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Find cheap flights from Chicago to Pebble Beach from $74

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 6/25. 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
Wed 7/10
Wed 7/17

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Good to know

Low season

January

High season

July

Cheapest flight

$74
Best time to beat the crowds with an average 1% drop in price.
Most popular time to fly with an average 16% increase in price.
Flight from Chicago O'Hare 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 28m.

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

    111 direct flights run between Chicago and Pebble Beach on a daily basis. On average, there are about 777 departures each week.

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

    Consider leaving on a Saturday and avoid Wednesdays 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 Mondays.

  • 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 Frontier for $74. Frontier offered a round-trip connection from $78 and Alaska Airlines from $144.

See more FAQs

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 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 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 9254 reviews
7.3Entertainment
8.2Boarding
7.3Food
7.9Comfort
8.6Crew
Airline reviews

The crew was the best I’ve had the experience of flying with. A misbehaving child was making things difficult for me with bopping my tray table, taking my snack, and continually tapping or bumping me. The crew quietly and respectfully moved me to another seat, and thanked me for my patience. They couldn’t have been more kind. Their professionalism really stood out to me and I am more than happy to leave a great review for them!

10.0 ExcellentCarolyn, Jun 2024ATL - SAN
Read more about Alaska Airlines reviews

The crew was the best I’ve had the experience of flying with. A misbehaving child was making things difficult for me with bopping my tray table, taking my snack, and continually tapping or bumping me. The crew quietly and respectfully moved me to another seat, and thanked me for my patience. They couldn’t have been more kind. Their professionalism really stood out to me and I am more than happy to leave a great review for them!

I would have appreciated notification that our flight was moved to another gate LAST MINUTE so that we would not have missed it. We got no such notice and had to spend another night to catch an available flight in the morning, which was huge inconvenience. We will never fly Alaska again.

Flight was delayed 2 hours. It was too cold inside the cabin. My seat mate had no jacket so she was shivering the entire flight. The stewardess says there’s no available blanket.

The airline was way too cold. We were freezing, I don’t know if that is normal. Overall it was pretty good flight. Always flown Alaska Airlines and I am not changing.

Mediocre is best way to describe. Bare bones narrow seats, Dirty pulldown tray, unfriendly cabin crew who were in a hurry to serve tiny drinks and tiny snacks. (Compared to much better Hawaiian Airlines experience, .. no comparison!)

The people who worked for Alaska Airlines, both on the ground at O'Hare and during the flight, made it remarkable for me. Their customer service is incredible; they're kind of like the Nordstrom of the sky.

I wasn't impressed with the entertainment selection, and the snack sizes were small. But the entire crew was professional and did a great job. For that I would fly Alaska again.

It was really good and that's why we choose AA over other airlines.

We loved the extra legroom on the flight and the fact that we didn’t have any one beside us.Everything was a n time and satisfactory.

In economy, there was actually a decent amount of legroom and it was shocking to be in a bathroom that actually had a little bit of space! It was far more spacious than Most airlines are today. It was pleasant because of that.

It was good until there was a 3 hour delay because there was not any pilots to fly the plane.

Had to change aircraft due to a faulty door. Surprisingly it only caused about an hour and a half of delay. Delta handled this situation as well as can be expected.

Your crew could maybe answer the call bell at least one of the times I pressed it. I pressed it first time with 2.5 hours left in our flight bc my partner was hungry and wanted a sandwich. We finally got the sandwich with 40 mins left in the flight.

The Flight crew didn’t serve us until about 1.5 hours into the flight because of turbulence but after it ended it was fine to move around. They served us water only and snacks and then NEVER, NOT ONE TIME came through to collect trash until right before landing about 1.5 hours later. There was absolutely no need for that. They crew was just standing around talking and visiting with each other and really never tried to see if we might want something besides water or even try to come pick up trash. This is VERY unusual for a Delta flight but it was not what I would have expected for a 4 hour flight.

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.

Flighty delayed on boarding - then group 1 had to check their carry on bags but groups 3 and beyond could carry bags on - very inconvenient for weekend business trip with no checked baggage. Then delayed on the runway - before take off. No communication from pilot on why or how long. Wifi/Entertainment didn't work for 4+ flight. Upon arrival, attendants announced wrong carousel for baggage claim - everyone was waiting at the wrong place for their checked bags. This was a mess united!

There was no screens on board AND the WiFi didn’t work. My seat was broken and couldn’t recline so I couldn’t even sleep. The flight attendants didn’t offer anything to make it more comfortable. It was such an old cramped plane, when the person in front of me reclined I couldn’t even open my tray table. All the United ads talk about guaranteeing everyone gets a screen!

I’ve had a couple flights this week on United that were delayed by an hour or more

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.

My husband and I pre-ordered our food, but they did not have my husband’s order, and my cheese plate was very average. I asked for a blanket and was told they don’t carry blankets on domestic routs. The flight was on time and smooth!

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

8 hr delay. had to buy another ticket with another airline

Four and a half hour delay in total. What frustrates me most is the poor communication and disorganization.

I appreciated the upgrade to free cary-on bag and seat selection at no charge

FRONTIER SUCKS! The agent downstairs tricked me into booking, just to get to the gate. At the gate, they told me they couldn't help. I then called Customer Service. They and the gate attendants kept blaming each other. Neither side was willing to help the customer.

The agent at check-in was strident, unwelcoming, and condescending to customers ahead of me.

Flight was delay 9hrs and nothing was provided at airport, had to go and get a room to sleep in, paid for Uber back and fort with no offers until we landed back home a 1hr later for a $75 voucher for a future flight.

It was delayed 9 hours for operational reasons, despite the plane arriving to the airport on time.

9hrs delay and didn’t provided anything until after flight landed $75 voucher for fiuture travel no meals or anything.

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

Book cheap flights from Chicago to Pebble Beach

Recent round-trip flight deals

9/14Sat
nonstopFrontier
4h 38mMDW-SFO
9/25Wed
nonstopFrontier
4h 11mSFO-MDW
$78
9/11Wed
nonstopFrontier
4h 38mMDW-SFO
9/28Sat
nonstopFrontier
4h 11mSFO-MDW
$80
10/30Wed
nonstopAlaska Airlines
4h 44mORD-SFO
11/2Sat
nonstopAlaska Airlines
4h 21mSFO-ORD
$145
11/2Sat
nonstopAlaska Airlines
4h 44mORD-SFO
11/9Sat
nonstopAlaska Airlines
4h 21mSFO-ORD
$146
8/15Thu
nonstopUnited Airlines
4h 40mORD-SFO
8/20Tue
1 stopUnited Airlines
5h 55mSFO-ORD
$185
7/2Tue
nonstopUnited Airlines
4h 44mORD-SFO
7/9Tue
nonstopUnited Airlines
4h 15mSFO-ORD
$193
8/1Thu
nonstopAmerican Airlines
4h 38mORD-SFO
8/6Tue
nonstopAmerican Airlines
4h 17mSFO-ORD
$217
9/26Thu
nonstopAmerican Airlines
4h 41mORD-SFO
9/29Sun
nonstopAmerican Airlines
4h 16mSFO-ORD
$218
9/11Wed
1 stopDelta
7h 23mMDW-SFO
9/17Tue
1 stopDelta
8h 24mSFO-MDW
$236
9/5Thu
1 stopDelta
6h 36mORD-SFO
9/14Sat
1 stopDelta
6h 37mSFO-ORD
$236

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Recent one-way flight deals

6/25Tue
1 stopFrontier
18h 17mORD-SFO
$74
6/17Mon
1 stopFrontier
17h 01mORD-SFO
$75
8/14Wed
nonstopAlaska Airlines
4h 37mORD-SFO
$76
9/1Sun
nonstopAmerican Airlines
4h 38mORD-SFO
$90
8/9Fri
nonstopAlaska Airlines
4h 37mORD-SFO
$97
7/2Tue
nonstopUnited Airlines
4h 44mORD-SFO
$104
8/8Thu
1 stopUnited Airlines
6h 23mORD-SFO
$109
8/9Fri
1 stopDelta
6h 21mMDW-SFO
$118
8/9Fri
1 stopDelta
9h 51mORD-SFO
$118
9/15Sun
nonstopAmerican Airlines
4h 43mORD-SFO
$149

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Last minute flights from Chicago to Pebble Beach

Last minute flight, train and bus deals

6/11Tue
multi-stopFrontier
18h 14mORD-SFO
6/21Fri
multi-stopFrontier
16h 54mSFO-ORD
$191
6/13Thu
multi-stopFrontier
22h 25mORD-SFO
6/21Fri
multi-stopFrontier
16h 54mSFO-ORD
$196
6/15Sat
nonstopAlaska Airlines
4h 37mORD-SFO
7/10Wed
multi-stopAlaska Airlines
15h 39mSFO-ORD
$458
6/11Tue
nonstopAlaska Airlines
4h 37mORD-SFO
7/5Fri
nonstopAlaska Airlines
4h 21mSFO-ORD
$469
6/11Tue
multi-stopAmerican Airlines
7h 25mORD-SFO
7/5Fri
nonstopAmerican Airlines
4h 14mSFO-ORD
$490
6/11Tue
nonstopUnited Airlines
4h 37mORD-SFO
7/4Thu
nonstopUnited Airlines
4h 18mSFO-ORD
$559
6/11Tue
multi-stopUnited Airlines
7h 00mORD-SFO
7/4Thu
nonstopUnited Airlines
4h 18mSFO-ORD
$569
6/11Tue
multi-stopDelta
9h 54mORD-SFO
6/12Wed
multi-stopDelta
8h 08mSFO-ORD
$602
6/11Tue
multi-stopAmerican Airlines
10h 53mORD-SFO
7/5Fri
multi-stopAmerican Airlines
6h 40mSFO-ORD
$603
6/10Mon
multi-stopDelta
8h 01mMDW-SFO
6/14Fri
multi-stopDelta
8h 38mSFO-MDW
$650

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Flights to Pebble Beach