166:05 am
SBP
- ORD
1 stop6h 49m
United Airlines
Wed 5/206:20 am
ORD
- SBP
1 stop7h 34m
United Airlines
Deal found 5/1![United Airlines logo]()
$367
This American Airlines deal was found by Cheapflights users on 5/2. 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 5/2812:51 pm
SBP
- ORD
1 stop9h 51m
American Airlines
Sun 5/315:00 am
ORD
- SBP
1 stop8h 43m
American Airlines
Deal found 5/2![American Airlines logo]()
$369
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 May 4, 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 May 4, 2026.
This United Airlines deal was found by Cheapflights users on 5/1. 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 6/22:06 pm
SBP
- ORD
1 stop6h 53m
United Airlines
Tue 6/96:10 pm
ORD
- SBP
1 stop7h 34m
United Airlines
Deal found 5/1![United Airlines logo]()
$275
This Alaska Airlines deal was found by Cheapflights users on 5/3. 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 6/22:59 pm
SBP
- ORD
1 stop20h 15m
Alaska Airlines
Tue 6/99:00 am
ORD
- SBP
1 stop7h 19m
Alaska Airlines
Deal found 5/3![Alaska Airlines logo]()
$275
This American Airlines deal was found by Cheapflights users on 5/2. 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 7/112:52 pm
SBP
- ORD
1 stop9h 47m
American Airlines
Sat 7/115:00 am
ORD
- SBP
1 stop8h 51m
American Airlines
Deal found 5/2![American Airlines logo]()
$368
This United Airlines deal was found by Cheapflights users on 5/2. 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.
Sat 9/1910:52 am
SBP
- ORD
1 stop7h 49m
United Airlines
Sat 9/2612:45 pm
ORD
- SBP
1 stop6h 27m
United Airlines
Deal found 5/2![United Airlines logo]()
$275
This Alaska Airlines deal was found by Cheapflights users on 4/30. 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 7/165:57 pm
SBP
- ORD
1 stop17h 24m
Alaska Airlines
Mon 7/207:59 pm
ORD
- SBP
1 stop23h 18m
Alaska Airlines
Deal found 4/30![Alaska Airlines logo]()
$349
This Expedia deal was found by Cheapflights users on 5/4. 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 7/175:50 pm
SBP
- ORD
1 stop9h 10m
Alaska Airlines
Mon 7/207:59 pm
ORD
- SBP
1 stop23h 18m
Alaska Airlines
Deal found 5/4![Alaska Airlines logo]()
$349
This Alaska Airlines deal was found by Cheapflights users on 5/2. 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 10/77:45 am
SBP
- ORD
1 stop13h 56m
Alaska Airlines
Mon 10/127:55 pm
ORD
- SBP
1 stop21h 11m
Alaska Airlines
Deal found 5/2![Alaska Airlines logo]()
$384
This Alaska Airlines deal was found by Cheapflights users on 5/4. 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 5/197:27 pm
SBP
- ORD
1 stop8h 53m
Alaska Airlines
Sat 5/237:59 pm
ORD
- SBP
1 stop20h 20m
Alaska Airlines
Deal found 5/4![Alaska Airlines logo]()
$387
This Alaska Airlines deal was found by Cheapflights users on 5/2. 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 9/157:33 am
SBP
- ORD
2 stops10h 12m
Alaska Airlines
Tue 10/67:00 am
ORD
- SBP
1 stop7h 38m
Alaska Airlines
Deal found 5/2![Alaska Airlines logo]()
$417
This Alaska Airlines deal was found by Cheapflights users on 4/30. 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.
Fri 5/154:14 pm
SBP
- ORD
1 stop12h 06m
Alaska Airlines
Tue 5/192:10 pm
ORD
- SBP
1 stop11h 43m
Alaska Airlines
Deal found 4/30![Alaska Airlines logo]()
$443
Last-minute flights from San Luis Obispo to ChicagoDiscover last-minute flight deals from San Luis Obispo to Chicago. Data last updated May 4, 2026 and is based on user searches.
Discover last-minute flight deals from San Luis Obispo to Chicago. Data last updated May 4, 2026 and is based on user searches.
This United Airlines deal was found by Cheapflights users on 5/1. 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.
Sat 5/166:05 am
SBP
- ORD
1 stop6h 49m
United Airlines
Wed 5/206:20 am
ORD
- SBP
1 stop7h 34m
United Airlines
Deal found 5/1![United Airlines logo]()
$367
This Alaska Airlines deal was found by Cheapflights users on 5/4. 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 5/197:27 pm
SBP
- ORD
1 stop8h 53m
Alaska Airlines
Sat 5/237:59 pm
ORD
- SBP
1 stop20h 20m
Alaska Airlines
Deal found 5/4![Alaska Airlines logo]()
$387
This American Airlines deal was found by Cheapflights users on 4/30. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/204:32 pm
SBP
- ORD
1 stop6h 00m
American Airlines
Tue 5/265:00 am
ORD
- SBP
1 stop8h 47m
American Airlines
Deal found 4/30![American Airlines logo]()
$397
This American Airlines deal was found by Cheapflights users on 5/2. 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 5/2812:51 pm
SBP
- ORD
1 stop9h 51m
American Airlines
Sun 5/315:00 am
ORD
- SBP
1 stop8h 43m
American Airlines
Deal found 5/2![American Airlines logo]()
$369
This United Airlines deal was found by Cheapflights users on 5/1. 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 6/22:06 pm
SBP
- ORD
1 stop6h 53m
United Airlines
Tue 6/910:53 am
ORD
- SBP
1 stop8h 31m
United Airlines
Deal found 5/1![United Airlines logo]()
$275
This Alaska Airlines deal was found by Cheapflights users on 5/1. 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 6/27:27 pm
SBP
- ORD
1 stop8h 53m
Alaska Airlines
Tue 6/99:00 am
ORD
- SBP
1 stop7h 19m
Alaska Airlines
Deal found 5/1![Alaska Airlines logo]()
$294
This American Airlines deal was found by Cheapflights users on 5/1. 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 6/212:28 pm
SBP
- ORD
2 stops9h 09m
American Airlines
Tue 6/95:00 am
ORD
- SBP
1 stop8h 47m
American Airlines
Deal found 5/1![American Airlines logo]()
$383
This American Airlines deal was found by Cheapflights users on 5/3. 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 6/1012:52 pm
SBP
- ORD
1 stop9h 47m
American Airlines
Sun 6/145:00 am
ORD
- SBP
1 stop8h 47m
American Airlines
Deal found 5/3![American Airlines logo]()
$415
This Expedia deal was found by Cheapflights users on 5/4. 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.
Sun 6/215:57 pm
SBP
- ORD
1 stop17h 24m
Alaska Airlines
Fri 6/262:20 pm
ORD
- SBP
1 stop11h 20m
Alaska Airlines
Deal found 5/4![Alaska Airlines logo]()
$384
This Expedia deal was found by Cheapflights users on 4/30. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/245:57 pm
SBP
- ORD
1 stop17h 24m
Alaska Airlines
Sat 7/115:59 pm
ORD
- SBP
1 stop7h 41m
Alaska Airlines
Deal found 4/30![Alaska Airlines logo]()
$349
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 May 4, 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 May 4, 2026.
This American Airlines deal was found by Cheapflights users on 4/30. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/1912:45 pm
SBP
- ORD
1 stop8h 14m
American Airlines
Deal found 4/30![American Airlines logo]()
$138
This American Airlines deal was found by Cheapflights users on 4/30. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/154:37 pm
SBP
- ORD
1 stop5h 59m
American Airlines
Deal found 4/30![American Airlines logo]()
$175
This American Airlines deal was found by Cheapflights users on 5/1. 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.
Sat 5/167:02 pm
SBP
- ORD
1 stop8h 19m
American Airlines
Deal found 5/1![American Airlines logo]()
$184
This United Airlines deal was found by Cheapflights users on 5/3. 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 5/2012:40 pm
SBP
- ORD
1 stop9h 16m
United Airlines
Deal found 5/3![United Airlines logo]()
$197
This United Airlines deal was found by Cheapflights users on 5/1. 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 5/178:42 pm
SBP
- ORD
1 stop7h 38m
United Airlines
Deal found 5/1![United Airlines logo]()
$210
This United Airlines deal was found by Cheapflights users on 4/30. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/212:06 pm
SBP
- ORD
1 stop8h 53m
United Airlines
Deal found 4/30![United Airlines logo]()
$261
This Alaska Airlines deal was found by Cheapflights users on 4/30. 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 10/156:07 am
SBP
- ORD
2 stops11h 48m
Alaska Airlines
Deal found 4/30![Alaska Airlines logo]()
$312
This Expedia deal was found by Cheapflights users on 5/1. 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 5/162:59 pm
SBP
- ORD
2 stops13h 21m
Alaska Airlines
Deal found 5/1![Alaska Airlines logo]()
$436
This Alaska Airlines deal was found by Cheapflights users on 5/1. 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 5/182:59 pm
SBP
- ORD
2 stops13h 21m
Alaska Airlines
Deal found 5/1![Alaska Airlines logo]()
$456
This Alaska Airlines deal was found by Cheapflights users on 5/3. 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 7/106:04 am
SBP
- ORD
2 stops11h 17m
Alaska Airlines
Deal found 5/3![Alaska Airlines logo]()
$472
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 May 4, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $275 (Alaska Airlines) |
One-way from | $138 (American Airlines) |
Popular in | November |
Cheapest in | August |
Average price | $434 |
Good round-trip deal | $1,156 or less |
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 May 4, 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 6/2
2:06 pm-10:59 pm
1 stop6h 53m
Chicago O'Hare Intl
Tue 6/9
6:10 pm-11:44 pm
1 stop7h 34m
$275
San Luis ObispoChicago
SBP - ORD
SBPORD
San Luis Obispo County
Tue 6/2
2:59 pm-1:14 pm
1 stop20h 15m
Chicago O'Hare Intl
Tue 6/9
9:00 am-2:19 pm
1 stop7h 19m
$275
Quickest round-trip
San Luis ObispoChicago
SBP - ORD
SBPORD
San Luis Obispo County
Sat 9/19
10:52 am-8:41 pm
1 stop7h 49m
Chicago O'Hare Intl
Sat 9/26
12:45 pm-5:12 pm
1 stop6h 27m
$275
San Luis ObispoChicago
SBP - ORD
SBPORD
San Luis Obispo County
Thu 7/16
5:57 pm-1:21 pm
1 stop17h 24m
Chicago O'Hare Intl
Mon 7/20
7:59 pm-5:17 pm
1 stop23h 18m
$349
San Luis ObispoChicago
SBP - ORD
SBPORD
San Luis Obispo County
Fri 7/17
5:50 pm-5:00 am
1 stop9h 10m
Chicago O'Hare Intl
Mon 7/20
7:59 pm-5:17 pm
1 stop23h 18m
$349
San Luis ObispoChicago
SBP - ORD
SBPORD
San Luis Obispo County
Wed 7/1
12:52 pm-12:39 am
1 stop9h 47m
Chicago O'Hare Intl
Sat 7/11
5:00 am-11:51 am
1 stop8h 51m
$368
San Luis ObispoChicago
SBP - ORD
SBPORD
San Luis Obispo County
Wed 10/7
7:45 am-11:41 pm
1 stop13h 56m
Chicago O'Hare Intl
Mon 10/12
7:55 pm-3:06 pm
1 stop21h 11m
$384
San Luis ObispoChicago
SBP - ORD
SBPORD
San Luis Obispo County
Tue 5/19
7:27 pm-6:20 am
1 stop8h 53m
Chicago O'Hare Intl
Sat 5/23
7:59 pm-2:19 pm
1 stop20h 20m
$387
San Luis ObispoChicago
SBP - ORD
SBPORD
San Luis Obispo County
Tue 9/15
7:33 am-7:45 pm
2 stops10h 12m
Chicago O'Hare Intl
Tue 10/6
7:00 am-12:38 pm
1 stop7h 38m
$417
San Luis ObispoChicago
SBP - ORD
SBPORD
San Luis Obispo County
Fri 5/15
4:14 pm-6:20 am
1 stop12h 06m
Chicago O'Hare Intl
Tue 5/19
2:10 pm-11:53 pm
1 stop11h 43m
$443
Showing 1-10 of 18 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 May.
| 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 June is currently the most expensive (average of $439). 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 May 4, 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 May 4, 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.
Crew
8.5
Comfort
7.8
Entertainment
7.0
Overall
7.9
Food
7.1
Boarding
8.1
Reviews
1 / 20
10.0
ExcellentFranzi,Mar 2026
SFO - PDX
Crew
8.5
Comfort
7.8
Entertainment
7.0
Overall
7.9
Food
7.1
Boarding
8.1
Reviews
1 / 20
10.0
ExcellentFranzi,Mar 2026
SFO - PDX
Crew
8.5
Comfort
7.8
Entertainment
7.0
Overall
7.9
Food
7.1
Boarding
8.1
Reviews
1 / 20
10.0
ExcellentFranzi,Mar 2026
SFO - PDX
Crew
8.5
Comfort
7.8
Entertainment
7.0
Overall
7.9
Food
7.1
Boarding
8.1
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
Hammond
Porter
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San Luis Obispo and Chicago flights
Browse other San Luis Obispo and Chicago flight options. Last updated on May 4, 2026.
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Browse through other flights departing from San Luis Obispo. Flights are based on user searches made on Cheapflights and were last updated on May 4, 2026.
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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 May 4, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$274 | Average$457 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$331 | Average$574 | FlexibilityNo cancel fee | On-time69% |