$128 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 2/9. 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.
1 adult
1 adult, Economy, 0 bags

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Everything you should know

Cheapest round-trip
$243
Overall average: $289
Delta
Tue 2/10Wed 2/18
MDW - SFO • 1 stop
Cheapest non-stop
$250
Typical prices: $332-$357
Southwest
Thu 2/26Sat 2/28
MDW - SFO • Non-stop
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Flight Deals
Useful Info
Flight Deals

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

Tue, Feb 10 - Wed, Feb 18
Delta Logo
12:46 pm - 8:25 pm
MDW
-
SFO
9h 39m
1 stop
Delta Logo
10:45 pm - 8:54 am
SFO
-
MDW
8h 09m
1 stop
$243Delta
Wed, Feb 11 - Fri, Feb 13
Frontier Logo
12:36 pm - 9:39 pm
ORD
-
SFO
11h 03m
1 stop
Frontier Logo
10:58 pm - 10:46 am
SFO
-
ORD
9h 48m
1 stop
$243Frontier
Sat, Feb 14 - Fri, Feb 20
Frontier Logo
9:15 am - 10:15 am
MDW
-
SFO
27h 00m
2 stops
Frontier Logo
3:18 pm - 11:41 pm
SFO
-
MDW
6h 23m
1 stop
$244Frontier
Fri, Mar 13 - Tue, Mar 17
Frontier Logo
7:00 am - 5:46 pm
ORD
-
SFO
12h 46m
1 stop
Frontier Logo
10:38 pm - 10:52 am
SFO
-
ORD
10h 14m
1 stop
$244Frontier
Wed, Mar 25 - Sun, Mar 29
Frontier Logo
6:00 am - 7:14 pm
MDW
-
SFO
15h 14m
1 stop
Frontier Logo
10:15 pm - 11:35 pm
SFO
-
MDW
23h 20m
1 stop
$245Frontier
Mon, Mar 16 - Tue, Mar 24
Frontier Logo
5:11 am - 3:21 pm
ORD
-
SFO
12h 10m
1 stop
Frontier Logo
10:38 pm - 10:52 am
SFO
-
ORD
10h 14m
1 stop
$245Frontier
Sat, Apr 11 - Wed, Apr 22
Multiple Airlines Logo
5:52 pm - 8:10 pm
ORD
-
SFO
28h 18m
1 stop
Multiple Airlines Logo
7:15 am - 7:03 pm
SFO
-
ORD
9h 48m
1 stop
$246Multiple Airlines
Tue, Feb 3 - Thu, Feb 26
Multiple Airlines Logo
8:00 am - 5:48 pm
ORD
-
SFO
11h 48m
2 stops
Multiple Airlines Logo
10:46 pm - 10:51 am
SFO
-
ORD
10h 05m
1 stop
$247Multiple Airlines
Wed, Feb 11 - Tue, Feb 24
Southwest Logo
8:10 am - 2:55 pm
MDW
-
SFO
8h 45m
2 stops
Southwest Logo
5:30 am - 6:45 pm
SFO
-
MDW
11h 15m
2 stops
$248Southwest
Wed, Mar 18 - Sun, May 17
United Airlines Logo
4:35 pm - 7:34 pm
ORD
-
SFO
4h 59mnonstop
United Airlines Logo
12:45 am - 7:07 am
SFO
-
ORD
4h 22mnonstop
$250United Airlines
Useful Info

Good to know

Low seasonJanuary
Cheapest flight$128
Best time to beat the crowds but there is an average 12% increase in price.
Most popular time to fly with an average 8% 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 4h 25m.

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

    79 direct flights run between Chicago and Big Sur on a daily basis. On average, there are about 556 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 Saturdays.

  • 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 JetBlue for $73. Frontier offered a round-trip connection from $90 and Hawaiian Airlines from $108.

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 83 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 11721 reviews
7.8Comfort
8.1Boarding
7.0Entertainment
7.1Food
8.5Crew
Airline reviews

The whole experience went smoothly with no hitches along the way.

10.0 ExcellentAnonymous, Jan 2026
SAN - SMF
Read more Alaska Airlines reviews

The whole experience went smoothly with no hitches along the way.

The flight was excellent and very friendly and helpful staff. Will travel again and recommend to friends. Thank you

I paid $168 each for myself and my daughter for an upgrade and we didn’t get any of the things mentioned by you/ site that comes with an upgrade. It was all just the same. One snack and one beverage. Nothing else. I don’t understand what the upgrade was.

One of the flight attendants treated my grandma who is 77 years old badly and would respond sarcastically. Example my grandma "do you have and honey by any chance" the flight attendant "does this look like a restaurant to you. She was also very rude to myself and my children giving us attitude and being sarcastic when answering.

we waited for 50 minutes to check a bag and missed a flight. do better.

The flight crew was very professional and pleasant. Our flight was delayed 3 hours, but Kayak informed me in advance

I really hate the seat assignment at the gate. I understand it is so families can sit together but it caused me and others a lot of unnecessary stress and confusion, enough for me to not fly Alaska again. The app is so awful that it did not even update my seat assignment on the boarding pass but sent me a notification of my seat... it showed in Apple Wallet but not in the Alaska app itself. That only made the stress worse. I think most people like myself prefer to know where they are seated at check in 24 hours before so they don't have to anxiously hang out at the gate the entire time. This is not a good use of your agents time either to be dealing with all of us asking where we are sitting. You should automatically assign the multiple seat purchases to be together before they check in and fill us solo travelers in those gaps as we check in.

Alaska Airlines have beautiful new airplanes that have comfortable seats but tight for a tall person like myself. They do provide upgrades to flyers but at a $140 cost. My flight went smooth and prompt as well as without a hitch. The flight crew were warm and friendly as well as very attentive. I'd recommend this airline over Frontier airlines any day.

Did not have In flight service on my round trip due to turbulence. I did not partake in In flight entertainment. Flight descending into LAX was very turbulent. It would have been nice if the pilot communicated with us during that rough descent into LAX to ease the minds of some of us more nervous flyers.

Before I even boarded this old white man , a fat Samoan lady, and a short brown guy were at the desk. They asked if we could have 15 volunteers to get free checked bags cause it was a full flight. I waited in line, I got up to the short brown guy and he asked for my boarding pass and I showed him, he said that he can’t check my bag because I wasn’t given a seat yet. So he had me go to the next line with the old white guy, but before I switched lines I asked him, well if I go to that line, will I be able to check my bag so I waited in line and he said yeah, it doesn’t matter , I’m good. So I switch lines and wait in the line of the old white man, with every guest before me he was very sweet , making small talk, smiling and had great eye contact( all of the people he was talking to was white) I come up and he doesn’t look at me , then says I’ll be right with you, I wait for him to initiate and when he does he’s like what’s up? I was like the man next to you told me I needed to get checked in before I can check my bag. He’s like what’s your last name and I say Valenzuela , and he said we’re not there yet, all while not smiling, no eye contact like he was with the other guests. He said we’re will call you when I get to you. So I go sit down and I’m sitting down for less than a minute and he calls me and someone else. I go up and say Valenzuela and he’s like who are you and I’m like Valenzuela , he’s like hmm and says don’t go anywhere and calls someone else. I finally get my seat and I go back to the short brown man and ask if I can check my bag and he said there isn’t any room available and I was like? Wait you told me and then the fat Samoan lady said yeah we don’t need anymore bags thank you. I was dumbfounded and just walked away. So rude. Terrible experience and terrible communication on their end.

3 hour delay. Had to change plans and was still delayed.

The staff was very friendly, professional, and courteous. The overall flight was a great experience.

The flight crew was extremely rude and especially not helpful when our flight was delayed.

The boarding and seat assignment system no longer works for me, but I know it is being replaced. Otherwise, I am good with the overall experience.

The lead steward kept singing about "San Francisco" and hotel California---more annoying than humorous....needs work. Flight was smooth and on time.

Still a fan of open seating. Flight was on schedule and arrived on time. The 737 MAX is very comfortable.

San Diego airport is brand new, spacious, airy and very smooth checkin at SW baggage drop.

Plane crashed into a bus or some other vehicle on the ground while pulling out of the gate. No injuries, but wing tip was damaged and returned to gate for “maintenance issues” and we departed 5 hours later because the plane went out of service and new plane was flown in from a nearby airport, Midway.

Ever since Southwest starting charging for bags, passengers don't want to pay to check their bags, so the gate agents have to beg people to check their roller bags now because there's "not enough space". This was a terrible business move by Southwest.

All was good. I just had a hard time getting connected to the WiFi/internet during the flight

They lost my luggage, so, not happy. The crew was nice but my suitcases never made it, still trying to find out what happened!

I understand weather is an issue, but making us chase our plane down at five scheduled gates across three terminals in an airport the size of O'Hare was unfair. They'd have probably been better off to leave gates as TBD until the inbound plane is in final approach instead of running us all over the place. Also, props to the consistently-unprepared ground crew in Richmond for once again leaving my lane parked short of the gate because they couldn't have a crew in place on time with 2 hours notice...

cabin crew was OK, food was OK, the trip from the US to Munich was actually pretty bad comfort wise. Noisy aircraft, lights never dimmed even in Business class (night flight) barely sufficient amenities for the price. I have millions of miles with United but TBH American is gaining ground and Delta has always been marginally better then United although on paper United has more longes and cheaper upgrades.

Essy to get on. The hostess gave very little pop, the plane was late getting in, and we are still waiting for our bags. This sucks. :/

Great flight. On time boarding. Smooth flight and on time arrival at EWR. The flight crew was marvelous and there was a great selection of movies on the entertainment system. Our bags were at the carousel before we got there. Another excellent flight from United.

I liked the snacks and the flight attendants were friendly.

After a delay at the gate, C3, at Ohare on Sunday, I left my Blk ski coat on the bench at the gate, lost! Please review my lob claim, thx.

Very thoughtful flight attendant offered me water immediately since I had run to make my connection.

Always wish for more healthy, gluten free options. We have to bring our own.

Having a long layover, I was very appreciative of the ability to stand by for an earlier flight. Other airlines like Delta have refused this to me in the past, just to be mean (because my ticket class wasn't high enough). United went out of their way to help me get to my destination early, which I really appreciated given that it was the third leg of a 24+ hour journey for me.

We were upgraded to First Class and it was a great flight

We experienced gate changes and a long delay. My seat was dirty when I boarded and I had to use wipes to clean it myself. There was an unpleasant and overpowering cleaning product scent on the plane as well that lingered through the flight.

My carry on baggage was damaged. Entire trip, I had to carry the baggage. When complained to the boarding crew, they got mad at me and still asked me to valet check in the cabin baggage. Rude boarding crew!!!

Crew were all friendly and helpful. It was a short flight so just a beverage service with a cookie. After we were boarded the plane took about 45 minutes to leave the gate but it was New Year’s Eve so not shocking there was some delay. Overall good experience and very grateful.

The boarding process needs to be fixed. The zone don't work, especially when there is hardly anyone in zones 3, 4,and 5, leaving the majority of the passengers backed up in the aisle, especially because passengers seated near the front are blocking passengers who are seated in the rear of the plane. It would also help if the size of carry on bags was more strictly enforced.

The boarding by groups is pointless. The first two groups worked fine, but almost Noone boarded in goups three thru five leaving the vast majority boarding when group six was called. It defeated the purpose of spreading out the crowd.

We loved the steward on the plane. He made the night enjoyable

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"

It was costly and difficult to check in. $85 to take a small suitcase with me, carry on or checked and $75 on the return trip, Plus $25 if I didn't check my self in check in $25, because I couldn't do it on the kiosk. Small very uncomfortable seats, waited on the runway for near an hour each way. It was my worst flight to date.

It was ok. It was expensive to check 2 bags ($75.00 per bag), and then it took a long time to wait for shuttle to take us from one terminal to the terminal where the plane was taking off at LAX. And all of this for a flight where we had to pay for any food or drink that was not water.

It didn’t happen. I booked it and then was told it wasn’t available and then forced to pay far higher prices for a worse option

A 630departure flight Delayed 6hours! They changed my gate, I moved to the new gate. Had our flight on the screen for 12noon departure. I go get above to eat, check screen again and the flight was gone, no notice no announcement, nothing!! They sent my bag on the flight I wasn’t on, got it back to me 3days later. Thank goodness they did refund my money but I will NEVER fly them again.

Due to weather, my flight was delayed, further delayed, then canceled. I eventually got through to a support person who helped me find a different route out of MSP, but to get to DIA, they didn't want to, but eventually did help with the connection ticket purchase. But even this replacement flight was delayed time and time again, and I would have missed my connecting flights and I didn't want to get stuck in a layover city, so after 12 hours at the airport with two young boys who were very tired, we just cancelled our plans and spent the week at home, instead of Nana's.

Plane and crew on board were fine. Everything else was terrible.

Better than expected. Staff were friendly and nice on both flights.

Terrible. The canceled my entire flight when I requested a refund for a trip frontier canceled trip one way.

i was unable to check in the flight. refund requested

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.

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

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