Find out what a flight from San Juan to Chicago Midway might cost

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

$74 is the best price recorded in the last 15 days.

Try shifting your departure forward or backward by a day to find better options. If you’re looking for a good deal, consider flying outside peak hours as well.

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.

Plan your perfect flight from San Juan 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 like Delta, United, American, 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.