Starting at $74
Starting at $90
Helping travelers to find the best flight offers
A direct flight is the easiest way to get to your destination. The following airlines operate non-stop flights from Chicago to San Juan:
We keep tight track on airlines' pre-holidays sales and other special offers occurences all the time to let you save maximum amount of funds while traveling to your family or just going out on vacation.
Starting at $74
Starting at $90
Flaut.Travel was designed and developed by a team dedicated to making the process of searching, comparing and booking airline tickets as easy and convenient as possible. Our service helps travelers to find and buy the cheapest flights from Chicago to San Juan. We have connected more than 40 airlines and airline ticketing agencies to help you find the most suitable and affordable flight option.
Below you will find a list of airlines operating flights on the Chicago — San Juan route and the starting prices for flights of each specific airline on it.
Spirit Airlines
Every day
Starting at $75
The cheapest one-way flight from Chicago to San Juan departs on 04/10/2025, is operated by Frontier Airlines and costs $49
The cheapest roundtrip flight from Chicago to San Juan departs on 02/22/2025, is operated by Frontier Airlines and costs $92
Fastest flight from Chicago to San Juan takes 4h 45m
There are direct flights on this route 2 days a week: Th and Fr
The distance between Chicago and San Juan is 3305km (2049 miles). There are 27 direct flights from Chicago to San Juan. The time difference between Chicago and San Juan is 2h . Flights from Chicago begin at 7:20 AM. The latest flight from Chicago departs at 2:20 PM.
We carefully collect statistics on the search and pricing of airlines and, based on these data, we make an assumption about future prices. Thus, you can better understand which season is the cheapest to fly from Chicago to San Juan
A direct flight is the most convenient and comfortable way to fly from Chicago to San Juan, despite the fact that sometimes flights with transfers can cost significantly less.
There appear to be no direct flights from Chicago to San Juan at this time.... Well, or something went wrong on our side and we couldn't find anything
The cheapest flight ticket from Chicago to San Juan according to data for the last 48 hours costs $49
Often the best time to buy tickets from Chicago to San Juan is 2 months before departure.
Based on statistics over the past years, the lowest prices for flights from Chicago to San Juan can be found flying in these months: March.
The fastest flights from Chicago to San Juan start from 4 hours 45 minutes in the air.
The following airlines operate direct flights on the route Chicago — San Juan:
We couldn't find any special offers for flights from Chicago to San Juan
