Starting at $129
Starting at $252
Starting at $53
Starting at $145
Helping travelers to find the best flight offers
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.
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.
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.
The Chicago — San Juan route is served by a wide range of airlines: 4 in total, including United Airlines, Spirit Airlines, JetBlue Airways, and Frontier Airlines. Competition among carriers gives passengers the opportunity to find tickets at attractive fares — with prices starting from $53. Our service helps compare all available offers within seconds and choose the most convenient option. You can filter flights by price, departure time, or baggage rules to make your trip as comfortable as possible. With so many airlines, there’s always a chance to catch special promotions and save.
Starting at $129
Starting at $252
Starting at $53
Starting at $145
Chicago — San Juan
12/23/2025
Departure
Direct flight
UA1996
Starting at $616
Chicago — San Juan
12/24/2025
Departure
Direct flight
UA695
Starting at $548
Chicago — San Juan
12/20/2025
Departure
Direct flight
UA695
Starting at $627
Chicago — San Juan
12/22/2025
Departure
Direct flight
NK1481
Starting at $252
Chicago — San Juan
12/26/2025
Departure
Direct flight
NK1481
Starting at $620
Chicago — San Juan
01/13/2026
Departure
Direct flight
UA695
Starting at $287
Chicago — San Juan
02/24/2026
Departure
Direct flight
UA695
Starting at $148
Chicago — San Juan
03/03/2026
Departure
Direct flight
UA1996
Starting at $129
Spirit Airlines
Su, Mo, Tu, We, Th, and Fr
Starting at $110
United Airlines
Su, Mo, Tu, We, Th, and Fr
Starting at $129
American Airlines
Su, Mo, Th, and Fr
Starting at $206
The cheapest one-way flight from Chicago to San Juan departs on 03/03/2026, is operated by JetBlue Airways and costs $53
The cheapest roundtrip flight from Chicago to San Juan departs on 02/24/2026, is operated by JetBlue Airways and costs $115
Fastest flight from Chicago to San Juan takes 8h 20m
There are no direct flights on this route.
The distance between Chicago and San Juan is 3305km (2049 miles). The average flight duration is 4h 32m. 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 5:40 AM. The latest flight from Chicago departs at 2:20 PM
The cheapest flight ticket from Chicago to San Juan according to data for the last 48 hours costs $53
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, February.
The fastest flights from Chicago to San Juan start from 8 hours 20 minutes in the air.
The following airlines operate direct flights on the route Chicago — San Juan: United Airlines, Spirit Airlines
The minimum one-way ticket price from Chicago to San Juan is $53 (March 2026), while the maximum is $55 (February 2026). On average, a ticket costs $54–$55.
We couldn't find any special offers for flights from Chicago to San Juan