Cheap flights from Chicago to San Juan, Puerto Rico (MDW - SJU)

As a rule, buying flight tickets from Chicago to San Juan expends a lot. Using our service of searching for cheap flight tickets, you will be able to save a significant sum of money! We will help tip to buy flight tickets from Chicago to San Juan at the most favorable prices.

Out service helps you to find tickets from Chicago to San Juan in the most reliable travel agencies and booking systems, including all the airline companies. We don't sell tickets and don't do any surcharges, we just find the best offers - you choose yourself where you want to buy flight tickets Chicago - San Juan at the best price!

We also recommend you to look through the prices for return tickets from San Juan to Chicago.

Flights price per day for Junio 2025

Chicago - San Juan
1 stop
109
Chicago - San Juan
115
Chicago - San Juan
115
Chicago - San Juan
115
Chicago - San Juan
115
Chicago - San Juan
1 stop
121
Chicago - San Juan
139
Chicago - San Juan
1 stop
156
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Airfares found by our users in the past 24 hours

The cheapest flight from Chicago to San Juan is 259 on Frontier Airlines, departing on 09.06.2025 and returning on 12.06.2025.
The price for these dates could change. Use search to get the best price.
AirlineDeparture dateReturn datePrice
Frontier Airlines09.06.202512.06.2025from 259

Average round-trip airfares from Chicago to San Juan by months

MesRound-Trip
Mayo 2025find now
Junio 202509.06 - 12.06from 259
Julio 2025find now
Agosto 2025find now
Septiembre 2025find now
Octubre 2025find now
Noviembre 2025find now
Diciembre 2025find now
Enero 2026find now
Febrero 2026find now
Marzo 2026find now
Abril 2026find now

The price which were found by our clients for the latest several days. Given ticket prices could change. It's connected with the presence of flight tickets while booking.

Airlines are flying from Chicago to San Juan

Southwest Airlines

Airports

Other airports in Chicago: Merrill C Meigs (CGX), Burqin (CHI), Melville Hall (DPA), Pevek (PWK).

Airports in San Juan: Isla Grande (SIG), Luis Munoz Marin (SJU).

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