Cheap Flights from Chicago to San Juan from $110

Frequently Asked Questions

• What are the cheapest flights from Chicago to San Juan (CHI-SJU)?

  Based on Trip.com data, Spirit Airlines offers one-way fares as low as $110 on Cheapest nonstop routes (e.g. ORD to SJU on Fri, May 22), while Spirit Airlines offers Cheapest nonstop round-trips from $192 departing on Tue, May 26 and returning on Thu, May 28.

• Which airlines offer direct flights from Chicago to San Juan?

  At the moment, you can catch a nonstop flight from Chicago to San Juan with the following airlines, including: United Airlines Frontier Airlines Spirit Airlines Delta Air Lines American Airlines Selected airlines are based on historical data collected from flight bookings users made on Trip.com within the last 90 days.

• How long does it take to fly from Chicago (CHI) to San Juan (SJU) and what is the distance?

  It takes around 4 hours 50 minutes to fly from Chicago (CHI) to San Juan (SJU).

• When is the best time to book flights from Chicago to San Juan?

  By analyzing data from all airlines on the Trip.com flight calendar, it looks like the best time to book a flight from Chicago to San Juan is around 40 days (6 weeks) in advance, and the best time to fly is usually on Tuesday, Wednesday, and Saturday. Tuesday typically offers the cheapest flights for departure, while Saturday offers the best return deals.

• How many flights are there per week from Chicago to San Juan?

  Based on Trip.com data in the past 4 weeks, there is 1 flight per week flying from Chicago to San Juan. You can check the weekly schedule for popular airlines on this route below: United Airlines: S/M/T/W/T/F/S -- UA1996 (09:11) American Airlines: -/M/T/-/-/-/- -- AA2845 (08:44)

• How can I find the best deals on flights from Chicago to San Juan?

  To find best deals on flights from Chicago to San Juan, you can use various tools on Trip.com:
  · Be flexible with your travel dates to get the cheapest flight deal. Now the cheapest flight deal is on Fri, May 22, with one-way flights priced at just $110.
  · Compare airlines strategically. Budget carriers often provide the lowest base fares, while we found the most affordable airline currently operating on this route is Spirit Airlines.
  · Set up price alerts to easily monitor ticket prices without having to check every day.
  · Check Trip.com flight deals and promo codes frequently.
  · Avoid peak season unless you book very early. It seems the peak season for San Juan travel is around July.
  · Get exclusive promo codes for Trip.com app users.

• When are flight tickets from Chicago (CHI) to San Juan (SJU) the cheapest?

  The cheapest months to fly from Chicago to San Juan is October, when demand for travel is lower.

• Which upcoming date is cheapest to fly from Chicago to San Juan on?

  After crunching the numbers on our May flight calendar, it's currently cheapest to fly from Chicago to San Juan on May 26, 2026 with Frontier Airlines, with prices starting at $180.

• Which airports can I fly to for San Juan from Chicago?

  You can land at any one of the following hubs in San Juan, with Chicago O'Hare International Airport to Luis Munoz Marin International Airport (ORD-SJU) is by far the most common option on this route: Luis Munoz Marin International Airport (SJU) Fernando Luis Ribas Dominicci Airport (SIG).

• Is there any time difference between Chicago and San Juan?

  The time difference between San Juan and Chicago is 2h.

• How do I change or cancel my ticket from Chicago to San Juan?

  Tickets can only be changed or canceled if permitted by airline policy. To submit a change or cancellation request, go to the flight bookings page, select the option to change or cancel your booking, choose the relevant passengers and segment, and submit a request. Please note that additional charges may apply according to the airline ticket policy. However, if the flight has been rescheduled and you would like to change or cancel your ticket, you can submit an involuntary cancellation request. For more details about change and cancellation policies, please check the customer support pages.