Airlines operating on route
Starting at $121
Starting at $124
Helping travelers to find the best flight offers
Starting at $121
Starting at $124
Chicago — San Juan
06/09/2025
Departure date
Direct flight
NK2535
Starting at $704
Chicago — San Juan
06/10/2025
Departure date
Direct flight
UA695
Starting at $323
Chicago — San Juan
06/12/2025
Departure date
Direct flight
UA1996
Starting at $390
Chicago — San Juan
06/14/2025
Departure date
Direct flight
NK2535
Starting at $304
Chicago — San Juan
06/18/2025
Departure date
Direct flight
UA695
Starting at $445
Chicago — San Juan
06/28/2025
Departure date
Direct flight
UA695
Starting at $222
Chicago — San Juan
07/21/2025
Departure date
Direct flight
UA695
Starting at $224
Chicago — San Juan
08/24/2025
Departure date
Direct flight
UA1996
Starting at $237
Chicago — San Juan
08/25/2025
Departure date
Direct flight
AA2852
Starting at $202
A direct flight is the easiest way to get to your destination. The following airlines operate non-stop flights from Chicago to San Juan:
Unable to find information about the schedule of direct flights from
The cheapest flight ticket from Chicago to San Juan according to data for the last 48 hours costs $115
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: June.
The fastest flights from Chicago to San Juan start from 7 hours 58 minutes in the air.
The following airlines operate direct flights on the route Chicago — San Juan: Spirit Airlines, United Airlines, American Airlines
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.
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.
We couldn't find any special offers for flights from Chicago to San Juan
The cheapest one-way flight from Chicago to San Juan departs on 08/26/2025, is operated by Spirit Airlines and costs $115
The cheapest roundtrip flight from Chicago to San Juan departs on 07/11/2025, is operated by Frontier Airlines and costs $52
Fastest flight from Chicago to San Juan takes 7h 58m
There are no direct flights on this route.
The distance between Chicago and San Juan is 3305km (2049 miles). There are 31 direct flights from Chicago to San Juan. The time difference between Chicago and San Juan is 2h . Flights from Chicago begin at 8:26 AM. The latest flight from Chicago departs at 6:03 PM.
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.
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.
