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$100+ 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 8/30. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — SFO
Aug 5 — Aug 121
Tue 8/5
Tue 8/12
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 September 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 July 31, 2025.

Round-trip from

$204
(Kiwi.com)

One-way from

$100
(Southwest)

Popular in

December

Cheapest in

September

Average price

$297
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. 7% potential increase in price ($27 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 July 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 July 31, 2025.

This Kiwi.com deal was found by Cheapflights users on 7/30. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/193:20 pmORD - SFO
1 stop10h 44mHawaiian Airlines
Wed 9/2411:30 amSFO - ORD
1 stop8h 37mHawaiian Airlines
Deal found 7/30$204
This American Airlines deal was found by Cheapflights users on 7/29. 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.
Sat 9/63:19 pmORD - SFO
Nonstop4h 42mAmerican Airlines
Fri 9/192:22 pmSFO - ORD
Nonstop4h 18mAmerican Airlines
Deal found 7/29$206
This Southwest deal was found by Cheapflights users on 7/29. 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 9/511:10 amMDW - SFO
Nonstop4h 35mSouthwest
Tue 9/910:45 amSFO - MDW
Nonstop4h 10mSouthwest
Deal found 7/29$207
This Southwest deal was found by Cheapflights users on 7/31. 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 8/237:00 amORD - SFO
1 stop6h 20mSouthwest
Sun 8/317:15 amSFO - ORD
1 stop8h 40mSouthwest
Deal found 7/31$208
This Trip.com deal was found by Cheapflights users on 7/28. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/151:39 pmORD - SFO
1 stop8h 00mMultiple Airlines
Wed 8/208:00 amSFO - ORD
1 stop18h 50mMultiple Airlines
Deal found 7/28$215
This United Airlines deal was found by Cheapflights users on 7/31. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/257:18 amORD - SFO
Nonstop4h 46mUnited Airlines
Sun 9/2811:33 pmSFO - ORD
Nonstop4h 22mUnited Airlines
Deal found 7/31$217
This Alaska Airlines deal was found by Cheapflights users on 7/30. 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.
Tue 10/78:20 amORD - SFO
1 stop7h 41mAlaska Airlines
Wed 10/810:26 amSFO - ORD
1 stop11h 33mAlaska Airlines
Deal found 7/30$220
This Cheapflightsfares deal was found by Cheapflights users on 7/29. 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 8/161:39 pmORD - SFO
1 stop8h 00mFrontier
Sat 8/2310:29 pmSFO - ORD
1 stop10h 10mFrontier
Deal found 7/29$234
This Frontier deal was found by Cheapflights users on 7/31. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/1211:39 amMDW - SFO
1 stop11h 08mFrontier
Wed 8/1311:30 pmSFO - MDW
1 stop11h 59mFrontier
Deal found 7/31$238
This Delta deal was found by Cheapflights users on 7/31. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/199:29 amMDW - SFO
1 stop6h 58mDelta
Sat 9/2012:45 amSFO - MDW
1 stop6h 04mDelta
Deal found 7/31$257
This Delta deal was found by Cheapflights users on 7/31. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/127:10 amORD - SFO
1 stop7h 35mDelta
Sun 9/2111:00 pmSFO - ORD
1 stop7h 05mDelta
Deal found 7/31$257

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 July 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

ORD - SFO

ORDSFO

Chicago O'Hare Intl

Fri 9/19

3:20 pm-12:04 am

1 stop10h 44m

San Francisco

Tue 9/30

2:42 pm-12:03 am

1 stop7h 21m

$204

ChicagoSan Francisco

ORD - SFO

ORDSFO

Chicago O'Hare Intl

Sat 9/6

3:19 pm-6:01 pm

Nonstop4h 42m

San Francisco

Fri 9/19

2:22 pm-8:40 pm

Nonstop4h 18m

$206

ChicagoSan Francisco

MDW - SFO

MDWSFO

Chicago Midway

Fri 9/5

11:10 am-1:45 pm

Nonstop4h 35m

San Francisco

Tue 9/9

10:45 am-4:55 pm

Nonstop4h 10m

$207

ChicagoSan Francisco

ORD - SFO

ORDSFO

Chicago O'Hare Intl

Sat 8/23

7:00 am-11:20 am

1 stop6h 20m

San Francisco

Sun 8/31

7:15 am-5:55 pm

1 stop8h 40m

$208

ChicagoSan Francisco

ORD - SFO

ORDSFO

Chicago O'Hare Intl

Fri 8/15

1:39 pm-7:39 pm

1 stop8h 00m

San Francisco

Wed 8/20

8:00 am-4:50 am

1 stop18h 50m

$215

ChicagoSan Francisco

ORD - SFO

ORDSFO

Chicago O'Hare Intl

Thu 9/25

7:18 am-10:04 am

Nonstop4h 46m

San Francisco

Sun 9/28

11:33 pm-5:55 am

Nonstop4h 22m

$217

ChicagoSan Francisco

ORD - SFO

ORDSFO

Chicago O'Hare Intl

Tue 10/7

8:20 am-2:01 pm

1 stop7h 41m

San Francisco

Wed 10/8

10:26 am-11:59 pm

1 stop11h 33m

$220

ChicagoSan Francisco

ORD - SFO

ORDSFO

Chicago O'Hare Intl

Sat 8/16

9:08 am-10:25 am

1 stop27h 17m

San Francisco

Sat 8/23

6:34 am-11:39 pm

1 stop15h 05m

$234

ChicagoSan Francisco

MDW - SFO

MDWSFO

Chicago Midway

Tue 8/12

11:39 am-8:47 pm

1 stop11h 08m

San Francisco

Wed 8/13

11:30 pm-1:29 pm

1 stop11h 59m

$238

ChicagoSan Francisco

MDW - SFO

MDWSFO

Chicago Midway

Fri 9/19

9:29 am-2:27 pm

1 stop6h 58m

San Francisco

Sat 9/20

12:45 am-8:49 am

1 stop6h 04m

$257

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/31

Showing 1-10 of 23 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 July 25, 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 $358). 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 July 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 Thursday evenings 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 July 31, 2025.

The most flights from CHI to B1G are scheduled on a Thursday (97 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (47 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 July 31, 2025.
Read through reviews of airlines operating flights from Chicago to Big Sur, such as Alaska Airlines, Southwest, and Delta. 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

Food

7.1

Entertainment

7.1

Boarding

8.1

Overall

8.0

Crew

8.5

Comfort

7.8

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

Food

7.1

Entertainment

7.1

Boarding

8.1

Overall

8.0

Crew

8.5

Comfort

7.8

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
4,246 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Food

7.1

Entertainment

7.1

Boarding

8.1

Overall

8.0

Crew

8.5

Comfort

7.8

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
7,981 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Food

7.1

Entertainment

7.1

Boarding

8.1

Overall

8.0

Crew

8.5

Comfort

7.8

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
Hawaiian Airlines
7.8
Good
2,611 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Food

7.1

Entertainment

7.1

Boarding

8.1

Overall

8.0

Crew

8.5

Comfort

7.8

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
8,900 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Food

7.1

Entertainment

7.1

Boarding

8.1

Overall

8.0

Crew

8.5

Comfort

7.8

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 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 $100. Hawaiian Airlines flights start at $103 while deals on American Airlines start at $116 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 Austrian Airlines (85%), ANA (82%) or Brussels Airlines (80%) 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 $97. On average you can expect to pay $1,249. The most popular route, (Chicago O'Hare Intl - San Francisco), can usually be booked for $197.

  • 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 $358). 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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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 July 31, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$90Average$255FlexibilityNo cancel feeOn-time62%
Hawaiian AirlinesCheapest$108Average$217FlexibilityNo cancel feeOn-time85%
Sun Country AirCheapest$112Average$305FlexibilityNo cancel feeOn-time83%
Spirit AirlinesCheapest$127Average$238FlexibilityNo cancel feeOn-time65%
DeltaCheapest$128Average$349FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$138Average$431FlexibilityNo cancel feeOn-time63%
United AirlinesCheapest$179Average$471FlexibilityNo cancel feeOn-time69%
Alaska AirlinesCheapest$187Average$287FlexibilityNo cancel feeOn-time75%
American AirlinesCheapest$197Average$484FlexibilityNo cancel feeOn-time71%

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