How much is a flight from San Juan to Chicago Midway?

Prices vary based on date, airline, and availability. Compare several options if you're flying between San Juan and Chicago.

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

Fares change often — checking several times throughout the week can make a big difference. Booking in advance often means access to lower prices for the San Juan - Chicago Midway route.

Flying between San Juan and Chicago? 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 San Juan: You can fly from either San Juan - Luis Muñoz Marín or Isla Grande.
• Airports in Chicago: Chicago has 3 airports - Midway, O'Hare, Rockford.

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

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

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 United States? Other users also viewed: Las Vegas, Los Angeles, Miami, New York City, Orlando.

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.