How much should you expect to spend for a flight from San José to Chicago Midway?

Flight prices from San José to Chicago change depending on demand and time of booking.

Pick a travel date to see today’s available fares.

Studies show that flying midweek — like on a Tuesday or Wednesday — can be cheaper than weekend flights. Still, airfares change frequently, so check updated prices on Jetcost.

Which departure and arrival airports are available?

Between San José and Chicago, flight options may depend on the combination of airports available.

• Airports in San José: Tobias Bolanos is another departure point near San José - Juan Santamaria International.
• Airports in Chicago: Chicago is served by 3 airports - Midway, O'Hare, Rockford.

Sometimes flying into a nearby city can be more cost-effective. When a city has multiple airports, it’s worth comparing different flight combinations.

Plan your perfect flight from San José to Chicago Midway

Jetcost gives you full control over your flight search. Filter by date, time, duration, price, and airline. See round-trip and one-way options from low-cost and full-service carriers and more.

Other popular destinations

Planning a trip to United States? Other frequent searches include: Atlanta, Los Angeles, Miami, New York City, Orlando.

Some airlines include baggage in the fare, others don’t — always check the details before booking. If you're looking for round-trip flights, you can easily see the most convenient combinations.