$186 Find Cheap Flights from San José to Chicago - Compare and Save

The cheapest return flight from San José to Chicago costs $491 on the route between San José (SJO) and Chicago O'Hare Intl Airport (ORD). It is also the most popular route.

If your flying dates are flexible, you should consider flying to Chicago on a Thursday, as we generally find the cheapest rates on that day for this route. On the other hand, Monday is the most expensive day to fly from San José to Chicago. For your return ticket, we recommend flying on a Tuesday and avoiding Saturdays for the best deals.

The cheapest month for flights from San José to Chicago is January, where tickets cost $385 (return) on average. On the other hand, the most expensive months are July and June, where the average cost of round-trip tickets is $638 and $561 respectively.

No, with an average price for the route of $528, prices are generally cheapest when you fly direct.

In the past 5 days, the cheapest round-trip tickets from San José to Chicago were found on Copa Airlines ($408) and Southwest ($414).

There are 3 airlines that fly nonstop from San José to Chicago. They are: American Airlines, Avianca and United Airlines. The cheapest price of all airlines flying this route was found with American Airlines at $332 for a round-trip flight. On average, the best prices for this route can be found at United Airlines.

Weekly flights between San José and Chicago historically see delays in approximately 7% of cases, with the average delay over the past year being 245 minutes.

Typically, flights leaving in the morning tend to face fewer delays, whereas flights in the early afternoon have historically encountered delays more often.

Statistically, Tuesday is the day of the week with the fewest delays on this flight route, while Friday has typically experienced more delays than other days.

Based on our data, American Airlines have experienced the fewest delays on this route in the past 12 months, with only about 5% of their flights encountering any delays.

Panama City (PTY) is the top choice – 35% of KAYAK users who clicked on 1-stop flights from San José to Chicago picked an itinerary connecting there.

Flights via Houston (IAH) offer the most affordable fares, with an average round-trip price of $362.

Consider flying via Guatemala City (GUA) for the shortest journey. The average one-way travel time for flights connecting there is 7h 20m.

If you prefer a quick connection, Fort Lauderdale (FLL) often has the shortest layovers from San José to Chicago, with an average of 1h 21m.