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

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

Select your dates to check current offers.

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.

Best airport options between San Juan and Chicago

If you're open to flying into or out of more than one airport, you’ll have more routes to compare.

• Airports in San Juan: An alternative to San Juan - Luis Muñoz Marín is Isla Grande.
• Airports in Chicago: In Chicago, 3 airports are available - Midway, O'Hare, Rockford.

Some airports offer extras like lounges, fast track, or self check-in — good to keep in mind. Comparing airports by services offered helps you balance cost and comfort.

Plan your perfect flight from San Juan to Chicago

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.