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Cheap flights from Chicago to San Luis Obispo from $250

This is the cheapest round-trip flight price found by a momondo user in the last 72 hours by searching for a flight from Chicago to San Luis Obispo departing on 9/20. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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Find the cheapest flights from Chicago to San Luis Obispo

Cheap round-trip flights

Hawaiian Airlines Logo
10:00 am - 5:37 pmORD-SBP
9h 37m1 stop
Hawaiian Airlines Logo
5:23 pm - 5:00 amSBP-ORD
9h 37m1 stop
$250Hawaiian Airlines
Find Deal
Sat, Sep 20 - Fri, Sep 26
American Airlines Logo
6:00 am - 11:34 amORD-SBP
7h 34m1 stop
American Airlines Logo
12:53 pm - 10:24 pmSBP-ORD
7h 31m1 stop
$269American Airlines
Find Deal
Fri, Sep 26 - Mon, Sep 29
American Airlines Logo
11:54 am - 6:43 pmORD-SBP
8h 49m2 stops
American Airlines Logo
12:24 pm - 11:59 pmSBP-ORD
9h 35m1 stop
$272American Airlines
Find Deal
Sat, Sep 20 - Fri, Sep 26
Alaska Airlines Logo
10:00 am - 7:01 pmORD-SBP
11h 01m1 stop
Alaska Airlines Logo
3:31 pm - 1:54 pmSBP-ORD
20h 23m2 stops
$282Alaska Airlines
Find Deal
Fri, Nov 14 - Mon, Nov 17
Alaska Airlines Logo
9:20 am - 11:26 pmORD-SBP
16h 06m1 stop
Alaska Airlines Logo
6:00 am - 11:59 pmSBP-ORD
15h 59m1 stop
$283Alaska Airlines
Find Deal
Wed, Nov 5 - Sun, Nov 9
Alaska Airlines Logo
8:20 am - 11:24 pmORD-SBP
17h 04m1 stop
Alaska Airlines Logo
7:50 pm - 6:24 amSBP-ORD
8h 34m1 stop
$291Alaska Airlines
Find Deal
Fri, Oct 17 - Mon, Oct 20
Alaska Airlines Logo
5:59 pm - 6:38 pmORD-SBP
26h 39m1 stop
Alaska Airlines Logo
2:03 pm - 5:01 amSBP-ORD
12h 58m2 stops
$307Alaska Airlines
Find Deal
Fri, Oct 10 - Wed, Oct 15
American Airlines Logo
5:00 am - 11:36 amORD-SBP
8h 36m1 stop
American Airlines Logo
4:18 pm - 12:12 amSBP-ORD
5h 54m1 stop
$314American Airlines
Find Deal
Thu, Oct 30 - Sun, Nov 2
United Airlines Logo
4:40 pm - 11:43 pmORD-SBP
9h 03m1 stop
United Airlines Logo
6:22 pm - 5:55 amSBP-ORD
9h 33m1 stop
$359United Airlines
Find Deal
Thu, Oct 2 - Sun, Oct 5
United Airlines Logo
9:13 am - 10:14 pmORD-SBP
15h 01m2 stops
United Airlines Logo
8:34 am - 11:15 pmSBP-ORD
12h 41m2 stops
$579United Airlines
Find Deal
Fri, Sep 26 - Sun, Sep 28

United Airlines flights from Chicago to San Luis Obispo

Our best United Airlines deals on Chicago to San Luis Obispo flight tickets
United Airlines
Oct 2
ORD4:40 pmChicago O'Hare Intl
9h 03m
1 stop
SBP11:43 pmSan Luis Obispo County
Oct 5
SBP6:22 pmSan Luis Obispo County
9h 33m
1 stop
ORD5:55 amChicago O'Hare Intl
$359
Find similar
United Airlines
Sep 26
ORD9:13 amChicago O'Hare Intl
15h 01m
2 stops
SBP10:14 pmSan Luis Obispo County
Sep 28
SBP8:34 amSan Luis Obispo County
12h 41m
2 stops
ORD11:15 pmChicago O'Hare Intl
$579
Find similar
United Airlines
Dec 28
ORD6:15 amChicago O'Hare Intl
19h 29m
1 stop
SBP11:44 pmSan Luis Obispo County
Jan 3
SBP6:23 pmSan Luis Obispo County
15h 02m
1 stop
ORD11:25 amChicago O'Hare Intl
$625
Find similar

Alaska Airlines flights from Chicago to San Luis Obispo

Our best Alaska Airlines deals on Chicago to San Luis Obispo flight tickets
Alaska Airlines
Nov 14
ORD10:00 amChicago O'Hare Intl
11h 01m
1 stop
SBP7:01 pmSan Luis Obispo County
Nov 17
SBP3:31 pmSan Luis Obispo County
20h 23m
2 stops
ORD1:54 pmChicago O'Hare Intl
$282
Find similar
Alaska Airlines
Nov 5
ORD9:20 amChicago O'Hare Intl
16h 06m
1 stop
SBP11:26 pmSan Luis Obispo County
Nov 9
SBP6:00 amSan Luis Obispo County
15h 59m
1 stop
ORD11:59 pmChicago O'Hare Intl
$283
Find similar
Alaska Airlines
Oct 17
ORD8:20 amChicago O'Hare Intl
17h 04m
1 stop
SBP11:24 pmSan Luis Obispo County
Oct 20
SBP7:50 pmSan Luis Obispo County
8h 34m
1 stop
ORD6:24 amChicago O'Hare Intl
$291
Find similar

momondo Fare Finder

 
Customize your flight search to find flights from Chicago to San Luis Obispo 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, momondo users made 832,500 searches. Data last updated July 31, 2025.
Use the filters below to find and compare flights from Chicago to San Luis Obispo that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

ChicagoSan Luis Obispo

ORD - SBP

ORDSBP

Chicago O'Hare Intl

Sat 9/20

10:00 am-5:37 pm

1 stop9h 37m

San Luis Obispo County

Fri 9/26

5:23 pm-5:00 am

1 stop9h 37m

$250

ChicagoSan Luis Obispo

ORD - SBP

ORDSBP

Chicago O'Hare Intl

Fri 9/26

6:00 am-11:34 am

1 stop7h 34m

San Luis Obispo County

Mon 9/29

12:53 pm-10:24 pm

1 stop7h 31m

$269

ChicagoSan Luis Obispo

ORD - SBP

ORDSBP

Chicago O'Hare Intl

Sat 9/20

11:54 am-6:43 pm

2 stops8h 49m

San Luis Obispo County

Fri 9/26

12:24 pm-11:59 pm

1 stop9h 35m

$272

ChicagoSan Luis Obispo

ORD - SBP

ORDSBP

Chicago O'Hare Intl

Fri 11/14

10:00 am-7:01 pm

1 stop11h 01m

San Luis Obispo County

Mon 11/17

3:31 pm-1:54 pm

2 stops20h 23m

$282

ChicagoSan Luis Obispo

ORD - SBP

ORDSBP

Chicago O'Hare Intl

Wed 11/5

9:20 am-11:26 pm

1 stop16h 06m

San Luis Obispo County

Sun 11/9

6:00 am-11:59 pm

1 stop15h 59m

$283

ChicagoSan Luis Obispo

ORD - SBP

ORDSBP

Chicago O'Hare Intl

Fri 10/17

8:20 am-11:24 pm

1 stop17h 04m

San Luis Obispo County

Mon 10/20

7:50 pm-6:24 am

1 stop8h 34m

$291

ChicagoSan Luis Obispo

ORD - SBP

ORDSBP

Chicago O'Hare Intl

Fri 10/10

5:59 pm-6:38 pm

1 stop26h 39m

San Luis Obispo County

Wed 10/15

2:03 pm-5:01 am

2 stops12h 58m

$307

ChicagoSan Luis Obispo

ORD - SBP

ORDSBP

Chicago O'Hare Intl

Thu 10/30

5:00 am-11:36 am

1 stop8h 36m

San Luis Obispo County

Sun 11/2

4:18 pm-12:12 am

1 stop5h 54m

$314

ChicagoSan Luis Obispo

ORD - SBP

ORDSBP

Chicago O'Hare Intl

Thu 10/2

4:40 pm-11:43 pm

1 stop9h 03m

San Luis Obispo County

Sun 10/5

6:22 pm-5:55 am

1 stop9h 33m

$359

ChicagoSan Luis Obispo

ORD - SBP

ORDSBP

Chicago O'Hare Intl

Fri 9/26

9:13 am-10:14 pm

2 stops15h 01m

San Luis Obispo County

Sun 9/28

8:34 am-11:15 pm

2 stops12h 41m

$579

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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See travel insights to San Luis Obispo from

How to get the cheapest flight ticket from Chicago to San Luis Obispo

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

What is the cheapest month to fly to San Luis Obispo?

In general, December is the cheapest month to fly from Chicago to San Luis Obispo. Due to it being the ‘off-season’ during this time, you can expect flight prices to be around $336. The month of November is another great option to travel to San Luis Obispo, with average flight prices from Chicago averaging around $346.

What is the cheapest day to depart on your flight to San Luis Obispo?

On average, the least expensive day to fly to San Luis Obispo from Chicago is on a Saturday. momondo users have found tickets for Saturday departures for as low as $452. However, this price may fluctuate depending on the airline, the season, and holidays. When flying out on a Sunday, the most expensive travel day of the week, you can expect to see flight prices from Chicago to San Luis Obispo for around $693.

What is the cheapest time of day to depart on your flight to San Luis Obispo?

Flying to San Luis Obispo from Chicago in the morning is the least expensive time of day to depart. momondo users have found prices as low as $563 when looking at flights departing in the morning. If you have a flexible travel schedule, then try to avoid flying in the evening when prices are $693 on average. Flights to San Luis Obispo from Chicago in the evening are generally more expensive because this time of day is more convenient for travelers’ schedules.

When to book flights from Chicago to San Luis Obispo

Are you open to changing your travel dates? Check out the ideal times to fly from Chicago to San Luis Obispo according to our flight data. Find out which month and days have the cheapest flights.
Estimated round-trip price

Cheap Chicago to San Luis Obispo (CHI to SBP) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Chicago to San Luis Obispo

Best Price Found

$378

Fastest flight time

5h 52m

Direct flights

None

Airports in San Luis Obispo

1 airport
The best one-way flight to San Luis Obispo from Chicago in the past 72 hours is $378. The best round-trip flight deal from Chicago to San Luis Obispo found on momondo in the last 72 hours is $250.
The fastest flight from Chicago to San Luis Obispo takes 5h 52m
There are no direct flights from Chicago to San Luis Obispo. Popular non-direct route for this connection is Chicago O'Hare Intl Airport - San Luis Obispo County Airport.
There is 1 airport near San Luis Obispo: San Luis Obispo County (SBP)
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  • How far is Chicago to San Luis Obispo County by plane?

    The distance between Chicago and San Luis Obispo County is about 1827.9 mi. 5h 52m is a normal flight duration for this route.

  • When did momondo last update prices for flights from Chicago to San Luis Obispo County Airport?

    Prices for flights from Chicago to San Luis Obispo County Airport refresh daily.

  • How many operators does momondo search for flights from Chicago to San Luis Obispo County Airport?

  • How old do you have to be to fly from Chicago to San Luis Obispo County Airport?

    The minimum age a child must be to fly alone is five but airlines that offer an unaccompanied minor (UNMR) service will have their own age restrictions, including rules around flight length, timings, and stopovers. We always recommend checking with the individual airline you are booking with to travel from Chicago to San Luis Obispo County Airport.

  • What documentation or ID do you need to fly to San Luis Obispo County Airport?

    The travel and health documents you'll need for your trip to San Luis Obispo County Airport may differ based on your itinerary and personal situation. Typically, you should have several documents on hand, such as a national ID card or driver's license and a passport that is valid for six months after your intended arrival at San Luis Obispo County Airport. It is always advisable to seek advice from your airline or a trusted third party, such as IATA.

  • What is the most popular airline from Chicago to San Luis Obispo?

Best airlines flying from Chicago to San Luis Obispo

Compare and see reviews for airlines that fly from Chicago to San Luis Obispo with momondo
Airline
Rating
Free Cancellation
Price
American AirlinesPriceFrom $326Free CancellationRating
7.2
10,000 reviews
Search American Airlines flights
United AirlinesPriceFrom $518Free CancellationRating
7.4
8,900 reviews
Search United Airlines flights

Traveling to a place near San Luis Obispo?

Book flights to San Luis Obispo if you plan to visit one of these locations
Pismo Beach
Morro Bay
Cambria
Paso Robles
Avila Beach
San Simeon
Cayucos
Atascadero
Arroyo Grande
Grover Beach

Why use momondo?

Why should I use momondo to find a flight deal from Chicago to San Luis Obispo?

Finding the right flight to San Luis Obispo from Chicago is quick and easy when you have a range of options in front of you, from reputable agents and recognisable airlines. Options that can then be filtered down to find the best fit. That is what momondo does. We make finding flights to San Luis Obispo quick and easy, saving you time and money.

Can I find flights from Chicago to San Luis Obispo with flexible booking policies on momondo?

Yes. momondo enables you to select and highlight flights to San Luis Obispo from Chicago with this policy.

How can momondo help me find flights from Chicago to San Luis Obispo?

momondo offers useful filters to help you find the right flight. Choose specific flight times, airports or even what payment method you prefer. We have numerous options to help you book your ideal flight from Chicago to San Luis Obispo.

I’m not ready to book a flight from Chicago to San Luis Obispo right now. Can momondo alert me if prices change?

Of course. momondo tracks the price of Chicago to San Luis Obispo flights. All you need is a valid email address and we will do the rest; it is that quick and easy.

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