$113+ 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 5/3. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — SFO
Apr 2 — Apr 91
1 adult, Economy
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Find cheap flights from Chicago to Palo Alto with Cheapflights
1. Tell us where you want to go
Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”2. Select your favorite providers
We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.3. Compare prices and book
Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.Cheapflights Tip: The best prices from Chicago to Palo Alto are usually found in April 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
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Best
Last-minute
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Cheapest flights from Chicago to Palo AltoExplore 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 March 3, 2026.
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 March 3, 2026.
This Southwest deal was found by Cheapflights users on 3/1. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/2510:00 am
MDW
- SFO
Nonstop4h 35m
Southwest
Wed 4/295:25 am
SFO
- MDW
Nonstop4h 10m
Southwest
Deal found 3/1![Southwest logo]()
$224
This Kiwi.com deal was found by Cheapflights users on 2/28. 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.
Fri 5/1510:07 pm
ORD
- SFO
1 stop16h 45m
Multiple Airlines
Sun 8/238:20 pm
SFO
- ORD
1 stop7h 03m
Multiple Airlines
Deal found 2/28![Multiple Airlines logo]()
$224
This Kiwi.com deal was found by Cheapflights users on 2/27. 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 4/142:15 pm
MDW
- SFO
1 stop29h 19m
Frontier
Thu 4/169:58 am
SFO
- MDW
2 stops26h 36m
Frontier
Deal found 2/27![Frontier logo]()
$225
This Kiwi.com deal was found by Cheapflights users on 3/1. 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 4/98:30 am
ORD
- SFO
2 stops17h 58m
Frontier
Mon 4/1310:50 pm
SFO
- ORD
1 stop29h 18m
Frontier
Deal found 3/1![Frontier logo]()
$225
This Kiwi.com deal was found by Cheapflights users on 3/1. 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.
Wed 4/156:30 am
MDW
- SFO
1 stop13h 04m
Frontier
Sat 4/186:00 am
SFO
- MDW
2 stops14h 14m
Frontier
Deal found 3/1![Frontier logo]()
$226
This Super.com deal was found by Cheapflights users on 2/26. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/259:28 am
ORD
- SFO
1 stop11h 46m
Frontier
Fri 3/279:04 pm
SFO
- ORD
1 stop25h 34m
Frontier
Deal found 2/26![Frontier logo]()
$226
This Southwest deal was found by Cheapflights users on 3/1. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/185:10 am
MDW
- SFO
1 stop8h 40m
Southwest
Sat 4/255:40 am
SFO
- MDW
2 stops9h 35m
Southwest
Deal found 3/1![Southwest logo]()
$227
This Booking.com deal was found by Cheapflights users on 2/26. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/43:35 pm
ORD
- SFO
1 stop7h 25m
Frontier
Sat 4/116:00 am
SFO
- ORD
1 stop16h 38m
Frontier
Deal found 2/26![Frontier logo]()
$227
This Kiwi.com deal was found by Cheapflights users on 3/1. 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.
Wed 4/156:30 am
MDW
- SFO
1 stop13h 04m
Frontier
Wed 4/227:00 am
SFO
- MDW
2 stops13h 14m
Frontier
Deal found 3/1![Frontier logo]()
$228
This Cheapflightsfares deal was found by Cheapflights users on 3/2. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/2112:44 pm
ORD
- SFO
1 stop8h 26m
Frontier
Tue 5/268:20 pm
SFO
- ORD
1 stop7h 03m
Frontier
Deal found 3/2![Frontier logo]()
$229
This Southwest deal was found by Cheapflights users on 2/26. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/89:00 pm
MDW
- SFO
Nonstop4h 35m
Southwest
Tue 4/145:25 am
SFO
- MDW
Nonstop4h 10m
Southwest
Deal found 2/26![Southwest logo]()
$230
This Frontier deal was found by Cheapflights users on 2/26. 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 8/1912:44 pm
ORD
- SFO
1 stop8h 26m
Frontier
Sun 8/238:20 pm
SFO
- ORD
1 stop7h 03m
Frontier
Deal found 2/26![Frontier logo]()
$230
Best flights from Chicago to Palo AltoDiscover carefully curated flight deals from Chicago to Palo Alto that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated March 3, 2026.
Discover carefully curated flight deals from Chicago to Palo Alto that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated March 3, 2026.
This United Airlines deal was found by Cheapflights users on 2/26. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/96:25 am
ORD
- SFO
Nonstop4h 51m
United Airlines
Mon 4/1311:52 pm
SFO
- ORD
Nonstop4h 28m
United Airlines
Deal found 2/26![United Airlines logo]()
$267
This Southwest deal was found by Cheapflights users on 3/1. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/1212:50 pm
MDW
- SFO
2 stops10h 35m
Southwest
Tue 5/1910:40 pm
SFO
- MDW
1 stop7h 45m
Southwest
Deal found 3/1![Southwest logo]()
$270
This Alaska Airlines deal was found by Cheapflights users on 3/1. 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.
Fri 8/285:55 pm
ORD
- SFO
1 stop8h 04m
Alaska Airlines
Wed 9/22:45 pm
SFO
- ORD
1 stop7h 14m
Alaska Airlines
Deal found 3/1![Alaska Airlines logo]()
$304
This Delta deal was found by Cheapflights users on 2/28. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/291:24 pm
MDW
- SFO
1 stop7h 39m
Delta
Sun 5/310:55 pm
SFO
- MDW
1 stop7h 52m
Delta
Deal found 2/28![Delta logo]()
$318
This Southwest deal was found by Cheapflights users on 2/25. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/812:50 pm
MDW
- SFO
2 stops10h 35m
Southwest
Sun 4/125:20 am
SFO
- MDW
Nonstop4h 10m
Southwest
Deal found 2/25![Southwest logo]()
$273
This United Airlines deal was found by Cheapflights users on 2/26. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 3/229:15 pm
ORD
- SFO
Nonstop5h 01m
United Airlines
Mon 4/276:29 pm
SFO
- ORD
Nonstop4h 30m
United Airlines
Deal found 2/26![United Airlines logo]()
$298
This Southwest deal was found by Cheapflights users on 3/1. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/159:00 pm
MDW
- SFO
Nonstop4h 35m
Southwest
Fri 4/179:15 pm
SFO
- MDW
1 stop8h 40m
Southwest
Deal found 3/1![Southwest logo]()
$275
This Delta deal was found by Cheapflights users on 2/27. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/191:15 pm
ORD
- SFO
1 stop8h 20m
Delta
Tue 6/238:55 am
SFO
- ORD
1 stop6h 35m
Delta
Deal found 2/27![Delta logo]()
$331
This Southwest deal was found by Cheapflights users on 2/26. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/77:30 am
MDW
- SFO
1 stop9h 30m
Southwest
Sun 5/105:20 am
SFO
- MDW
Nonstop4h 10m
Southwest
Deal found 2/26![Southwest logo]()
$282
This Delta deal was found by Cheapflights users on 2/28. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/187:00 am
ORD
- SFO
1 stop10h 11m
Delta
Sun 6/217:00 am
SFO
- ORD
1 stop8h 30m
Delta
Deal found 2/28![Delta logo]()
$349
This United Airlines deal was found by Cheapflights users on 3/1. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/288:55 am
ORD
- SFO
Nonstop4h 49m
United Airlines
Sat 5/3012:50 am
SFO
- ORD
Nonstop4h 26m
United Airlines
Deal found 3/1![United Airlines logo]()
$351
This Southwest deal was found by Cheapflights users on 2/27. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/306:35 pm
MDW
- SFO
2 stops7h 35m
Southwest
Wed 4/15:55 am
SFO
- MDW
2 stops8h 15m
Southwest
Deal found 2/27![Southwest logo]()
$315
This Delta deal was found by Cheapflights users on 2/26. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/2111:00 am
ORD
- SFO
1 stop10h 03m
Delta
Sat 4/2510:32 am
SFO
- ORD
2 stops8h 46m
Delta
Deal found 2/26![Delta logo]()
$373
This Southwest deal was found by Cheapflights users on 2/27. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/142:55 pm
MDW
- SFO
1 stop9h 50m
Southwest
Thu 4/168:05 am
SFO
- MDW
2 stops7h 35m
Southwest
Deal found 2/27![Southwest logo]()
$325
This Delta deal was found by Cheapflights users on 3/1. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/247:09 pm
ORD
- SFO
1 stop6h 45m
Delta
Mon 4/278:00 pm
SFO
- ORD
2 stops10h 01m
Delta
Deal found 3/1![Delta logo]()
$386
This Southwest deal was found by Cheapflights users on 3/1. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/2010:00 am
MDW
- SFO
Nonstop4h 35m
Southwest
Tue 5/265:25 am
SFO
- MDW
Nonstop4h 10m
Southwest
Deal found 3/1![Southwest logo]()
$333
This Southwest deal was found by Cheapflights users on 3/2. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/57:45 am
ORD
- SFO
2 stops12h 45m
Southwest
Fri 5/81:25 pm
SFO
- ORD
2 stops8h 30m
Southwest
Deal found 3/2![Southwest logo]()
$334
This Southwest deal was found by Cheapflights users on 2/27. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/64:05 pm
MDW
- SFO
2 stops8h 30m
Southwest
Tue 4/148:55 am
SFO
- MDW
2 stops11h 20m
Southwest
Deal found 2/27![Southwest logo]()
$340
This Southwest deal was found by Cheapflights users on 3/2. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/412:35 pm
ORD
- SFO
2 stops11h 40m
Southwest
Tue 7/72:15 pm
SFO
- ORD
1 stop6h 40m
Southwest
Deal found 3/2![Southwest logo]()
$358
This Southwest deal was found by Cheapflights users on 2/27. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/26:15 am
ORD
- SFO
2 stops13h 10m
Southwest
Sun 5/105:00 am
SFO
- ORD
2 stops8h 00m
Southwest
Deal found 2/27![Southwest logo]()
$366
This Southwest deal was found by Cheapflights users on 3/1. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/265:00 am
MDW
- SFO
1 stop7h 00m
Southwest
Thu 4/211:05 am
SFO
- MDW
1 stop8h 35m
Southwest
Deal found 3/1![Southwest logo]()
$371
This Southwest deal was found by Cheapflights users on 2/27. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/154:15 pm
ORD
- SFO
2 stops9h 30m
Southwest
Mon 5/181:25 pm
SFO
- ORD
2 stops8h 30m
Southwest
Deal found 2/27![Southwest logo]()
$373
Last-minute flights from Chicago to Palo AltoDiscover last-minute flight deals from Chicago to Palo Alto. Data last updated March 3, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to Palo Alto. Data last updated March 3, 2026 and is based on user searches.
This Super.com deal was found by Cheapflights users on 2/26. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/259:28 am
ORD
- SFO
1 stop11h 46m
Frontier
Fri 3/279:04 pm
SFO
- ORD
1 stop25h 34m
Frontier
Deal found 2/26![Frontier logo]()
$226
This Booking.com deal was found by Cheapflights users on 2/26. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/43:35 pm
ORD
- SFO
1 stop7h 25m
Frontier
Sat 4/116:00 am
SFO
- ORD
1 stop16h 38m
Frontier
Deal found 2/26![Frontier logo]()
$227
This Southwest deal was found by Cheapflights users on 2/26. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/89:00 pm
MDW
- SFO
Nonstop4h 35m
Southwest
Tue 4/145:25 am
SFO
- MDW
Nonstop4h 10m
Southwest
Deal found 2/26![Southwest logo]()
$230
This Kiwi.com deal was found by Cheapflights users on 3/1. 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 4/98:30 am
ORD
- SFO
2 stops17h 58m
Frontier
Mon 4/1310:50 pm
SFO
- ORD
1 stop29h 18m
Frontier
Deal found 3/1![Frontier logo]()
$225
This Kiwi.com deal was found by Cheapflights users on 2/28. 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.
Fri 4/102:29 pm
ORD
- SFO
1 stop11h 59m
Multiple Airlines
Sat 4/187:40 pm
SFO
- ORD
1 stop7h 45m
Multiple Airlines
Deal found 2/28![Multiple Airlines logo]()
$230
This Kiwi.com deal was found by Cheapflights users on 2/26. 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.
Sun 4/127:55 am
ORD
- SFO
2 stops39h 28m
Frontier
Sun 4/1910:38 pm
SFO
- ORD
1 stop10h 54m
Frontier
Deal found 2/26![Frontier logo]()
$224
This Kiwi.com deal was found by Cheapflights users on 2/27. 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 4/142:15 pm
MDW
- SFO
1 stop29h 19m
Frontier
Thu 4/169:58 am
SFO
- MDW
2 stops26h 36m
Frontier
Deal found 2/27![Frontier logo]()
$225
This Kiwi.com deal was found by Cheapflights users on 3/1. 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.
Wed 4/156:30 am
MDW
- SFO
1 stop13h 04m
Frontier
Sat 4/186:00 am
SFO
- MDW
2 stops14h 14m
Frontier
Deal found 3/1![Frontier logo]()
$226
This Kiwi.com deal was found by Cheapflights users on 3/1. 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.
Wed 4/156:30 am
MDW
- SFO
1 stop13h 04m
Frontier
Wed 4/227:00 am
SFO
- MDW
2 stops13h 14m
Frontier
Deal found 3/1![Frontier logo]()
$228
This Kiwi.com deal was found by Cheapflights users on 2/28. 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.
Wed 4/157:51 am
ORD
- SFO
1 stop15h 48m
Multiple Airlines
Sun 4/1910:38 pm
SFO
- ORD
1 stop10h 54m
Multiple Airlines
Deal found 2/28![Multiple Airlines logo]()
$229
This Southwest deal was found by Cheapflights users on 3/1. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/185:10 am
MDW
- SFO
1 stop8h 40m
Southwest
Sat 4/255:40 am
SFO
- MDW
2 stops9h 35m
Southwest
Deal found 3/1![Southwest logo]()
$227
This Southwest deal was found by Cheapflights users on 3/1. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/2510:00 am
MDW
- SFO
Nonstop4h 35m
Southwest
Wed 4/295:25 am
SFO
- MDW
Nonstop4h 10m
Southwest
Deal found 3/1![Southwest logo]()
$224
One-way flights from Chicago to Palo AltoSearch for one-way flight options from Chicago to Palo Alto. Find affordable one-way fares based on user searches. Data last updated March 3, 2026.
Search for one-way flight options from Chicago to Palo Alto. Find affordable one-way fares based on user searches. Data last updated March 3, 2026.
This Kiwi.com deal was found by Cheapflights users on 2/26. 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.
Sun 5/36:20 am
MDW
- SFO
2 stops37h 08m
Frontier
Deal found 2/26![Frontier logo]()
$113
This Kiwi.com deal was found by Cheapflights users on 3/3. 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.
Mon 4/204:14 pm
MDW
- SFO
2 stops33h 11m
Frontier
Deal found 3/3![Frontier logo]()
$114
This Super.com deal was found by Cheapflights users on 3/2. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/109:28 am
ORD
- SFO
1 stop11h 46m
Frontier
Deal found 3/2![Frontier logo]()
$114
This Southwest deal was found by Cheapflights users on 2/26. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/79:00 pm
MDW
- SFO
Nonstop4h 35m
Southwest
Deal found 2/26![Southwest logo]()
$115
This Frontier deal was found by Cheapflights users on 2/28. 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 5/184:09 pm
MDW
- SFO
1 stop8h 22m
Frontier
Deal found 2/28![Frontier logo]()
$116
This Kiwi.com deal was found by Cheapflights users on 2/26. 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 4/142:15 pm
MDW
- SFO
2 stops35h 10m
Frontier
Deal found 2/26![Frontier logo]()
$117
This Kiwi.com deal was found by Cheapflights users on 3/2. 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.
Sun 4/267:50 am
ORD
- SFO
2 stops29h 21m
Frontier
Deal found 3/2![Frontier logo]()
$117
This CheapOair deal was found by Cheapflights users on 2/27. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/288:48 pm
ORD
- SFO
1 stop14h 39m
Alaska Airlines
Deal found 2/27![Alaska Airlines logo]()
$118
This Delta deal was found by Cheapflights users on 3/2. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/11:10 pm
MDW
- SFO
1 stop7h 57m
Delta
Deal found 3/2![Delta logo]()
$119
This Delta deal was found by Cheapflights users on 3/1. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/247:25 am
ORD
- SFO
1 stop10h 39m
Delta
Deal found 3/1![Delta logo]()
$119
This Kiwi.com deal was found by Cheapflights users on 3/3. 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.
Sat 5/96:00 am
MDW
- SFO
2 stops29h 08m
Frontier
Deal found 3/3![Frontier logo]()
$120
This United Airlines deal was found by Cheapflights users on 2/26. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/116:25 am
ORD
- SFO
Nonstop4h 51m
United Airlines
Deal found 2/26![United Airlines logo]()
$120
Find 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 March 3, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $224 (Southwest) |
One-way from | $113 (Kiwi.com) |
Popular in | December |
Cheapest in | April |
Average price | $364 |
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 March 3, 2026.
Use the filters below to find and compare flights from Chicago to Palo Alto that are best for you.
Fly from
Fly to
Route
Depart
Return
ChicagoSan Francisco
ORD - SFO
ORDSFO
Chicago O'Hare Intl
Thu 4/9
6:25 am-9:16 am
Nonstop4h 51m
San Francisco
Mon 4/13
11:52 pm-6:20 am
Nonstop4h 28m
$267
ChicagoSan Francisco
MDW - SFO
MDWSFO
Chicago Midway
Tue 5/12
12:50 pm-9:25 pm
2 stops10h 35m
San Francisco
Tue 5/19
10:40 pm-8:25 am
1 stop7h 45m
$270
ChicagoSan Francisco
MDW - SFO
MDWSFO
Chicago Midway
Wed 4/8
12:50 pm-9:25 pm
2 stops10h 35m
San Francisco
Sun 4/12
5:20 am-11:30 am
Nonstop4h 10m
$273
ChicagoSan Francisco
MDW - SFO
MDWSFO
Chicago Midway
Wed 4/15
9:00 pm-11:35 pm
Nonstop4h 35m
San Francisco
Fri 4/17
9:15 pm-7:55 am
1 stop8h 40m
$275
ChicagoSan Francisco
MDW - SFO
MDWSFO
Chicago Midway
Thu 5/7
7:30 am-3:00 pm
1 stop9h 30m
San Francisco
Sun 5/10
5:20 am-11:30 am
Nonstop4h 10m
$282
ChicagoSan Francisco
ORD - SFO
ORDSFO
Chicago O'Hare Intl
Sun 3/22
9:15 pm-12:16 am
Nonstop5h 01m
San Francisco
Mon 4/27
6:29 pm-12:59 am
Nonstop4h 30m
$298
ChicagoSan Francisco
ORD - SFO
ORDSFO
Chicago O'Hare Intl
Fri 8/28
5:55 pm-11:59 pm
1 stop8h 04m
San Francisco
Wed 9/2
2:45 pm-11:59 pm
1 stop7h 14m
$304
ChicagoSan Francisco
MDW - SFO
MDWSFO
Chicago Midway
Mon 3/30
6:35 pm-12:10 am
2 stops7h 35m
San Francisco
Wed 4/1
5:55 am-4:10 pm
2 stops8h 15m
$315
ChicagoSan Francisco
MDW - SFO
MDWSFO
Chicago Midway
Wed 4/29
1:24 pm-7:03 pm
1 stop7h 39m
San Francisco
Sun 5/3
10:55 pm-8:47 am
1 stop7h 52m
$318
ChicagoSan Francisco
MDW - SFO
MDWSFO
Chicago Midway
Tue 4/14
2:55 pm-10:45 pm
1 stop9h 50m
San Francisco
Thu 4/16
8:05 am-5:40 pm
2 stops7h 35m
$325
Showing 1-10 of 45 resultsSorted by cheapest first
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.
MDW-SFO
ORD-SFO
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
CHI-P4L
MDW-SFO
ORD-SFO
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 February 27, 2026.
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, October is the cheapest month in which you can book a flight from Chicago to Palo Alto (average of $80). Flying from Chicago to Palo Alto in February is currently the most expensive (average of $211). 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 March 3, 2026.
A simple way to save on the total cost of your ticket is to fly from Chicago to Palo Alto in the evening. If you’re flexible enough to do this you can expect to save up to 25% on your trip compared to booking a flight in the morning.
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 February 21, 2026.
Travelers seeking maximum savings on their Chicago to Palo Alto flight should consider departing on Tuesday afternoons when fares are most often at their lowest. Sunday at noon flights should be avoided if possible as fares are typically the most expensive at this time.
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 March 3, 2026.
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.
Comfort
7.8
Crew
8.5
Boarding
8.1
Entertainment
7.0
Food
7.1
Overall
8.0
Reviews
1 / 20
10.0
Excellentrobert,Feb 2026
LAS - SAN
Comfort
7.8
Crew
8.5
Boarding
8.1
Entertainment
7.0
Food
7.1
Overall
8.0
Reviews
1 / 20
10.0
Excellentrobert,Feb 2026
LAS - SAN
Comfort
7.8
Crew
8.5
Boarding
8.1
Entertainment
7.0
Food
7.1
Overall
8.0
Reviews
1 / 20
10.0
Excellentrobert,Feb 2026
LAS - SAN
Comfort
7.8
Crew
8.5
Boarding
8.1
Entertainment
7.0
Food
7.1
Overall
8.0
Reviews
1 / 20
10.0
Excellentrobert,Feb 2026
LAS - SAN
Comfort
7.8
Crew
8.5
Boarding
8.1
Entertainment
7.0
Food
7.1
Overall
8.0
Reviews
1 / 20
10.0
Excellentrobert,Feb 2026
LAS - SAN
Comfort
7.8
Crew
8.5
Boarding
8.1
Entertainment
7.0
Food
7.1
Overall
8.0
Reviews
1 / 20
10.0
Excellentrobert,Feb 2026
LAS - SAN
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.
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Complete your trip
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Search flights from Chicago to Palo Alto by cabin class
Find flights from Chicago to Palo Alto, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Chicago and Palo Alto flights
Browse other Chicago and Palo Alto flight options. Last updated on March 3, 2026.
Other flights from Chicago
Browse through other flights departing from Chicago. Flights are based on user searches made on Cheapflights and were last updated on March 3, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Top 10 airlines flying from Chicago to Palo Alto
Discover the top 10 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 March 3, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$80 | Average$209 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$83 | Average$215 | FlexibilityNo cancel fee | On-time65% | |
| Cheapest$108 | Average$217 | FlexibilityNo cancel fee | On-time85% | |
| Cheapest$112 | Average$374 | FlexibilityNo cancel fee | On-time83% | |
| Cheapest$128 | Average$349 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$138 | Average$419 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$147 | Average$264 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$186 | Average$317 | FlexibilityNo cancel fee | On-time75% | |
| Cheapest$197 | Average$427 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$207 | Average$427 | FlexibilityNo cancel fee | On-time69% |