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This Weekend's Flight Deals from San Juan to Chicago

This weekend's flight prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.

Airfares from $89 One Way, $173 Round Trip from San Juan to Chicago

Prices starting at $173 for return flights and $89 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.

Chicago economy flight packages

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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
Distance2073 mi
Direct Flight AirlinesAmerican Airlines, Air Canada, Alaska Airlines, Frontier Airlines, Air New Zealand, United Airlines
Earliest Flight Arrival2:43PM UTC
Latest Flight Arrival11:46PM UTC

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 combines guaranteed low prices with cutting-edge mobile tools for travel from San Juan to Chicago to give you a travel experience that is second to none.

Bargain Travel at Your Fingertips

Orbitz provides the cheapest fares from San Juan to Chicago. When reserving your flight you can mix and match a range of low cost airlines for you departing and returning domestic or international flights. This way you can travel on a budget while selecting the flights that suit your schedule.

Modern Tools for Fast-Paced Travel

Orbitz makes use of the latest technology to ensure that you are always kept up-to-date on the status of your San Juan to Chicago flights. Through easy-to-use mobile Android and iPhone apps you can book low cost flights from San Juan to Chicago and choose a range of cheap hotels to stay in.

Enjoy Stress-Free Travel with Flight Alerts

Once you have booked your flights from San Juan to Chicago on Orbitz you will always be kept informed of any changes to your flight. When you opt into Orbitz’s free email and SMS alerts on your San Juan to Chicago flights you can ask Orbitz to send the flight details to up to 6 other contacts, so keeping your family and business team informed is a cinch.

Frequent Flyer Program

For loyal Orbitz customers who fly from San Juan to Chicago the chance to join our frequent flyer program is an added bonus. Simply log-on to your online account and input your frequent flyer number for future flights.

Flights from San Juan to Chicago - Frequently Asked Questions

Are there non-stop flights from San Juan to Chicago?

Get ready to click "book" because there are no less than 9 airlines that advertise nonstop services between Isla Verde Intl. Airport and ORD. Cruise in comfort on board one of these leading carriers:

  • United Airlines
  • United Airlines
  • Frontier Airlines
  • American Airlines
  • Frontier Airlines
What is the shortest flight from San Juan to Chicago?

Traveling from Luis Munoz Marin Intl. Airport (SJU) to Midway Airport will take you at least 5 hours and 50 minutes. Enjoy a beverage and read a few magazines — here's your chance to chill out.

What airlines fly from San Juan to Chicago most frequently?

These airlines operate the most flights from San Juan to Chicago. Cruise in comfort with one of these leading carriers: United Airlines - (UA) with 60 flights every month Frontier Airlines - (F9) with 60 flights every month Frontier Airlines - (F9) with 60 flights every month American Airlines - (AA) with 60 flights every month United Airlines - (UA) with 60 flights every month American Airlines - (AA) with 60 flights every month

If I am not able to travel due to COVID-19, can I cancel my flight to Chicago?

We get that traveling right now has its challenges, so it's good to know that many reservations booked through us are able to be cancelled or changed. If your travel plans to Chicago have been affected by COVID-19, a lot of airlines are making things easier by offering credits to use at a later date. Just sign in to your account and you'll quickly see what options are available. Our Customer Service Portal is the place to go for more information.

Are there flights to Chicago with flexible change policies?

In most cases you'll have the option to reschedule your flight to Chicago without a change fee. All you have to do then is pay the difference between the old flight and the new one. Look for the "no change fees" filter and book with confidence.

What is the cheapest day of the week to fly?

Consider flying out early in the week to save on your airfare. Orbitz data from 2020 shows that Monday is the cheapest day to depart, followed by Tuesday. Saturday showed the highest average ticket prices likely because many travelers prefer to start their vacation on a weekend.

What is the cheapest month to fly?

We won't keep you guessing, according to Orbitz data the cheapest month to fly is August. Perfect for those who need a weekend getaway, or just a break from it all before the weather changes. Be aware that the most expensive time to fly is the height of summer, with ticket prices peaking in the month of June.

How can I save money on flights?

To really save big on your next vacation, think outside the box. Select two different airlines or fare types for your return trip and you'll generally get a much better deal. Those who tried this on Orbitz in 2020 saved up to 45% on their airfares. Get mixing and matching today!

*According to flight demand on from January to December 2020. Savings are subject to change based on departure location, date and destination.

Fare, taxes & fees: Fares include all taxes and fees, except baggage fees. Rates shown reflect fares found by other Orbitz users over the past 7 days. Due to rapidly changing airline prices & seat availability, these fares may no longer be available.

Refunds/changes/cancellations: Itinerary changes, if permitted for the fare, will have a $30 service fee charged by Orbitz. Additional airline charges may apply.

Other conditions: Schedules, fares and rules are subject to change without notice. Seats are limited and may not be available on all flights/dates or in all markets. Lower fares may be available. Fares will not be honored retroactively or in exchange for any wholly/partially unused ticket. Tickets are non-transferable and non-refundable. Fare rules are provided for the selected itinerary before booking.