SBP - ORD

$175 Find Cheap Flights from San Luis Obispo to Chicago - Compare and Save

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from San Luis Obispo to Chicago departing on 10/15. 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 Chicago O'Hare Intl Airport

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

Cheapest round-trip
$349
Typical prices: $384-$550
American Airlines
Tue 9/1Sat 9/5
SBP - ORD • 1 stop
Cheapest one-way
$175
Typical prices: $144-$269
Alaska Airlines
Thu 10/15
SBP - ORD • 1 stop
Top airlines
Cheapest • from $349 (round-trip)
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 San Luis Obispo and Chicago. You'll need at least 1 connection.
Insights
Insights
Insights
Insights
Top layover airports
Cheapest • Avg $511 (round-trip)
Shortest trip • 6h 08m (one-way)
Insights
Insights
Insights
Insights
When to travel
Cheapest • 41% price drop
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 Chicago!
Flight Deals
Booking Insights
Flight Deals

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

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from San Luis Obispo to Chicago 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 San Luis Obispo to Chicago

Tue, Sep 1 - Sat, Sep 5
American Airlines Logo
12:29 pm - 10:13 pm
SBP
-
ORD
7h 44m
1 stop
American Airlines Logo
5:00 am - 12:05 pm
ORD
-
SBP
9h 05m
1 stop
$349American Airlines
Tue, Sep 1 - Sat, Sep 5
American Airlines Logo
12:51 pm - 12:18 am
SBP
-
ORD
9h 27m
2 stops
American Airlines Logo
6:00 am - 11:39 am
ORD
-
SBP
7h 39m
1 stop
$354American Airlines
Tue, Sep 1 - Sat, Sep 5
American Airlines Logo
12:51 pm - 12:18 am
SBP
-
ORD
9h 27m
2 stops
American Airlines Logo
5:00 am - 12:05 pm
ORD
-
SBP
9h 05m
2 stops
$359American Airlines
Wed, Sep 2 - Fri, Sep 4
Alaska Airlines Logo
6:00 am - 7:21 pm
SBP
-
ORD
11h 21m
1 stop
Alaska Airlines Logo
8:17 pm - 2:44 pm
ORD
-
SBP
20h 27m
1 stop
$384Alaska Airlines
Tue, Sep 15 - Tue, Oct 6
American Airlines Logo
1:00 pm - 11:30 pm
SBP
-
ORD
8h 30m
2 stops
American Airlines Logo
5:00 am - 12:07 pm
ORD
-
SBP
9h 07m
2 stops
$394American Airlines
Thu, Jul 9 - Mon, Jul 13
American Airlines Logo
7:02 pm - 6:25 am
SBP
-
ORD
9h 23m
1 stop
American Airlines Logo
5:00 am - 11:43 am
ORD
-
SBP
8h 43m
1 stop
$419American Airlines
Mon, Jul 27 - Sat, Aug 1
American Airlines Logo
4:07 pm - 12:51 am
SBP
-
ORD
6h 44m
1 stop
American Airlines Logo
5:00 am - 11:49 am
ORD
-
SBP
8h 49m
2 stops
$420American Airlines
Wed, Nov 11 - Sun, Nov 15
Alaska Airlines Logo
6:00 am - 7:00 pm
SBP
-
ORD
11h 00m
1 stop
Alaska Airlines Logo
7:56 pm - 4:01 pm
ORD
-
SBP
22h 05m
2 stops
$441Alaska Airlines
Thu, Sep 3 - Tue, Sep 8
American Airlines Logo
12:51 pm - 11:30 pm
SBP
-
ORD
8h 39m
1 stop
American Airlines Logo
5:00 am - 12:05 pm
ORD
-
SBP
9h 05m
2 stops
$442American Airlines
Fri, Aug 21 - Mon, Aug 24
American Airlines Logo
12:29 pm - 11:30 pm
SBP
-
ORD
9h 01m
1 stop
American Airlines Logo
5:00 am - 12:05 pm
ORD
-
SBP
9h 05m
2 stops
$447American Airlines
Booking Insights

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

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

How much is a round-trip flight from San Luis Obispo to Chicago O'Hare Intl Airport?

This analysis is based on the cheapest round-trip price found on KAYAK in the last 12 months by searching for a flight from San Luis Obispo to Chicago O'Hare Intl Airport departing in September.

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

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from San Luis Obispo to Chicago O'Hare Intl Airport, 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 San Luis Obispo to Chicago O'Hare Intl Airport is January, where tickets cost $298 (return) on average. On the other hand, the most expensive months are June and July, where the average cost of round-trip tickets is $758 and $711 respectively.

Good to know

Low seasonJanuary
Cheapest flight$175
Best time to beat the crowds with an average 42% drop in price.
Most popular time to fly with an average 39% increase in price.
Flight from San Luis Obispo to Chicago

When to book flights from San Luis Obispo to Chicago

Are your dates flexible? Find out the best times to travel from San Luis Obispo to Chicago 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 San Luis Obispo to Chicago flights

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

    In the last 5 days, the lowest price for a flight from San Luis Obispo to Chicago O'Hare Intl Airport was $175 for a one-way ticket and $349 for a round-trip.

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

    No, a passport isn't needed to fly from San Luis Obispo to Chicago. However, local authorities might ask for an official ID.

  • Which airports will I be using when flying from San Luis Obispo to Chicago?

    San Luis Obispo and Chicago are both served by 1 main airport. You will leave San Luis Obispo from San Luis Obispo County and will be arriving at Chicago O'Hare Intl.

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

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

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

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

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

    The two airlines most popular with KAYAK users for flights from San Luis Obispo to Chicago are United Airlines and American Airlines. With an average price for the route of $575 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 $432 and an overall rating of 7.1.

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

    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 San Luis Obispo to Chicago.

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

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Chicago from San Luis Obispo 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 San Luis Obispo to Chicago?

    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 Chicago with an airline and back to San Luis Obispo with another airline. Booking your flights between San Luis Obispo and ORD 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 San Luis Obispo to Chicago?

    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 Chicago from San Luis Obispo 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 San Luis Obispo to Chicago

 
See real verified KAYAK customer reviews for airlines flying from San Luis Obispo to Chicago. 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 San Luis Obispo to Chicago? 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 9894 reviews
7.7Boarding
7.3Comfort
6.6Food
7.1Entertainment
8.1Crew
Airline reviews

Crew was great (professional, attentive, prompt). Snacks for 4 hrs flight is deplorable.

8.0 ExcellentDarly, Feb 2026
LAX - ORD
Read more United Airlines reviews

Crew was great (professional, attentive, prompt). Snacks for 4 hrs flight is deplorable.

It was a pretty standard flight... until the almost hour and a half spent on the taxi way. I get that the weather has been poor but the delay had nothing to do with the weather and more to do with a plane with several issues tying up the gate. I get that that happens from time to time but this has been EVERY flight I've been on for the past 5 years and I fly 3 to 5 times a year. This isn't just United... it's American, it's Delta. It's an issue with the entire industry. I work for UPS and packages on a cargo plane get better service than people do these days. Anymore I HATE flying.

While the staff was pleasant and helpful, the following observations are for your awareness. There was some delay on the tarmac on take off and landing. The paid lunch/food offerings were limited. Entertainment was only available on WiFi at a cost.

The first flight was better in terms of the aircraft.

As usual, United scheduling is completely misleading. A 54-minute layover at O’Hare is too short to make a lot of connections, especially since the flight landed “on time” but had to wait on the taxiway 15 minutes for a gate to open up. Then it takes another 10 minutes to exit the plane before one can run to another concourse to catch a connecting flight.

when you can say you don't remember being at any point upset during a flight, the airline is winning .

I had a great flight. Everything went smoothly and the flight arrived early.

United WiFi is consistently unusable (it can take 10 mins to load a single web page). If you need Wifi to do work, be prepared to lose half a day of productivity.

The Palm Springs to Chicago O’Hare was on Time and Palm Springs airport is easier navigate. As our connection was only an approximately 50 minutes, we asked staff for insights for the Chicago airport in terms of transferring into the other terminal from which our flight left, and they were unhelpful. However, the United App was very helpful in terms of notifications and even providing directions. The Chicago to Detroit flight was significantly delayed which we all know does happen. However, there were very few updates or notifications as to why this was happening when we would actually arrive. It took nearly 30 minutes for bags to make it to baggage claim. We arrived nearly 1 hour late on a 40 minute flight.

Wifi did not work. Cut off on and off every 10 min

The flight from LA to Chicago was smooth and service was very good overall.

The chicken wrap was tiny ($13 for what looked like a 1/3 of a normal wrap?) and disgusting.

We flew in first class. The crew did not offer drinks before the flight took off, but they treated us well during the flight. The food was excellent. There was actually too much food served, but it was nice to have all the options.

Was not able to watch most shows on the entertainment site. They would not load

The plane was late and then sat on the runway for almost 45 minutes before taking off.

Had to wait on pilot and crew to depart and had to wait to arrive at the gate because they only had 2 crews working. Delays, delays....Planes just keep getting smaller and tighter and they nickle and dime for everything. When will an airline actually wake up and make flying more enjoyable?

It was nice being on a flight that had working wifi. The boarding was quick - why don’t all airlines have small boarding groups window to aisle? Makes so much sense!!! I was disappointed to be the first person stopped to have to gate check my carryon. Especially when there was plenty of overhead space at the back! But I get it…keeps it moving. Crew was nice.

The flight encountered a delay exceeding 4 hours. The food voucher issued was valued at $12, insufficient to cover our meal expenses. Consequently, I was unable to take my medication, leading to a drop in blood sugar levels and exacerbating my anxiety.

The flight was uneventful. What was a problem was I was delayed getting home one entire day because the flight from Sacramento was delayed. That made getting to my connecting flight impossible. I had to stay another night at the hotel and incur that expense as a result.

Seats were very uncomfortable. I paid extra for a seat with more leg room, the seat was no different than a seat at the back of the plane. Flight attendant was rude.

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

Information on your arrival and departure airports