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Find cheap flights from Chicago to Big Sur from $42

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 6/1. 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
0 bags
Fri 6/7
Fri 6/14

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Good to know

Low season

January

High season

December

Cheapest flight

$42
Best time to beat the crowds with an average 1% drop in price.
Most popular time to fly and prices are also 3% lower on average.
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 28m.

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

    106 direct flights run between Chicago and Big Sur on a daily basis. On average, there are about 746 departures each week.

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

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

  • 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 Frontier for $42. Frontier offered a round-trip connection from $88 and Alaska Airlines from $179.

See more FAQs

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 51 days before departure, on average.
  • Book at least 1 week before departure in order to get a below-average price.
  • High season is considered to be February, March and April. The cheapest month to fly is September.
See more tips

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 9141 reviews
8.2Boarding
7.3Food
8.6Crew
7.9Comfort
7.3Entertainment
Airline reviews

Ground crew was great in Austin, flight crew left a lot to be desired. Not particularly friendly, helpful or nice.

6.0 GoodAnonymous, May 2024AUS - SFO
Read more about Alaska Airlines reviews

Ground crew was great in Austin, flight crew left a lot to be desired. Not particularly friendly, helpful or nice.

My baggage was in another flight, anit was delayed for one hour.

They canceled the flight 30 minutes prior to departure without any heads up.

Like South West(2 check in baggage free) if Alaskan Airlines could give at least one check in baggage free then it would be great.

Up on arrival, due to twisted ankle, I wasn’t able to walk. Requested for a wheelchair. They immediately asked for it. After 10 minutes wait a young man named Carlos picked me up at the gate, got my baggage and took me to the pick up area. It was a great service. Thanks Alaska Air line

Staff great. Tight seating. Pretzels and drink same as any other airline.

We had a very scary attempted landing in Palm Springs and were redirected to Ontario. It was a stressful flight.

Every thing means , crew, service, timing, boarding is very good.

My boarding pass birthdate was printed incorrectly causing me to spend an extra hour in a check-in and then again TSA line and to miss a chance to have dinner pre-flight. My window seat was given away and was replaced with a middle seat. I would have liked an opportunity to charge my phone and take advantage of movies but many of the departure gate chargers weren’t operational and I don’t know of an in-flight charging option, The flight left 45 late after trouble with unruly passengers, and I was glad staff removed them.

Horrible. I likely will have to spend several thousand dollars to rebook my international flights, due to their delays, plus a hotel in SF. I can’t wait to never fly them again!

There was a loud squeaky sound the whole time we were flying.

Had a broken tray in business class. Crew just shrugged it off.

I didn’t like that I could not select my seat and was assigned a seat when I checked in at LAX

Great experience overall. Check in at Austin was congested as they only have about 6 check in kiosks, one was broken, and there was a lot of Spring Break travelers.

Bag drop off was slow and annoying. Only 2 agents at the entire delta desk, and no one directing traffic for what line to be in, many confused people slowed down the process. Boarding was fine. Seats in Delta comfort plus were fine. Snacks were great! Definitely a bonus. The entertainment system was awful — old, slow, not responsive, and completely unable to play games due to some kind of error. But on the other hand, thank you to Delta for the free WiFi. That made it better.

Everything was very good other than I had selected a specific seat when I booked the flight and they changed it once I checked-in the day before my flight. I was still in first class but lost my aisle seat for a window seat. Being tall, the aisle offers more comfort so I always select an aisle seat.

Flight diverted in SD. Later take off in Seattle by 1.3hrs

Horrible. Flight ORD to CGH was okay, but Paris was a nightmare. Old planes, delays, involuntary downgrades, broken planes, terrible communication. CGH to CPT was my worst flight ever.

Crew was not friendly when I went to request a seat change.

Really impressive staff at airport and on plane, especially given how busy it was

Great! The plane was decently sized and comfortable. The staff was nice and there was great in flight entertainment

Last minute gate change nearly caused us to miss our flight. Change was not announced or displayed in the main board at the old gate. Terrible communication. When we landed we had to wait 20 minutes because there was another plane at the assigned gate. Not the crew’s fault, but adding 20 minutes to a 45 minute flight sucked.

delay several times and wait extra long to board. no entertainment service because there are problem for some rows. always encounter some delays for the last flight of the day.

The flight experience was very good! Especially the United Club!

I was not able to buy food in the flight. They refer to include your Credit card in the APP, and if you are not from USA (i have a credit card form Canada) it is not possible

The flight from Ottawa to Chicago took a lot longer due to DC in Ottawa. We got to Chicago and went to our gate to catch our flight. We only had nine minutes I found that very stressful.

Good boarding. Crew started quick with drinks and food. They came around several times for trash which I really liked. Other than turbulence due to storms in the area, flight was great.

The control panel for the seat back screen did not work at all after takeoff.

Plane was so old it had cigarette butt trays in the seat

Everything was good, hard to really comfortable on a flight that long.

Good flights. Departure and arrivals were on time. DFW was a little problematic in that the Skytrain without prior notice bypassed the Echo terminal so that delayed my arrival at my connecting flight.

Because I can’t stand very long in one place, I was allowed to reword.

5 hour flight - full flight - not enough room to use my computer - slightly delayed - Admirals club was excellent quality food, drink made up for flight seating. No food offerred on flight, you ahd to prebook.

Excellent- plan was barely populated. I cannot remember a flight where I was able/encouraged to stretch out!

Great flight. Boarding was efficient and quick. On time departure and smooth flight. Flight arrived early at destination. Good experience.

Had technical issue which delayed the flight period. Flight crew knew there was 5 passengers that the connecting flight was within 15 minutes once at the gate. Rather than identify the 5 passengers to assure they got first. The flight attended mentioned it but didn't assist to assure passengers with connecting flights off first. This caused a hardship and our party of 3 missed the connecting flight.

I don't like that I have to pay if I want extra leg room. The seats are so expensive; I sit in normal seats and my legs and knees cramp the entire flight. I never feel comfortable on AA flights.

Flight was delayed at departure due to weather and the need for de-icing. The flight was smooth but there was a delay at arrival due to weather. We were in a hold for 20 minutes or more. The flight arrived more than 30 minutes late. Airlines have no control over the weather and I'm glad that they follow all safety procedures. Had to wait a long time for my checked luggage. Whole process was slow and the bags arrived wet due to the rain. The onboard wifi and entertainment access was spotty and the signal was dropped several times. Otherwise the crew was great and friendly. They tried to get everyone's bags stowed and seated so we could take off.

Regarding the boarding: it needs more efforts to make it more convenient

Deicing in Denver took forever and I almost missed my connection. De-ice faster! Not Americans fault.

Frontier is a crappy airline nothing about it is honest

I didn't get to do this flight l, hard to review

They cancelled the flight then did nothing to help us rebook. It was awful - I won’t fly with them again

The truck that was refueling the plane drove away with the hose still connected to the plane and ripped part of the plane off with it

The boarding time. I was in Section 1 the lady in charge just let people in section 3 without see us. Make a line , I have to step out and ask her. We were in the line and she just take my ticket and that’s it, so if I don’t ask her she could leave us at the end! We paid more for that privilege and. She doesn’t care….

Was just ok with over selling I guess. A lot of people in a short space and when we finally arrive i20 minutes, waiting to get out from the plain because we were waiting authorization for out boarding? Something like that.

See my previous comment which is mostly about our flight from Phoenix to SFO

They changed my flight and did not want to accommodate me or try to help me in any way. They do not care about their customers.

The check in at the airport was awful. Told I need to pay for a bag. The item was taken at screening. I went back to get my $ back and they gave me a coupon with a QR code that doesn’t work. Worst costumer service ever!!!!!

4 hour delay because they used our aircraft to fly a different segment (per the captain)

Book cheap flights from Chicago to Big Sur

Recent round-trip flight deals

8/21Wed
nonstopFrontier
4h 38mMDW-SFO
9/4Wed
nonstopFrontier
4h 11mSFO-MDW
$88
9/21Sat
nonstopFrontier
4h 38mMDW-SFO
9/25Wed
nonstopFrontier
4h 11mSFO-MDW
$96
8/7Wed
nonstopAlaska Airlines
4h 37mORD-SFO
8/10Sat
nonstopAlaska Airlines
4h 21mSFO-ORD
$179
7/17Wed
nonstopAmerican Airlines
4h 45mORD-SFO
8/13Tue
nonstopAmerican Airlines
4h 17mSFO-ORD
$184
9/10Tue
1 stopAlaska Airlines
9h 47mORD-SFO
9/17Tue
nonstopAlaska Airlines
4h 20mSFO-ORD
$188
8/7Wed
nonstopUnited Airlines
4h 39mORD-SFO
8/21Wed
nonstopUnited Airlines
4h 24mSFO-ORD
$194
5/25Sat
nonstopUnited Airlines
4h 44mORD-SFO
5/28Tue
nonstopUnited Airlines
4h 20mSFO-ORD
$202
6/8Sat
nonstopAmerican Airlines
4h 40mORD-SFO
6/11Tue
nonstopAmerican Airlines
4h 18mSFO-ORD
$213
6/18Tue
1 stopDelta
6h 52mMDW-SFO
7/13Sat
1 stopDelta
8h 55mSFO-MDW
$242
9/18Wed
1 stopDelta
10h 06mMDW-SFO
9/24Tue
1 stopDelta
8h 30mSFO-MDW
$246

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Recent one-way flight deals

6/1Sat
nonstopFrontier
4h 29mMDW-SFO
$42
6/1Sat
nonstopFrontier
4h 29mMDW-SFO
$44
8/14Wed
nonstopAlaska Airlines
4h 37mORD-SFO
$90
5/30Thu
nonstopAlaska Airlines
4h 44mORD-SFO
$95
5/25Sat
nonstopAmerican Airlines
4h 45mORD-SFO
$108
8/10Sat
nonstopAmerican Airlines
4h 38mORD-SFO
$114
5/26Sun
nonstopUnited Airlines
4h 42mORD-SFO
$120
5/31Fri
1 stopDelta
6h 17mMDW-SFO
$123
7/3Wed
1 stopDelta
9h 07mORD-SFO
$123
6/22Sat
1 stopUnited Airlines
6h 23mORD-SFO
$124

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Last minute flights from Chicago to Big Sur

Last minute flight, train and bus deals

5/13Mon
multi-stopFrontier
12h 45mMDW-SFO
5/18Sat
multi-stopFrontier
13h 22mSFO-MDW
$223
5/13Mon
multi-stopFrontier
15h 28mMDW-SFO
5/18Sat
multi-stopFrontier
9h 16mSFO-MDW
$228
5/13Mon
multi-stopAlaska Airlines
8h 47mORD-SFO
5/18Sat
nonstopAlaska Airlines
4h 23mSFO-ORD
$346
5/13Mon
multi-stopAlaska Airlines
8h 47mORD-SFO
5/20Mon
nonstopAlaska Airlines
4h 23mSFO-ORD
$360
5/11Sat
nonstopUnited Airlines
4h 53mORD-SFO
5/14Tue
nonstopUnited Airlines
4h 21mSFO-ORD
$394
5/11Sat
multi-stopUnited Airlines
6h 37mORD-SFO
5/14Tue
nonstopUnited Airlines
4h 21mSFO-ORD
$403
5/11Sat
multi-stopDelta
7h 32mMDW-SFO
5/30Thu
multi-stopDelta
6h 07mSFO-MDW
$429
5/11Sat
multi-stopAmerican Airlines
8h 03mORD-SFO
5/13Mon
nonstopAmerican Airlines
4h 17mSFO-ORD
$452
5/9Thu
multi-stopAmerican Airlines
8h 27mORD-SFO
5/14Tue
nonstopAmerican Airlines
4h 22mSFO-ORD
$453
5/11Sat
multi-stopDelta
7h 32mMDW-SFO
5/18Sat
multi-stopDelta
8h 50mSFO-MDW
$469

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Flights to Big Sur

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