$117 Find Cheap Flights from Chicago to Big Sur

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Chicago to Big Sur departing on 11/3. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
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Cheap Flights from Chicago to Big Sur (CHI-SFO)

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Chicago to Big Sur that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Chicago to Big Sur

Fri, Nov 14 - Sun, Nov 16
Frontier Logo
11:24 am - 9:11 pmORD-SFO
11h 47m1 stop
Frontier Logo
10:23 pm - 10:41 amSFO-ORD
10h 18m1 stop
$234Frontier
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Fri, Oct 31 - Sat, Nov 8
Frontier Logo
6:30 am - 9:05 pmORD-SFO
16h 35m1 stop
Frontier Logo
6:34 am - 11:00 pmSFO-ORD
14h 26m2 stops
$235Frontier
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Thu, Nov 20 - Mon, Dec 1
Multiple Airlines Logo
7:00 am - 8:47 pmORD-SFO
15h 47m2 stops
Multiple Airlines Logo
6:32 pm - 5:32 amSFO-ORD
9h 00m1 stop
$237Multiple Airlines
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Tue, Nov 18 - Tue, Dec 2
Alaska Airlines Logo
9:20 am - 10:01 pmORD-SFO
14h 41m1 stop
Alaska Airlines Logo
7:00 am - 11:50 pmSFO-ORD
14h 50m1 stop
$238Alaska Airlines
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Tue, Dec 16 - Sun, Jan 11
Alaska Airlines Logo
8:59 pm - 8:06 amORD-SFO
13h 07m1 stop
Alaska Airlines Logo
7:40 pm - 11:55 pmSFO-ORD
26h 15m1 stop
$241Alaska Airlines
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Mon, Oct 27 - Wed, Oct 29
Multiple Airlines Logo
12:23 pm - 9:52 pmORD-SFO
11h 29m1 stop
Multiple Airlines Logo
8:00 am - 12:59 amSFO-ORD
14h 59m2 stops
$244Multiple Airlines
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Wed, Dec 24 - Wed, Dec 24
Delta Logo
7:25 am - 12:21 pmORD-SFO
6h 56m1 stop
Delta Logo
12:10 am - 9:25 amSFO-ORD
7h 15m1 stop
$253Delta
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Wed, Dec 24 - Tue, Dec 30
Delta Logo
4:01 pm - 9:20 pmORD-SFO
7h 19m1 stop
Delta Logo
12:10 am - 9:25 amSFO-ORD
7h 15m1 stop
$257Delta
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Fri, Oct 31 - Tue, Nov 4
Southwest Logo
2:25 pm - 7:00 pmMDW-SFO
6h 35m1 stop
Southwest Logo
6:10 am - 12:15 pmSFO-MDW
4h 05mnonstop
$278Southwest
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Fri, Oct 31 - Tue, Nov 4
Southwest Logo
6:30 am - 1:00 pmMDW-SFO
8h 30m2 stops
Southwest Logo
6:10 am - 12:15 pmSFO-MDW
4h 05mnonstop
$283Southwest
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Everything you should know

Cheapest round-trip
$234
Overall average: $375
Frontier
Fri 11/14Sun 11/16
ORD - SFO • 1 stop
Cheapest non-stop
$255
Southwest
Wed 12/10Thu 1/1
MDW - SFO • Non-stop
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We hope you love your trip to Big Sur!
Useful Info

Good to know

Low seasonJanuary
Cheapest flight$117
Best time to beat the crowds with an average 5% drop in price.
Most popular time to fly with an average 15% increase in price.
Flight from Chicago Midway Airport to San Francisco

When to book flights from Chicago to Big Sur

Are your dates flexible? Find out the best times to travel from Chicago to Big Sur based on our flight data from the last year. Discover the cheapest month and even day to fly.
Estimated round-trip price

FAQs for booking flights from Chicago to Big Sur

  • Which airports will I be using when flying from Chicago to Big Sur?

    When flying out of Chicago you’ll be using one of these airports: Chicago Midway or Chicago O'Hare Intl. Big Sur does not have its own airport so you’ll be flying into nearby San Francisco airport, which is 98.5 mi away.

  • How long does a flight from Chicago to Big Sur take?

    Direct flights cover the 1,855 miles separating Chicago and Big Sur in about 6h 22m.

  • How many flights are there between Chicago and Big Sur?

    97 direct flights run between Chicago and Big Sur on a daily basis. On average, there are about 681 departures each week.

  • What’s the cheapest day of the week to fly between Chicago and Big Sur?

    Consider leaving on a Friday and avoid Sundays if you are looking for the best rates. For your return to Chicago, you’ll find the best rates on Mondays and the most expensive ones on Fridays.

  • How does KAYAK find such low prices on flights from Chicago to Big Sur?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Chicago to Big Sur.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Chicago to Big Sur?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Big Sur from Chicago is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights from Chicago to Big Sur?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly to Big Sur with an airline and back to Chicago with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Chicago to Big Sur?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying to Big Sur from Chicago up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

  • Which airlines provide the cheapest flights from Chicago to Big Sur?

    In the last 72 hours, the cheapest one-way ticket between Chicago and Big Sur found on KAYAK was with American Airlines for $117. Frontier offered a round-trip connection from $234 and Alaska Airlines from $238.

Top tips for finding cheap flights from Chicago to Big Sur

  • There is no airport in Big Sur. Instead, you’ll be flying into San Francisco Airport when flying between Chicago and Big Sur.
  • The cheapest flight from Chicago to Big Sur was found 48 days before departure, on average.
  • Book at least 2 weeks before departure in order to get a below-average price.
  • High season is considered to be November, December and January. The cheapest month to fly is July.

Reviews of the top 5 airlines serving Chicago to Big Sur

 
Need help choosing which airline to fly with from Chicago to Big Sur? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
8.0
Alaska AirlinesOverall score based on 11095 reviews
7.8Comfort
8.5Crew
7.0Entertainment
8.1Boarding
7.1Food
Airline reviews

this was the THIRD time in four Alaska flights that were 2 hours late. Only one was due to weather. The intentionally posted each flight as only 1 hour and 55 minutes late so that they wouldn't have to give out vouchers. And then the flights all ended up more than 2 hours late. Makes United look like a premium carrier.

2.0 MediocreKEN, Oct 2025PAE - SFO
Read more Alaska Airlines reviews

this was the THIRD time in four Alaska flights that were 2 hours late. Only one was due to weather. The intentionally posted each flight as only 1 hour and 55 minutes late so that they wouldn't have to give out vouchers. And then the flights all ended up more than 2 hours late. Makes United look like a premium carrier.

It was fine, mostly I was just happy to be on my last leg home. No in flight entertainment but that's forgivable since it was only a 2 hour flight.

Flight was cancelled, then rebooked on a flight that I was unable to get through since they had closed the gate.

This was likely the smallest, oldest plane I've been on. It didn't handle turbulence well and we were all jostled a lot more than I'm used to. At least it was a short flight.

Flight was delayed two hours; for an hour and a half flight?! And so we missed our connecting flight to Rome because of the long walk between the terminals. Hoping to hear back from Alaska about some compensation for our missed flight and night stay in Los Angeles.

Excellent service from staff at the gate as well as flight attendants on board. Seats had more room than many other airlines and if they were just a little better cushioned they would have been perfect.

Look at my previous review I just wrote on this survey. It was awful!

When I bought my tickets I up great my seats for extra $104 each seats 8A and 8B in the way back from Portland to Palm Springs they gave me the seats 15. I thought it was for round trip same seats . So I was very disappointed ☹️

Alaska Airlines adds time to flight time to make up for late departures. Also Alaska Airlines destroyed my suitcase and I had to buy another suitcase for return flight. Very frustrating and not sure I would fly Alaska Airlines again.

Landed and parked in back of larger jet. Cabin filled with jet exhaust. Left many with headache. I got sick to my stomach. Scrambled to find airsick bags

Connecting flight is on time and boarding was a breeze!

Better and more food and drinks. Put msnbc and free speech tv on the news channel selection list.

Very smooth checking in our luggage with a super pleasant SW agent. I enjoyed a fun entertaining movie.

after landing, we stay 2 hours on the taxi way before reaching the gate The airline and the crew were good though

First time traveling on Southwest since bag fees were implemented. Usual good service. Just more expensive now.

I'm not a fan of Southwest's model. I don't like the herding style of boarding.

It was a perfect flight in all aspects! Both legs!

Boarding process, crew were good. But the seats were so uncomfortable that was all I could focus on. I literally had to sit forward so that all 3 of us could fit in row. I will try to avoid Southwest in the future for any flights over 60 minutes.

Great flight, 47 passengers on a 180 seat plane. Stewardess was pleasant and cheerful.

Great experience flying Southwest. The crew was really kind and helpful, and very friendly with our toddler.

I will never book a flight through Cheap fare. They booked me from Portland Main . And would not give me a refund, so I bought 2 tickets one for 299. From Portland Main to ORD. Then I had to buy a ticket from Oregon PDX to ORD that was another 440. So Just so you know they even told me it was there fault but no refund. Bad bussniess. I did inform United but they said they couldn't help me due to the fact I booked through Cheap Tickets. Never again. And I'm spreding the word. I let everyone know at my 50th class reunion

Crew and customer service were excellent. This flight also had plenty of leg room and seat mounted screens for entertainment. A very pleasant flight all around!

It would have been better if the crew has supported my husband's reasons for needing to keep the space clear around his feet, rather than insisting that he put his knapsack in that space.

Subject: Formal Complaint: Discriminatory and Unprofessional Conduct – Request for Immediate Action & Compensation Dear [Airline Customer Relations Team], I am writing to file a formal complaint regarding my recent travel experience with [Airline], which was by far the worst I have ever encountered. What occurred was not only unprofessional, but in several instances discriminatory, unsafe, and unacceptable. On the first leg of my trip, I arrived only four minutes past check-in. Instead of making any attempt to resolve the matter, your representative flatly denied me boarding and made me wait while she attended to passengers who arrived after me. By the time a manager intervened, it was too late to board, costing me time, money, and unnecessary frustration. The second leg of my trip (Chicago–San Francisco) raised even more serious concerns. From the outset, it was apparent that the staff—particularly two attendants—prioritized Caucasian passengers while dismissing African American and minority passengers. • When a Caucasian passenger in the exit row refused to comply with federal safety requirements, I, as a first responder, immediately offered to switch seats and assume the responsibility. My offer was blatantly ignored, and instead, a Caucasian passenger seated further up was chosen. This was discriminatory and deeply insulting, especially as I was actively de-escalating the situation that could have delayed the flight further. • During a lengthy tarmac delay of over 90 minutes, passengers were given conflicting and unreasonable instructions that created unnecessary distress and tension. • Throughout the flight, a visibly intoxicated passenger directly in front of me was disruptive, rude to others, failed to comply with seatbelt and electronic device rules, and yet faced no enforcement from the crew. In stark contrast, I was singled out for repeated compliance checks even though I was following every rule. This unequal treatment was so obvious that multiple passengers around me spoke up in my defense. This pattern of behavior demonstrated a clear lack of professionalism, disregard for passenger safety, and discriminatory treatment. I expect far better from an airline of your stature. As a paying customer subjected to this unacceptable treatment, I am formally requesting: 1. A full investigation into the conduct of the staff on both flights. 2. A written apology acknowledging the discriminatory and unprofessional behavior I endured. 3. Appropriate compensation for the distress, inconvenience, and mishandling of my travel. If this matter is not addressed promptly and thoroughly, I will have no choice but to escalate my complaint further, including filing with the U.S. Department of Transportation and sharing my experience through other channels. I trust [Airline] will take this complaint seriously and provide a timely resolution.

Check in was quick and easy during early hours. Flight was on time, and customer services was a plus.

Once we got in the air the pilot made up some of the time of the delay. So that was really nice.

Excellent flight. Boarding was efficient and departure was on time. Smooth flight with on time arrival. Deplaning was also efficient.

It was delayed instead of departing at 9:20pm, we departed at 11pm… putting us in Columbus after 2am! It was awful. Had I known about the delay, I could have spent some time in the United Lounge… I was starving because I started my journey in Budapest… so I was exhausted and hungry. Plus I had to make new arrangements to be picked up at the airport in Columbus, instead of midnight it was 2:30 am after getting luggage and out of airport. Not feasible. I would have just stayed in Chicago for the night and gotten a morning flight.

It was great, I’m very grateful for the pilots and crew flight attendants for everything.

Evidently, my seat had the only broken TV. I couldn’t plug it in, get it to come on, or watch anything, and of course, no one could fix it while we were on the plane. The service was good and the boarding was quick

The plane was late, when we did board the plane was as cold as a freezer. I was freezing the entire flight, no blankets. Lost miserable flight I’ve ever had.

3 hour weather delay followed by 1 hour (and counting) maintenance delay. UGH!

After we'd boarded , they canceled the flight. The crew didn't even know , we just all received text messages. Then after they deplaned us , AA was just like "too bad, go F your self, we sure ain't gonna help you"

After a two hour delay, my flight was CANCELLED! No pilot available. Such BS.

Amazing food, great staff, with one noticable detail missing ...but no seat entertainment in any of aircraft ...I am not a fan

I wish American Airlines would change the airline industry by loading the plane back to front instead of front to back. Planes would board so much more smoothly and quickly.

I have long legs, my foot was out in the aisle and when a flight attendant came walking by and I didn't notice, instead of saying "excuse me" or anything like that, she kicked my foot. Extremely rude

Excellent! The gate agents were kind enough to rebook me on an earlier flight saving me from a 6 hour layover. Even my luggage made it despite the fact that the connection was technically too narrow. The flight itself was very comfortable, roomy, and clean. Plenty of space for my carryon items with plugs to charge my phone. After a long international flight of 14 hours, this was an excellent way to end my travels!

Great experience. Flight boarded easily. Departed early. Smooth flight. Great arrival in DC--almost no taxing! Almost direct to gate from runway. Crew was terrific. Same cookies and beverages in main cabin. I did not use the entertainment system on this flight.

Most of the delay was due to weather which is not what was at issue here. One delay was due to a missing flashlight and in the end the flashlight was actually found on the plane. The entertainment system is very limited. Live TV options offer only a few channels that are not very appealing. Boarding and deplaning are always difficult. It just takes too much time to get on and off the plane. On the plus side, I missed my connecting flight, but was easily able to book a later flight from the app while enroute.

Boarding was on time and plane departed as scheduled. There are obviously no amenities (food, drink, entertainment) on Frontier, but there also didn't seem to be any issues with luggage space either.

Inbound plane was on time and flight departed on time with no issues while boarding.

I knew going into this that Frontier, being a low cost carrier, would be pretty bare bones and charge for most extras but this was made up for by the fact that the airplane was a reasonably new Airbus, every employee was great and best of all, Everett Washington is an amazing airport - thanks Frontier for flying there!!!

i was unable to check in the flight. refund requested

It was well done. It was my first time flying with them and I was nervous b/c I have heard of many cancelled and/or delray flights. Everything went smoothly.

Just know that everything, and I mean everything is “ala cart”. 60$ just to put something in the overhead bin. I will never fly Frontier again nor do I recommend them to anyone else.

The single worst check in experience I could imagine. I’ll never do any business with Frontier or any affiliated company

Too many extra fees, uncomfortable, little leg room. Will not recommend this airline.

I think Frontier was very good at communication. Their app worked very well. Loading was great and the flight was nice and easy.

Great for the price. No wifi or entertainment, but gate agents and crew were fantastic and we boarded quickly and left on time.

Everything you need to know for your flight from Chicago to Big Sur

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