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Big Sur

$127+ 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 1/18. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — SFO
Jan 17 — Jan 241
Sat 1/17
Sat 1/24
1 adult, Economy
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Find cheap flights from Chicago to Big Sur with Cheapflights

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Cheapflights Tip: The best prices from Chicago to Big Sur are usually found in July or September, booked 83 days in advance, depart on a Thursday or Friday and return on a Wednesday

Cheap 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 December 18, 2025.

This Kiwi.com deal was found by Cheapflights users on 12/17. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/247:00 amORD - SFO
1 stop19h 24mFrontier
Wed 1/74:01 pmSFO - ORD
1 stop27h 31mFrontier
Deal found 12/17$241
This Expedia deal was found by Cheapflights users on 12/16. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/253:27 pmORD - SFO
1 stop18h 21mFrontier
Thu 1/16:24 amSFO - ORD
1 stop15h 48mFrontier
Deal found 12/16$258
This Cheapflightsfares deal was found by Cheapflights users on 12/15. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/247:00 amORD - SFO
1 stop27h 23mFrontier
Mon 1/511:20 pmSFO - ORD
1 stop11h 34mFrontier
Deal found 12/15$273
This Expedia deal was found by Cheapflights users on 12/16. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/247:00 amORD - SFO
1 stop27h 23mFrontier
Thu 1/16:24 amSFO - ORD
1 stop15h 48mFrontier
Deal found 12/16$278
This Frontier deal was found by Cheapflights users on 12/16. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/196:12 amMDW - SFO
1 stop9h 01mFrontier
Sat 1/1011:20 pmSFO - MDW
1 stop10h 11mFrontier
Deal found 12/16$282
This Frontier deal was found by Cheapflights users on 12/16. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/196:00 amORD - SFO
1 stop9h 13mFrontier
Sat 1/1011:20 pmSFO - ORD
1 stop10h 15mFrontier
Deal found 12/16$282
This Kiwi.com deal was found by Cheapflights users on 12/16. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/253:27 pmORD - SFO
1 stop18h 21mFrontier
Wed 12/311:29 pmSFO - ORD
2 stops28h 54mFrontier
Deal found 12/16$300
This Priceline deal was found by Cheapflights users on 12/16. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/196:00 amORD - SFO
1 stop9h 13mFrontier
Mon 1/1911:46 pmSFO - ORD
1 stop12h 11mFrontier
Deal found 12/16$301
This CheapOair deal was found by Cheapflights users on 12/16. 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 12/196:12 amMDW - SFO
1 stop9h 01mFrontier
Mon 1/1911:46 pmSFO - MDW
1 stop10h 19mFrontier
Deal found 12/16$302
This Frontier deal was found by Cheapflights users on 12/16. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/226:00 amORD - SFO
1 stop9h 13mFrontier
Sat 1/1011:20 pmSFO - ORD
1 stop10h 15mFrontier
Deal found 12/16$312
This Delta deal was found by Cheapflights users on 12/17. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/256:00 amORD - SFO
1 stop9h 02mDelta
Wed 12/316:00 amSFO - ORD
2 stops16h 02mDelta
Deal found 12/17$315
This Frontier deal was found by Cheapflights users on 12/16. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/196:00 amORD - SFO
1 stop9h 13mFrontier
Sun 1/1111:35 pmSFO - ORD
1 stop10h 00mFrontier
Deal found 12/16$317

Find 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 December 18, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$238
(Delta)

One-way from

$127
(CheapOair)

Popular in

December

Cheapest in

July

Average price

$449
Provider with most accurate pricing for Chicago (CHI)-San Francisco flight deals.
Search Deals
Provider most trusted by Cheapflights users for Chicago (CHI)-San Francisco flights.
Search Deals
From Chicago (CHI) to Big Sur
Search Deals
One-way flight from Chicago (CHI) to Big Sur
Search Deals
Highest demand for flights based on searches. 15% potential increase in price ($59 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($11 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in December 2025
Search Deals

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 December 18, 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

Tue 1/13

9:00 am-4:32 pm

1 stop9h 32m

San Francisco

Mon 1/26

2:30 pm-11:50 pm

1 stop7h 20m

$239

ChicagoSan Francisco

ORD - SFO

ORDSFO

Chicago O'Hare Intl

Fri 1/23

6:06 pm-8:11 am

1 stop16h 05m

San Francisco

Wed 1/28

11:41 am-11:37 pm

1 stop9h 56m

$239

ChicagoSan Francisco

ORD - SFO

ORDSFO

Chicago O'Hare Intl

Fri 1/30

3:44 pm-10:47 pm

1 stop9h 03m

San Francisco

Tue 2/3

2:52 pm-11:37 pm

1 stop6h 45m

$239

ChicagoSan Francisco

ORD - SFO

ORDSFO

Chicago O'Hare Intl

Sat 2/7

3:44 pm-10:47 pm

1 stop9h 03m

San Francisco

Mon 2/9

9:42 pm-1:10 pm

1 stop13h 28m

$246

ChicagoSan Francisco

ORD - SFO

ORDSFO

Chicago O'Hare Intl

Thu 1/22

9:00 am-4:32 pm

1 stop9h 32m

San Francisco

Wed 1/28

9:16 am-11:37 pm

1 stop12h 21m

$246

ChicagoSan Francisco

MDW - SFO

MDWSFO

Chicago Midway

Sun 2/15

1:28 pm-6:36 pm

1 stop7h 08m

San Francisco

Wed 2/18

6:00 am-5:37 pm

1 stop9h 37m

$248

ChicagoSan Francisco

MDW - SFO

MDWSFO

Chicago Midway

Tue 2/24

1:26 pm-6:36 pm

1 stop7h 10m

San Francisco

Wed 3/4

12:40 am-9:06 am

1 stop6h 26m

$248

ChicagoSan Francisco

MDW - SFO

MDWSFO

Chicago Midway

Sun 3/1

7:17 pm-11:47 pm

1 stop6h 30m

San Francisco

Tue 3/3

6:00 am-5:37 pm

1 stop9h 37m

$248

ChicagoSan Francisco

MDW - SFO

MDWSFO

Chicago Midway

Wed 1/21

1:49 pm-8:59 pm

1 stop9h 10m

San Francisco

Sun 1/25

10:54 pm-8:52 am

1 stop7h 58m

$248

ChicagoSan Francisco

MDW - SFO

MDWSFO

Chicago Midway

Fri 1/9

7:16 pm-11:47 pm

1 stop6h 31m

San Francisco

Sun 1/18

5:45 am-5:34 pm

1 stop9h 49m

$248

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/16

Showing 1-10 of 44 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 December 12, 2025.

Booking 83 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 November is currently the most expensive (average of $207). 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 December 18, 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 34% 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. Monday evenings flights should be avoided if possible as fares are typically the most expensive at this time.

How much does it cost to fly round-trip from Chicago to Big Sur?

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 December 18, 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
11,474 reviews

Comfort

7.8

Boarding

8.1

Food

7.1

Overall

8.0

Entertainment

7.0

Crew

8.5

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
11,474 reviews
Alaska Airlines
8.0
Very good
11,474 reviews

Comfort

7.8

Boarding

8.1

Food

7.1

Overall

8.0

Entertainment

7.0

Crew

8.5

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
7.9
Good
4,249 reviews
Alaska Airlines
8.0
Very good
11,474 reviews

Comfort

7.8

Boarding

8.1

Food

7.1

Overall

8.0

Entertainment

7.0

Crew

8.5

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
9,092 reviews
Alaska Airlines
8.0
Very good
11,474 reviews

Comfort

7.8

Boarding

8.1

Food

7.1

Overall

8.0

Entertainment

7.0

Crew

8.5

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
11,053 reviews
Alaska Airlines
8.0
Very good
11,474 reviews

Comfort

7.8

Boarding

8.1

Food

7.1

Overall

8.0

Entertainment

7.0

Crew

8.5

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
3,082 reviews
Alaska Airlines
8.0
Very good
11,474 reviews

Comfort

7.8

Boarding

8.1

Food

7.1

Overall

8.0

Entertainment

7.0

Crew

8.5

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 $248, Alaska Airlines can have you in Big Sur from Chicago in 7h 08m. Airlines will cover a distance of 1849 mi. This flight may include one or multiple stops.

  • What are the cheapest airlines to fly from Chicago to Big Sur one-way?

    To fly one-way, consider booking your trip with Frontier, which is currently one of the cheapest options available, starting at $71. JetBlue flights start at $73 while deals on Alaska Airlines start at $89 one-way.

  • 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 China Southern (83%) 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 $125. On average you can expect to pay $1,255. The most popular route, (Chicago O'Hare Intl - San Francisco), can usually be booked for $171.

  • 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 November is currently the most expensive (average of $207). 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 10 airlines flying from Chicago to Big Sur

Discover the top 10 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 December 18, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$80Average$223FlexibilityNo cancel feeOn-time62%
Hawaiian AirlinesCheapest$108Average$217FlexibilityNo cancel feeOn-time85%
Sun Country AirCheapest$112Average$375FlexibilityNo cancel feeOn-time83%
SouthwestCheapest$138Average$435FlexibilityNo cancel feeOn-time63%
Spirit AirlinesCheapest$142Average$201FlexibilityNo cancel feeOn-time65%
DeltaCheapest$159Average$355FlexibilityNo cancel feeOn-timeN/A
JetBlueCheapest$183Average$427FlexibilityNo cancel feeOn-time62%
Alaska AirlinesCheapest$188Average$319FlexibilityNo cancel feeOn-time75%
American AirlinesCheapest$197Average$504FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$204Average$471FlexibilityNo cancel feeOn-time69%

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