Big Sur

$99+ 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 4/29. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — SFO
Apr 5 — Apr 121
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Find cheap flights from Chicago to Big Sur with Cheapflights

1. Tell us where you want to go
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Cheapflights Tip: The best prices from Chicago to Big Sur are usually found in September or April, booked 83 days in advance, depart on a Wednesday or Thursday 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 March 31, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$207
(Southwest)

One-way from

$99
(Southwest)

Popular in

December

Cheapest in

September

Average price

$373
Provider with most accurate pricing for Chicago (CHI)-San Francisco flight deals.
Provider most trusted by Cheapflights users for Chicago (CHI)-San Francisco flights.
From Chicago (CHI) to Big Sur
One-way flight from Chicago (CHI) to Big Sur
Highest demand for flights based on searches. 7% potential increase in price ($23 potential increase over avg. RT price).
Cheapest flight prices on average. 1% potential price decrease ($6 potential savings vs. average RT price).
Average for round-trip flights in March 2025

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 March 31, 2025.

This Southwest deal was found by Cheapflights users on 3/31. 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.
Sat 4/1912:40 pmMDW - SFO
1 stop6h 20mSouthwest
Sat 4/267:20 amSFO - MDW
1 stop7h 30mSouthwest
Deal found 3/31$207
This Hawaiian Airlines deal was found by Cheapflights users on 3/31. 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.
Thu 5/16:58 pmORD - SFO
Nonstop4h 59mHawaiian Airlines
Tue 5/611:48 amSFO - ORD
Nonstop4h 32mHawaiian Airlines
Deal found 3/31$207
This Alaska Airlines deal was found by Cheapflights users on 3/30. 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.
Sat 4/197:16 pmORD - SFO
Nonstop4h 59mAlaska Airlines
Tue 4/298:00 amSFO - ORD
1 stop8h 01mAlaska Airlines
Deal found 3/30$208
This American Airlines deal was found by Cheapflights users on 3/31. 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.
Thu 9/186:35 pmORD - SFO
Nonstop4h 54mAmerican Airlines
Tue 9/236:10 amSFO - ORD
Nonstop4h 22mAmerican Airlines
Deal found 3/31$209
This Southwest deal was found by Cheapflights users on 3/30. 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 5/306:55 pmORD - SFO
1 stop6h 25mSouthwest
Sat 6/76:25 amSFO - ORD
1 stop9h 30mSouthwest
Deal found 3/30$213
This Expedia deal was found by Cheapflights users on 3/30. 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.
Sat 4/197:16 pmORD - SFO
Nonstop4h 59mMultiple Airlines
Sun 4/2012:08 amSFO - ORD
1 stop9h 09mMultiple Airlines
Deal found 3/30$214
This United Airlines deal was found by Cheapflights users on 3/30. 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 4/2510:35 amORD - SFO
Nonstop5h 01mUnited Airlines
Sun 4/2710:46 pmSFO - ORD
Nonstop4h 22mUnited Airlines
Deal found 3/30$217
This Cheapflightsfares deal was found by Cheapflights users on 3/30. 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.
Sat 5/103:16 pmORD - SFO
1 stop9h 06mFrontier
Sat 5/1711:50 pmSFO - ORD
1 stop9h 10mFrontier
Deal found 3/30$234
This Mytrip deal was found by Cheapflights users on 3/30. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/72:12 pmMDW - SFO
1 stop10h 10mFrontier
Tue 5/1311:50 pmSFO - MDW
1 stop9h 36mFrontier
Deal found 3/30$235
This Delta deal was found by Cheapflights users on 3/30. 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.
Sat 4/193:02 pmMDW - SFO
1 stop7h 12mDelta
Sat 4/266:30 amSFO - MDW
1 stop5h 52mDelta
Deal found 3/30$257
This Delta deal was found by Cheapflights users on 3/30. 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.
Tue 5/206:24 amORD - SFO
1 stop9h 05mDelta
Mon 6/212:40 amSFO - ORD
1 stop9h 07mDelta
Deal found 3/30$257
This Sun Country Air deal was found by Cheapflights users on 3/31. 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.
Thu 8/78:10 pmORD - SFO
1 stop13h 58mSun Country Air
Sun 8/1011:59 pmSFO - ORD
1 stop17h 12mSun Country Air
Deal found 3/31$315

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 March 31, 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

MDW - SFO

MDWSFO

Chicago Midway

Sat 4/19

12:40 pm-5:00 pm

1 stop6h 20m

San Francisco

Sat 4/26

7:20 am-4:50 pm

1 stop7h 30m

$207

ChicagoSan Francisco

ORD - SFO

ORDSFO

Chicago O'Hare Intl

Thu 5/1

6:58 pm-9:57 pm

Nonstop4h 59m

San Francisco

Tue 5/6

11:48 am-6:20 pm

Nonstop4h 32m

$207

ChicagoSan Francisco

ORD - SFO

ORDSFO

Chicago O'Hare Intl

Sat 4/19

7:16 pm-10:15 pm

Nonstop4h 59m

San Francisco

Tue 4/29

8:00 am-6:01 pm

1 stop8h 01m

$208

ChicagoSan Francisco

ORD - SFO

ORDSFO

Chicago O'Hare Intl

Sat 4/19

8:15 am-11:08 am

Nonstop4h 53m

San Francisco

Sat 4/26

7:05 am-5:36 pm

1 stop8h 31m

$210

ChicagoSan Francisco

ORD - SFO

ORDSFO

Chicago O'Hare Intl

Fri 5/30

6:55 pm-11:20 pm

1 stop6h 25m

San Francisco

Sat 6/7

6:25 am-5:55 pm

1 stop9h 30m

$213

ChicagoSan Francisco

ORD - SFO

ORDSFO

Chicago O'Hare Intl

Sat 4/19

7:16 pm-10:15 pm

Nonstop4h 59m

San Francisco

Sun 4/20

12:08 am-11:17 am

1 stop9h 09m

$214

ChicagoSan Francisco

ORD - SFO

ORDSFO

Chicago O'Hare Intl

Fri 4/25

10:35 am-1:36 pm

Nonstop5h 01m

San Francisco

Sun 4/27

10:46 pm-5:08 am

Nonstop4h 22m

$217

ChicagoSan Francisco

ORD - SFO

ORDSFO

Chicago O'Hare Intl

Sat 5/10

3:16 pm-10:22 pm

1 stop9h 06m

San Francisco

Sat 5/17

11:50 pm-11:00 am

1 stop9h 10m

$234

ChicagoSan Francisco

MDW - SFO

MDWSFO

Chicago Midway

Wed 5/7

2:12 pm-10:22 pm

1 stop10h 10m

San Francisco

Tue 5/13

11:50 pm-11:26 am

1 stop9h 36m

$235

ChicagoSan Francisco

MDW - SFO

MDWSFO

Chicago Midway

Sat 4/19

1:16 pm-8:37 pm

1 stop9h 21m

San Francisco

Tue 4/29

6:30 am-2:22 pm

1 stop5h 52m

$257

Flights are sorted by cheapest round-trip flights first.

Deals found on 3/30

Showing 1-10 of 25 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 March 28, 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 $393). 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 March 31, 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 Friday afternoons 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 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 March 31, 2025.

The most flights from CHI to B1G are scheduled on a Monday (72 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (34 on average).

Rainfall in Big Sur by month

Plan your trip to Big Sur by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Big Sur 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 Big Sur when rainfall is around 0.0 in.

Temperature in Big Sur by month

Plan your trip to Big Sur by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Big Sur, 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 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 March 31, 2025.
See what other customers who have flown with Alaska Airlines, Southwest and Delta from Chicago to Big Sur have to say. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.

Overall

8.0

Comfort

7.9

Crew

8.5

Boarding

8.2

Entertainment

7.1

Food

7.1

Reviews

1 / 20
10.0
Excellent

Seleste,Dec 2024

FAT - SAN

The attention and efficiency of the staff and the good handling of the pilot

Overall

8.0

Comfort

7.9

Crew

8.5

Boarding

8.2

Entertainment

7.1

Food

7.1

Reviews

1 / 20
10.0
Excellent

Seleste,Dec 2024

FAT - SAN

The attention and efficiency of the staff and the good handling of the pilot

Overall

8.0

Comfort

7.9

Crew

8.5

Boarding

8.2

Entertainment

7.1

Food

7.1

Reviews

1 / 20
10.0
Excellent

Seleste,Dec 2024

FAT - SAN

The attention and efficiency of the staff and the good handling of the pilot
8.0
Very good

Overall

8.0

Comfort

7.9

Crew

8.5

Boarding

8.2

Entertainment

7.1

Food

7.1

Reviews

1 / 20
10.0
Excellent

Seleste,Dec 2024

FAT - SAN

The attention and efficiency of the staff and the good handling of the pilot

Overall

8.0

Comfort

7.9

Crew

8.5

Boarding

8.2

Entertainment

7.1

Food

7.1

Reviews

1 / 20
10.0
Excellent

Seleste,Dec 2024

FAT - SAN

The attention and efficiency of the staff and the good handling of the pilot

Overall

8.0

Comfort

7.9

Crew

8.5

Boarding

8.2

Entertainment

7.1

Food

7.1

Reviews

1 / 20
10.0
Excellent

Seleste,Dec 2024

FAT - SAN

The attention and efficiency of the staff and the good handling of the pilot

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

    To fly one-way, consider booking your trip with Southwest, which is currently one of the cheapest options available, starting at $99. Alaska Airlines flights start at $99 while deals on American Airlines start at $100 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 (92%), Air China (92%) or British Airways (88%) 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 $98. On average you can expect to pay $1,423. The most popular route, (Chicago O'Hare Intl - San Francisco), can usually be booked for $184.

  • 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 $393). 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

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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.

Top 8 airlines flying from Chicago to Big Sur

Discover the top 8 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 March 31, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$78Average$219FlexibilityNo cancel feeOn-time62%
DeltaCheapest$128Average$389FlexibilityNo cancel feeOn-timeN/A
Spirit AirlinesCheapest$133Average$245FlexibilityNo cancel feeOn-time65%
Alaska AirlinesCheapest$140Average$323FlexibilityNo cancel feeOn-time75%
United AirlinesCheapest$141Average$489FlexibilityNo cancel feeOn-time69%
Hawaiian AirlinesCheapest$144Average$303FlexibilityNo cancel feeOn-time85%
American AirlinesCheapest$197Average$483FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$257Average$464FlexibilityNo cancel feeOn-time63%
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