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Fares from $100 One Way, $174 Round Trip from San Juan to Chicago

Prices starting at $174 for return flights and $100 for one-way flights to Chicago were the cheapest prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.

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More About Flying To Chicago from San Juan

Route Information for Flights from San Juan to Chicago

Origin Airport IATA CodeSJU
Destination Airport IATA CodeCHI
Direct Flight Airlines
Earliest Flight Arrival
Latest Flight Arrival

Flights Review

Feb 29, 2020

Free carrie on luggage would be nice

Feb 6, 2020

Flight delay was inconvenient. Safety first important to me.

Jan 6, 2020

Thank you.

Jun 29, 2019

Everything exellent

Jan 22, 2019

Lower you rates

Jan 16, 2019

Was disappointed seat did not recline (was told it was because I was in front of wing seats-would have liked to know at seat selection time).

Aug 17, 2018

On SJU Puerto Rico DIDN'T bring the first access to the military without uniform we as military can't use the uniform to get a civilian fly

Jul 5, 2018

no in-flight entertainment, like American offers

Jun 12, 2018

No in-flight entertainment besides the limited wifi, which worked for a while (you have to pay if you want to see a movie o tv show).

Apr 17, 2018

Best attentive staff I’ve ever experienced. All attendants were friendly and smiling. Best trip I’ve had thank you!!

San Juan to Chicago

Orbitz guarantees you low prices on flights from San Juan to Chicago. In addition to low fares on San Juan to Chicago flights, Orbitz offers fantastic savings on hotels, cruises, vacation packages, and more.

Earn Miles While Saving

Besides helping you fly for the lowest fares, Orbitz lets you earn miles for your frequent flyer program for certain flights from San Juan to Chicago. If you are a member of the frequent flyer or loyalty program offered by the airline you booked through Orbitz or a partner airline’s, simply add your frequent flyer number to your Orbitz reservation to get credit for your San Juan to Chicago flights.

Travel Planning Made Easy

We help take some of the anxiety out of your San Juan to Chicago flights with free flight alerts. We will let you know of flight changes and delays to your flights from San Juan to Chicago by email, voicemail, or text messages to your mobile phone. Alerts can also be sent to up to six other contacts to keep family and business teams informed.

Use Mobile Apps with Orbitz

Orbitz lets you find the best deals on San Juan to Chicago flights while on the go, with our easy-to-use Android and iPhone mobile apps. Easily check flight status, gate numbers, and other flight details all in one place with our app—which is great when you are in a hurry. You can use the apps to access great mobile deals on flights and amazing hotel rooms.

^Savings based on all package bookings with Flight + Hotel made on from January 1, 2019 to December 31, 2019 as compared to the price of the same components booked separately. Savings will vary based on origin/destination, length of trip, stay dates and selected travel supplier(s). Savings not available on all packages.