$132 Find Cheap Flights from Chicago to Palo Alto

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 Palo Alto departing on 7/6. 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

KAYAK searches hundreds of travel sites at once for deals on flights from Chicago to Palo Alto

Travelers love KAYAK
41,299,237 searches in the past 7 days on KAYAK

Save 24% or moreCompare multiple travel sites with one search.

Track pricesNot ready to book? Create a price alert for when prices drop.

Free to useThere are no hidden charges or fees.

Filter your dealsChoose cabin class, free Wi-Fi and more.

Everything you should know

Cheapest round-trip
$270
Typical prices: $567-$400
Frontier
Sat 7/18Sun 7/19
MDW - SFO • 1 stop
Cheapest non-stop
$272
Typical prices: $431-$261
United Airlines
Tue 7/14Tue 7/21
ORD - SFO • Non-stop
Arrival airport
You can't fly directly to Palo Alto. It is served by San Francisco (SFO), located 17.9 miles from Palo Alto.
FAQs
FAQs
FAQs
FAQs
Start a new search
KAYAK searches 100s of sites at once to find you the best travel deals.
We hope you love your trip to Palo Alto!
Flight Deals
Useful Info
Flight Deals

Cheap Flights from Chicago to Palo Alto (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 Palo Alto 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 Palo Alto

Sat, Jul 18 - Sun, Jul 19
Frontier Logo
6:00 am - 7:13 pm
MDW
-
SFO
15h 13m
1 stop
Frontier Logo
12:24 am - 2:27 pm
SFO
-
MDW
12h 03m
1 stop
$270Frontier
Sat, Oct 31 - Thu, Nov 12
Frontier Logo
6:00 am - 3:00 pm
ORD
-
SFO
11h 00m
1 stop
Frontier Logo
6:15 am - 9:35 pm
SFO
-
ORD
13h 20m
1 stop
$270Frontier
Wed, Jun 10 - Wed, Jun 10
Frontier Logo
7:20 am - 2:16 pm
ORD
-
SFO
8h 56m
1 stop
Frontier Logo
8:45 pm - 5:07 am
SFO
-
ORD
6h 22m
1 stop
$271Frontier
Thu, Jun 4 - Tue, Jun 9
United Airlines Logo
7:30 am - 10:19 am
ORD
-
SFO
4h 49mnonstop
United Airlines Logo
6:34 pm - 12:59 am
SFO
-
ORD
4h 25mnonstop
$272United Airlines
Tue, Jul 14 - Tue, Jul 21
Southwest Logo
9:30 pm - 12:10 am
MDW
-
SFO
4h 40mnonstop
Southwest Logo
6:00 am - 4:55 pm
SFO
-
MDW
8h 55m
2 stops
$272Southwest
Fri, May 29 - Mon, Jun 8
Frontier Logo
6:55 am - 7:34 pm
ORD
-
SFO
14h 39m
1 stop
Frontier Logo
10:50 pm - 5:07 am
SFO
-
ORD
28h 17m
1 stop
$273Frontier
Wed, May 27 - Mon, Jun 1
Frontier Logo
6:00 am - 7:34 pm
MDW
-
SFO
15h 34m
1 stop
Frontier Logo
10:05 pm - 11:12 am
SFO
-
MDW
11h 07m
1 stop
$274Frontier
Tue, Aug 4 - Wed, Aug 5
Delta Logo
5:10 pm - 11:54 pm
MDW
-
SFO
8h 44m
1 stop
Delta Logo
10:10 pm - 9:59 am
SFO
-
MDW
9h 49m
1 stop
$277Delta
Tue, Jul 7 - Wed, Jul 15
Delta Logo
3:22 pm - 10:49 pm
ORD
-
SFO
9h 27m
1 stop
Delta Logo
11:45 am - 11:18 pm
SFO
-
ORD
9h 33m
1 stop
$277Delta
Thu, Jun 4 - Wed, Jun 10
Southwest Logo
9:30 pm - 12:10 am
MDW
-
SFO
4h 40mnonstop
Southwest Logo
3:10 pm - 12:05 am
SFO
-
MDW
6h 55m
1 stop
$282Southwest
Useful Info

Good to know

Low seasonJanuary
Cheapest flight$132
Best time to beat the crowds but there is an average 5% increase in price.
Most popular time to fly and prices are also 3% lower on average.
Flight from Chicago O'Hare Airport to San Francisco

When to book flights from Chicago to Palo Alto

Are your dates flexible? Find out the best times to travel from Chicago to Palo Alto 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 Palo Alto

  • Which airports will I be using when flying from Chicago to Palo Alto?

    When flying out of Chicago you’ll be using one of these airports: Chicago Midway or Chicago O'Hare Intl. Palo Alto does not have its own airport so you’ll be flying into nearby San Francisco airport, which is 17.9 mi away.

  • How long does a flight from Chicago to Palo Alto take?

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

  • How many flights are there between Chicago and Palo Alto?

    95 direct flights run between Chicago and Palo Alto on a daily basis. On average, there are about 669 departures each week.

  • What’s the cheapest day of the week to fly between Chicago and Palo Alto?

    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 Fridays and the most expensive ones on Saturdays.

  • How does KAYAK find such low prices on flights from Chicago to Palo Alto?

    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 Palo Alto.

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

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

    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 Palo Alto 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 Palo Alto?

    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 Palo Alto 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 Palo Alto?

    In the last 72 hours, the cheapest one-way ticket between Chicago and Palo Alto found on KAYAK was with JetBlue for $73. Hawaiian Airlines offered a round-trip connection from $108 and Frontier from $116.

Top tips for finding cheap flights from Chicago to Palo Alto

  • There is no airport in Palo Alto. Instead, you’ll be flying into San Francisco Airport when flying between Chicago and Palo Alto.
  • The cheapest flight from Chicago to Palo Alto was found 74 days before departure, on average.
  • Book at least 3 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 September.

Reviews of the top 5 airlines serving Chicago to Palo Alto

 
Need help choosing which airline to fly with from Chicago to Palo Alto? 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
SouthwestOverall score based on 4299 reviews
7.0Food
8.1Boarding
8.6Crew
7.5Entertainment
8.0Comfort
Airline reviews

Plane was clean and comfortable. Flight attendants and gate staff were professional, friendly and efficient. Boarding and deplaning were orderly and efficient. All in all, the typical excellent Southwest experience.

10.0 ExcellentRobert, May 2026
LAS - SFO
Read more Southwest reviews

Plane was clean and comfortable. Flight attendants and gate staff were professional, friendly and efficient. Boarding and deplaning were orderly and efficient. All in all, the typical excellent Southwest experience.

Not having a five hour delay with little notice! The crew was very kind, though, and just as tired as we passengers were. The flight didn't depart until nearly 1 am...and no reason was ever given.

This leg was much better, but we did have to have a 3 hour lay o er after coming from a very exhausting hiccup with our flight from BNA to Den

The Air hostess were very rude on my flight from Houston to Austin . Their regular communication itself felt a they are shouting at people.

I flew twice this week on Southwest, was delayed over 2 hours both ways. From Pittsburgh to Chicago it was due to weather but the gate agents, pilot etc were great at updating everyone. Today from Midway to Pittsburgh the plane had come from an international location, kept getting delayed, no information was given until we were delayed for the third time. It was ridiculous, whoever scheduled that plane to fly to Pittsburgh after didn’t consider a lot of things.

Boarding was easy. The seats are small and fairly uncomfortable

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.

It departed an hour and a half late because the crew got in late the previous night due to weather related problems. So we got into LA later than anticipated and traffic was much worse.

Good. I didn’t order food and there was no entertainment available.

It is a hassle to not have entertainment screens on the backs of the seats.

I had to cancel this trip due to medical reasons. I took out flight insurance but I was unable to cancel my reservation on either Kayak or Alaska. I need proof that I did not take this flight to get my refund. I have tried for a week and a half together that information from either Kayak or Alaska but so far I have gotten no response. I am very disappointed!

I had to change my flight last minute due to a medical emergency. Their agent was compassionate and extremely helpful. This airlines really cares about making travel, for fun, work, or an emergency a customer-focused experience. Thank you!

See what I wrote in the previous section. This was a terrible experience. I would like refund.. I even paid an extra $70 for an aisle seat closer to the front to ensure that I got off early enough to catch the next flight. The fact that the plane did not wait, and even left eearlier, knowing that the first flight came in late, and was moved to a terminal three train stops away is appalling. My friend that flew JetBlue, their flight was delayed and came in later and the connecting flight WAITED for them. How is it that JetBlue could do that, and Alaska could not.

The seat on the plane out was broken and would not lean back. I have back problems and sitting up straight was hard on my lower back and caused pain for over half the flight. Since I paid extra for First Class so I would not have these issues. This needs to be addressed.

No headphones provided. No gf food. Only 1 beverage cart run sAN to HNL. Rarely saw crew members

Thanks for all you do to keep us safe and on time!

The check-in crew for Alaska was rude, unhelpful, and the opposite of customer-centric. We arrived 50 minutes before our flight and were told it was too late to check baggage. When I asked what the cutoff was, the agent started speaking in codes “D50” and yelling to their manager who also spoke in codes. They then tried to speak to me using these codes and all I wanted to know was the time of the cutoff, which they would not — or could not — articulate. They booked me and my family on the next flight while smirking.

A long delay. Don't travel late in the day.

Super friendly with lots of drink options an entertainment. Friendly crew.

The crew was great. Very friendly and responsive. The plane was old, small and tight. We ran out of overhead space and I had to check. Middle seat was particularly tight.

Several missed and almost missed connections. It felt like everything was being patched together last minute without enough resources and it ended up being an extremely stressful experience that basically ruined our weekend on the west coast. What a waste.

Crew was friendly. Seats are too narrow, particularly when a big person is in the adjacent seat, but I understand this is due to smaller planes usually flight into Lincoln. I have experienced several flight delays going out and coming into Lincoln airport, I say maybe 50% or higher of the flights I've taken out of this airport have been delayed.

Great flight. Boarded efficiently. Arrived early at CLT. There was no in flight entertainment on this aircraft. Great crew.

The seat was comfortable. There was a lot of turbulence. If it weren't for that,it would have been okay.

Poor communication, flight was delayed for preventable reasons. I missed my connection.

No meal service to the back of the plane as it started late or was too slow to get it out before it was time to land.

Terrible, if possible won't be flying again anytime soon!

The airplane was an old model, the overhead didn’t have enough room for people’s items and made boarding and boarding disappointing and stressful. Crew allowed passengers to bring more than the permitted baggage sizes.

Original flight was on time, then late, then changed gates...4 times. Once our newest plane came in, it was fine.

I almost missed my flight and they helped me out enormously

Delays experienced in boarding/take off due to incoming plane delayed. However, the boarding time/depart time in the app was significantly delayed in providing these updates. Usually not updated until an hour after we should have already boarded. Poorly managed.

Moved to earlier flight which unexpectedly had maintenance issues initially indicated as quick fix to ultimately plane changes. Moved back to original flight, also delayed. In all cases customer updates and communication very unclear, no updates on drivers for delays.

Typical AA - late by 90+ mn. Gate changed twice... Changed the departure time 6 times No explanation, no communication on reasons for delay I travel with AA twice a year... and it is consistently very poor.. I will continue to use AA only when i have to.

Pretty awful. 2 hours late due to operational issues and finally deboarded around 2am.

The gate got changed several times and the flight was delayed over an hour. Awful experience

American continues to decline in their customer service and its beyond disappointing.

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.

The staff at the check in counter was so rude. Made you feel Incompetent

Frontier scheduled a 40 minute connection in DEN. What they failed to mention was that they “close the doors” 20 mins prior to departure, which means you only have 20 mins. Not enough time. Possibly against DOT regulations. Filing complaint.

Flight was scheduled at 9:40pm. Got delayed to 10 am, the next day. crazy

The bag check, flight check-in, and onboard experience convinced my wife and me that we will actively go out of our way to avoid flying Frontier Airlines in the future. At bag check, we were informed that check-in could only be completed via the Frontier mobile app. Unfortunately, the app was extremely frustrating—sending us through repetitive, confusing loops that repeatedly forced us to decline add-on services with nearly every click. While most airline apps upsell, this one felt intentionally exhausting. As the process dragged on, we became genuinely concerned that my phone battery would die before check-in could be completed. We approached the bag check staff—who were standing together talking—and explained both our frustration and our predicament. They laughed. Later, my wife described the interaction as “gaslighting,” which felt accurate. We were then informed it would cost $25 per person simply to have our boarding passes printed. From that point forward, the tone of the experience was consistently hostile. The bag check employees were condescending and combative, behaving more like bullies than customer service staff. Unfortunately, that same attitude continued onboard. One flight attendant argued with me when I attempted to stow my backpack in the overhead bin. I explained that we had each paid $75 to check our bags specifically so we would not need to use carry-on space and could have adequate legroom. She demanded to see my ticket, pointed out that it said “no carry-on”—which I acknowledged—and I reiterated that this was precisely why we paid to check our bags. Her response was, “I don’t make the rules.” She then walked away, but not before asking if I “truly wanted to fly back to Chicago today?”—an unnecessary and unmistakable threat. It is also worth noting that despite booking our tickets together in the same transaction, we were not seated together. Upon our return to Chicago—where we could once again sit together—we compared onboard experiences. We both remarked on how unhappy the flight attendants appeared and how each of us was separately asked whether we would like to purchase a beverage. We declined. At no point was water mentioned as an option, leaving us with the clear impression that even water came at a cost—or that complimentary water, if available at all, was deliberately left unmentioned. Overall, the experience was shocking and deeply disappointing, but it was also a profound learning experience—one we will not forget and will not repeat. -Steve

Plane was hot and miserable and the crew was rude!

12 hour delay required getting on and off plane 3 times - would have at least liked to have been offered a snack or drink

They didn’t offer a water, even after I asked

They switched our terminal 3 times and we were delayed for four plus hours!!!

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 !!!!!!!

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

Everything you need to know for your flight from Chicago to Palo Alto

Complete your trip to Palo Alto with a hotel stay or car rental