Wed Mar 19th 2025 Alaska Airlines · AS 329 Depart at 9:00am from Chicago (ORD) Fly for 4h 50m Arrive at 11:50am in Seattle (SEA)
Layover in Seattle for 0h 55m
Wed Mar 19th 2025 Alaska Airlines · AS 1114 Depart at 12:45pm from Seattle (SEA) Fly for 2h 10m Arrive at 2:55pm in San Jose (SJC)
Tue Mar 18th 2025 Alaska Airlines · AS 329 Depart at 9:00am from Chicago (ORD) Fly for 4h 50m Arrive at 11:50am in Seattle (SEA)
Layover in Seattle for 0h 55m
Tue Mar 18th 2025 Alaska Airlines · AS 1114 Depart at 12:45pm from Seattle (SEA) Fly for 2h 10m Arrive at 2:55pm in San Jose (SJC)
Tue Mar 18th 2025 Alaska Airlines · AS 587 Depart at 6:30am from Chicago (ORD) Fly for 4h 51m Arrive at 9:21am in Seattle (SEA)
Layover in Seattle for 1h 14m
Tue Mar 18th 2025 Alaska Airlines · AS 1080 Depart at 10:35am from Seattle (SEA) Fly for 2h 13m Arrive at 12:48pm in San Jose (SJC)
Tue Mar 18th 2025 Alaska Airlines · AS 329 Depart at 9:00am from Chicago (ORD) Fly for 4h 50m Arrive at 11:50am in Seattle (SEA)
Layover in Seattle for 3h 10m
Tue Mar 18th 2025 Alaska Airlines · AS 1046 Depart at 3:00pm from Seattle (SEA) Fly for 2h 9m Arrive at 5:09pm in San Jose (SJC)
Wed Mar 12th 2025 Alaska Airlines · AS 587 Depart at 6:30am from Chicago (ORD) Fly for 4h 51m Arrive at 9:21am in Seattle (SEA)
Layover in Seattle for 3h 24m
Wed Mar 12th 2025 Alaska Airlines · AS 1114 Depart at 12:45pm from Seattle (SEA) Fly for 2h 10m Arrive at 2:55pm in San Jose (SJC)
Tue Mar 18th 2025 Alaska Airlines · AS 587 Depart at 6:30am from Chicago (ORD) Fly for 4h 51m Arrive at 9:21am in Seattle (SEA)
Layover in Seattle for 3h 24m
Tue Mar 18th 2025 Alaska Airlines · AS 1114 Depart at 12:45pm from Seattle (SEA) Fly for 2h 10m Arrive at 2:55pm in San Jose (SJC)
Wed Mar 12th 2025 Alaska Airlines · AS 587 Depart at 6:30am from Chicago (ORD) Fly for 4h 51m Arrive at 9:21am in Seattle (SEA)
Layover in Seattle for 1h 14m
Wed Mar 12th 2025 Alaska Airlines · AS 1080 Depart at 10:35am from Seattle (SEA) Fly for 2h 13m Arrive at 12:48pm in San Jose (SJC)
Tue Mar 18th 2025 United Airlines · UA 1069 Depart at 7:40pm from Chicago (ORD) Fly for 4h 36m Arrive at 10:16pm in San Jose (SJC)
Tue Mar 18th 2025 United Airlines · UA 2187 Depart at 2:18pm from Chicago (ORD) Fly for 8h 25m Arrive at 8:43pm in San Jose (SJC)
Tue Mar 18th 2025 United Airlines · UA 1875 Depart at 3:55pm from Chicago (ORD) Fly for 2h 40m Arrive at 5:35pm in Denver (DEN)
Layover in Denver for 1h 27m
Tue Mar 18th 2025 United Airlines · UA 2187 Depart at 7:02pm from Denver (DEN) Fly for 2h 41m Arrive at 8:43pm in San Jose (SJC)
Tue Mar 18th 2025 United Airlines · UA 2666 Depart at 5:00am from Chicago (ORD) Fly for 2h 37m Arrive at 6:37am in Denver (DEN)
Layover in Denver for 1h 38m
Tue Mar 18th 2025 United Airlines · UA 397 Depart at 8:15am from Denver (DEN) Fly for 2h 41m Arrive at 9:56am in San Jose (SJC)
Tue Mar 18th 2025 United Airlines · UA 2249 Depart at 12:45pm from Chicago (ORD) Fly for 2h 38m Arrive at 2:23pm in Denver (DEN)
Layover in Denver for 1h 34m
Tue Mar 18th 2025 United Airlines · UA 1813 Depart at 3:57pm from Denver (DEN) Fly for 2h 46m Arrive at 5:43pm in San Jose (SJC)
Tue Mar 18th 2025 United Airlines · UA 2180 Depart at 6:00am from Chicago (ORD) Fly for 2h 45m Arrive at 8:45am in Houston (IAH)
Layover in Houston for 0h 55m
Tue Mar 18th 2025 United Airlines · UA 2293 Depart at 9:40am from Houston (IAH) Fly for 4h 18m Arrive at 11:58am in San Jose (SJC)
Tue Mar 18th 2025 United Airlines · UA 711 Depart at 7:15am from Chicago (ORD) Fly for 2h 40m Arrive at 8:55am in Denver (DEN)
Layover in Denver for 2h 50m
Tue Mar 18th 2025 United Airlines · UA 535 Depart at 11:45am from Denver (DEN) Fly for 2h 41m Arrive at 1:26pm in San Jose (SJC)
Tue Mar 18th 2025 United Airlines · UA 1803 Depart at 10:50am from Chicago (ORD) Fly for 2h 34m Arrive at 12:24pm in Denver (DEN)
Layover in Denver for 3h 33m
Tue Mar 18th 2025 United Airlines · UA 1813 Depart at 3:57pm from Denver (DEN) Fly for 2h 46m Arrive at 5:43pm in San Jose (SJC)
Wed Mar 12th 2025 Alaska Airlines · AS 335 Depart at 7:00am from Chicago (ORD) Fly for 4h 44m Arrive at 9:44am in Portland (PDX)
Layover in Portland for 0h 41m
Wed Mar 12th 2025 Alaska Airlines · AS 3350 Depart at 10:25am from Portland (PDX) Fly for 1h 45m Arrive at 12:10pm in San Jose (SJC)
Wed Mar 12th 2025 Alaska Airlines · AS 329 Depart at 9:00am from Chicago (ORD) Fly for 4h 50m Arrive at 11:50am in Seattle (SEA)
Layover in Seattle for 0h 55m
Wed Mar 12th 2025 Alaska Airlines · AS 1114 Depart at 12:45pm from Seattle (SEA) Fly for 2h 10m Arrive at 2:55pm in San Jose (SJC)
Fri Mar 14th 2025 Alaska Airlines · AS 587 Depart at 6:30am from Chicago (ORD) Fly for 4h 51m Arrive at 9:21am in Seattle (SEA)
Layover in Seattle for 1h 14m
Fri Mar 14th 2025 Alaska Airlines · AS 1080 Depart at 10:35am from Seattle (SEA) Fly for 2h 13m Arrive at 12:48pm in San Jose (SJC)
Fri Mar 14th 2025 Alaska Airlines · AS 407 Depart at 2:05pm from Chicago (ORD) Fly for 4h 48m Arrive at 4:53pm in Seattle (SEA)
Layover in Seattle for 2h 37m
Fri Mar 14th 2025 Alaska Airlines · AS 1192 Depart at 7:30pm from Seattle (SEA) Fly for 2h 8m Arrive at 9:38pm in San Jose (SJC)
Wed Mar 12th 2025 Alaska Airlines · AS 407 Depart at 2:05pm from Chicago (ORD) Fly for 4h 48m Arrive at 4:53pm in Seattle (SEA)
Layover in Seattle for 2h 37m
Wed Mar 12th 2025 Alaska Airlines · AS 1192 Depart at 7:30pm from Seattle (SEA) Fly for 2h 8m Arrive at 9:38pm in San Jose (SJC)
Wed Mar 12th 2025 Alaska Airlines · AS 329 Depart at 9:00am from Chicago (ORD) Fly for 4h 50m Arrive at 11:50am in Seattle (SEA)
Layover in Seattle for 3h 10m
Wed Mar 12th 2025 Alaska Airlines · AS 1046 Depart at 3:00pm from Seattle (SEA) Fly for 2h 9m Arrive at 5:09pm in San Jose (SJC)
Wed Mar 12th 2025 Alaska Airlines · AS 335 Depart at 7:00am from Chicago (ORD) Fly for 4h 44m Arrive at 9:44am in Portland (PDX)
Layover in Portland for 3h 56m
Wed Mar 12th 2025 Alaska Airlines · AS 3379 Depart at 1:40pm from Portland (PDX) Fly for 1h 45m Arrive at 3:25pm in San Jose (SJC)
Tue Mar 18th 2025 United Airlines · UA 2297 Depart at 8:55am from Chicago (ORD) Fly for 2h 35m Arrive at 10:30am in Denver (DEN)
Layover in Denver for 1h 15m
Tue Mar 18th 2025 United Airlines · UA 535 Depart at 11:45am from Denver (DEN) Fly for 2h 41m Arrive at 1:26pm in San Jose (SJC)
Tue Mar 18th 2025 Alaska Airlines · AS 335 Depart at 7:00am from Chicago (ORD) Fly for 4h 44m Arrive at 9:44am in Portland (PDX)
Layover in Portland for 0h 41m
Tue Mar 18th 2025 Alaska Airlines · AS 3350 Depart at 10:25am from Portland (PDX) Fly for 1h 45m Arrive at 12:10pm in San Jose (SJC)
Tue Mar 18th 2025 Alaska Airlines · AS 407 Depart at 2:05pm from Chicago (ORD) Fly for 4h 48m Arrive at 4:53pm in Seattle (SEA)
Layover in Seattle for 2h 37m
Tue Mar 18th 2025 Alaska Airlines · AS 1192 Depart at 7:30pm from Seattle (SEA) Fly for 2h 8m Arrive at 9:38pm in San Jose (SJC)
Tue Mar 18th 2025 Alaska Airlines · AS 335 Depart at 7:00am from Chicago (ORD) Fly for 4h 44m Arrive at 9:44am in Portland (PDX)
Layover in Portland for 3h 56m
Tue Mar 18th 2025 Alaska Airlines · AS 3379 Depart at 1:40pm from Portland (PDX) Fly for 1h 45m Arrive at 3:25pm in San Jose (SJC)
Tue Mar 18th 2025 Alaska Airlines · AS 587 Depart at 6:30am from Chicago (ORD) Fly for 4h 51m Arrive at 9:21am in Seattle (SEA)
Layover in Seattle for 1h 59m
Tue Mar 18th 2025 Alaska Airlines · AS 1039 Depart at 11:20am from Seattle (SEA) Fly for 0h 54m Arrive at 12:14pm in Portland (PDX)
Layover in Portland for 1h 26m
Tue Mar 18th 2025 Alaska Airlines · AS 3379 Depart at 1:40pm from Portland (PDX) Fly for 1h 45m Arrive at 3:25pm in San Jose (SJC)
Wed Mar 19th 2025 Alaska Airlines · AS 587 Depart at 6:30am from Chicago (ORD) Fly for 4h 51m Arrive at 9:21am in Seattle (SEA)
Layover in Seattle for 1h 59m
Wed Mar 19th 2025 Alaska Airlines · AS 1039 Depart at 11:20am from Seattle (SEA) Fly for 0h 54m Arrive at 12:14pm in Portland (PDX)
Layover in Portland for 1h 26m
Wed Mar 19th 2025 Alaska Airlines · AS 3379 Depart at 1:40pm from Portland (PDX) Fly for 1h 45m Arrive at 3:25pm in San Jose (SJC)
Wed Mar 12th 2025 Alaska Airlines · AS 587 Depart at 6:30am from Chicago (ORD) Fly for 4h 51m Arrive at 9:21am in Seattle (SEA)
Layover in Seattle for 1h 59m
Wed Mar 12th 2025 Alaska Airlines · AS 1039 Depart at 11:20am from Seattle (SEA) Fly for 0h 54m Arrive at 12:14pm in Portland (PDX)
Layover in Portland for 1h 26m
Wed Mar 12th 2025 Alaska Airlines · AS 3379 Depart at 1:40pm from Portland (PDX) Fly for 1h 45m Arrive at 3:25pm in San Jose (SJC)
Sat Mar 15th 2025 Alaska Airlines · AS 587 Depart at 6:30am from Chicago (ORD) Fly for 4h 51m Arrive at 9:21am in Seattle (SEA)
Layover in Seattle for 1h 59m
Sat Mar 15th 2025 Alaska Airlines · AS 1039 Depart at 11:20am from Seattle (SEA) Fly for 0h 54m Arrive at 12:14pm in Portland (PDX)
Layover in Portland for 1h 26m
Sat Mar 15th 2025 Alaska Airlines · AS 3379 Depart at 1:40pm from Portland (PDX) Fly for 1h 45m Arrive at 3:25pm in San Jose (SJC)
Mon Mar 17th 2025 Alaska Airlines · AS 587 Depart at 6:30am from Chicago (ORD) Fly for 4h 51m Arrive at 9:21am in Seattle (SEA)
Layover in Seattle for 1h 14m
Mon Mar 17th 2025 Alaska Airlines · AS 1080 Depart at 10:35am from Seattle (SEA) Fly for 2h 13m Arrive at 12:48pm in San Jose (SJC)
Mon Mar 17th 2025 United Airlines · UA 1069 Depart at 7:40pm from Chicago (ORD) Fly for 4h 36m Arrive at 10:16pm in San Jose (SJC)
Wed Mar 19th 2025 United Airlines · UA 1069 Depart at 7:40pm from Chicago (ORD) Fly for 4h 36m Arrive at 10:16pm in San Jose (SJC)
Fri Mar 14th 2025 United Airlines · UA 1069 Depart at 7:40pm from Chicago (ORD) Fly for 4h 36m Arrive at 10:16pm in San Jose (SJC)
Mon Mar 17th 2025 Alaska Airlines · AS 335 Depart at 7:00am from Chicago (ORD) Fly for 4h 44m Arrive at 9:44am in Portland (PDX)
Layover in Portland for 0h 41m
Mon Mar 17th 2025 Alaska Airlines · AS 3350 Depart at 10:25am from Portland (PDX) Fly for 1h 45m Arrive at 12:10pm in San Jose (SJC)
Mon Mar 17th 2025 Alaska Airlines · AS 335 Depart at 7:00am from Chicago (ORD) Fly for 4h 44m Arrive at 9:44am in Portland (PDX)
Layover in Portland for 3h 56m
Mon Mar 17th 2025 Alaska Airlines · AS 3379 Depart at 1:40pm from Portland (PDX) Fly for 1h 45m Arrive at 3:25pm in San Jose (SJC)
Mon Mar 17th 2025 Alaska Airlines · AS 587 Depart at 6:30am from Chicago (ORD) Fly for 4h 51m Arrive at 9:21am in Seattle (SEA)
Layover in Seattle for 3h 24m
Mon Mar 17th 2025 Alaska Airlines · AS 1114 Depart at 12:45pm from Seattle (SEA) Fly for 2h 10m Arrive at 2:55pm in San Jose (SJC)
Mon Mar 17th 2025 Alaska Airlines · AS 587 Depart at 6:30am from Chicago (ORD) Fly for 4h 51m Arrive at 9:21am in Seattle (SEA)
Layover in Seattle for 1h 59m
Mon Mar 17th 2025 Alaska Airlines · AS 1039 Depart at 11:20am from Seattle (SEA) Fly for 0h 54m Arrive at 12:14pm in Portland (PDX)
Layover in Portland for 1h 26m
Mon Mar 17th 2025 Alaska Airlines · AS 3379 Depart at 1:40pm from Portland (PDX) Fly for 1h 45m Arrive at 3:25pm in San Jose (SJC)
Fri Mar 14th 2025 Alaska Airlines · AS 587 Depart at 6:30am from Chicago (ORD) Fly for 4h 51m Arrive at 9:21am in Seattle (SEA)
Layover in Seattle for 1h 59m
Fri Mar 14th 2025 Alaska Airlines · AS 1039 Depart at 11:20am from Seattle (SEA) Fly for 0h 54m Arrive at 12:14pm in Portland (PDX)
Layover in Portland for 1h 26m
Fri Mar 14th 2025 Alaska Airlines · AS 3379 Depart at 1:40pm from Portland (PDX) Fly for 1h 45m Arrive at 3:25pm in San Jose (SJC)
Wed Mar 19th 2025 Alaska Airlines · AS 325 Depart at 1:10pm from Chicago (ORD) Fly for 4h 44m Arrive at 3:54pm in Portland (PDX)
Layover in Portland for 0h 36m
Wed Mar 19th 2025 Alaska Airlines · AS 422 Depart at 4:30pm from Portland (PDX) Fly for 2h 25m Arrive at 6:55pm in Los Angeles (LAX)
Layover in Los Angeles for 2h 0m
Wed Mar 19th 2025 Alaska Airlines · AS 3387 Depart at 8:55pm from Los Angeles (LAX) Fly for 1h 14m Arrive at 10:09pm in San Jose (SJC)
Sun Mar 16th 2025 United Airlines · UA 1069 Depart at 7:40pm from Chicago (ORD) Fly for 4h 36m Arrive at 10:16pm in San Jose (SJC)
Have flexible travel plans or looking for alternative routes given the chaos? Check out all the connection possibilities via a super helpful site created by @ismaelyws flightlist.io thanks to @andy_travels for the recommendation #travel #flights
There seem to be lots of sites launching at the moment that promise to find you cheap flights but not many have the professional finish of Flightlist by @ismaelyws #travel #flights
@ismaelyws Just tried out Flightlist for the first time. Really nice idea, well made, and just what I need at the moment 👍
Did you spot my recent article about how to score cheap one way flights? ✈️ FlightList is my new secret tool for discovering cheap routes, within a departure date range. Plus you can also search by country/region for departures & destinations. Powerful! 💪
Tips to help you find the cheapest flights from Chicago to San Jose (CHI to SJC).
❝As someone who works remotely & travels frequently, I always book one way flights and I'm flexible on my departure dates. I look for the best deals. Most sites require you to enter a specific departure date and clutter the page with uneccessary options, images and ads. I want something simple and minimal which allows me to search by departure date range & display a list of flights with the ability to filter according to my needs. So, I built FlightList to solve my own problem & help other travelers who may have the same frustration. It's how I imagine a flight booking site should be.❞
- Hans Desjarlais, Founder & Creator 