Cheap Flights from San Jose to Chicago

Prices were available within the past 7 days and starts at $129 for one-way flights and $170 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Reviews from verified customers

Mar 2, 2020

It was excellent fly.

Feb 26, 2020

These seats were really uncomfortable for a short person

Feb 21, 2020

I tried to re use my plastic glass.... the steward told me he is not allowed to reuse glasses.... That’s unacceptable...

Feb 6, 2020

The in flight staff was some of the best ever. The first class food was awful. The beef cooked dry and was uneatable. The vegetables were over cooked and gray. The salad looked uneatable. Potatoes and gravy were okay.

Jan 6, 2019


Apr 30, 2018

We did not have a free checked bag. Also not a purchase through Expedia but daughter on the same flight even after asking was not charged an infant charge until arrival at airport and it took over 30 minutes to get the rate from United’s actuary. It was stressful.

Apr 16, 2017

anytime someone puts their seat back it hits my knees and my knees are sore for 1 or 2 days. Seats are just to close

San Jose to Chicago route information

Origin Airport Juan Santamaria Intl.
Destination Airport O'Hare Intl.
Airlines Serving Aeromexico, Air Canada, Alaska Airlines, American Airlines, Avianca, Copa, Delta, JetBlue Airways, Spirit Airlines, United
Flight Price $169
Distance 2,220 mi

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