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Palo Alto

$99+ Cheap flights from Chicago (CHI) to Palo Alto, CA

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 11/1. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — SFO
Aug 19 — Aug 261
Tue 8/19
Tue 8/26
1 adult, Economy
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Cheapflights Tip: The best prices from Chicago to Palo Alto are usually found in September or July, booked 83 days in advance, depart on a Thursday or Friday and return on a Wednesday

Cheap flight deals from Chicago to Palo Alto

Keep the following information in mind while searching for Chicago to Palo Alto flight deals. Data was last updated August 14, 2025.

Round-trip from

$198
(Frontier)

One-way from

$99
(Southwest)

Popular in

December

Cheapest in

September

Average price

$317
From Chicago (CHI) to Palo Alto
Search Deals
One-way flight from Chicago (CHI) to Palo Alto
Search Deals
Highest demand for flights based on searches. 7% potential increase in price ($26 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($7 potential savings vs. average RT price).
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Average for round-trip flights in August 2025
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Find flight deals from Chicago to Palo Alto

Cheapest flights from Chicago to Palo Alto
Explore the most affordable flight options available from Chicago to Palo Alto. Find the lowest fares from popular airlines and budget airlines, with prices last updated on August 14, 2025.

This Frontier deal was found by Cheapflights users on 8/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/166:24 pmMDW - SFO
1 stop7h 50mFrontier
Sun 10/198:27 pmSFO - MDW
2 stops12h 46mFrontier
Deal found 8/13$198
This American Airlines deal was found by Cheapflights users on 8/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/316:45 amORD - SFO
Nonstop4h 30mAmerican Airlines
Fri 9/51:21 pmSFO - ORD
Nonstop4h 24mAmerican Airlines
Deal found 8/12$198
This American Airlines deal was found by Cheapflights users on 8/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/66:45 amORD - SFO
Nonstop4h 39mAmerican Airlines
Sat 9/131:21 pmSFO - ORD
Nonstop4h 24mAmerican Airlines
Deal found 8/14$199
This Frontier deal was found by Cheapflights users on 8/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/193:48 pmMDW - SFO
2 stops10h 27mFrontier
Sun 9/2111:57 pmSFO - MDW
1 stop11h 14mFrontier
Deal found 8/13$200
This Kiwi.com deal was found by Cheapflights users on 8/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/219:45 pmORD - SFO
1 stop17h 30mFrontier
Mon 8/2510:29 pmSFO - ORD
1 stop13h 04mFrontier
Deal found 8/13$200
This Frontier deal was found by Cheapflights users on 8/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/1810:13 amMDW - SFO
2 stops15h 02mFrontier
Mon 9/226:29 amSFO - MDW
1 stop7h 24mFrontier
Deal found 8/14$201
This Frontier deal was found by Cheapflights users on 8/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/187:05 amORD - SFO
2 stops12h 59mFrontier
Fri 10/2410:23 pmSFO - ORD
1 stop11h 12mFrontier
Deal found 8/14$201
This Frontier deal was found by Cheapflights users on 8/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/256:31 pmMDW - SFO
1 stop7h 48mFrontier
Thu 9/411:57 pmSFO - MDW
1 stop11h 14mFrontier
Deal found 8/13$202
This Kiwi.com deal was found by Cheapflights users on 8/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/148:20 amORD - SFO
1 stop7h 41mMultiple Airlines
Sun 10/191:29 pmSFO - ORD
1 stop6h 55mMultiple Airlines
Deal found 8/14$202
This Frontier deal was found by Cheapflights users on 8/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/176:44 pmORD - SFO
2 stops16h 00mFrontier
Sun 9/2111:00 pmSFO - ORD
1 stop9h 31mFrontier
Deal found 8/14$203
This Alaska Airlines deal was found by Cheapflights users on 8/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/147:59 pmORD - SFO
1 stop20h 02mAlaska Airlines
Tue 10/2110:26 amSFO - ORD
1 stop11h 33mAlaska Airlines
Deal found 8/14$204
This Frontier deal was found by Cheapflights users on 8/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/154:48 pmMDW - SFO
1 stop9h 28mFrontier
Thu 9/185:45 amSFO - MDW
2 stops14h 13mFrontier
Deal found 8/14$205

Cheapflights Fare Finder

 
Customize your flight search to find flights from Chicago to Palo Alto that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated August 14, 2025.
Use the filters below to find and compare flights from Chicago to Palo Alto that are best for you.

Fly from

Chicago

Fly to

Palo Alto

Route

Depart

Return

Price

ChicagoSan Francisco

MDW - SFO

MDWSFO

Chicago Midway

Thu 10/23

6:24 pm-12:14 am

1 stop7h 50m

San Francisco

Sun 10/26

8:27 pm-11:13 am

2 stops12h 46m

$198

ChicagoSan Francisco

MDW - SFO

MDWSFO

Chicago Midway

Fri 10/31

9:15 am-11:50 am

Nonstop4h 35m

San Francisco

Tue 11/4

5:50 am-3:55 pm

1 stop8h 05m

$198

ChicagoSan Francisco

ORD - SFO

ORDSFO

Chicago O'Hare Intl

Thu 9/11

7:55 am-1:22 pm

1 stop7h 27m

San Francisco

Fri 9/19

11:00 pm-11:27 am

1 stop10h 27m

$199

ChicagoSan Francisco

MDW - SFO

MDWSFO

Chicago Midway

Thu 9/18

10:13 am-11:15 pm

2 stops15h 02m

San Francisco

Mon 9/22

6:29 am-3:53 pm

1 stop7h 24m

$201

ChicagoSan Francisco

ORD - SFO

ORDSFO

Chicago O'Hare Intl

Tue 10/14

7:59 pm-2:01 pm

1 stop20h 02m

San Francisco

Tue 10/21

10:26 am-11:59 pm

1 stop11h 33m

$204

ChicagoSan Francisco

ORD - SFO

ORDSFO

Chicago O'Hare Intl

Tue 10/14

3:50 pm-2:01 pm

1 stop24h 11m

San Francisco

Wed 10/22

10:26 am-11:59 pm

1 stop11h 33m

$204

ChicagoSan Francisco

ORD - SFO

ORDSFO

Chicago O'Hare Intl

Wed 10/8

7:59 pm-8:05 am

1 stop14h 06m

San Francisco

Tue 10/14

10:26 am-11:59 pm

1 stop11h 33m

$204

ChicagoSan Francisco

ORD - SFO

ORDSFO

Chicago O'Hare Intl

Tue 10/28

2:54 pm-10:01 pm

1 stop9h 07m

San Francisco

Tue 11/11

7:00 am-11:59 pm

1 stop14h 59m

$204

ChicagoSan Francisco

ORD - SFO

ORDSFO

Chicago O'Hare Intl

Tue 10/7

8:20 am-2:01 pm

1 stop7h 41m

San Francisco

Tue 10/21

10:26 am-11:59 pm

1 stop11h 33m

$204

ChicagoSan Francisco

ORD - SFO

ORDSFO

Chicago O'Hare Intl

Sat 11/8

2:54 pm-9:55 pm

1 stop9h 01m

San Francisco

Wed 11/12

7:00 am-6:59 pm

1 stop9h 59m

$204

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/12

Showing 1-10 of 36 results
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Best time to book a flight from Chicago to Palo Alto

Have a flexible travel schedule? Discover the best time to fly to Palo Alto from Chicago with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

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

How far ahead should I book a flight from Chicago to Palo Alto?

Use this chart to determine the optimal time to book a round-trip flight from Chicago to Palo Alto. Price data was last updated on August 8, 2025.

To ensure you get the cheapest price possible for a flight from Chicago to Palo Alto, you should look to book at least 83 days in advance of your intended travel date. The price of your flight may increase if you delay and leave booking until a week or so before departure.

What is the cheapest month to book a flight from Chicago to Palo Alto?

Currently, January is the cheapest month in which you can book a flight from Chicago to Palo Alto (average of $276). Flying from Chicago to Palo Alto in June is currently the most expensive (average of $358). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

What is the cheapest time of day to fly from CHI to P4L?

Find hourly flight availability from Chicago to Palo Alto. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated August 14, 2025.

When flying from Chicago to Palo Alto, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

What is the cheapest day to fly from Chicago to Palo Alto?

Use this chart to determine the cheapest time to fly round-trip from Chicago to Palo Alto. Price data was last updated on December 16, 2024.

Travelers seeking maximum savings on their Chicago to Palo Alto flight should consider departing on Thursday evenings when fares are most often at their lowest. Sunday afternoons flights should be avoided if possible as fares are typically the most expensive at this time.

Weekly flight availability from Chicago to Palo Alto

Explore weekly flight availability from Chicago to Palo Alto. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated August 14, 2025.

The most flights from CHI to P4L are scheduled on a Thursday (98 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (31 on average).

Reviews of airlines servicing Palo Alto

Get insights into the airlines that provide service to Palo Alto. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Palo Alto. Reviews last updated August 14, 2025.
See what other customers who have flown with Alaska Airlines, Southwest, and United Airlines from Chicago to Palo Alto have to say. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
Alaska Airlines
8.0
Very good
10,000 reviews

Crew

8.5

Food

7.1

Boarding

8.1

Comfort

7.8

Overall

8.0

Entertainment

7.0

Reviews

1 / 20
8.0
Excellent

Anonymous,Aug 2025

BOI - LAX

flying in first class, my husband froze the entire flight and was miserable. first class does not offer blankets or any entertainment. (TV etc)
Alaska Airlines
8.0
Very good
10,000 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Crew

8.5

Food

7.1

Boarding

8.1

Comfort

7.8

Overall

8.0

Entertainment

7.0

Reviews

1 / 20
8.0
Excellent

Anonymous,Aug 2025

BOI - LAX

flying in first class, my husband froze the entire flight and was miserable. first class does not offer blankets or any entertainment. (TV etc)
Southwest
8.0
Very good
4,244 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Crew

8.5

Food

7.1

Boarding

8.1

Comfort

7.8

Overall

8.0

Entertainment

7.0

Reviews

1 / 20
8.0
Excellent

Anonymous,Aug 2025

BOI - LAX

flying in first class, my husband froze the entire flight and was miserable. first class does not offer blankets or any entertainment. (TV etc)
United Airlines
7.4
Good
8,916 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Crew

8.5

Food

7.1

Boarding

8.1

Comfort

7.8

Overall

8.0

Entertainment

7.0

Reviews

1 / 20
8.0
Excellent

Anonymous,Aug 2025

BOI - LAX

flying in first class, my husband froze the entire flight and was miserable. first class does not offer blankets or any entertainment. (TV etc)
American Airlines
7.2
Good
10,000 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Crew

8.5

Food

7.1

Boarding

8.1

Comfort

7.8

Overall

8.0

Entertainment

7.0

Reviews

1 / 20
8.0
Excellent

Anonymous,Aug 2025

BOI - LAX

flying in first class, my husband froze the entire flight and was miserable. first class does not offer blankets or any entertainment. (TV etc)
Frontier
5.8
Fair
3,217 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Crew

8.5

Food

7.1

Boarding

8.1

Comfort

7.8

Overall

8.0

Entertainment

7.0

Reviews

1 / 20
8.0
Excellent

Anonymous,Aug 2025

BOI - LAX

flying in first class, my husband froze the entire flight and was miserable. first class does not offer blankets or any entertainment. (TV etc)

Related info for your journey

Find useful and relevant information for your journey from Chicago to Palo Alto. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What are the cheapest airlines to fly from Chicago to Palo Alto one-way?

    $99 is the cheapest one-way deal found within the past few days, from Southwest. You may also be able to find cheap deals on United Airlines and American Airlines, with prices starting from $99 and $100, respectively.

  • What are the most reliable airlines from Chicago to Palo Alto?

    The top 3 most reliable airlines when flying from Chicago to Palo Alto are ANA (82%), Air China (79%) and Austrian Airlines (78%).

  • What are the cheapest flights from Chicago to Palo Alto?

    Looking at all options, your cheapest flight can be booked for $98. While the most popular route (Chicago O'Hare Intl - San Francisco) can be booked for $179 on average our data indicates $779 when flying from Chicago to Palo Alto.

  • Can I find deals for flights from Chicago to Palo Alto that include hotel bookings?

    Yes. In addition to deals on Chicago to Palo Alto flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Chicago to Palo Alto?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Chicago to Palo Alto.

  • Can I find deals for business class flights from Chicago to Palo Alto?

    Yes. Cheapflights offers flight deals from Chicago to Palo Alto by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Chicago to Palo Alto?

    Currently, January is the cheapest month in which you can book a flight from Chicago to Palo Alto (average of $276). Flying from Chicago to Palo Alto in June is currently the most expensive (average of $358). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

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Alternative routes for Chicago to Palo Alto

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Top 8 airlines flying from Chicago to Palo Alto

Discover the top 8 airlines that operate flights from Chicago to Palo Alto. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated August 14, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$90Average$254FlexibilityNo cancel feeOn-time62%
Hawaiian AirlinesCheapest$108Average$217FlexibilityNo cancel feeOn-time85%
Spirit AirlinesCheapest$119Average$229FlexibilityNo cancel feeOn-time65%
DeltaCheapest$128Average$349FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$141Average$405FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$180Average$408FlexibilityNo cancel feeOn-time63%
Alaska AirlinesCheapest$187Average$286FlexibilityNo cancel feeOn-time75%
American AirlinesCheapest$197Average$394FlexibilityNo cancel feeOn-time71%

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