$52 Cheap flight deals from Chicago (CHI) to San Juan (SJU)

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This Weekend's Flight Deals from Chicago to San Juan

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.

Fri, Jun 7 - Tue, Jun 11
MDW
Midway Intl.
SJU
Luis Munoz Marin Intl.
$208 Roundtrip, found 12 hours ago
$208
Roundtrip
found 12 hours ago
Select Frontier Airlines flight, departing Fri, Jun 7 from Midway Intl. to Luis Munoz Marin Intl., returning Tue, Jun 11, priced at $208 found 12 hours ago
Sat, Jun 8 - Sat, Jun 15
ORD
O'Hare Intl.
SJU
Luis Munoz Marin Intl.
$239 Roundtrip, found 6 hours ago
$239
Roundtrip
found 6 hours ago
Select Frontier Airlines flight, departing Sat, Jun 8 from O'Hare Intl. to Luis Munoz Marin Intl., returning Sat, Jun 15, priced at $239 found 6 hours ago

Airfares from $52 One Way, $110 Round Trip from Chicago to San Juan

Prices starting at $110 for return flights and $52 for one-way flights to San Juan were the cheapest prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.

Tue, Aug 27 - Wed, Aug 28
ORD
Chicago
SJU
San Juan
$110 Roundtrip, found 1 day ago
$110
Roundtrip
found 1 day ago
Select Spirit Airlines flight, departing Tue, Aug 27 from Chicago to San Juan, returning Wed, Aug 28, priced at $110 found 1 day ago
Tue, Aug 27 - Wed, Aug 28
ORD
Chicago
SJU
San Juan
$117 Roundtrip, found 1 day ago
$117
Roundtrip
found 1 day ago
Select Spirit Airlines flight, departing Tue, Aug 27 from Chicago to San Juan, returning Wed, Aug 28, priced at $117 found 1 day ago
Tue, Aug 27 - Wed, Aug 28
ORD
Chicago
SJU
San Juan
$125 Roundtrip, found 1 day ago
$125
Roundtrip
found 1 day ago
Select Spirit Airlines flight, departing Tue, Aug 27 from Chicago to San Juan, returning Wed, Aug 28, priced at $125 found 1 day ago
Mon, Sep 9 - Wed, Sep 11
ORD
Chicago
SJU
San Juan
$132 Roundtrip, found 1 day ago
$132
Roundtrip
found 1 day ago
Select Spirit Airlines flight, departing Mon, Sep 9 from Chicago to San Juan, returning Wed, Sep 11, priced at $132 found 1 day ago
Tue, Aug 27 - Wed, Aug 28
ORD
Chicago
SJU
San Juan
$139 Roundtrip, found 1 day ago
$139
Roundtrip
found 1 day ago
Select Spirit Airlines flight, departing Tue, Aug 27 from Chicago to San Juan, returning Wed, Aug 28, priced at $139 found 1 day ago

San Juan economy flight packages

Price found within the past 48 hours. Click for updated prices.
El Colonial - Adults Only
3.5-star property

El Colonial - Adults Only

9.6/10 Exceptional! (882 reviews)

Jul 3 - Jul 7

4 night stay

Chicago (CHI) to San Juan (SJU)

Spirit Airlines • Roundtrip • Coach
Save 100% on your flight
per person
found 1 day ago
El Colonial was a great place to stay. Walking distance to everything in Old San Juan. It’s a very old building so the floors seemed not so clean in the room we had, but I wore slipper socks. Beds were very comfortable and bath all were clean. Free beer and wine and other alcohol free, soda and free coffee in the morning. It was quiet enough with the AC fan providing a white noise- outside noises on Cinco de Mayo were a bit loud. Staff was very friendly and helpful.

Reviewed on May 6, 2024

Numero Uno Beach House
3.0-star property

Numero Uno Beach House

9.2/10 Wonderful! (258 reviews)

Jul 4 - Jul 11

7 night stay

Chicago (ORD) to San Juan (SJU)

Spirit Airlines • Roundtrip • Coach
Save 100% on your flight
per person
found 1 day ago
The staff was amazing!!!!! They treated us like family. Every single one of them. Roniel, alondra, alaya, paola, braulio and the one and only Oki were amazing in every single way. Their energy was contagious. So grateful for this place and the people. They made the trip even that more special. Gorgeous place and drinks were divine! HIGHLY RECOMMEND! Will return.

Reviewed on Mar 20, 2024

San Juan Water and Beach Club
4.0-star property

San Juan Water and Beach Club

7.2/10 Good! (1,006 reviews)

Jul 3 - Jul 7

4 night stay

Chicago (CHI) to San Juan (SJU)

Spirit Airlines • Roundtrip • Coach
Save 100% on your flight
per person
found 1 day ago
The views very nice from the pool

Reviewed on Feb 11, 2024

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San Juan business class flight packages

Price found within the past 48 hours. Click for updated prices.
El Colonial - Adults Only
3.5-star property

El Colonial - Adults Only

9.6/10 Exceptional! (882 reviews)

Jul 7 - Jul 14

7 night stay

Chicago (ORD) to San Juan (SJU)

American Airlines • Roundtrip • BusinessClass
per person
found 13 hours ago
El Colonial was a great place to stay. Walking distance to everything in Old San Juan. It’s a very old building so the floors seemed not so clean in the room we had, but I wore slipper socks. Beds were very comfortable and bath all were clean. Free beer and wine and other alcohol free, soda and free coffee in the morning. It was quiet enough with the AC fan providing a white noise- outside noises on Cinco de Mayo were a bit loud. Staff was very friendly and helpful.

Reviewed on May 6, 2024

Fairmont El San Juan Hotel
5.0-star property

Fairmont El San Juan Hotel

8/10 Very Good! (1,273 reviews)

Jul 7 - Jul 14

7 night stay

Chicago (ORD) to San Juan (SJU)

American Airlines • Roundtrip • BusinessClass
Save 100% on your flight
per person
found 13 hours ago
An excellent hotel. The staff, the restaurants, the different entertainment alternatives, the rooms, in short, a great hotel experience that you should not miss if you are looking for an option in Isla Verde, Puerto Rico.

Reviewed on May 31, 2024

CIQALA Luxury Suites
4.0-star property

CIQALA Luxury Suites

7/10 Good! (1,005 reviews)

Jul 7 - Jul 14

7 night stay

Chicago (ORD) to San Juan (SJU)

American Airlines • Roundtrip • BusinessClass
per person
found 13 hours ago
The property was off the main strip but it was still in a decent area. The staff was awesome! Wish there was more places to eat in the area and there was early check in available.

Reviewed on Feb 20, 2024

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More About Flying To San Juan from Chicago

Route Information for Flights from Chicago to San Juan

Origin Airport IATA Code
CHI
Destination Airport IATA Code
SJU
Distance
2073 mi
Direct Flight Airlines
American Airlines, Alaska Airlines, Air Canada, Air New Zealand, United Airlines, Spirit Airlines
Earliest Flight Arrival
6:09PM UTC
Latest Flight Arrival
3:54AM UTC

Chicago to San Juan

Using Orbitz can save you a significant amount of money and time when booking Chicago to San Juan flights. With cutting-edge mobile tools for on-the-move travel planning and guaranteed low prices, Orbitz is the ultimate resource for travelers looking for great deals.

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Orbitz now offers free apps for iPad, iPhone, and Android users. You can use Orbitz on these devices to search for affordable fares and to book flights from Chicago to San Juan. Mobile apps also allow users to view, compare, and book hotel rooms with just a few taps on the screen and let you access up-to-date flight and baggage claim information in a matter of seconds.

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Keep Everyone Updated With Flight Alerts

Orbitz is the ideal way to book flights from Chicago to San Juan. Free Orbitz alerts can be sent to you and as many as six of your contacts about changes to your Chicago to San Juan flights. This keeps everyone notified of flight delays or any other disruptions that might impact your arrival time.

Orbitz Makes It Easy to Plan Your Trips on a Budget

You can always find affordable flights from Chicago to San Juan on Orbitz. Use different airlines to book arrival and departure flights, take advantage of vacation package deals, and secure exclusive rewards.

Frequently asked questions

Am I able to catch a flight from Chicago to San Juan now?
Go right to our Covid-19 Travel Advisor for the most up-to-date information on quarantine and travel restrictions when catching a flight from Chicago to San Juan.
Are there non-stop flights from Chicago to San Juan?
You betcha. In fact, there are 3 airlines that fly direct from ORD to Isla Verde Intl. Airport. Book a ticket with one of these popular carriers:
  • American Airlines
  • Frontier Airlines
  • United Airlines
  • American Airlines
  • Frontier Airlines
  • United Airlines
What is the shortest flight from Chicago to San Juan?
From Chicago, the unique sights and sounds of San Juan are at least 4 hours and 46 minutes away. Lock in your favorite seat, or maybe even one with extra legroom, and fly to your destination in comfort.
What airlines fly from Chicago to San Juan most frequently?
American Airlines (AA) is one of the airlines with the most flights from ORD to Isla Verde Intl. Airport. It offers 60 flights each month on this route. Taking off on a vacation is one of life’s greatest pleasures, and this carrier will get you to your destination quickly and safely. Also check out the great airfares from Frontier Airlines (F9). Offering 30 flights each month between Chicago and San Juan, they’ll ensure your journey is just as delightful as the destination.
If I am not able to travel due to COVID-19, can I cancel my flight to San Juan?
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 San Juan 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 San Juan with flexible change policies?
In most cases you’ll have the option to reschedule your flight to San Juan 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!

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.