Starting at $133
Starting at $146
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 San Juan to Chicago:
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 $133
Starting at $146
The cheapest one-way flight from San Juan to Chicago departs on 06/21/2025, is operated by Frontier Airlines and costs $132
The cheapest roundtrip flight from San Juan to Chicago departs on 07/10/2025, is operated by Frontier Airlines and costs $52
Fastest flight from San Juan to Chicago takes 5h 16m
There are direct flights on this route 1 day a week: Tu
The distance between San Juan and Chicago is 3305km (2049 miles). There are 30 direct flights from San Juan to Chicago. The time difference between San Juan and Chicago is 2h . Flights from San Juan begin at 6:09 AM. The latest flight from San Juan departs at 3:56 PM.
San Juan — Chicago
06/09/2025
Departure date
Direct flight
UA2088
Starting at $356
San Juan — Chicago
06/10/2025
Departure date
Direct flight
AA1184
Starting at $191
San Juan — Chicago
06/21/2025
Departure date
Direct flight
NK2534
Starting at $165
San Juan — Chicago
10/01/2025
Departure date
Direct flight
UA2088
Starting at $217
Unable to find information about the schedule of direct flights from
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 San Juan to Chicago
Below you will find a list of airlines operating flights on the San Juan — Chicago route and the starting prices for flights of each specific airline on it.
A direct flight is the most convenient and comfortable way to fly from San Juan to Chicago, despite the fact that sometimes flights with transfers can cost significantly less.
We couldn't find any special offers for flights from San Juan to Chicago
The cheapest flight ticket from San Juan to Chicago according to data for the last 48 hours costs $132
Often the best time to buy tickets from San Juan to Chicago is 2 months before departure.
The fastest flights from San Juan to Chicago start from 5 hours 16 minutes in the air.
The following airlines operate direct flights on the route San Juan — Chicago: United Airlines, American Airlines, Spirit Airlines
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 San Juan to Chicago. We have connected more than 40 airlines and airline ticketing agencies to help you find the most suitable and affordable flight option.
