Cheap Flights from Chicago to San Juan Starting at $115

Helping travelers to find the best flight offers

Cheapest flights from Chicago to San Juan

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.

Airfare from Chicago to San Juan by month

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

Airlines operating on route

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.

Starting at $110

Starting at $158

Starting at $205

Direct Flights 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.

San Juan city image

ChicagoSan Juan

CHISJU

06/26/2025

Departure date

Direct flight

United Airlines

UA695

Starting at $268

San Juan city image

ChicagoSan Juan

CHISJU

04/28/2025

Departure date

Direct flight

United Airlines

UA695

Starting at $385

San Juan city image

ChicagoSan Juan

CHISJU

05/01/2025

Departure date

Direct flight

Spirit Airlines

NK261

Starting at $212

San Juan city image

ChicagoSan Juan

CHISJU

05/02/2025

Departure date

Direct flight

Spirit Airlines

NK261

Starting at $212

San Juan city image

ChicagoSan Juan

CHISJU

06/27/2025

Departure date

Direct flight

Spirit Airlines

NK2535

Starting at $424

Schedule of direct flights from Chicago to San Juan

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

Chicago airports overview

ORD
American Airlines
United Airlines
Frontier Airlines
Spirit Airlines
Airlines flying to this airport
$115
Starting at
$192
on average

San Juan airports overview

SJU
United Airlines
American Airlines
Frontier Airlines
Spirit Airlines
Airlines flying to this airport
$111
Starting at
$175
on average

Frequently asked questions (FAQ)

Answers to questions about the route that travelers are most interested in.

Special offers and sales on air tickets 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.

🫤

We couldn't find any special offers for flights from Chicago to San Juan

Alternative routes