SBP - ORD

$159 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 7/4. 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
$295
Typical prices: $384-$550
Alaska Airlines
Tue 9/1Sat 9/5
SBP - ORD • 1 stop
Cheapest one-way
$159
Typical prices: $391-$656
United Airlines
Sat 7/4
SBP - ORD • 1 stop
Top airlines
Cheapest • from $295 (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 $472 (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
Alaska Airlines Logo
3:24 pm - 1:22 pm
SBP
-
ORD
19h 58m
1 stop
Alaska Airlines Logo
6:01 am - 2:44 pm
ORD
-
SBP
10h 43m
1 stop
$295Alaska Airlines
Thu, Sep 17 - Tue, Sep 22
Alaska Airlines Logo
3:24 pm - 11:59 pm
SBP
-
ORD
6h 35m
1 stop
Alaska Airlines Logo
2:18 pm - 11:50 pm
ORD
-
SBP
11h 32m
1 stop
$322Alaska Airlines
Fri, Jul 3 - Tue, Jul 7
Alaska Airlines Logo
5:57 pm - 1:21 pm
SBP
-
ORD
17h 24m
1 stop
Alaska Airlines Logo
6:20 am - 5:17 pm
ORD
-
SBP
12h 57m
1 stop
$338Alaska Airlines
Sat, Aug 22 - Wed, Aug 26
United Airlines Logo
5:00 am - 1:30 pm
SBP
-
ORD
6h 30m
1 stop
United Airlines Logo
10:35 am - 3:22 pm
ORD
-
SBP
6h 47m
1 stop
$344United Airlines
Tue, Sep 15 - Tue, Oct 6
Alaska Airlines Logo
3:24 pm - 1:22 pm
SBP
-
ORD
19h 58m
1 stop
Alaska Airlines Logo
7:20 am - 2:56 pm
ORD
-
SBP
9h 36m
1 stop
$349Alaska 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
Fri, Jul 3 - Tue, Jul 7
Alaska Airlines Logo
5:57 pm - 1:21 pm
SBP
-
ORD
17h 24m
1 stop
Alaska Airlines Logo
6:20 am - 5:17 pm
ORD
-
SBP
12h 57m
1 stop
$373Alaska Airlines
Wed, Aug 19 - Tue, Aug 25
American Airlines Logo
12:45 pm - 12:18 am
SBP
-
ORD
9h 33m
2 stops
American Airlines Logo
5:00 am - 12:05 pm
ORD
-
SBP
9h 05m
2 stops
$379American Airlines
Thu, Aug 20 - Sun, Aug 23
United Airlines Logo
2:20 pm - 12:59 am
SBP
-
ORD
8h 39m
1 stop
United Airlines Logo
5:55 am - 10:11 am
ORD
-
SBP
6h 16m
1 stop
$382United 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$159
Best time to beat the crowds with an average 42% drop in price.
Most popular time to fly and prices are also 13% lower on average.
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 $159 for a one-way ticket and $295 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 $565 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 9860 reviews
7.3Comfort
7.1Entertainment
6.7Food
8.1Crew
7.7Boarding
Airline reviews

Very easy ! Use the kiosk and bag drop and right to security within 10 min

10.0 ExcellentJoanne, Jun 2026
DEN - ORD
Read more United Airlines reviews

Very easy ! Use the kiosk and bag drop and right to security within 10 min

Over 5 hour delay with minimal updates or ability to standby for alternative flights. During boarding and 1 hr+ wait for takeoff, seats were drenched w water from air conditioning condensation and always leftover crumbs on carpet and seats

Boarded early, left early, arrived 40 mins early! A win win for me!

These airplanes should be illegal. The seats are two tight, it is a safety issue. Wheelchair support was ridiculously slow. We almost missed our flight.

This flight is a quick way to get to Chicago, but a bit expensive.

O’hsre taxi and deboarding took 40 minutes. Needed 20 minutes extra time between connecting flights to avoid running through terminal.

Standard flight with a drinks and a snack- overall very quick flight. The flight attendants were very strict, bordered on rude.

Delayed - weather wasn't bad at either end. Also sat on tarmac in ORD.

boarded early to only find out that flight would sit at gate for 45 min to an hour. Landed in chicago and sat on runway for over an hour before got to gate. Total delay was extensive for a 45 min flight door to door.

The flight was significantly delayed. The inbound flight from EWR was delayed departing because of mechanical problems. My original departure from CLT was 5:28 pm but due to the delay of the inbound flight, after arrival, deplaning, cleaning, boarding, we did not push back from the gate until 9:00 pm. Once in the air, the flight was smooth and what was originally supposed to be an arrival in ORD at 7:30 pm local time turned out to be 9:35 pm.

We had a mechanical delay which made us 90 minutes late (9:30 PM) then land and put into the penalty box because a plane was in our gate? What the hell! We should get priority.Damn American.

The seats were extremely cramped, with very little legroom or personal space. There was no room left in the overhead bins for a backpack, and the space under the seat in front was so limited that I could barely fit my bag underneath. Overall, the seating arrangement felt very uncomfortable and overcrowded.

weather delay of almost 2 hours then we landed and our gate wasn't available so we waited another 30 min

Delayed flight more than I hour. When boarding we spent some additional time on the plane before takeoff ....

The flight was delayed significantly and we sat on runway after landing for awhile. Best thing was the flight attendant, Jenny, in first class, who was very professional and attentive. She was excellent - the rest of the flight was not.

The flight attendants were extremely sourly and borderline rude. I did not feel appreciated as an AA customer once.

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

The Mario was so helpful and provided amazing customer service however l have being waiting for a callback for almost a week now and have not heard anything further after l informed them l wanted to change my date of traveling because of my hospital appointment even send them proof and l was unable to use manag your booking on their website is a bit frustrating and l would appreciate an update on My request as soon as possible. And have called them times without numbers no response

Awful, tons of delays, I got into Chicago multiple hours late meaning I hit the very traffic I tried so desperately to avoid. Just empty apologies from American Airlines text alerts. Trash behavior from a trash airline.

They lost my baggage and I am still struggling to the information and update

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

Information on your arrival and departure airports