$90 Find Cheap Flights from Chicago to Pebble Beach

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 Pebble Beach departing on 9/30. 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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Cheap Flights from Chicago to Pebble Beach (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 Pebble Beach 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 Pebble Beach

Fri, Aug 22 - Tue, Aug 26
Southwest Logo
11:10 am - 1:45 pmMDW-SFO
4h 35mnonstop
Southwest Logo
10:45 am - 4:55 pmSFO-MDW
4h 10mnonstop
$179Southwest
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Tue, Jul 1 - Sat, Jul 5
American Airlines Logo
3:19 pm - 5:57 pmORD-SFO
4h 38mnonstop
American Airlines Logo
8:00 am - 2:15 pmSFO-ORD
4h 15mnonstop
$179American Airlines
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Wed, Jul 30 - Wed, Aug 6
Hawaiian Airlines Logo
7:18 pm - 10:06 pmORD-SFO
4h 48mnonstop
Hawaiian Airlines Logo
11:55 am - 6:18 pmSFO-ORD
4h 23mnonstop
$184Hawaiian Airlines
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Wed, Jul 30 - Wed, Aug 6
Hawaiian Airlines Logo
7:18 pm - 10:06 pmORD-SFO
4h 48mnonstop
Hawaiian Airlines Logo
11:55 am - 6:18 pmSFO-ORD
4h 23mnonstop
$186Hawaiian Airlines
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Thu, Jun 26 - Mon, Jun 30
Frontier Logo
2:55 pm - 9:26 pmMDW-SFO
8h 31m1 stop
Frontier Logo
5:45 am - 2:56 pmSFO-MDW
7h 11m1 stop
$188Frontier
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Mon, Jun 30 - Tue, Jul 8
Frontier Logo
6:25 am - 12:19 pmMDW-SFO
7h 54m1 stop
Frontier Logo
10:03 pm - 10:40 amSFO-MDW
10h 37m1 stop
$189Frontier
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Wed, Jul 30 - Wed, Aug 6
Alaska Airlines Logo
7:18 pm - 10:06 pmORD-SFO
4h 48mnonstop
Alaska Airlines Logo
11:55 am - 6:18 pmSFO-ORD
4h 23mnonstop
$194Alaska Airlines
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Fri, Jul 4 - Sun, Jul 13
United Airlines Logo
8:50 am - 11:29 amORD-SFO
4h 39mnonstop
United Airlines Logo
6:43 pm - 12:59 amSFO-ORD
4h 16mnonstop
$198United Airlines
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Fri, Jul 4 - Mon, Jul 14
Alaska Airlines Logo
7:18 pm - 10:06 pmORD-SFO
4h 48mnonstop
Alaska Airlines Logo
11:55 am - 6:18 pmSFO-ORD
4h 23mnonstop
$218Alaska Airlines
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Tue, Jul 1 - Tue, Jul 1
United Airlines Logo
8:50 am - 11:29 amORD-SFO
4h 39mnonstop
United Airlines Logo
11:25 pm - 5:39 amSFO-ORD
4h 14mnonstop
$269United Airlines
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Good to know

Low seasonJanuary
High seasonJuly
Cheapest flight$90
Best time to beat the crowds with an average 5% drop in price.
Most popular time to fly and prices are also 5% lower on average.
Flight from Chicago Midway Airport to San Francisco

When to book flights from Chicago to Pebble Beach

Are your dates flexible? Find out the best times to travel from Chicago to Pebble Beach 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 Pebble Beach

  • Which airports will I be using when flying from Chicago to Pebble Beach?

    When flying out of Chicago you’ll be using one of these airports: Chicago Midway or Chicago O'Hare Intl. Pebble Beach does not have its own airport so you’ll be flying into nearby San Francisco airport, which is 76.2 mi away.

  • How long does a flight from Chicago to Pebble Beach take?

    Direct flights cover the 1,855 miles separating Chicago and Pebble Beach in about 4h 30m.

  • How many flights are there between Chicago and Pebble Beach?

    94 direct flights run between Chicago and Pebble Beach on a daily basis. On average, there are about 660 departures each week.

  • What’s the cheapest day of the week to fly between Chicago and Pebble Beach?

    Consider leaving on a Friday and avoid Mondays 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 Saturdays.

  • How does KAYAK find such low prices on flights from Chicago to Pebble Beach?

    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 Pebble Beach.

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

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Pebble Beach 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 Pebble Beach?

    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 Pebble Beach 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 Pebble Beach?

    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 Pebble Beach 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 Pebble Beach?

    In the last 72 hours, the cheapest one-way ticket between Chicago and Pebble Beach found on KAYAK was with Southwest for $90. American Airlines offered a round-trip connection from $179 and Southwest from $179.

Top tips for finding cheap flights from Chicago to Pebble Beach

  • There is no airport in Pebble Beach. Instead, you’ll be flying into San Francisco Airport when flying between Chicago and Pebble Beach.
  • The cheapest flight from Chicago to Pebble Beach 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 September.

Top 5 airlines serving Chicago to Pebble Beach

 
Need help choosing which airline to fly with from Chicago to Pebble Beach? 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
8.5Crew
7.1Entertainment
8.1Boarding
7.1Food
7.8Comfort
Airline reviews

Both flights were delayed going to our destination and leaving, and communication about the delays was not great by the airlines, now the crews were phenomenal and great to be around!!

6.0 GoodAnna, Jun 2025SEA - BUR
Read more Alaska Airlines reviews

Both flights were delayed going to our destination and leaving, and communication about the delays was not great by the airlines, now the crews were phenomenal and great to be around!!

Delayed. It's not our first flight with them either, it's actually our 3rd and all 3 were delayed by hours each time. It was a myriad of delays. On one flight we boarded after being delayed for a little over an hr, only to be told we were going to sit in the plane for another hour before departing. Once landed, we waited another 40ish min to get to our gate. On another flight, flight was delayed just under 3 hrs but atleast we got to wait it out at the airport terminal. Its just a bad experience overall flying with Alaska Airlines.

Flight was delayed for weather, then delayed for mechanical, then just cancelled. Once mechanical problems started I wish you had just started offering rebooking options (at the same airport). I felt my trip was not a priority for you. I called you, I asked for a better option (than changing airports), then I had to literally run around the airport making it happen. Do better.

I would've liked to have the seat tablets like before to view movies, with long travels not everyone carries tablets to view movies. And phones are not worth it because screens to small.

Flight was delayed 5 hours. Missed connecting flight. Very little apology or attempt to make anything better. Got a $150 credit for next flight. There won’t be another flight. First time on Alaska - last time. Keep your credit. Should have done something more

Horrible! No blanket or pillow available! We had bulkhead seats but the seats were worn out and no cushion old. No meal or even a sandwich for our 5 hour flight just a little bag of pretzels. Crabby attendant female with long brown hair. We will not book Alaska Airlines again

On time, smooth take off and landing, efficient boarding. Gate staff excellent, stewardess grumpy, but civil enough.

No WiFi available. It was too late to order food also. Guy next to me was huge (not fat) so had his shoulder & thigh next to me the whole way. Plane was delayed leaving PDX due to 8 other planes waiting. Not my best Alaska airlines flight.

I do wish the the actual airplane I flew on was bigger. But, I made it work.

It is very bad they do not give you money back

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.

Plane late from DC to Austin 30 minutes. Crew made up much of the time enroute to San Diego.

Fine, but how to board on SW versus othrr airlines, is just lame. Goood staff though and all was solid otherwise.

One of the crew performed a hilarious skit to accompany the standard instructions. Passengers enjoyed it so much they applauded at the end!

Excellent experience. WiFi worked on this leg of My trip

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.

Delays took 2hours and thirty minutes making me miss my connecting flight and make me sit in the Chicago airport for 9 hours

Had a short delay once we boarded the aircraft in Chicago, but it was fixed in no time flat then we were on our way. The pilot was able to make up the time lost and we landed 5 minute later then schedualed . Great service

Our seats were all the way in back of the plane,

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.

The meals were mediocre and the alcohol selection was poor. I enjoyed the selection of movies and other entertainment.

I chatted with the captain before the flight, and similarly during the welcome announcement, he warned of a turbulent flight that may impact the in-flight service. However, once at altitude, he announced that the weather changed and he immediately turned off the seatbelt sign. But it appeared the cabin crew had already decided to take off this flight. They remained seated and then just chatted in the galley. The flight was fully catered, but only first class received service.

My flight attendant was attentive! The elderly person next to me was flatulent and the flight attendant could see that I was in distress and brought me some face masks

My boarding pass wouldn't pull up in the app very easily and had to really dig through my email. That caused a delay in TSA..

I had a TERRIBLE experience with the AA crew. I believe it was disability-related. It’s unlikely I will fly AA again.

Since you have to pay for overhead bags then they shouldn't be running out of space and asking individuals who paid to remove stuff from the overhead

Cancelled flight after I arrived at airport after 75 min drive and parking. Next flight was 4 days in the future. Had to scramble and buy a much more expensive flight on another carrier.

Book with frontier airlines with the mentality that they'll cancel your flight, kick you off and lose your luggage. Anything besides that is a win. Compare prices with other airlines (to include luggage) and if frontier is still worth it, book it but know all of their policies.

You get what you pay for nothing essentially but a hard uncomfortable seat that doesn’t recline and kids screaming all around you and chaotic boarding and limited check bag weight allowance when compared to other airlines

Plane was down graded and I lost my uncharged exit row with more leg room. No mention or offer of refund from podium. Flight attendant was nice to explain this happens often and that I could request a refund via online form submission. I did this and have heard nothing back.

Horrendous. I do not recommend Frontier. The passengers lack manners and decency, and the flight attendants lack professionalism. If I wasn’t in a bind to fly with 48 hours notice for a job interview, I would not have selected a flight with Frontier and I never plan to fly with them in the future.

The seats were hard molded plastic covered in plastic vinyl. And the scam to charge people extra to sit together. Don’t they know we can just ask someone to trade seats. And watching the staff separate young children from parents… super classy. We had to guilt them into offering up our seats. This companies policies suck. Don’t give them your money.

Everything went as planned. Crew was great. Seats were still not that comfortable.

No frills for sure. No gate announcements about flight delay, not even water to drink on the flight.

The plane was clean, the crew was friendly and helpful. It’s a low cost airline so there was no food, drinks or in flight entertainment but we didn’t expect any of these things. In the room for improvement department, they should install USB ports in seats to charge mobile devices.

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