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Pebble Beach

$99+ Cheap flights from Chicago (CHI) to Pebble Beach, CA

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 5/13. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — SFO
Apr 22 — Apr 291
Tue 4/22
Tue 4/29
1 adult, Economy
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Cheapflights Tip: The best prices from Chicago to Pebble Beach are usually found in September or February, booked 83 days in advance, depart on a Wednesday or Thursday and return on a Wednesday

Cheap flight deals from Chicago to Pebble Beach

Keep the following information in mind while searching for Chicago to Pebble Beach flight deals. Data was last updated April 17, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$201
(CheapOair)

One-way from

$99
(Alaska Airlines)

Popular in

December

Cheapest in

September

Average price

$288
Provider with most accurate pricing for Chicago (CHI)-San Francisco flight deals.
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Provider most trusted by Cheapflights users for Chicago (CHI)-San Francisco flights.
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From Chicago (CHI) to Pebble Beach
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One-way flight from Chicago (CHI) to Pebble Beach
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Highest demand for flights based on searches. 7% potential increase in price ($24 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease ($6 potential savings vs. average RT price).
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Average for round-trip flights in April 2025
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Find flight deals from Chicago to Pebble Beach

Cheapest flights from Chicago to Pebble Beach
Explore the most affordable flight options available from Chicago to Pebble Beach. Find the lowest fares from popular airlines and budget airlines, with prices last updated on April 17, 2025.

This CheapOair deal was found by Cheapflights users on 4/16. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/164:15 pmORD - SFO
1 stop23h 00mFrontier
Sun 5/182:53 pmSFO - ORD
1 stop12h 17mFrontier
Deal found 4/16$201
This Trip.com deal was found by Cheapflights users on 4/16. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/152:45 pmMDW - SFO
1 stop10h 21mFrontier
Sun 5/189:59 pmSFO - MDW
1 stop12h 25mFrontier
Deal found 4/16$205
This Southwest deal was found by Cheapflights users on 4/16. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/15:15 amMDW - SFO
1 stop6h 10mSouthwest
Tue 7/87:45 pmSFO - MDW
1 stop7h 15mSouthwest
Deal found 4/16$207
This United Airlines deal was found by Cheapflights users on 4/16. 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 5/89:05 pmORD - SFO
Nonstop4h 54mUnited Airlines
Tue 5/1311:20 pmSFO - ORD
Nonstop4h 25mUnited Airlines
Deal found 4/16$207
This Hawaiian Airlines deal was found by Cheapflights users on 4/16. 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 Hawaiian Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/307:59 pmORD - SFO
Nonstop4h 50mHawaiian Airlines
Tue 6/36:49 pmSFO - ORD
1 stop8h 51mHawaiian Airlines
Deal found 4/16$208
This Lucky2Go deal was found by Cheapflights users on 4/17. 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 Lucky2Go is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/95:21 pmORD - SFO
1 stop8h 48mMultiple Airlines
Tue 5/1311:48 amSFO - ORD
Nonstop4h 32mMultiple Airlines
Deal found 4/17$212
This Alaska Airlines deal was found by Cheapflights users on 4/16. 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 5/86:58 pmORD - SFO
Nonstop4h 59mAlaska Airlines
Mon 5/1211:48 amSFO - ORD
Nonstop4h 32mAlaska Airlines
Deal found 4/16$217
This American Airlines deal was found by Cheapflights users on 4/17. 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 5/164:51 pmORD - SFO
Nonstop4h 46mAmerican Airlines
Sun 5/1811:49 pmSFO - ORD
Nonstop4h 18mAmerican Airlines
Deal found 4/17$237
This Delta deal was found by Cheapflights users on 4/16. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/256:24 amORD - SFO
1 stop9h 05mDelta
Sat 5/311:45 pmSFO - ORD
1 stop8h 14mDelta
Deal found 4/16$256
This Delta deal was found by Cheapflights users on 4/16. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/11:09 pmMDW - SFO
1 stop7h 04mDelta
Tue 7/1512:40 amSFO - MDW
1 stop5h 56mDelta
Deal found 4/16$257
This Gotogate deal was found by Cheapflights users on 4/16. 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 Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/176:15 pmORD - SFO
1 stop17h 07mSun Country Air
Sun 7/2011:59 pmSFO - ORD
1 stop15h 16mSun Country Air
Deal found 4/16$304
This Southwest deal was found by Cheapflights users on 4/15. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/36:15 amORD - SFO
2 stops10h 05mSouthwest
Wed 5/76:00 amSFO - ORD
1 stop8h 45mSouthwest
Deal found 4/15$312

Cheapflights Fare Finder

Customize your flight search to find flights from Chicago to Pebble Beach 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 April 17, 2025.
Use the filters below to find and compare flights from Chicago to Pebble Beach that are best for you.

Fly from

Chicago

Fly to

Pebble Beach

Route

Depart

Return

Price

ChicagoSan Francisco

ORD - SFO

ORDSFO

Chicago O'Hare Intl

Fri 5/16

4:15 pm-1:15 pm

1 stop23h 00m

San Francisco

Sun 5/18

2:53 pm-5:10 am

1 stop12h 17m

$201

ChicagoSan Francisco

MDW - SFO

MDWSFO

Chicago Midway

Thu 5/15

2:45 pm-11:06 pm

1 stop10h 21m

San Francisco

Sun 5/18

9:59 pm-12:24 pm

1 stop12h 25m

$205

ChicagoSan Francisco

MDW - SFO

MDWSFO

Chicago Midway

Tue 7/1

5:15 am-9:25 am

1 stop6h 10m

San Francisco

Wed 7/9

7:45 pm-5:00 am

1 stop7h 15m

$207

ChicagoSan Francisco

ORD - SFO

ORDSFO

Chicago O'Hare Intl

Thu 5/8

6:58 pm-9:57 pm

Nonstop4h 59m

San Francisco

Tue 5/13

11:48 am-6:20 pm

Nonstop4h 32m

$207

ChicagoSan Francisco

ORD - SFO

ORDSFO

Chicago O'Hare Intl

Fri 5/9

5:21 pm-12:09 am

1 stop8h 48m

San Francisco

Tue 5/13

11:48 am-6:20 pm

Nonstop4h 32m

$212

ChicagoSan Francisco

ORD - SFO

ORDSFO

Chicago O'Hare Intl

Thu 5/8

5:05 am-9:36 am

1 stop6h 31m

San Francisco

Mon 5/12

12:10 am-6:30 am

Nonstop4h 20m

$217

ChicagoSan Francisco

ORD - SFO

ORDSFO

Chicago O'Hare Intl

Thu 5/29

7:59 pm-10:49 pm

Nonstop4h 50m

San Francisco

Sat 5/31

12:33 pm-6:59 pm

Nonstop4h 26m

$229

ChicagoSan Francisco

ORD - SFO

ORDSFO

Chicago O'Hare Intl

Fri 5/16

4:51 pm-7:37 pm

Nonstop4h 46m

San Francisco

Sun 5/18

11:49 pm-6:07 am

Nonstop4h 18m

$237

ChicagoSan Francisco

ORD - SFO

ORDSFO

Chicago O'Hare Intl

Sun 5/25

6:24 am-1:29 pm

1 stop9h 05m

San Francisco

Sat 5/31

1:45 pm-11:59 pm

1 stop8h 14m

$256

ChicagoSan Francisco

MDW - SFO

MDWSFO

Chicago Midway

Tue 7/1

1:09 pm-6:13 pm

1 stop7h 04m

San Francisco

Fri 7/18

10:45 pm-8:40 am

1 stop7h 55m

$257

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/15

Showing 1-10 of 25 results
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Best time to book a flight from Chicago to Pebble Beach

Have a flexible travel schedule? Discover the best time to fly to Pebble Beach from Chicago with our price prediction graph.
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 Chicago to Pebble Beach

How far ahead should I book a flight from Chicago to Pebble Beach?

Use this chart to determine the optimal time to book a round-trip flight from Chicago to Pebble Beach. Price data was last updated on April 11, 2025.

The price you pay for your flight from Chicago to Pebble Beach may vary depending on when you book. For the best chance of a lower fare, look to book 83 days in advance of your trip. Fares are likely to increase a fortnight or so before your departure date.

What is the cheapest month to book a flight from Chicago to Pebble Beach?

Currently, January is the cheapest month in which you can book a flight from Chicago to Pebble Beach (average of $276). Flying from Chicago to Pebble Beach in June is currently the most expensive (average of $393). 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 CHI to P3L?

Find hourly flight availability from Chicago to Pebble Beach. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated April 17, 2025.

When flying from Chicago to Pebble Beach, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

What is the cheapest day to fly from Chicago to Pebble Beach?

Use this chart to determine the cheapest time to fly round-trip from Chicago to Pebble Beach. Price data was last updated on December 16, 2024.

Travelers seeking maximum savings on their Chicago to Pebble Beach flight should consider departing on Friday afternoons when fares are most often at their lowest. Sunday afternoons flights should be avoided if possible as fares are typically the most expensive at this time.

Weekly flight availability from Chicago to Pebble Beach

Explore weekly flight availability from Chicago to Pebble Beach. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated April 17, 2025.

The most flights from CHI to P3L are scheduled on a Thursday (81 on average). You will have fewer flight options on Sunday, which is when the least amount of flights are scheduled (47 on average).

Rainfall in Pebble Beach by month

Plan your trip to Pebble Beach by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Pebble Beach ranges from 0.0 - 4.4 inches per month. January is typically the wettest month, when rainfall can reach 4.4 in. July is typically the driest time to visit Pebble Beach when rainfall is around 0.0 in.

Temperature in Pebble Beach by month

Plan your trip to Pebble Beach by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Pebble Beach, use this chart to help with planning. For those seeking warmer temperatures, September is the ideal time of year to visit, when temperatures reach an average of 62.6 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 51.8 F).

Reviews of airlines servicing Pebble Beach

Get insights into the airlines that provide service to Pebble Beach. 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 Pebble Beach. Reviews last updated April 17, 2025.
Read through reviews of airlines operating flights from Chicago to Pebble Beach, such as Alaska Airlines, Southwest and Delta. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
Alaska Airlines
8.0
Very good
9,887 reviews

Entertainment

7.1

Comfort

7.9

Crew

8.5

Overall

8.0

Food

7.1

Boarding

8.1

Reviews

1 / 20
4.0
Okay

Anonymous,Apr 2025

LAS - STS

flight was delayed both ways even tho the weather was clear >
Alaska Airlines
8.0
Very good
9,887 reviews
Alaska Airlines
8.0
Very good
9,887 reviews

Entertainment

7.1

Comfort

7.9

Crew

8.5

Overall

8.0

Food

7.1

Boarding

8.1

Reviews

1 / 20
4.0
Okay

Anonymous,Apr 2025

LAS - STS

flight was delayed both ways even tho the weather was clear >
Southwest
8.0
Very good
4,280 reviews
Alaska Airlines
8.0
Very good
9,887 reviews

Entertainment

7.1

Comfort

7.9

Crew

8.5

Overall

8.0

Food

7.1

Boarding

8.1

Reviews

1 / 20
4.0
Okay

Anonymous,Apr 2025

LAS - STS

flight was delayed both ways even tho the weather was clear >
Delta
8.0
Very good
7,916 reviews
Alaska Airlines
8.0
Very good
9,887 reviews

Entertainment

7.1

Comfort

7.9

Crew

8.5

Overall

8.0

Food

7.1

Boarding

8.1

Reviews

1 / 20
4.0
Okay

Anonymous,Apr 2025

LAS - STS

flight was delayed both ways even tho the weather was clear >
Hawaiian Airlines
7.9
Good
2,380 reviews
Alaska Airlines
8.0
Very good
9,887 reviews

Entertainment

7.1

Comfort

7.9

Crew

8.5

Overall

8.0

Food

7.1

Boarding

8.1

Reviews

1 / 20
4.0
Okay

Anonymous,Apr 2025

LAS - STS

flight was delayed both ways even tho the weather was clear >
United Airlines
7.4
Good
8,667 reviews
Alaska Airlines
8.0
Very good
9,887 reviews

Entertainment

7.1

Comfort

7.9

Crew

8.5

Overall

8.0

Food

7.1

Boarding

8.1

Reviews

1 / 20
4.0
Okay

Anonymous,Apr 2025

LAS - STS

flight was delayed both ways even tho the weather was clear >

Related info for your journey

Find useful and relevant information for your journey from Chicago to Pebble Beach. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What are the cheapest airlines to fly from Chicago to Pebble Beach one-way?

    One-way options have recently been found by users for as low as $99 on Alaska Airlines. Other airlines that offer cheap prices include Frontier from $100 and Southwest from $108 one-way.

  • What are the most reliable airlines from Chicago to Pebble Beach?

    Looking for the most reliable airlines to get you to your destination on time? Our data shows these are most likely to get you from Chicago to Pebble Beach on time: ANA (97%), Air China (94%), China Southern (89%).

  • What are the cheapest flights from Chicago to Pebble Beach?

    On average you can expect to pay $817 for a flight from Chicago to Pebble Beach. The cheapest flight overall is $98 while the most popular route, (Chicago O'Hare Intl - San Francisco) is currently priced at $179.

  • Can I find deals for flights from Chicago to Pebble Beach that include hotel bookings?

    Yes. In addition to deals on Chicago to Pebble Beach flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Chicago to Pebble Beach?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Chicago to Pebble Beach.

  • Can I find deals for business class flights from Chicago to Pebble Beach?

    Yes. Cheapflights offers flight deals from Chicago to Pebble Beach by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Chicago to Pebble Beach?

    Currently, January is the cheapest month in which you can book a flight from Chicago to Pebble Beach (average of $276). Flying from Chicago to Pebble Beach in June is currently the most expensive (average of $393). 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.

See more FAQs

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Alternative routes for Chicago to Pebble Beach

See prices for flight routes from nearby airports that may be better suited for you.
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Top 8 airlines flying from Chicago to Pebble Beach

Discover the top 8 airlines that operate flights from Chicago to Pebble Beach. 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 April 17, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$78Average$236FlexibilityNo cancel feeOn-time62%
Hawaiian AirlinesCheapest$108Average$268FlexibilityNo cancel feeOn-time85%
DeltaCheapest$128Average$388FlexibilityNo cancel feeOn-timeN/A
Spirit AirlinesCheapest$129Average$243FlexibilityNo cancel feeOn-time65%
Alaska AirlinesCheapest$140Average$321FlexibilityNo cancel feeOn-time75%
United AirlinesCheapest$179Average$441FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$197Average$455FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$247Average$437FlexibilityNo cancel feeOn-time63%

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