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Big Sur

$130+ Cheap flights from Chicago (CHI) to Big Sur, 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 12/3. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — SFO
Dec 3 — Dec 101
Wed 12/3
Wed 12/10
1 adult, Economy
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Cheapflights Tip: The best prices from Chicago to Big Sur are usually found in July or February, booked 83 days in advance, depart on a Thursday or Friday and return on a Wednesday

Cheap flight deals from Chicago to Big Sur

Keep the following information in mind while searching for Chicago to Big Sur flight deals. Data was last updated November 3, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$262
(Alaska Airlines)

One-way from

$130
(Kiwi.com)

Popular in

November

Cheapest in

July

Average price

$387
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 Big Sur
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One-way flight from Chicago (CHI) to Big Sur
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Highest demand for flights based on searches. 12% potential increase in price ($46 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 November 2025
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Find flight deals from Chicago to Big Sur

Cheapest flights from Chicago to Big Sur
Explore the most affordable flight options available from Chicago to Big Sur. Find the lowest fares from popular airlines and budget airlines, with prices last updated on November 3, 2025.

This Kissandfly.com deal was found by Cheapflights users on 11/2. 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.
Mon 11/246:00 amORD - SFO
1 stop10h 01mHawaiian Airlines
Wed 12/37:00 amSFO - ORD
1 stop14h 50mHawaiian Airlines
Deal found 11/2$262
This Kiwi.com deal was found by Cheapflights users on 11/1. 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.
Wed 12/102:49 pmMDW - SFO
1 stop24h 29mFrontier
Sat 12/1311:33 pmSFO - MDW
1 stop16h 39mFrontier
Deal found 11/1$263
This Alaska Airlines deal was found by Cheapflights users on 11/2. 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 12/28:59 pmORD - SFO
1 stop16h 04mAlaska Airlines
Sun 12/78:09 amSFO - ORD
1 stop13h 41mAlaska Airlines
Deal found 11/2$263
This Kiwi.com deal was found by Cheapflights users on 11/1. 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 12/227:38 pmORD - SFO
1 stop16h 46mMultiple Airlines
Tue 1/66:30 pmSFO - ORD
2 stops14h 19mMultiple Airlines
Deal found 11/1$264
This Kiwi.com deal was found by Cheapflights users on 11/2. 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.
Sun 11/1610:43 pmORD - SFO
1 stop16h 42mFrontier
Thu 12/44:07 pmSFO - ORD
1 stop6h 05mFrontier
Deal found 11/2$265
This Alaska Airlines deal was found by Cheapflights users on 11/3. 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.
Wed 12/178:55 amORD - SFO
2 stops10h 29mAlaska Airlines
Wed 1/710:12 amSFO - ORD
1 stop11h 25mAlaska Airlines
Deal found 11/3$266
This Booking.com deal was found by Cheapflights users on 11/2. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/1412:30 pmMDW - SFO
1 stop13h 44mFrontier
Sun 11/166:34 amSFO - MDW
1 stop26h 56mFrontier
Deal found 11/2$267
This Kiwi.com deal was found by Cheapflights users on 11/2. 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 11/112:31 pmORD - SFO
2 stops31h 39mMultiple Airlines
Mon 11/171:10 pmSFO - ORD
1 stop9h 49mMultiple Airlines
Deal found 11/2$267
This Kiwi.com deal was found by Cheapflights users on 11/2. 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 11/243:31 pmMDW - SFO
1 stop10h 53mFrontier
Fri 11/289:03 amSFO - MDW
2 stops33h 55mFrontier
Deal found 11/2$268
This Kiwi.com deal was found by Cheapflights users on 11/2. 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 11/1111:00 amORD - SFO
1 stop7h 43mFrontier
Thu 11/131:10 pmSFO - ORD
1 stop9h 49mFrontier
Deal found 11/2$268
This Kiwi.com deal was found by Cheapflights users on 11/1. 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.
Fri 12/128:05 amMDW - SFO
2 stops15h 20mFrontier
Fri 12/1211:38 pmSFO - MDW
1 stop19h 44mFrontier
Deal found 11/1$269
This Kiwi.com deal was found by Cheapflights users on 11/1. 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.
Fri 11/146:00 amORD - SFO
1 stop10h 40mMultiple Airlines
Tue 12/26:00 amSFO - ORD
1 stop21h 32mMultiple Airlines
Deal found 11/1$269

Cheapflights Fare Finder

 
Customize your flight search to find flights from Chicago to Big Sur 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 November 3, 2025.
Use the filters below to find and compare flights from Chicago to Big Sur that are best for you.

Fly from

Chicago

Fly to

Big Sur

Route

Depart

Return

Price

ChicagoSan Francisco

ORD - SFO

ORDSFO

Chicago O'Hare Intl

Sat 1/31

9:00 am-2:22 pm

1 stop7h 22m

San Francisco

Tue 2/3

2:52 pm-11:37 pm

1 stop6h 45m

$262

ChicagoSan Francisco

ORD - SFO

ORDSFO

Chicago O'Hare Intl

Fri 1/30

8:00 am-5:59 pm

1 stop11h 59m

San Francisco

Tue 2/3

11:41 am-11:37 pm

1 stop9h 56m

$272

ChicagoSan Francisco

ORD - SFO

ORDSFO

Chicago O'Hare Intl

Wed 1/7

7:30 am-1:38 pm

1 stop8h 08m

San Francisco

Sat 1/10

2:39 pm-11:53 pm

1 stop7h 14m

$283

ChicagoSan Francisco

ORD - SFO

ORDSFO

Chicago O'Hare Intl

Thu 1/1

8:39 am-12:27 am

1 stop17h 48m

San Francisco

Wed 1/7

10:12 am-11:37 pm

1 stop11h 25m

$290

ChicagoSan Francisco

ORD - SFO

ORDSFO

Chicago O'Hare Intl

Sat 12/13

3:05 pm-11:03 am

1 stop21h 58m

San Francisco

Sun 1/18

9:00 am-11:37 pm

2 stops12h 37m

$306

ChicagoSan Francisco

MDW - SFO

MDWSFO

Chicago Midway

Mon 11/24

8:10 am-3:05 pm

1 stop8h 55m

San Francisco

Wed 12/3

6:10 am-12:15 pm

Nonstop4h 05m

$308

ChicagoSan Francisco

MDW - SFO

MDWSFO

Chicago Midway

Mon 11/24

7:02 pm-12:12 am

1 stop7h 10m

San Francisco

Mon 12/1

12:30 am-9:19 am

1 stop6h 49m

$318

ChicagoSan Francisco

MDW - SFO

MDWSFO

Chicago Midway

Wed 12/17

1:50 pm-8:28 pm

1 stop8h 38m

San Francisco

Wed 1/7

10:54 pm-8:54 am

1 stop8h 00m

$319

ChicagoSan Francisco

MDW - SFO

MDWSFO

Chicago Midway

Wed 11/26

1:25 pm-4:05 pm

Nonstop4h 40m

San Francisco

Wed 12/3

6:10 am-12:15 pm

Nonstop4h 05m

$329

ChicagoSan Francisco

ORD - SFO

ORDSFO

Chicago O'Hare Intl

Wed 12/24

5:31 pm-11:57 pm

1 stop8h 26m

San Francisco

Sun 1/4

12:47 am-11:47 am

1 stop9h 00m

$335

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/1

Showing 1-10 of 43 results
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Best time to book a flight from Chicago to Big Sur

Have a flexible travel schedule? Discover the best time to fly to Big Sur 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 Big Sur

How far ahead should I book a flight from Chicago to Big Sur?

Use this chart to determine the optimal time to book a round-trip flight from Chicago to Big Sur. Price data was last updated on October 31, 2025.

Booking 48 days in advance of your planned departure date is, on average, the best time to get cheap flights from Chicago to Big Sur. The general trend is that the closer you book to the departure date, the more expensive your flight will be.

What is the cheapest month to book a flight from Chicago to Big Sur?

Currently, October is the cheapest month in which you can book a flight from Chicago to Big Sur (average of $80). Flying from Chicago to Big Sur in December is currently the most expensive (average of $203). 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 B1G?

Find hourly flight availability from Chicago to Big Sur. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated November 3, 2025.

One of the essential ways to save on airfare from Chicago to Big Sur is to remain as flexible as possible. Flights that are in the evening tend to be the most expensive. A flight in the afternoon could potentially save you up to 35% on airfare.

What is the cheapest day to fly from Chicago to Big Sur?

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

Travelers seeking maximum savings on their Chicago to Big Sur flight should consider departing on Tuesday afternoons 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 Big Sur

Explore weekly flight availability from Chicago to Big Sur. 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 November 3, 2025.

The most flights from CHI to B1G are scheduled on a Sunday (65 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (22 on average).

Reviews of airlines servicing Big Sur

Get insights into the airlines that provide service to Big Sur. 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 Big Sur. Reviews last updated November 3, 2025.
Read through reviews of airlines operating flights from Chicago to Big Sur, such as Alaska Airlines, Southwest, and United Airlines. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Alaska Airlines
8.0
Very good
11,235 reviews

Overall

8.0

Food

7.1

Boarding

8.1

Entertainment

7.0

Crew

8.5

Comfort

7.8

Reviews

1 / 20
6.0
Good

Hannah,Aug 2025

SFO - SAN

Ticket said TSA pre check, but then the TSA agent said that Alaska Airlines has not actually entered the pre check information for the ticket, so I had to use regular security. During boarding, I have a disability and need to board early. The Alaska Airlines employee announced disability boarding, but then immediately announced 2 other groups to board, so I still had to fight the crowds. On the plane, the stewardess was brusk and rude. Seats were very uncomfortable, especially on lower back.
Alaska Airlines
8.0
Very good
11,235 reviews
Alaska Airlines
8.0
Very good
11,235 reviews

Overall

8.0

Food

7.1

Boarding

8.1

Entertainment

7.0

Crew

8.5

Comfort

7.8

Reviews

1 / 20
6.0
Good

Hannah,Aug 2025

SFO - SAN

Ticket said TSA pre check, but then the TSA agent said that Alaska Airlines has not actually entered the pre check information for the ticket, so I had to use regular security. During boarding, I have a disability and need to board early. The Alaska Airlines employee announced disability boarding, but then immediately announced 2 other groups to board, so I still had to fight the crowds. On the plane, the stewardess was brusk and rude. Seats were very uncomfortable, especially on lower back.
Southwest
8.0
Very good
4,238 reviews
Alaska Airlines
8.0
Very good
11,235 reviews

Overall

8.0

Food

7.1

Boarding

8.1

Entertainment

7.0

Crew

8.5

Comfort

7.8

Reviews

1 / 20
6.0
Good

Hannah,Aug 2025

SFO - SAN

Ticket said TSA pre check, but then the TSA agent said that Alaska Airlines has not actually entered the pre check information for the ticket, so I had to use regular security. During boarding, I have a disability and need to board early. The Alaska Airlines employee announced disability boarding, but then immediately announced 2 other groups to board, so I still had to fight the crowds. On the plane, the stewardess was brusk and rude. Seats were very uncomfortable, especially on lower back.
United Airlines
7.4
Good
8,997 reviews
Alaska Airlines
8.0
Very good
11,235 reviews

Overall

8.0

Food

7.1

Boarding

8.1

Entertainment

7.0

Crew

8.5

Comfort

7.8

Reviews

1 / 20
6.0
Good

Hannah,Aug 2025

SFO - SAN

Ticket said TSA pre check, but then the TSA agent said that Alaska Airlines has not actually entered the pre check information for the ticket, so I had to use regular security. During boarding, I have a disability and need to board early. The Alaska Airlines employee announced disability boarding, but then immediately announced 2 other groups to board, so I still had to fight the crowds. On the plane, the stewardess was brusk and rude. Seats were very uncomfortable, especially on lower back.
American Airlines
7.2
Good
11,036 reviews
Alaska Airlines
8.0
Very good
11,235 reviews

Overall

8.0

Food

7.1

Boarding

8.1

Entertainment

7.0

Crew

8.5

Comfort

7.8

Reviews

1 / 20
6.0
Good

Hannah,Aug 2025

SFO - SAN

Ticket said TSA pre check, but then the TSA agent said that Alaska Airlines has not actually entered the pre check information for the ticket, so I had to use regular security. During boarding, I have a disability and need to board early. The Alaska Airlines employee announced disability boarding, but then immediately announced 2 other groups to board, so I still had to fight the crowds. On the plane, the stewardess was brusk and rude. Seats were very uncomfortable, especially on lower back.
Frontier
5.8
Fair
3,117 reviews
Alaska Airlines
8.0
Very good
11,235 reviews

Overall

8.0

Food

7.1

Boarding

8.1

Entertainment

7.0

Crew

8.5

Comfort

7.8

Reviews

1 / 20
6.0
Good

Hannah,Aug 2025

SFO - SAN

Ticket said TSA pre check, but then the TSA agent said that Alaska Airlines has not actually entered the pre check information for the ticket, so I had to use regular security. During boarding, I have a disability and need to board early. The Alaska Airlines employee announced disability boarding, but then immediately announced 2 other groups to board, so I still had to fight the crowds. On the plane, the stewardess was brusk and rude. Seats were very uncomfortable, especially on lower back.

Related info for your journey

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

  • How long is the flight from Chicago to Big Sur?

    For as low as $262, Alaska Airlines can have you in Big Sur from Chicago in 7h 22m. Airlines will cover a distance of 1841 mi. This flight may include one or multiple stops.

  • What are the most reliable airlines from Chicago to Big Sur?

    No one likes to see their flight delayed. When booking a flight from Chicago to Big Sur consider choosing ANA (90%), Air China (86%) or Qantas Airways (82%) as they are the most reliable in getting you off to your destination on time.

  • What are the cheapest flights from Chicago to Big Sur?

    The cheapest flight price from Chicago to Big Sur is $134. On average you can expect to pay $1,293. The most popular route, (Chicago O'Hare Intl - San Francisco), can usually be booked for $157.

  • Can I find deals for flights from Chicago to Big Sur that include hotel bookings?

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

  • How can I find direct flights from Chicago to Big Sur?

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

  • Can I find deals for business class flights from Chicago to Big Sur?

    Yes. Cheapflights offers flight deals from Chicago to Big Sur 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 Big Sur?

    Currently, October is the cheapest month in which you can book a flight from Chicago to Big Sur (average of $80). Flying from Chicago to Big Sur in December is currently the most expensive (average of $203). 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 Big Sur

See prices for flight routes from nearby airports that may be better suited for you.
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Top 9 airlines flying from Chicago to Big Sur

Discover the top 9 airlines that operate flights from Chicago to Big Sur. 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 November 3, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$80Average$261FlexibilityNo cancel feeOn-time62%
Hawaiian AirlinesCheapest$108Average$217FlexibilityNo cancel feeOn-time85%
Sun Country AirCheapest$112Average$375FlexibilityNo cancel feeOn-time83%
DeltaCheapest$128Average$352FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$138Average$436FlexibilityNo cancel feeOn-time63%
Spirit AirlinesCheapest$142Average$220FlexibilityNo cancel feeOn-time65%
Alaska AirlinesCheapest$192Average$324FlexibilityNo cancel feeOn-time75%
American AirlinesCheapest$197Average$511FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$203Average$474FlexibilityNo cancel feeOn-time69%

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