Skip to main content
Beginning of main content

Cheap Flights from San Jose to Chicago $238.4

Search over 321,000 hotels worldwide and 400 airlines worldwide.
Secure incredible value with Expedia's Price Guarantee.
No Expedia cancellation fee to change or cancel almost any hotel reservation.

Cheapest Flights from San Jose to Chicago (SJC to MDW)

Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.

Interesting Facts About Flights from San Jose to Chicago (SJC to MDW)

Question : Is this route your best bet for getting to Chicago with minimal delays?
Answer : Using the combined on-time percentage and average delay breakdown, San Jose to Chicago currently has a 3 out of a possible 5 star rating. A 3-star rating means you should feel slightly worried about getting to Chicago on time.

Question : About how long is the flight from San Jose to Chicago?
Answer : On average, the flight time from SJC to MDW is four hours and six minutes.

Question : Which airline is struggling to get to Chicago on time?
Answer : XOJET is delayed on 100% of flights from Norman Y. Mineta San Jose International Airport (SJC) to Chicago Midway International Airport (MDW) at the moment. If you should choose this airline, be sure to track the flight status to stay on top of the departure time.

Question : How often is the Norman Y. Mineta San Jose International Airport (SJC) to Chicago Midway International Airport (MDW) route delayed?
Answer : The San Jose to Chicago route has a 78% on-time rate, ranking in the top half of the world in getting their passengers to their destinations on schedule. If a flight is late, though, expect an average of less than half an hour added to your flight time.

Question : How many departure times from Norman Y. Mineta San Jose International Airport (SJC) to Chicago Midway International Airport (MDW) are there on a daily basis?
Answer : Of course the day of the week matters, but on average, only one flight time exists when you fly from SJC to MDW. That is lower than the national average of five.

Question : What is the cheapest round-trip ticket you can get to Chicago?
Answer : Delta Air Lines is the leader in keeping prices down for their passengers over the next three months. Fares are being booked at just $264, which is quite a deal when compared to the high-end bookings of $871.

Question : Which airline has been the most dependable in getting passengers to their destination on time?
Answer : Delta Air Lines will have you to MDW on schedule 100% of the time. Don't spend more time waiting in an airport than you have to and stick with Delta Air Lines on this route. Hopefully they keep that perfect record alive.