Book Chicago to San Juan Flights

Book Chicago to San Juan flights at the cheapest fares with Rehlat’s competitive pricing and attractive offers. Our platform lets you filter the flight options as per the airline, duration, departure, or arrival time, with stops or non-stop easily. Chicago to San Juan flight fares start from 328.04 AUD, and a total of 13 flights connect the cities. The shortest flight duration between Chicago to San Juan is 10h 39m. To maximize your savings, book your return San Juan to Chicago flight ticket as well.

Airfares From Chicago to San Juan

Airline

From

To

Fare

05:20

Chicago

10h 39m
NonStop

16:59

San Juan

AUD 328.04

AUD 328.04

Book

12:15

Chicago

07h 04m
NonStop

20:19

San Juan

AUD 376.08

AUD 376.08

Book

05:00

Chicago

07h 50m
NonStop

13:50

San Juan

AUD 378.16

AUD 378.16

Book

06:00

Chicago

08h 48m
NonStop

15:48

San Juan

AUD 392.24

AUD 392.24

Book

06:00

Chicago

06h 16m
NonStop

13:16

San Juan

AUD 445.25

AUD 445.25

Book

07:00

Chicago

06h 52m
NonStop

14:52

San Juan

AUD 458.5

AUD 458.5

Book

12:34

Chicago

09h 19m
NonStop

22:53

San Juan

AUD 515.25

AUD 515.25

Book

08:26

Chicago

04h 39m
NonStop

14:05

San Juan

AUD 523.53

AUD 523.53

Book

06:59

Chicago

07h 13m
NonStop

15:12

San Juan

AUD 530.57

AUD 530.57

Book

10:44

Chicago

05h 57m
NonStop

17:41

San Juan

AUD 608.44

AUD 608.44

Book

Chicago to San Juan Fare Guide

How to book cheap flights from Chicago to San Juan?

Our platform offers cheap Chicago to San Juan flights by calculating the fares using a robust algorithm considering the dynamic pricing, airline availability and historic data. Our custom deals further ensure maximum savings on flight bookings.
Here’s the detailed way to book cheap Chicago to San Juan flights:

  • Login to Rehlat website or app
  • Enter the details and click on search
  • Select the itinerary and fill traveler details
  • Use code: MARHABA to get Save up to 66 TND
  • Proceed to payment
Post booking, you will get alerts regarding departure time, delayed flights, connecting flight changes, check-in baggage information and more on Whatsapp. Browse through our flight schedule to find the perfect flight that suits your travel plans.

Tips to find cheap flights from Chicago to San Juan

If you're looking to book cheapest Chicago to San Juan flight, here are some tips to help you save money:

  • Start searching for flights at least 65 days before your planned departure to increase the chances of finding cheaper deals.
  • Confirm your Chicago San Juan flight booking at least 4 weeks before your departure to avoid last-minute surcharges.
  • Consider booking red eye flights as they are 40% cheaper than daytime flights.
  • Be open to alternate airports for Chicago to San Juan flight route as they may offer cheaper fares.
  • . Avoid traveling during peak times like holidays, or special events to avoid higher airfares.
Insider tip: We recommend you to book your ChicagoSan Juan flight during 12AM-6AM since the flight fares tend less expensive during this period.

How can I web check-in for my upcoming Chicago to San Juan flight?

Web check-in is generally available from 24 hours up to 60 minutes before the scheduled departure time of your flight. However, it is always recommended to check the airline's web check-in policy and timing.
To check-in your Chicago to San Juan flight:

  • Visit the airline website
  • Click on web check-in option
  • Enter the PNR number and your name
  • Proceed further to generate the boarding pass
You can also choose an online web check-in service while booking a flight and skip the long queues at the airport. Our team will web check-in for your Chicago to San Juan flight and secure your preferred seat.

How do I cancel Chicago to San Juan flight tickets?

You can cancel your Chicago to San Juan flights ticket easily in two ways on Rehlat:

  • Contacting our customer support team.
  • Through the Self-help section.
Customer Support Team: Self-help Section:

Tips for travelers flying between Chicago and San Juan

Arrive early at the airport: If you have checked bags, it's best to go to Chicago airport at least two hours before your flight is due to depart so that you'll have enough time to check in, get through security, and get to the boarding gate before it closes.
Be ready with travel documents: Before you depart for the airport, double-check that you have all of your travel documents, including your passport or ID card, airline ticket, and any other relevant documents required by San Juan. This will assist you in avoiding any unforeseen problems or delays.
Pack wisely: Carry just what you absolutely must have on Chicago to San Juan flight. You'll be able to move around more easily and save money by not checking additional bags.
Stay in touch: Bring a functional mobile phone or other form of communication with you on your journey in case you need to call someone in an emergency or keep up with any news or changes regarding your travel plans.
Dress appropriately: In both Chicago and San Juan, dress comfortably and in accordance with the weather. A lightweight jacket or jumper may be something you want to take because the air aboard a flight may occasionally feel chilly.
Be mindful of local customs: Keep in mind that there are rigorous social and clothing norms in Puerto Rico that you must abide by. Before going to San Juan, make sure you learn about and abide by the local laws and traditions.
Plan and book in advance: Advance planning can help you save money and prevent last-minute difficulties when booking a ticket and lodging. To obtain the cheapest pricing, search online for special discounts and get your tickets in advance.

Which documents must I bring with me on Chicago to San Juan flight?

A few documents that is advised to carry on Chicago to San Juan flight are as follows:

  • Valid passport
  • ID card
  • Airline ticket
Additionally, it is crucial to determine and carry other additional travel papers, such as health certifications or visas, based on your nationality and the intention of your trip.