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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 7/15. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — SFO
jun. 16 — jun. 231
lun. 6/16
lun. 6/23
1 adult, Economy
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Cheapflights Tip: The best prices from Chicago to Pebble Beach are usually found in September or October, booked 84 days in advance, depart on a Friday 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 junio 11, 2025.

Round-trip from

$203
(FlightHub)

One-way from

$99
(Southwest)

Popular in

December

Cheapest in

September

Average price

$326
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. 8% potential increase in price ($28 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 June 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 junio 11, 2025.

This FlightHub deal was found by Cheapflights users on 6/9. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lun. 8/1812:35 pmMDW - SFO
1 stop13h 44mFrontier
sáb. 8/2310:29 pmSFO - MDW
1 stop9h 39mFrontier
Deal found 6/9$203
This American Airlines deal was found by Cheapflights users on 6/11. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 8/296:50 pmORD - SFO
Nonstop4h 43mAmerican Airlines
lun. 9/16:10 amSFO - ORD
Nonstop4h 20mAmerican Airlines
Deal found 6/11$203
This Southwest deal was found by Cheapflights users on 6/9. 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.
sáb. 8/166:15 amORD - SFO
1 stop9h 30mSouthwest
sáb. 8/239:05 pmSFO - ORD
1 stop12h 45mSouthwest
Deal found 6/9$204
This Southwest deal was found by Cheapflights users on 6/9. 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.
mar. 7/1512:50 pmMDW - SFO
Nonstop4h 30mSouthwest
mar. 7/227:45 pmSFO - MDW
1 stop7h 15mSouthwest
Deal found 6/9$207
This Alaska Airlines deal was found by Cheapflights users on 6/9. 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.
jue. 8/77:18 pmORD - SFO
Nonstop4h 48mAlaska Airlines
mié. 8/137:55 pmSFO - ORD
1 stop7h 45mAlaska Airlines
Deal found 6/9$208
This Hawaiian Airlines deal was found by Cheapflights users on 6/10. 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.
mié. 8/67:00 amORD - SFO
1 stop7h 24mHawaiian Airlines
dom. 8/1011:55 amSFO - ORD
Nonstop4h 23mHawaiian Airlines
Deal found 6/10$227
This Kissandfly.com deal was found by Cheapflights users on 6/10. 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 Kissandfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 7/47:18 pmORD - SFO
Nonstop4h 48mMultiple Airlines
mar. 7/87:20 amSFO - ORD
1 stop13h 47mMultiple Airlines
Deal found 6/10$233
This Kiwi.com deal was found by Cheapflights users on 6/10. 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.
dom. 9/285:12 pmORD - SFO
1 stop7h 52mFrontier
sáb. 10/181:20 pmSFO - ORD
1 stop7h 00mFrontier
Deal found 6/10$240
This Delta deal was found by Cheapflights users on 6/10. 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.
mar. 7/14:26 pmMDW - SFO
1 stop8h 22mDelta
lun. 8/412:50 amSFO - MDW
1 stop5h 55mDelta
Deal found 6/10$257
This Delta deal was found by Cheapflights users on 6/11. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 7/111:00 amORD - SFO
1 stop9h 13mDelta
mar. 7/155:50 amSFO - ORD
1 stop8h 43mDelta
Deal found 6/11$257
This United Airlines deal was found by Cheapflights users on 6/10. 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.
vie. 8/222:25 pmORD - SFO
Nonstop4h 42mUnited Airlines
mar. 8/2611:10 pmSFO - ORD
Nonstop4h 13mUnited Airlines
Deal found 6/10$269
This Sun Country Air deal was found by Cheapflights users on 6/10. 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 Sun Country Air is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb. 6/286:10 amORD - SFO
1 stop7h 10mSun Country Air
vie. 7/46:13 pmSFO - ORD
1 stop20h 56mSun Country Air
Deal found 6/10$295

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 junio 11, 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

mié. 10/1

8:31 am-11:15 am

Nonstop4h 44m

San Francisco

dom. 10/5

11:25 pm-5:31 am

Nonstop4h 06m

$202

ChicagoSan Francisco

MDW - SFO

MDWSFO

Chicago Midway

lun. 8/18

12:35 pm-12:19 am

1 stop13h 44m

San Francisco

sáb. 8/23

10:29 pm-10:08 am

1 stop9h 39m

$203

ChicagoSan Francisco

ORD - SFO

ORDSFO

Chicago O'Hare Intl

sáb. 9/27

7:20 am-10:29 pm

1 stop17h 09m

San Francisco

vie. 10/3

11:40 am-9:02 pm

1 stop7h 22m

$203

ChicagoSan Francisco

MDW - SFO

MDWSFO

Chicago Midway

sáb. 9/6

9:45 am-6:20 pm

2 stops10h 35m

San Francisco

sáb. 9/13

6:20 pm-5:10 am

1 stop8h 50m

$204

ChicagoSan Francisco

ORD - SFO

ORDSFO

Chicago O'Hare Intl

sáb. 8/16

6:15 am-1:45 pm

1 stop9h 30m

San Francisco

sáb. 8/23

9:05 pm-11:50 am

1 stop12h 45m

$204

ChicagoSan Francisco

ORD - SFO

ORDSFO

Chicago O'Hare Intl

jue. 8/7

7:18 pm-10:06 pm

Nonstop4h 48m

San Francisco

mié. 8/13

7:55 pm-5:40 am

1 stop7h 45m

$208

ChicagoSan Francisco

ORD - SFO

ORDSFO

Chicago O'Hare Intl

vie. 7/11

7:18 pm-10:06 pm

Nonstop4h 48m

San Francisco

mar. 7/15

2:45 pm-11:59 pm

1 stop7h 14m

$220

ChicagoSan Francisco

ORD - SFO

ORDSFO

Chicago O'Hare Intl

vie. 7/4

7:18 pm-10:06 pm

Nonstop4h 48m

San Francisco

mar. 7/8

7:20 am-11:07 pm

1 stop13h 47m

$233

ChicagoSan Francisco

MDW - SFO

MDWSFO

Chicago Midway

mar. 7/1

4:26 pm-10:48 pm

1 stop8h 22m

San Francisco

lun. 8/4

12:50 am-8:45 am

1 stop5h 55m

$257

ChicagoSan Francisco

ORD - SFO

ORDSFO

Chicago O'Hare Intl

mié. 7/2

7:05 am-2:34 pm

1 stop9h 29m

San Francisco

mié. 7/9

11:39 am-9:30 pm

1 stop7h 51m

$267

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/9

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 June 9, 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 84 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 $364). 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 junio 11, 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 at noon 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 junio 11, 2025.

The most flights from CHI to P3L are scheduled on a Wednesday (90 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (57 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 junio 11, 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
10,000 reviews

Comfort

7.9

Crew

8.5

Entertainment

7.1

Overall

8.0

Boarding

8.1

Food

7.1

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
Alaska Airlines
8.0
Very good
10,000 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Comfort

7.9

Crew

8.5

Entertainment

7.1

Overall

8.0

Boarding

8.1

Food

7.1

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
Southwest
8.0
Very good
4,287 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Comfort

7.9

Crew

8.5

Entertainment

7.1

Overall

8.0

Boarding

8.1

Food

7.1

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
Delta
8.0
Very good
7,945 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Comfort

7.9

Crew

8.5

Entertainment

7.1

Overall

8.0

Boarding

8.1

Food

7.1

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
Hawaiian Airlines
7.9
Good
2,493 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Comfort

7.9

Crew

8.5

Entertainment

7.1

Overall

8.0

Boarding

8.1

Food

7.1

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
United Airlines
7.4
Good
8,784 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Comfort

7.9

Crew

8.5

Entertainment

7.1

Overall

8.0

Boarding

8.1

Food

7.1

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.

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 Hawaiian Airlines from $99 and Alaska Airlines from $101 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: Austrian Airlines (90%), ANA (90%), Brussels Airlines (88%).

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

    On average you can expect to pay $1,238 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 $364). 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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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 junio 11, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$78Average$242FlexibilityNo cancel feeOn-time62%
Hawaiian AirlinesCheapest$108Average$226FlexibilityNo cancel feeOn-time85%
Spirit AirlinesCheapest$127Average$239FlexibilityNo cancel feeOn-time65%
DeltaCheapest$128Average$393FlexibilityNo cancel feeOn-timeN/A
Alaska AirlinesCheapest$167Average$324FlexibilityNo cancel feeOn-time75%
United AirlinesCheapest$179Average$426FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$197Average$449FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$246Average$433FlexibilityNo cancel feeOn-time63%

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