Beginning of main content
Trip Type
Flight 1
Flight 2
Flight 3
Flight 4
Flight 5

Search over 895,000 properties worldwide and 550 airlines worldwide.

Search over a million flights, hotels, packages, and more

No Expedia cancellation fee to change or cancel almost any hotel reservation.

Cheap ORD to SJU Flights

Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.

Chicago to San Juan Route Information
Origin Airport O'Hare Intl.
Destination Airport Luis Munoz Marin Intl.
Flight Price $208
Distance 2,073 mi
Airlines Serving American Airlines, Frontier Airlines, JetBlue Airways, Spirit Airlines, United

Chicago

$318.40

Cheap ORD to SJU Flights

  • Question : What day has the most flight time options?
    Answer : When you’re flying from ORD to SJU, the day with the most flight times is Saturday, with seven different options. The day of the week with the least amount of times is Thursday with only three departures.
  • Question : What is the cheapest day to fly?
    Answer : The cheapest day to fly from Chicago to San Juan is on Tuesday. So, if you want to save some money on your next business trip look for flights on Tuesday.
  • Question : What is the cheapest airline flying from Chicago to San Juan?
    Answer : Flight prices are hitting highs of $1,443 over the next three months when flying to SJU from ORD. Check out Spirit Airlines, as customers have been purchasing tickets at just $238.
  • Question : How long does it take to fly from Chicago to San Juan?
    Answer : United Airlines currently holds the shortest travel time with four hours and 25 minutes. So, you would arrive in San Juan at 2:05 PM AST if you left Chicago at 7:40 AM CST. Remember, there is a time change of two hours.
  • Question : Can I change the date of my flight?
    Answer : You sure can and you may save money by changing when you take off. The cheapest day to fly in February is Tuesday. Being flexible with your travel days can provide you extra savings when booking.
  • Question : How many flights are there per day from Chicago to San Juan?
    Answer : The number of flight times varies by day of the week, but on average, ORD to SJU sees five different options. That is lower than the national average of nine.
  • Question : What is the cheapest day to fly to San Juan?
    Answer : As of Jan 21st, the cheapest day to fly from Chicago to San Juan is Jan 28th. Tickets are presently $238, which is 36% below the average price for this route.

Dec 24, 2018

Keep up the good work

Dec 22, 2018

Just wish it had left on time, instead of taxiing for almost 30min before take off

Dec 19, 2018

Quick smooth check in and flight.

Dec 6, 2018

we need free food on this route chicago san juan, since is outside of US mainland, flight attendants were great.

Dec 2, 2018

Flight was delayed and planes changed but it wasn’t too bad.

Nov 29, 2018

Felt very cramped and head cushion should be adjustable to accommodate all size passengers not just tall.

Nov 20, 2018

I'm still waiting for my luggage to arrive.

Oct 22, 2018

The WiFi is TERRIBLE! But the economy seats were fine, boarding was quick, and staff very friendly

Sep 27, 2018

Free carry on bag charges were included in flight ticket payment Great advance and good purchase

Sep 26, 2018

Verry good