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Find cheap flights from Chicago to Palo Alto from $44

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 9/4. 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
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Thu 6/6
Thu 6/13

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Good to know

Low season

January

High season

December

Cheapest flight

$44
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 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 28m.

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

    106 direct flights run between Chicago and Palo Alto on a daily basis. On average, there are about 743 departures each week.

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

    Consider leaving on a Saturday and avoid Fridays 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 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 Frontier for $44. Frontier offered a round-trip connection from $88 and American Airlines from $179.

See more FAQs

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 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 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
Alaska AirlinesOverall score based on 9137 reviews
7.9Comfort
8.2Boarding
7.3Food
8.6Crew
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.

Not good 😐 Over priced baggage fees Small hard seats No wifi or entertainment options 😕

Didn't like anything!! Horrible flight. Small seating area and hard seats. Butt was sore after 2 hour flight to Seattle No entertainment or free refreshments No wifi or USB charging receptacles to charge phone entoute like other airliners Luggage rates were 3 times as much as competitors. Difficult to navigate online luggue process to pre pay before flight Overall bad experience WILL NEVER RIDE OR RECOMMEND FRONTIER TO FRIENDS OR FAMILY MEMBERS!!! THIS IS A SHAME!! MOST MESERIBLE FLIGHT OF MY LIFE!! AND I THOUGHT SPIRIT WAS 👎 YOU GOT THEM BEAD HANDS DOWN!!

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 Palo Alto

Recent round-trip flight deals

9/14Sat
nonstopFrontier
4h 38mMDW-SFO
9/21Sat
nonstopFrontier
4h 11mSFO-MDW
$88
8/9Fri
nonstopFrontier
4h 38mMDW-SFO
8/24Sat
nonstopFrontier
4h 11mSFO-MDW
$108
9/14Sat
nonstopAmerican Airlines
4h 39mORD-SFO
9/21Sat
nonstopAmerican Airlines
4h 16mSFO-ORD
$179
5/29Wed
nonstopAlaska Airlines
4h 44mORD-SFO
5/29Wed
nonstopAlaska Airlines
4h 23mSFO-ORD
$183
9/10Tue
1 stopAlaska Airlines
9h 47mORD-SFO
9/17Tue
nonstopAlaska Airlines
4h 20mSFO-ORD
$188
7/17Wed
nonstopUnited Airlines
4h 39mORD-SFO
7/22Mon
nonstopUnited Airlines
4h 18mSFO-ORD
$217
7/17Wed
1 stopUnited Airlines
6h 23mORD-SFO
7/22Mon
nonstopUnited Airlines
4h 18mSFO-ORD
$226
7/2Tue
nonstopAmerican Airlines
4h 40mORD-SFO
7/23Tue
nonstopAmerican Airlines
4h 13mSFO-ORD
$253
7/4Thu
1 stopDelta
6h 48mMDW-SFO
7/8Mon
1 stopDelta
7h 45mSFO-MDW
$262
10/9Wed
1 stopDelta
10h 15mORD-SFO
10/12Sat
1 stopDelta
6h 16mSFO-ORD
$262

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Recent one-way flight deals

9/4Wed
nonstopFrontier
4h 38mMDW-SFO
$44
6/1Sat
nonstopFrontier
4h 29mMDW-SFO
$47
5/30Thu
nonstopAlaska Airlines
4h 37mORD-SFO
$95
8/13Tue
nonstopUnited Airlines
4h 40mORD-SFO
$99
5/31Fri
1 stopAlaska Airlines
8h 41mORD-SFO
$104
8/8Thu
1 stopUnited Airlines
6h 23mORD-SFO
$114
5/29Wed
1 stopDelta
6h 15mMDW-SFO
$118
5/30Thu
1 stopDelta
6h 40mORD-SFO
$118
6/15Sat
nonstopAmerican Airlines
4h 40mORD-SFO
$160
7/8Mon
nonstopAmerican Airlines
4h 35mORD-SFO
$219

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Last minute flights from Chicago to Palo Alto

Last minute flight, train and bus deals

5/11Sat
nonstopFrontier
4h 39mMDW-SFO
5/14Tue
nonstopFrontier
4h 11mSFO-MDW
$192
5/7Tue
nonstopFrontier
4h 39mMDW-SFO
5/14Tue
nonstopFrontier
4h 11mSFO-MDW
$195
5/11Sat
multi-stopDelta
7h 25mORD-SFO
5/17Fri
multi-stopDelta
7h 46mSFO-ORD
$320
5/8Wed
nonstopUnited Airlines
4h 53mORD-SFO
5/14Tue
nonstopUnited Airlines
4h 21mSFO-ORD
$394
5/11Sat
multi-stopUnited Airlines
8h 11mORD-SFO
5/21Tue
nonstopUnited Airlines
4h 21mSFO-ORD
$395
5/8Wed
multi-stopAmerican Airlines
8h 17mORD-SFO
5/14Tue
nonstopAmerican Airlines
4h 22mSFO-ORD
$402
5/8Wed
multi-stopDelta
9h 31mMDW-SFO
5/14Tue
multi-stopDelta
7h 56mSFO-MDW
$413
5/11Sat
nonstopAlaska Airlines
4h 46mORD-SFO
5/22Wed
nonstopAlaska Airlines
4h 23mSFO-ORD
$427
5/7Tue
nonstopAlaska Airlines
4h 52mORD-SFO
5/14Tue
multi-stopAlaska Airlines
6h 50mSFO-ORD
$448
5/7Tue
nonstopAmerican Airlines
4h 44mORD-SFO
5/13Mon
multi-stopAmerican Airlines
8h 12mSFO-ORD
$452

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