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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 11/1. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — SFO
Aug 18 — Aug 251
Mon 8/18
Mon 8/25
1 adult, Economy
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Cheapflights Tip: The best prices from Chicago to Pebble Beach are usually found in September or July, booked 83 days in advance, depart on a Thursday or Friday 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 August 13, 2025.

Round-trip from

$198
(American Airlines)

One-way from

$99
(Southwest)

Popular in

December

Cheapest in

September

Average price

$317
From Chicago (CHI) to Pebble Beach
Search Deals
One-way flight from Chicago (CHI) to Pebble Beach
Search Deals
Highest demand for flights based on searches. 7% potential increase in price ($26 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease ($7 potential savings vs. average RT price).
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Average for round-trip flights in August 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 August 13, 2025.

This American Airlines deal was found by Cheapflights users on 8/12. 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.
Sun 8/316:45 amORD - SFO
Nonstop4h 30mAmerican Airlines
Fri 9/51:21 pmSFO - ORD
Nonstop4h 24mAmerican Airlines
Deal found 8/12$198
This Kiwi.com deal was found by Cheapflights users on 8/12. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/612:46 pmORD - SFO
1 stop10h 35mMultiple Airlines
Sat 9/138:00 amSFO - ORD
1 stop11h 32mMultiple Airlines
Deal found 8/12$201
This Alaska Airlines deal was found by Cheapflights users on 8/12. 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.
Tue 10/78:20 amORD - SFO
1 stop7h 41mAlaska Airlines
Wed 10/2210:26 amSFO - ORD
1 stop11h 33mAlaska Airlines
Deal found 8/12$204
This Kiwi.com deal was found by Cheapflights users on 8/12. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/299:54 pmORD - SFO
1 stop25h 27mFrontier
Sat 10/181:14 pmSFO - ORD
1 stop6h 55mFrontier
Deal found 8/12$206
This Southwest deal was found by Cheapflights users on 8/12. 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.
Fri 10/312:55 pmMDW - SFO
Nonstop4h 30mSouthwest
Wed 10/86:30 amSFO - MDW
Nonstop4h 05mSouthwest
Deal found 8/12$207
This United Airlines deal was found by Cheapflights users on 8/12. 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.
Fri 10/109:13 pmORD - SFO
Nonstop4h 46mUnited Airlines
Tue 10/1411:00 pmSFO - ORD
Nonstop4h 13mUnited Airlines
Deal found 8/12$207
This Kiwi.com deal was found by Cheapflights users on 8/12. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/911:15 amORD - SFO
1 stop12h 06mMultiple Airlines
Sat 9/206:00 amSFO - ORD
1 stop10h 14mMultiple Airlines
Deal found 8/12$208
This Trip.com deal was found by Cheapflights users on 8/12. 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.
Wed 10/88:20 amORD - SFO
1 stop7h 41mMultiple Airlines
Sat 10/111:14 pmSFO - ORD
1 stop6h 55mMultiple Airlines
Deal found 8/12$209
This Kiwi.com deal was found by Cheapflights users on 8/11. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/117:00 amORD - SFO
1 stop7h 09mFrontier
Thu 10/161:49 pmSFO - ORD
1 stop6h 55mFrontier
Deal found 8/11$210
This Kiwi.com deal was found by Cheapflights users on 8/12. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/89:54 pmORD - SFO
1 stop25h 27mMultiple Airlines
Wed 9/108:00 amSFO - ORD
1 stop8h 51mMultiple Airlines
Deal found 8/12$211
This Kiwi.com deal was found by Cheapflights users on 8/12. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/47:55 amORD - SFO
1 stop7h 27mMultiple Airlines
Wed 9/108:00 amSFO - ORD
1 stop8h 51mMultiple Airlines
Deal found 8/12$212
This Kiwi.com deal was found by Cheapflights users on 8/11. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/187:00 amORD - SFO
1 stop7h 09mFrontier
Wed 10/226:34 amSFO - ORD
1 stop15h 19mFrontier
Deal found 8/11$213

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 August 13, 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

Sat 8/30

4:20 pm-9:25 pm

1 stop7h 05m

San Francisco

Sun 8/31

11:25 am-11:40 pm

1 stop10h 15m

$204

ChicagoSan Francisco

ORD - SFO

ORDSFO

Chicago O'Hare Intl

Wed 10/8

7:59 pm-8:05 am

1 stop14h 06m

San Francisco

Tue 10/14

10:26 am-11:59 pm

1 stop11h 33m

$204

ChicagoSan Francisco

ORD - SFO

ORDSFO

Chicago O'Hare Intl

Tue 10/28

2:54 pm-10:01 pm

1 stop9h 07m

San Francisco

Tue 11/11

7:00 am-11:59 pm

1 stop14h 59m

$204

ChicagoSan Francisco

ORD - SFO

ORDSFO

Chicago O'Hare Intl

Tue 10/7

8:20 am-2:01 pm

1 stop7h 41m

San Francisco

Tue 10/21

10:26 am-11:59 pm

1 stop11h 33m

$204

ChicagoSan Francisco

ORD - SFO

ORDSFO

Chicago O'Hare Intl

Fri 9/26

9:13 pm-11:59 pm

Nonstop4h 46m

San Francisco

Wed 10/1

11:33 pm-5:55 am

Nonstop4h 22m

$207

ChicagoSan Francisco

ORD - SFO

ORDSFO

Chicago O'Hare Intl

Wed 9/10

8:26 pm-11:09 pm

Nonstop4h 43m

San Francisco

Fri 9/12

11:25 pm-5:31 am

Nonstop4h 06m

$207

ChicagoSan Francisco

MDW - SFO

MDWSFO

Chicago Midway

Sat 11/8

8:15 am-11:00 am

Nonstop4h 45m

San Francisco

Wed 11/12

2:15 pm-10:15 pm

1 stop6h 00m

$207

ChicagoSan Francisco

ORD - SFO

ORDSFO

Chicago O'Hare Intl

Thu 9/18

9:13 pm-11:59 pm

Nonstop4h 46m

San Francisco

Tue 9/23

11:10 pm-5:23 am

Nonstop4h 13m

$207

ChicagoSan Francisco

ORD - SFO

ORDSFO

Chicago O'Hare Intl

Wed 10/8

6:45 am-9:22 am

Nonstop4h 37m

San Francisco

Sun 10/12

11:25 pm-5:34 am

Nonstop4h 09m

$207

ChicagoSan Francisco

MDW - SFO

MDWSFO

Chicago Midway

Sat 10/25

8:15 am-10:50 am

Nonstop4h 35m

San Francisco

Sun 11/2

5:15 am-11:20 am

Nonstop4h 05m

$207

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/11

Showing 1-10 of 35 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 August 8, 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 $358). 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 August 13, 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 Thursday evenings 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 August 13, 2025.

The most flights from CHI to P3L are scheduled on a Monday (94 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (55 on average).

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 August 13, 2025.
Read reviews from past customers who have flown Alaska Airlines, Southwest, and United Airlines from Chicago to Pebble Beach. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
Alaska Airlines
8.0
Very good
10,000 reviews

Entertainment

7.0

Food

7.1

Boarding

8.1

Overall

8.0

Crew

8.5

Comfort

7.8

Reviews

1 / 20
8.0
Excellent

Anonymous,Aug 2025

BOI - LAX

flying in first class, my husband froze the entire flight and was miserable. first class does not offer blankets or any entertainment. (TV etc)
Alaska Airlines
8.0
Very good
10,000 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Entertainment

7.0

Food

7.1

Boarding

8.1

Overall

8.0

Crew

8.5

Comfort

7.8

Reviews

1 / 20
8.0
Excellent

Anonymous,Aug 2025

BOI - LAX

flying in first class, my husband froze the entire flight and was miserable. first class does not offer blankets or any entertainment. (TV etc)
Southwest
8.0
Very good
4,246 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Entertainment

7.0

Food

7.1

Boarding

8.1

Overall

8.0

Crew

8.5

Comfort

7.8

Reviews

1 / 20
8.0
Excellent

Anonymous,Aug 2025

BOI - LAX

flying in first class, my husband froze the entire flight and was miserable. first class does not offer blankets or any entertainment. (TV etc)
United Airlines
7.4
Good
8,920 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Entertainment

7.0

Food

7.1

Boarding

8.1

Overall

8.0

Crew

8.5

Comfort

7.8

Reviews

1 / 20
8.0
Excellent

Anonymous,Aug 2025

BOI - LAX

flying in first class, my husband froze the entire flight and was miserable. first class does not offer blankets or any entertainment. (TV etc)
American Airlines
7.2
Good
10,000 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Entertainment

7.0

Food

7.1

Boarding

8.1

Overall

8.0

Crew

8.5

Comfort

7.8

Reviews

1 / 20
8.0
Excellent

Anonymous,Aug 2025

BOI - LAX

flying in first class, my husband froze the entire flight and was miserable. first class does not offer blankets or any entertainment. (TV etc)
Frontier
5.8
Fair
3,221 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Entertainment

7.0

Food

7.1

Boarding

8.1

Overall

8.0

Crew

8.5

Comfort

7.8

Reviews

1 / 20
8.0
Excellent

Anonymous,Aug 2025

BOI - LAX

flying in first class, my husband froze the entire flight and was miserable. first class does not offer blankets or any entertainment. (TV etc)

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 Southwest. Other airlines that offer cheap prices include United Airlines from $99 and American Airlines from $100 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 (82%), Air China (79%), Austrian Airlines (78%).

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

    On average you can expect to pay $779 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 $184.

  • 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 $358). 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.

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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 August 13, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$90Average$254FlexibilityNo cancel feeOn-time62%
Hawaiian AirlinesCheapest$108Average$217FlexibilityNo cancel feeOn-time85%
Spirit AirlinesCheapest$119Average$229FlexibilityNo cancel feeOn-time65%
DeltaCheapest$128Average$349FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$141Average$424FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$180Average$408FlexibilityNo cancel feeOn-time63%
Alaska AirlinesCheapest$187Average$286FlexibilityNo cancel feeOn-time75%
American AirlinesCheapest$197Average$448FlexibilityNo cancel feeOn-time71%

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