How to get the best price from Chicago Midway to San José?

Depending on when you travel and how far in advance you book, fares between Chicago and San José can differ a lot.

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

Search engines like Jetcost can highlight price changes in just seconds. For example, some users find better prices by flying on one day of the week over another — try several searches to spot the cheapest day.

Flying between Chicago and San José? Consider these airports

Depending on your destination and where you’re starting from, it might make sense to look beyond the main hubs.

• Airports in Chicago: Chicago has 3 airports - Midway, O'Hare, Rockford.
• Airports in San José: Besides San José - Juan Santamaria International, also consider Tobias Bolanos.

Check if your destination airport has a rail link — it can make getting around easier. Jetcost lets you view options from all Chicago airports in a single search.

Match your flight search to your preferences: Chicago Midway – San José

Jetcost makes it easy to find the right flight. Set filters for flight time, price, number of stops, and preferred airline. You’ll see offers from the best airlines and travel agencies.

Other popular destinations

Thinking about traveling to Costa Rica? Other users also viewed: Golfito, Liberia, Quepos, San José, Tamarindo.

Don’t forget to check change or cancellation policies, especially if your plans aren’t final. For a more targeted search, you can also set price limits directly in the filters.