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

Airfare from Chicago to San Juan by month

June 2025
Lowest price
on average:
$162
  • Avg Price

Airlines operating on route

Starting at $121

Starting at $124

Direct Flights from Chicago to San Juan

San Juan city image

ChicagoSan Juan

CHISJU

06/09/2025

Departure date

Direct flight

Spirit Airlines

NK2535

Starting at $704

San Juan city image

ChicagoSan Juan

CHISJU

06/10/2025

Departure date

Direct flight

United Airlines

UA695

Starting at $323

San Juan city image

ChicagoSan Juan

CHISJU

06/12/2025

Departure date

Direct flight

United Airlines

UA1996

Starting at $390

San Juan city image

ChicagoSan Juan

CHISJU

06/14/2025

Departure date

Direct flight

Spirit Airlines

NK2535

Starting at $304

San Juan city image

ChicagoSan Juan

CHISJU

06/18/2025

Departure date

Direct flight

United Airlines

UA695

Starting at $445

San Juan city image

ChicagoSan Juan

CHISJU

06/28/2025

Departure date

Direct flight

United Airlines

UA695

Starting at $222

San Juan city image

ChicagoSan Juan

CHISJU

07/21/2025

Departure date

Direct flight

United Airlines

UA695

Starting at $224

San Juan city image

ChicagoSan Juan

CHISJU

08/24/2025

Departure date

Direct flight

United Airlines

UA1996

Starting at $237

San Juan city image

ChicagoSan Juan

CHISJU

08/25/2025

Departure date

Direct flight

American Airlines

AA2852

Starting at $202

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:

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Unable to find information about the schedule of direct flights from

Chicago airports overview

ORD
United Airlines
American Airlines
Spirit Airlines
Frontier Airlines
Airlines flying to this airport
$116
Starting at
$198-50%
on average
MDW
Southwest Airlines
Airlines flying to this airport
$297
Starting at
$297
on average

San Juan airports overview

SJU
+2
American Airlines
Spirit Airlines
Frontier Airlines
Airlines flying to this airport
$116
Starting at
$207
on average

Frequently asked questions (FAQ)

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

How much is the cheapest flight ticket from Chicago to San Juan?

The cheapest flight ticket from Chicago to San Juan according to data for the last 48 hours costs $115

When is the best time to buy air tickets on the route Chicago — San Juan?

Often the best time to buy tickets from Chicago to San Juan is 2 months before departure.

When is the cheapest time of year to fly from Chicago to San Juan?

Based on statistics over the past years, the lowest prices for flights from Chicago to San Juan can be found flying in these months: June.

How long does it take to fly from Chicago to San Juan?

The fastest flights from Chicago to San Juan start from 7 hours 58 minutes in the air.

Which airline can fly direct from Chicago to San Juan?

The following airlines operate direct flights on the route Chicago — San Juan: Spirit Airlines, United Airlines, American Airlines

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