Cheap flights from San Juan to Chicago

One-way fares from $109 · SJU → CHI · prices found by travellers in the last 48 hours

Compare all dates Chicago → San Juan
Cheapest fare
$109

Frontier Airlines · Tue, Jan 12

Cheapest month
January

from $109

Direct flights
Not recently

Usually 1+ stop

Quickest trip
6h 38m

3,300 km

Get a price alert

We'll email you when San Juan → Chicago drops to your price. It's free, and you can stop any time.

Today's cheapest fare is $109. We'll send one email to confirm. See our privacy policy.

Cheapest month to fly from San Juan to Chicago

Lowest one-way fare per person in each month. Choose a month to see every date.

  1. December 2026 $124
  2. January 2027 Cheapest $109

Cheapest dates in January 2027

The lowest fares we've seen for each day, cheapest first.

Frontier Airlines
Depart02:41 Tue, Jan 12SJU → ORD 6h 49m · 1 stop
$109one way, per person
View deal
See every date in January 2027 →

Plan the rest of your trip to Chicago

Where to stay, what to do and getting around, from our travel partners.

Where to stay

Hotels in ChicagoCompare places to stay on Booking.com Find hotels →

Things to do

Things to do in ChicagoTours, attractions and day trips on Klook Explore →

Getting around

Airport transfer in ChicagoPre-book a driver to meet you at arrivals, with Kiwitaxi Book a transfer → Car hire in ChicagoCompare rental cars from major brands on EconomyBookings Compare cars →

Stay connected

eSIM for United StatesMobile data from the moment you land, by Airalo Get eSIM →

About flights from San Juan to Chicago

San Juan (SJU) and Chicago (CHI) are about 3,300 km apart. We haven't seen direct fares on this route recently, so expect at least one stop; the quickest journey we've seen takes about 6h 38m. Over the next few months, one-way fares start from $109, and January 2027 is currently the cheapest month to fly.

These prices come from searches travellers made in the last 48 hours, so they move quickly. If you see a good fare, it's worth booking soon. FlightsExp is free to use: you book directly with our travel partner.

Frequently asked questions

How much is a flight from San Juan to Chicago?

The cheapest one-way fare we've seen recently is $109 with Frontier Airlines, departing Tuesday, January 12, 2027. Over the coming months, the lowest fare in each month ranges from $109 to $124.

What is the cheapest month to fly from San Juan to Chicago?

January 2027 currently has the lowest fares, from $109 one way.

Are there direct flights from San Juan to Chicago?

We haven't seen direct fares recently, so most journeys include at least one stop.

How long is the flight from San Juan to Chicago?

The quickest journey we've seen takes about 6h 38m. San Juan and Chicago are around 3,300 km apart.

Which airlines fly from San Juan to Chicago?

Recent fares on this route were with Frontier Airlines.

More cheap flights from San Juan

Compare flights to Chicago from other cities →