HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Big Sur

$101+ 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 10/17. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — SFO
Oct 15 — Oct 221
Wed 10/15
Wed 10/22
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Chicago to Big Sur with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

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 September 15, 2025.

Round-trip from

$208
(Frontier)

One-way from

$101
(Cheapflightsfares)

Popular in

December

Cheapest in

July

Average price

$297
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. 8% potential increase in price ($28 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($6 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in September 2025
Search Deals

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 September 15, 2025.

This Kiwi.com deal was found by Cheapflights users on 9/15. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/218:20 amORD - SFO
1 stop7h 41mMultiple Airlines
Sun 10/268:21 pmSFO - ORD
1 stop11h 15mMultiple Airlines
Deal found 9/15$208
This Cheapflightsfares deal was found by Cheapflights users on 9/15. 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.
Mon 9/229:54 pmORD - SFO
1 stop25h 27mFrontier
Thu 9/2510:37 pmSFO - ORD
1 stop20h 22mFrontier
Deal found 9/15$210
This Kiwi.com deal was found by Cheapflights users on 9/15. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/205:25 amORD - SFO
1 stop12h 35mMultiple Airlines
Wed 10/228:00 amSFO - ORD
1 stop10h 48mMultiple Airlines
Deal found 9/15$211
This Frontier deal was found by Cheapflights users on 9/14. 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.
Thu 10/22:07 pmORD - SFO
1 stop7h 01mFrontier
Thu 10/910:25 pmSFO - ORD
1 stop12h 33mFrontier
Deal found 9/14$213
This SmartFares deal was found by Cheapflights users on 9/13. 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 SmartFares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/21:53 pmMDW - SFO
1 stop7h 15mFrontier
Thu 10/93:25 pmSFO - MDW
1 stop7h 11mFrontier
Deal found 9/13$214
This Frontier deal was found by Cheapflights users on 9/13. 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.
Sun 10/195:25 amORD - SFO
1 stop12h 35mFrontier
Fri 10/2410:23 pmSFO - ORD
1 stop11h 12mFrontier
Deal found 9/13$214
This Kiwi.com deal was found by Cheapflights users on 9/13. 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 10/111:15 amORD - SFO
1 stop12h 06mMultiple Airlines
Mon 10/611:00 pmSFO - ORD
1 stop12h 47mMultiple Airlines
Deal found 9/13$215
This CheapOair deal was found by Cheapflights users on 9/13. 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.
Sat 10/256:15 amMDW - SFO
1 stop17h 08mFrontier
Fri 10/315:53 pmSFO - MDW
2 stops25h 42mFrontier
Deal found 9/13$216
This Frontier deal was found by Cheapflights users on 9/14. 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.
Thu 11/136:00 amORD - SFO
2 stops10h 09mFrontier
Mon 11/173:35 pmSFO - ORD
1 stop6h 40mFrontier
Deal found 9/14$216
This Kiwi.com deal was found by Cheapflights users on 9/13. 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 10/147:15 amORD - SFO
1 stop17h 12mFrontier
Thu 10/1610:25 pmSFO - ORD
1 stop12h 33mFrontier
Deal found 9/13$217
This CheapOair deal was found by Cheapflights users on 9/14. 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.
Sat 9/276:15 amMDW - SFO
1 stop17h 06mFrontier
Mon 9/2911:00 pmSFO - MDW
1 stop14h 58mFrontier
Deal found 9/14$218
This Alaska Airlines deal was found by Cheapflights users on 9/15. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/218:20 amORD - SFO
1 stop7h 41mAlaska Airlines
Wed 10/2210:26 amSFO - ORD
1 stop11h 33mAlaska Airlines
Deal found 9/15$218

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 September 15, 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

Fri 12/12

9:15 am-9:46 pm

1 stop14h 31m

San Francisco

Mon 12/15

9:57 pm-2:09 pm

1 stop14h 12m

$241

ChicagoSan Francisco

ORD - SFO

ORDSFO

Chicago O'Hare Intl

Wed 10/8

6:05 pm-11:33 pm

1 stop7h 28m

San Francisco

Sat 10/11

12:35 am-8:30 am

1 stop5h 55m

$241

ChicagoSan Francisco

ORD - SFO

ORDSFO

Chicago O'Hare Intl

Wed 10/22

9:13 pm-11:59 pm

Nonstop4h 46m

San Francisco

Tue 10/28

11:44 pm-6:02 am

Nonstop4h 18m

$255

ChicagoSan Francisco

ORD - SFO

ORDSFO

Chicago O'Hare Intl

Thu 12/11

9:15 am-9:46 pm

1 stop14h 31m

San Francisco

Sun 12/14

7:00 am-6:54 pm

1 stop9h 54m

$263

ChicagoSan Francisco

ORD - SFO

ORDSFO

Chicago O'Hare Intl

Fri 12/5

3:05 pm-8:06 am

1 stop19h 01m

San Francisco

Sun 12/7

7:00 am-11:50 pm

1 stop14h 50m

$263

ChicagoSan Francisco

ORD - SFO

ORDSFO

Chicago O'Hare Intl

Sat 10/18

7:00 am-12:23 pm

1 stop7h 23m

San Francisco

Tue 10/28

7:00 am-6:59 pm

1 stop9h 59m

$270

ChicagoSan Francisco

MDW - SFO

MDWSFO

Chicago Midway

Sat 12/13

2:45 pm-8:20 pm

1 stop7h 35m

San Francisco

Mon 1/12

2:00 pm-9:50 pm

1 stop5h 50m

$272

ChicagoSan Francisco

MDW - SFO

MDWSFO

Chicago Midway

Wed 11/5

3:15 pm-9:50 pm

1 stop8h 35m

San Francisco

Thu 11/13

5:00 am-4:20 pm

2 stops9h 20m

$274

ChicagoSan Francisco

ORD - SFO

ORDSFO

Chicago O'Hare Intl

Sat 10/25

10:35 am-1:21 pm

Nonstop4h 46m

San Francisco

Wed 10/29

5:10 am-11:30 am

Nonstop4h 20m

$287

ChicagoSan Francisco

MDW - SFO

MDWSFO

Chicago Midway

Sat 10/25

8:15 am-10:50 am

Nonstop4h 35m

San Francisco

Wed 10/29

6:30 am-12:35 pm

Nonstop4h 05m

$287

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/14

Showing 1-10 of 45 results
1
2
3
...
5

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 September 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, January is the cheapest month in which you can book a flight from Chicago to Big Sur (average of $276). Flying from Chicago to Big Sur in June is currently the most expensive (average of $357). 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 September 15, 2025.

When flying from Chicago to Big Sur, 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 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 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 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 September 15, 2025.

The most flights from CHI to B1G are scheduled on a Monday (95 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (60 on average).

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 September 15, 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
10,000 reviews

Overall

8.0

Boarding

8.1

Comfort

7.8

Crew

8.5

Entertainment

7.0

Food

7.1

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
10,000 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Overall

8.0

Boarding

8.1

Comfort

7.8

Crew

8.5

Entertainment

7.0

Food

7.1

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
4,242 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Overall

8.0

Boarding

8.1

Comfort

7.8

Crew

8.5

Entertainment

7.0

Food

7.1

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
8,929 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Overall

8.0

Boarding

8.1

Comfort

7.8

Crew

8.5

Entertainment

7.0

Food

7.1

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
10,000 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Overall

8.0

Boarding

8.1

Comfort

7.8

Crew

8.5

Entertainment

7.0

Food

7.1

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
3,172 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Overall

8.0

Boarding

8.1

Comfort

7.8

Crew

8.5

Entertainment

7.0

Food

7.1

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 $255, Alaska Airlines can have you in Big Sur from Chicago in 4h 46m. Airlines will cover a distance of 1841 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 Hawaiian Airlines, which is currently one of the cheapest options available, starting at $109. Alaska Airlines flights start at $115 while deals on Frontier start at $127 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 Air China (79%), ANA (79%) or Austrian Airlines (75%) 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 $89. On average you can expect to pay $924. The most popular route, (Chicago O'Hare Intl - San Francisco), can usually be booked for $165.

  • 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, January is the cheapest month in which you can book a flight from Chicago to Big Sur (average of $276). Flying from Chicago to Big Sur in June is currently the most expensive (average of $357). 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

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for Chicago to Big Sur

See prices for flight routes from nearby airports that may be better suited for you.
O'Hare Intl to Las Vegas flights
O'Hare Intl to Los Angeles flights
O'Hare Intl to San Francisco flights
Midway to Las Vegas flights
O'Hare Intl to Santa Ana flights
O'Hare Intl to San Diego flights
O'Hare Intl to Ontario flights
St. Louis to Las Vegas flights
Midway to Los Angeles flights
O'Hare Intl to Palm Springs flights
Midway to San Francisco flights
O'Hare Intl to Burbank flights
O'Hare Intl to Sacramento flights
O'Hare Intl to San Jose flights
St. Louis to Los Angeles flights
Midway to San Diego flights
St. Louis to San Francisco flights
O'Hare Intl to Oakland flights
O'Hare Intl to Reno flights
Rockford to Las Vegas flights
Midway to Santa Ana flights
Midway to Ontario flights
O'Hare Intl to Fresno flights
Midway to Palm Springs flights
St. Louis to San Diego flights
Midway to San Jose flights
O'Hare Intl to Santa Barbara flights
St. Louis to Ontario flights
Midway to Oakland flights
Midway to Burbank flights
Moline to Las Vegas flights
Midway to Sacramento flights
St. Louis to Santa Ana flights
Peoria to Las Vegas flights
St. Louis to Palm Springs flights
O'Hare Intl to Long Beach flights
St. Louis to San Jose flights
St. Louis to Sacramento flights
O'Hare Intl to Monterey flights
Bloomington to Las Vegas flights
St. Louis to Long Beach flights
O'Hare Intl to San Luis Obispo flights
Midway to Reno flights
Midway to Long Beach flights
St. Louis to Burbank flights
Midway to Fresno flights
Evansville to Las Vegas flights
Peoria to San Francisco flights
Moline to San Diego flights
Moline to San Jose flights

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 September 15, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$90Average$263FlexibilityNo cancel feeOn-time62%
Hawaiian AirlinesCheapest$108Average$217FlexibilityNo cancel feeOn-time85%
Sun Country AirCheapest$112Average$335FlexibilityNo cancel feeOn-time83%
DeltaCheapest$128Average$351FlexibilityNo cancel feeOn-timeN/A
Spirit AirlinesCheapest$133Average$257FlexibilityNo cancel feeOn-time65%
SouthwestCheapest$180Average$431FlexibilityNo cancel feeOn-time63%
Alaska AirlinesCheapest$188Average$328FlexibilityNo cancel feeOn-time75%
American AirlinesCheapest$197Average$488FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$204Average$490FlexibilityNo cancel feeOn-time69%

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.