$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 4/27. 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
$223
Typical prices: $239-$400
Frontier
Sun 4/19Wed 4/22
ORD - SFO • 2 stops
Cheapest non-stop
$234
Typical prices: $266-$562
Southwest
Sat 4/4Sat 4/11
MDW - SFO • Non-stop
Arrival airport
You can't fly directly to Big Sur. It is served by San Francisco (SFO), located 98.5 miles from Big Sur.
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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

Sun, Apr 19 - Wed, Apr 22
Frontier Logo
5:11 am - 5:34 pm
ORD
-
SFO
38h 23m
2 stops
Frontier Logo
7:40 pm - 6:08 am
SFO
-
ORD
8h 28m
1 stop
$223Frontier
Mon, Apr 20 - Thu, Apr 23
Frontier Logo
6:00 am - 5:34 pm
MDW
-
SFO
13h 34m
1 stop
Frontier Logo
9:58 am - 9:50 pm
SFO
-
MDW
33h 52m
2 stops
$225Frontier
Mon, Mar 30 - Thu, Apr 16
Frontier Logo
8:55 pm - 6:37 pm
ORD
-
SFO
23h 42m
1 stop
Frontier Logo
11:56 am - 9:50 am
SFO
-
ORD
19h 54m
1 stop
$225Frontier
Sat, May 2 - Sat, May 9
Southwest Logo
6:10 am - 2:25 pm
MDW
-
SFO
10h 15m
1 stop
Southwest Logo
5:40 am - 5:15 pm
SFO
-
MDW
9h 35m
2 stops
$226Southwest
Sat, Apr 18 - Sat, Apr 25
Southwest Logo
7:00 am - 4:10 pm
ORD
-
SFO
11h 10m
2 stops
Southwest Logo
5:40 am - 2:20 pm
SFO
-
ORD
6h 40m
1 stop
$226Southwest
Fri, May 8 - Sun, May 10
Frontier Logo
6:00 am - 4:54 pm
MDW
-
SFO
12h 54m
1 stop
Frontier Logo
10:03 am - 2:49 pm
SFO
-
MDW
26h 46m
2 stops
$227Frontier
Sat, Apr 4 - Thu, Apr 16
Frontier Logo
3:35 pm - 9:00 pm
ORD
-
SFO
7h 25m
1 stop
Frontier Logo
11:35 am - 6:08 am
SFO
-
ORD
16h 33m
1 stop
$227Frontier
Mon, Apr 20 - Thu, Apr 23
Frontier Logo
6:00 am - 5:34 pm
MDW
-
SFO
13h 34m
1 stop
Frontier Logo
9:58 am - 9:50 pm
SFO
-
MDW
33h 52m
2 stops
$228Frontier
Thu, Apr 16 - Sat, Apr 18
Frontier Logo
5:01 am - 5:34 pm
ORD
-
SFO
14h 33m
2 stops
Frontier Logo
6:29 pm - 5:50 am
SFO
-
ORD
9h 21m
1 stop
$228Frontier
Wed, Apr 15 - Sat, Apr 18
Southwest Logo
5:30 am - 11:05 am
MDW
-
SFO
7h 35m
1 stop
Southwest Logo
11:25 pm - 5:40 am
SFO
-
MDW
4h 15mnonstop
$229Southwest
Useful Info

Good to know

Low seasonJanuary
Cheapest flight$117
Best time to beat the crowds but there is an average 12% increase in price.
Most popular time to fly and prices are also 17% 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 35m.

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

    102 direct flights run between Chicago and Big Sur on a daily basis. On average, there are about 719 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. Hawaiian Airlines offered a round-trip connection from $108 and Frontier from $110.

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 January, February and March. 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 12016 reviews
7.0Entertainment
7.8Comfort
7.1Food
8.1Boarding
8.5Crew
Airline reviews

The airport crew and on board experience was fine. The problem with Alaska air is that there is zero customer service over the phone when you’re trying to buy your ticket or change anything.

8.0 ExcellentMary, Mar 2026
LAS - STS
Read more Alaska Airlines reviews

The airport crew and on board experience was fine. The problem with Alaska air is that there is zero customer service over the phone when you’re trying to buy your ticket or change anything.

The front desk attendant was rude to everyone in an absolutely careless way.

Good as usual. Just wished my seat was assigned at online check in. Thanks anyways

I like flying Alaska Airlines. I think the staff are happy, the plane is comfortable, the entertainment reasonable, the food acceptable.

The flight attendant was friendly and attentive. Although our interaction was brief—- it made a difference. The crew was upfront about turbulence. I like the Maui pretzels.

The boarding process could be clearer, there's never a call for group f

I bought tickets MONTHS ago for a flight that left SAN at 14:30. That is what it says on our tickets. I was never notified of any time changes. During online check-in. I discovered the flight time had been changed to 15:45. This was unacceptable and had I been notified, I would have changed flights, or airlines. That departure time was unworkable with our plans. We called Alaska and asked for an explanation. They said flight time was changed 11/08/25. No proof of notification could be offered. We asked to be moved to an earlier flight. After much pleading, the rep said she would allow a “one time exception..” While I appreciate being moved, this was YOUR fault Alaska Airlines.

Representatives both at the gate and on the plane have zero interest in helping you! It’s really unfortunate…

The planes were in very nice condition. Comfortable enough leg room. I had a very quick connection on my return home I made it just fine and so did my luggage!!

We left late; had to land in Minneapolis unscheduled to refuel and then landed in interior instead of lax at 2am......

The problem with the seat assignments is that there were a lot of rows in the front that were empty but my row at the back was full. Just not so pleasant.

No food or entertainment, just a quick 40 minute flight. A little bumpy due to Santa Ana winds but pilot has no control over that. Good flight and landing!

Good but I prefer choose your own seat. With the new assigned seats they should board from the back I see no advantage to this new boarding. Just like every other airline

Mediocre. Boarding is now unpleasant. The employees, once friendly and nice, are now regularly speaking sternly to passengers, badgering them to do things right so they can take off on time and gate check bags because they don't have enough overhead bin space. The pretzel snack was crushed flat and broken into even smaller pieces, which happens frequently lately. Drink service was suspended before they reached my row.

The charges were ridiculous for an hour flight and the turbulence was very scary.

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.

This trip did not start off well. The inbound flight was delayed about 20 minutes. Then, after initial onboarding, the passengers had to deplane due to a mechanical problem. That took about 30 minutes to fix and be cleared. Then, reboarding was chaotic. It took a long time to sort passengers and two passengers on standby were ticketed but there was no seat. So, they had to deplane. One of the flight crew was trying to help passengers figure out a place to put their carry-on bags and that took more time. In the end, our scheduled 10:30 am departure did not actually take off until about 12:05 pm CST. The flight itself was long but we got to Houston. Some passengers missed their connecting flights and had to rebook. Not the best of flights I've had.

We were delayed for about an hour from taking off due to traffic control procedures at the destination airport. But once in the air, the flight went well. The crew members were great and provided cabin service despite moderate turbulence during much of the flight.

Short flight, but no drink/snack service. The flights both going and coming were delayed.

Not being stranded in Chicago for her airport to 11:30 tomorrow morning the 3rd

I was fully checked in the prior night and i was unchecked and then didn’t have a seat when I boarded. Instead of an aisle seat, I was out in the middle seat of the very last row of the plane.

In overall it was a good experience, the only down point was that the entertainment screen was working properly.

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. :/

It was an older plane. First Class was not especially roomy or comfortable. It was a short flight so there were no meal but they did offer mixed nuts which used to be normal but now is rare. Crew member was very polite and professional.

Flight to Tampa was delayed taking off due to plane arriving late but no other issues

As previously stated the delay I experienced flying from Wichita to Chicago caused a host of issues. When I finally was able to be booked on the last remaining American flight from Chicago to Cincinnati, the gate changed four times with the last change occurring very near the scheduled boarding time. While I didn't have a problem moving from gate to gate, I did notice and make note of others that had mobility issues and had to move each time for the gate change.

Maintenance took a very long time and then we were in a holding pattern. While a one-off maintenance issue is standard, there were delays on both of my flights for this trip based on maintenance issues with the planes, which delayed both flights over 45 minutes. Thankfully, I didn't have any connections but it wasn't an experience that would make me pick AA if I have other options.

No Snacks or Entertainment. The flight was short, snacks should still be given.

See prior comment about how Kayak mishandled my reservation and delayed my arrival by 6 hours.

Boarding delayed 20 minutes for no reason, no wifi, in flight entertainment, or snacks / waters?

Delayed an hour due to operational issues. Minimal apologies or care for the significant inconvenience caused. Landed at nearly 1am and they still couldn’t find ground staff to get us off the plane promptly.

The aircraft had several problems - from excess fuel to non operational ac. Two hours of delay in Chicago could have been avoided with proper planning and aircraft maintenance.

Crew in Columbia was not prepared for landing. It was a bit of a disaster and getting bags took forever.

Flight was canceled. Most upsetting was message from Kayak, stating that the flight was canceled and click with Kayak for details regarding rebook, refund details. THERE'S NO INFORMATION PROVIDED BY KAYAK EXCEPT THAT FLIGHT IS CANCELED. AND NOW THIS SURVEY TO FIND OUT HOW WAS THE FLIGHT !!!!!!!

The flight never took off and we spent 7 hours at the airport

Gate not determined until I got to the airport - hard to plan the trip to the airport.

Our flight was canceled. I will never use Kayak nor Frontier for travel again. The entire experience was a headache.

Frontier.. nickel and dime add-ons. Flight late, on time, late again, last minute gate change, arrival gate required a shuttle to the terminal. They sure keep you guessing.. if you like a little chaos and airport anxiety, this is the airline for you!

This is my second time flying with Frontier. My current experience was very favorable. The staff from the gate to the plane was friendly, warm and professional. The food options lacked in my opinion. This area needs some attention in my opinion.

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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