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 are most convenient between Chicago and San Juan?

Whether it’s cost or connection time, the right airport combination can make a difference.

• Airports in Chicago: There are 3 airports in Chicago - Midway, O'Hare, Rockford.
• Airports in San Juan: Isla Grande is also worth considering.

In some cases, flying into a secondary airport can also reduce transfer costs. Connections from multiple airports give you more flight options and airlines.

Find flights from Chicago Midway to San Juan that suit your schedule

Use Jetcost to sort and filter results based on your preferred flight time, number of stops, price range, or airline. View deals from the best airlines and travel agencies.

Other popular destinations

Interested in Puerto Rico? These cities are also in demand: Aguadilla, Culebra Airport, Ponce, San Juan, Vieques Airport.

Connecting flights can be cheaper but often mean longer layovers. You can easily select either direct or connecting flights with a single click using the filters.