Spirit Airlines
Su, Mo, Tu, We, Th, and Fr
starting at $110
United Airlines
Su, Mo, Tu, We, Th, and Fr
starting at $130
American Airlines
Su, Mo, Th, and Fr
starting at $207
Compare airlines, prices, and flight durations for your trip
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 easiest way to get to your destination. The following airlines operate non-stop flights from Chicago to San Juan:
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Answers to questions about the route that travelers are most interested in.
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.
Spirit Airlines
Su, Mo, Tu, We, Th, and Fr
starting at $110
United Airlines
Su, Mo, Tu, We, Th, and Fr
starting at $130
American Airlines
Su, Mo, Th, and Fr
starting at $207
A non-stop 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.
Chicago — San Juan
02/07/2026
Departure
Direct flight
NK2205
starting at $161
Chicago — San Juan
03/17/2026
Departure
Direct flight
AA1060
starting at $127
Chicago — San Juan
04/02/2026
Departure
Direct flight
NK2205
starting at $242
Chicago — San Juan
04/28/2026
Departure
Direct flight
AA2845
starting at $126
Chicago — San Juan
02/13/2026
Departure
Direct flight
NK2205
starting at $411
Chicago — San Juan
05/06/2026
Departure
Direct flight
UA1996
starting at $257
Chicago — San Juan
05/07/2026
Departure
Direct flight
NK2205
starting at $205
starting at $98
starting at $126
starting at $257
starting at $51
The Chicago — San Juan route is served by a wide range of airlines: 4 in total, including Spirit Airlines, American Airlines, United Airlines, and JetBlue Airways. Competition among carriers gives passengers the opportunity to find tickets at attractive fares — with prices starting from $51. 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.
The cheapest one-way flight from Chicago to San Juan departs on 05/06/2026, is operated by JetBlue Airways and costs $51
The cheapest roundtrip flight from Chicago to San Juan departs on 03/04/2026, is operated by JetBlue Airways and costs $139
Fastest flight from Chicago to San Juan takes 4h 32m
There are direct flights on this route 5 days a week: Tu, We, Th, Fr, and Sa
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
We couldn't find any special offers for flights from Chicago to San Juan
The cheapest flight ticket from Chicago to San Juan according to data for the last 48 hours costs $51
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: May, March, April.
The fastest flights from Chicago to San Juan start from 4 hours 32 minutes in the air.
The following airlines operate direct flights on the route Chicago — San Juan: Spirit Airlines, American Airlines, United Airlines
The minimum one-way ticket price from Chicago to San Juan is $80 (May 2026), while the maximum is $111 (February 2026). On average, a ticket costs $98–$104.