ORD - SBP

$185 Find Cheap Flights from Chicago to San Luis Obispo

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Chicago to San Luis Obispo departing on 4/16. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
1 adult, Economy, 0 bags

KAYAK searches hundreds of travel sites at once for deals on flights to San Luis Obispo

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to San Luis Obispo, as well as popular online travel agencies
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to San Luis Obispo, as well as popular online travel agencies
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Everything you should know

Cheapest round-trip
$309
Overall average: $449
United Airlines
Thu 7/16Tue 7/21
ORD - SBP • 1 stop
Cheapest one-way
$185
Alaska Airlines
Thu 4/16
ORD - SBP • 1 stop
Top airlines
United Airlines
Cheapest • from $309 (round-trip)
United Airlines
Best reviews • 7.4 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
Nonstop flights
Not available
There are currently no direct flights between Chicago and San Luis Obispo. You'll need at least 1 connection.
Insights
Insights
Insights
Insights
Top layover airports
San Francisco (SFO)
Cheapest • Avg $349 (round-trip)
Los Angeles (LAX)
Shortest trip • 6h 45m (one-way)
Insights
Insights
Insights
Insights
When to travel
January
Cheapest • 33% price drop
October
Most popular
Good to know
Good to know
+1
+1
Good to know
Good to know
+1
Start a new search
KAYAK searches 100s of sites at once to find you the best travel deals.
We hope you love your trip to San Luis Obispo!
Flight Deals
Booking Insights
Flight Deals

Cheap Flights from Chicago to San Luis Obispo (ORD-SBP)

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Chicago to San Luis Obispo that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Chicago to San Luis Obispo

Thu, Jul 16 - Tue, Jul 21
United Airlines Logo
6:10 pm - 11:44 pm
ORD
-
SBP
7h 34m
1 stop
United Airlines Logo
6:05 pm - 4:51 am
SBP
-
ORD
8h 46m
1 stop
$309United Airlines
Fri, Apr 10 - Mon, Apr 13
American Airlines Logo
5:00 am - 12:10 pm
ORD
-
SBP
9h 10m
1 stop
American Airlines Logo
7:02 pm - 5:21 am
SBP
-
ORD
8h 19m
1 stop
$334American Airlines
Tue, Mar 24 - Sat, Mar 28
United Airlines Logo
4:35 pm - 11:59 pm
ORD
-
SBP
9h 24m
1 stop
United Airlines Logo
5:00 am - 1:15 pm
SBP
-
ORD
6h 15m
1 stop
$340United Airlines
Fri, Mar 6 - Tue, Mar 10
United Airlines Logo
2:45 pm - 9:04 pm
ORD
-
SBP
8h 19m
1 stop
United Airlines Logo
2:15 pm - 11:38 pm
SBP
-
ORD
7h 23m
1 stop
$359United Airlines
Fri, Mar 6 - Tue, Mar 10
American Airlines Logo
6:00 am - 12:02 pm
ORD
-
SBP
8h 02m
1 stop
American Airlines Logo
12:50 pm - 11:36 pm
SBP
-
ORD
8h 46m
2 stops
$364American Airlines
Fri, Apr 10 - Mon, Apr 13
American Airlines Logo
6:04 am - 12:10 pm
ORD
-
SBP
8h 06m
1 stop
American Airlines Logo
7:02 pm - 5:21 am
SBP
-
ORD
8h 19m
1 stop
$379American Airlines
Wed, Aug 19 - Sat, Aug 22
American Airlines Logo
11:54 am - 6:22 pm
ORD
-
SBP
8h 28m
2 stops
American Airlines Logo
4:35 pm - 12:35 am
SBP
-
ORD
6h 00m
1 stop
$384American Airlines
Fri, Mar 6 - Tue, Mar 10
Alaska Airlines Logo
8:20 am - 11:17 pm
ORD
-
SBP
16h 57m
1 stop
Alaska Airlines Logo
6:00 am - 2:58 pm
SBP
-
ORD
6h 58m
1 stop
$404Alaska Airlines
Fri, May 1 - Mon, May 4
Alaska Airlines Logo
8:48 pm - 1:47 pm
ORD
-
SBP
18h 59m
1 stop
Alaska Airlines Logo
5:36 pm - 6:40 am
SBP
-
ORD
11h 04m
2 stops
$405Alaska Airlines
Fri, Mar 6 - Tue, Mar 10
American Airlines Logo
5:00 am - 12:02 pm
ORD
-
SBP
9h 02m
1 stop
American Airlines Logo
12:50 pm - 11:36 pm
SBP
-
ORD
8h 46m
2 stops
$409American Airlines
Booking Insights

KAYAK's insights & trends for Chicago to San Luis Obispo flights

Get data-powered insights and trends into flights from Chicago to San Luis Obispo to help you find the cheapest flights, the best time to fly and much more.

What is the cheapest month to fly from Chicago O'Hare Intl Airport to San Luis Obispo?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Chicago O'Hare Intl Airport to San Luis Obispo, removes the top 0.1% to account for outliers, and then takes the median of all values for each month.

The cheapest month for flights from Chicago O'Hare Intl Airport to San Luis Obispo is January, where tickets cost $288 (return) on average. On the other hand, the most expensive months are December and June, where the average cost of round-trip tickets is $599 and $572 respectively.

Good to know

Low seasonJanuary
Cheapest flight$185
Best time to beat the crowds with an average 33% drop in price.
Most popular time to fly and prices are also 15% lower on average.
Flight from Chicago to San Luis Obispo

When to book flights from Chicago to San Luis Obispo

Are your dates flexible? Find out the best times to travel from Chicago to San Luis Obispo based on our flight data from the last year. Discover the cheapest month and even day to fly.
Estimated round-trip price
KAYAK looks at all historical flight data for each date to provide a predicted price for one-way trips or round-trips with a duration up to 40 days. While we try to provide actual minimum prices for each date, some prices are predictions and actual prices may differ.

FAQs for booking Chicago to San Luis Obispo flights

  • What is the cheapest flight from Chicago O'Hare Intl Airport to San Luis Obispo?

    In the last 3 days, the lowest price for a flight from Chicago O'Hare Intl Airport to San Luis Obispo was $185 for a one-way ticket and $309 for a round-trip.

  • Do I need a passport to fly between Chicago and San Luis Obispo?

    Even though you are not required to have a passport, keep in mind that an official ID is needed to board the airplane.

  • Which aircraft models fly most regularly from Chicago to San Luis Obispo?

    We unfortunately don’t have that data for this specific route.

  • Which airline alliances offer flights from Chicago to San Luis Obispo?

    Star Alliance, and oneworld are the airline alliances operating flights between Chicago and San Luis Obispo, with Star Alliance being the most commonly used for this route.

  • Which is the best airline for flights from Chicago to San Luis Obispo, United Airlines or American Airlines?

    The two airlines most popular with KAYAK users for flights from Chicago to San Luis Obispo are United Airlines and American Airlines. With an average price for the route of $426 and an overall rating of 7.4, United Airlines is the most popular choice. American Airlines is also a great choice for the route, with an average price of $458 and an overall rating of 7.2.

  • How does KAYAK find such low prices on flights from Chicago to San Luis Obispo?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Chicago to San Luis Obispo.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Chicago to San Luis Obispo?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to San Luis Obispo from Chicago is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights from Chicago to San Luis Obispo?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly to San Luis Obispo with an airline and back to Chicago with another airline. Booking your flights between Chicago and SBP can sometimes prove cheaper using this method.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Chicago to San Luis Obispo?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying to San Luis Obispo from Chicago up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

Reviews of the top airlines flying from Chicago to San Luis Obispo

 
See real verified KAYAK customer reviews for airlines flying from Chicago to San Luis Obispo. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
Need help choosing which airline to fly with from Chicago to San Luis Obispo? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
7.4
United AirlinesOverall score based on 9342 reviews
7.7Boarding
7.3Comfort
7.1Entertainment
6.6Food
8.1Crew
Airline reviews

We were delayed for about an hour from taking off due to traffic control procedures at the destination airport. But once in the air, the flight went well. The crew members were great and provided cabin service despite moderate turbulence during much of the flight.

8.0 ExcellentDr. Joseph, Feb 2026
ORD - DCA
Read more United Airlines reviews

We were delayed for about an hour from taking off due to traffic control procedures at the destination airport. But once in the air, the flight went well. The crew members were great and provided cabin service despite moderate turbulence during much of the flight.

Short flight, but no drink/snack service. The flights both going and coming were delayed.

Not being stranded in Chicago for her airport to 11:30 tomorrow morning the 3rd

I was fully checked in the prior night and i was unchecked and then didn’t have a seat when I boarded. Instead of an aisle seat, I was out in the middle seat of the very last row of the plane.

In overall it was a good experience, the only down point was that the entertainment screen was working properly.

They lost my luggage, so, not happy. The crew was nice but my suitcases never made it, still trying to find out what happened!

I understand weather is an issue, but making us chase our plane down at five scheduled gates across three terminals in an airport the size of O'Hare was unfair. They'd have probably been better off to leave gates as TBD until the inbound plane is in final approach instead of running us all over the place. Also, props to the consistently-unprepared ground crew in Richmond for once again leaving my lane parked short of the gate because they couldn't have a crew in place on time with 2 hours notice...

cabin crew was OK, food was OK, the trip from the US to Munich was actually pretty bad comfort wise. Noisy aircraft, lights never dimmed even in Business class (night flight) barely sufficient amenities for the price. I have millions of miles with United but TBH American is gaining ground and Delta has always been marginally better then United although on paper United has more longes and cheaper upgrades.

Essy to get on. The hostess gave very little pop, the plane was late getting in, and we are still waiting for our bags. This sucks. :/

Great flight. On time boarding. Smooth flight and on time arrival at EWR. The flight crew was marvelous and there was a great selection of movies on the entertainment system. Our bags were at the carousel before we got there. Another excellent flight from United.

As previously stated the delay I experienced flying from Wichita to Chicago caused a host of issues. When I finally was able to be booked on the last remaining American flight from Chicago to Cincinnati, the gate changed four times with the last change occurring very near the scheduled boarding time. While I didn't have a problem moving from gate to gate, I did notice and make note of others that had mobility issues and had to move each time for the gate change.

Maintenance took a very long time and then we were in a holding pattern. While a one-off maintenance issue is standard, there were delays on both of my flights for this trip based on maintenance issues with the planes, which delayed both flights over 45 minutes. Thankfully, I didn't have any connections but it wasn't an experience that would make me pick AA if I have other options.

No Snacks or Entertainment. The flight was short, snacks should still be given.

See prior comment about how Kayak mishandled my reservation and delayed my arrival by 6 hours.

Boarding delayed 20 minutes for no reason, no wifi, in flight entertainment, or snacks / waters?

Delayed an hour due to operational issues. Minimal apologies or care for the significant inconvenience caused. Landed at nearly 1am and they still couldn’t find ground staff to get us off the plane promptly.

The aircraft had several problems - from excess fuel to non operational ac. Two hours of delay in Chicago could have been avoided with proper planning and aircraft maintenance.

Crew in Columbia was not prepared for landing. It was a bit of a disaster and getting bags took forever.

We were upgraded to First Class and it was a great flight

We experienced gate changes and a long delay. My seat was dirty when I boarded and I had to use wipes to clean it myself. There was an unpleasant and overpowering cleaning product scent on the plane as well that lingered through the flight.

Everything you need to know for your flight from Chicago to San Luis Obispo

Information on your arrival and departure airports