Cheap Flights from Chicago to San Juan Starting at $91

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

Airlines operating on route

Starting at $91

Starting at $122

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

07/02/2025

Departure date

Direct flight

Spirit Airlines

NK2535

Starting at $291

San Juan city image

ChicagoSan Juan

CHISJU

09/19/2025

Departure date

Direct flight

United Airlines

UA1996

Starting at $179

San Juan city image

ChicagoSan Juan

CHISJU

08/22/2025

Departure date

Direct flight

Spirit Airlines

NK2080

Starting at $216

San Juan city image

ChicagoSan Juan

CHISJU

08/28/2025

Departure date

Direct flight

United Airlines

UA1996

Starting at $161

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:

Chicago airports overview

MDW
Frontier Airlines
Airlines flying to this airport
$91
Starting at
$91-38%
on average
ORD
United Airlines
Spirit Airlines
Frontier Airlines
Airlines flying to this airport
$91
Starting at
$126
on average

San Juan airports overview

SJU
+2
American Airlines
Spirit Airlines
Frontier Airlines
Airlines flying to this airport
$115
Starting at
$207
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.

Alternative routes