Flight prices from Chicago Midway to San Juan

There’s no fixed price — fares between Chicago and San Juan can vary a lot by day or time.

Choose a date to explore the best fares now.

The lowest fares are often found with some flexibility in travel dates. If your plans are flexible, you’ll have a better chance of finding cheap flights.

Which airports serve Chicago and San Juan?

When planning a trip of about 2059 mi, it's a good idea to check flights from surrounding airports too.

• Airports in Chicago: Chicago is connected to 3 airports - Midway, O'Hare, Rockford.
• Airports in San Juan: Another nearby option is Isla Grande.

The closest airport isn’t always the cheapest — it’s worth checking the alternatives too. In some cities, smaller airports offer lower fares than the main ones.

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

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 Expedia, Ryanair, British Airways, Easyjet, and more.

Other popular destinations

Thinking about traveling to Puerto Rico? Other users also viewed: Aguadilla, Culebra Airport, Ponce, San Juan, Vieques Airport.

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.