$71 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 10/30. 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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1 adult, Economy

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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

Sun, Oct 19 - Sat, Oct 25
Frontier Logo
6:50 am - 2:22 pmORD-SFO
9h 32m1 stop
Frontier Logo
1:29 pm - 10:24 pmSFO-ORD
6h 55m1 stop
$153Frontier
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Sat, Oct 4 - Sat, Oct 18
Frontier Logo
12:22 pm - 9:21 pmORD-SFO
10h 59m1 stop
Frontier Logo
1:29 pm - 10:24 pmSFO-ORD
6h 55m1 stop
$154Frontier
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Thu, Oct 2 - Mon, Oct 6
Frontier Logo
10:42 am - 12:16 amORD-SFO
15h 34m1 stop
Frontier Logo
7:07 pm - 11:53 pmSFO-ORD
26h 46m1 stop
$155Frontier
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Sat, Aug 30 - Tue, Sep 9
American Airlines Logo
6:50 pm - 9:33 pmORD-SFO
4h 43mnonstop
American Airlines Logo
12:47 am - 6:56 amSFO-ORD
4h 09mnonstop
$188American Airlines
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Sat, Sep 6 - Sat, Sep 13
United Airlines Logo
8:50 am - 11:43 amORD-SFO
4h 53mnonstop
United Airlines Logo
3:00 pm - 9:24 pmSFO-ORD
4h 24mnonstop
$197United Airlines
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Sat, Aug 30 - Sun, Sep 7
United Airlines Logo
6:35 pm - 9:23 pmORD-SFO
4h 48mnonstop
United Airlines Logo
11:59 pm - 6:24 amSFO-ORD
4h 25mnonstop
$198United Airlines
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Wed, Oct 8 - Tue, Oct 14
Alaska Airlines Logo
8:20 am - 2:01 pmORD-SFO
7h 41m1 stop
Alaska Airlines Logo
10:26 am - 11:59 pmSFO-ORD
11h 33m1 stop
$204Alaska Airlines
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Sat, Aug 30 - Sat, Sep 6
American Airlines Logo
6:50 pm - 9:33 pmORD-SFO
4h 43mnonstop
American Airlines Logo
11:25 pm - 5:42 amSFO-ORD
4h 17mnonstop
$206American Airlines
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Sat, Oct 4 - Sat, Oct 11
Southwest Logo
5:15 pm - 9:25 pmMDW-SFO
6h 10m1 stop
Southwest Logo
10:40 am - 4:45 pmSFO-MDW
4h 05mnonstop
$207Southwest
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Wed, Oct 8 - Sun, Oct 12
Southwest Logo
5:20 pm - 9:50 pmMDW-SFO
6h 30m1 stop
Southwest Logo
6:00 am - 12:05 pmSFO-MDW
4h 05mnonstop
$217Southwest
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Good to know

Low seasonJanuary
Cheapest flight$71
Best time to beat the crowds with an average 6% drop in price.
Most popular time to fly with an average 20% 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 7h 01m.

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

    99 direct flights run between Chicago and Big Sur on a daily basis. On average, there are about 699 departures each week.

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

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

  • 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.

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 September.

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 10000 reviews
8.1Boarding
8.5Crew
7.0Entertainment
7.8Comfort
7.1Food
Airline reviews

I like the friendliness of the staff. The food choices were OK. I wish there was more options. The entertainment through the movie portal was alright.

10.0 ExcellentJohn, Aug 2025PDX - LAX
Read more Alaska Airlines reviews

I like the friendliness of the staff. The food choices were OK. I wish there was more options. The entertainment through the movie portal was alright.

Good experience on flight. But flight was delayed for takeoff by an hour, and Alaska posted the wrong landing time on its website. So the person who was designated to pick me up arrived 1 hour early and sat waiting for a long time at 11pm at night. This could have been avoided with better text and website communication by Alaska/Hawaiin Airlines

2 FLIGHT DELAYS? what an inconvenience to stay @the airport HALF THE DAY😳from 1pm till boarding @ 4pm pass 😠exhausting !

There was a very drunk man behind me who kept talking loudly to no one in particular. He was slurring his words and at times he didn’t know where we were going or whether or not we landed. He was also loudly using a lot of profanity. The attendants didn’t seem to notice or care and in fact continued to serve him alcohol. He was allowed to purchase 4 little bottles.

Loved the staff ease of flying snacks and free movies and WiFi

Would have been nice if my flight was on time and I didn't miss my connection and had to spend the night in Seattle, losing one night at the VRBO I paid for in Sitka. And, my connecting flight was still at the gate when my flight was taxiing to it's gate. But, it took off. Too bad for me. I really can't believe you even want me to review or comment on my experience.

boarding was late worst was going back LAX to SFO delayed not once ? but TWICE😡I was at the airport practically almost 5 hours of previous time , very inconvenient! i would have spend longer time with family , I was wanting to avoid TSA line? but it just got me to spend unwanted time @ d airport

Flight was delayed - we left at 11:30 pm instead of 10:30 and it was extremely inconvenient. It affected both the day of the flight and the next day

Very pleasant , a flight attendant Jo did a great job mixing me up a beverage and just brightened the trip .

Plane boarded and left on time or very close to the stated departure. Arrived on time. Staff was subdued. Could not hear the flight attendant too well. No announcement from the pilot which is always nice. Biggest complaint absolutely no little snacks! But the important thing is we left and arrived on time and we survived.

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.

My flight to Chicago left and landed early. My return flight left two minutes late and arrived 2 minutes late. My seat selections were ideal! There were no snacks going to Chicago and no snacks on the return trip. There are no charging outlets on board.

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

I was charged for my daughters bag when I am supposed to receive two free checked bags with my United Explorer card.

The schedule to Moline changed 5 times. The gate changed 6 times. That is a pathetic way to run an airline. No wonder that no one in our company flies on United Express to or from Moline. Changes happen most of the time. I learned my lesson on this trip…never again!

Flight was great. Efficient boarding. Short flight. Early arrival. Friendly flight crew. The entertainment system did not work well. Could not access it until the aircraft reached 10K feet or more. Lots of glitches.

A bit rush for transit. Food and entertainment are not available

Smooth boarding process. Early departure, smooth flight, early arrival. The entertainment package has very good recent movie options. The flight crew were friendly and professional.

My flight was scheduled for about 6:05 departure. There were 11 gate changes from 4-7pm and the flight was 3 hours delayed due to operational issues. The plane taxied around the airport for about half an hour before stopping to be de-iced. It would have been nice if we were alerted of the plan to de-ice prior to the 30 minute drive around the airport. The flight attendant was friendly, which was the only redeeming thing about this flight. As a former flight attendant for United, I was extremely disappointed.

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.

You were more on time than United. I'm so over united delays.

sluggish boarding and arrival procedures, fake nice flight attendants, and lots of delays.

Disaster. They lied every step of the way. We ended up being delayed due to crew and then allegedly abandoned the flight because of a curfew at LGA. No rebooking to LGA at any reasonable time. No hotel. No meal vouchers. Had to sleep in the airport and fly to Newark instead. Will never fly Frontier again.

What I expected, nickeled and dined and a frontier flight attendant loudly complained about her job and lack of communication as she headed to the gate on her cell phone. Not professional.

As every law enforcement agency I could imagine surrounded the plane and we didn’t disembark for 2 hours and then had to stick around for another hour to go get our personal belongings after leaving them behind and being bused away from the plane, it was scary and inconvenient. We were given no information as to why this was happening. Lack of communication with passengers was disappointing.

After boarding and un-boarding twice over 6+hours, the flight was canceled.

Severe turbulence. Captain never came on to reassure passengers after things settled down.

My first flight was delayed 5 hours. The 2nd flight was canceled til the next day and the never even tried to compensate for it. Worse I was delayed again on the flight the rebooked me on.

Boarding in Orlando was not good. Giant mob at the gate, should have been lines.

Decent clean onboard experience. Okay discount airline experience. Unfortunately, any customer service interactions are difficult and unhelpful. There is no service. Also, a premium seat only gets you premium boarding if you line up first. Once they start general boarding you must go to the back of the line. Not very premium

baggage clamed had to wait over a hour and half for all people on my flight it was terrible

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