FromTo
Departure·1 pax, Economy

Cheapest flights for Chicago – San Juan (CHI – SJU)

Aviasales.ge will find you the cheapest airfare for Chicago – San Juan by comparing the ticket prices to San Juan using 45 agencies, five booking systems, and 728 airlines. Where exactly you buy your tickets for Chicago – San Juan is up to you.

Chicago – San Juan is most popular in November. During this period the average ticket price is 551.

Direct flight for from Chicago to San Juan

The easiest way to to get to your destination is a direct flight. Direct flights for from Chicago to San Juan are offered by:

  • United Airlines (daily UA1996)
  • American Airlines (daily AA2852)
  • Spirit Airlines (2 days per week, flight NK2080)

San Juan is served by 2 airports: Luis Munoz Marin International Airport and Isla Grande. Direct flights for Chicago – San Juan are operated by:
  • American Airlines, Spirit Airlines, United Airlines from O'Hare International Airport to Luis Munoz Marin International Airport
  • Southwest Airlines from Chicago Midway International Airport to Luis Munoz Marin International Airport
Flight with layover for the route from Chicago to San Juan

An alternative option for Chicago – San Juan (round-trip) would be a flight with a layover. Prices start at 551 up to 1 056.

A flight with a layover on the route Chicago – San Juan will allow you to make your trip more interesting. The layover could be in:

  • Tampa (flight WN994 Southwest Airlines)
  • New York (flight AA2485 American Airlines)
  • Atlanta (flight DL2400 Delta Air Lines)

This is a great chance to get to know these cities. Layovers are usually at least six hours.

Please keep in mind that depending on the number of days remaining until your departure, ticket prices for Chicago – San Juan could change by more than 62%.

Aviasales.ge suggests buying tickets for Chicago – San Juan in advance in order to choose the conditions for your flight that best suit your preferences and budget.

General information on flight Chicago – San Juan (CHI – SJU)
3,305 km
Distance
2 ⁠hr
Current time difference
21
Number of flights per week
₾376
Lowest price
₾0
Average ticket price
08:28
Earliest flight out
21:06
Latest flight out

Ticket prices for Chicago – San Juan by month *

Month One-way Round-trip
November 2025 01.11.2025
21.11 - 27.11.2025

* Prices found by users over the last 48 hours (they do not represent an offer).

Cheapest flight for from Chicago to San Juan found by our users over the last 48 hours: ticket with Spirit Airlines with a departure on 21.11.2025 and a price of 551 GEL.
Airlines flying from Chicago to San Juan
Airports serving Chicago – San Juan

Chicago airports serving flights to San Juan:

  • Chicago Midway International Airport (MDW)
  • O'Hare International Airport (ORD)

San Juan airports accepting flights from Chicago:

  • Luis Munoz Marin International Airport (SJU)