$69 Cheap flight deals from Chicago (CHI) to San Juan (SJU)

Earn rewards on top of your airline miles with Orbitz Rewards

Many airlines offer flexible change policies

Sign up to receive text alerts about your trip

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, Nov 29 - Sun, Dec 8
ORD
O'Hare Intl.
SJU
Luis Munoz Marin Intl.
$244 Roundtrip, just found
$244
Roundtrip
just found
Select Spirit Airlines flight, departing Fri, Nov 29 from O'Hare Intl. to Luis Munoz Marin Intl., returning Sun, Dec 8, priced at $244 just found
Fri, Nov 29 - Sat, Jan 11
MDW
Midway Intl.
SJU
Luis Munoz Marin Intl.
$450 Roundtrip, found 3 days ago
$450
Roundtrip
found 3 days ago
Select Delta flight, departing Fri, Nov 29 from Midway Intl. to Luis Munoz Marin Intl., returning Sat, Jan 11, priced at $450 found 3 days ago

Airfares from $69 One Way, $118 Round Trip from Chicago to San Juan

Prices starting at $118 for return flights and $69 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.

Wed, Jan 29 - Fri, Jan 31
ORD
Chicago
SJU
San Juan
$118 Roundtrip, found 6 hours ago
$118
Roundtrip
found 6 hours ago
Select Spirit Airlines flight, departing Wed, Jan 29 from Chicago to San Juan, returning Fri, Jan 31, priced at $118 found 6 hours ago
Wed, Jan 1 - Tue, Jan 14
ORD
Chicago
SJU
San Juan
$130 Roundtrip, found 9 hours ago
$130
Roundtrip
found 9 hours ago
Select Spirit Airlines flight, departing Wed, Jan 1 from Chicago to San Juan, returning Tue, Jan 14, priced at $130 found 9 hours ago
Mon, Dec 9 - Tue, Dec 10
MDW
Chicago
SJU
San Juan
$133 Roundtrip, found 6 days ago
$133
Roundtrip
found 6 days ago
Select Frontier Airlines flight, departing Mon, Dec 9 from Chicago to San Juan, returning Tue, Dec 10, priced at $133 found 6 days ago
Mon, Jan 13 - Mon, Jan 27
MDW
Chicago
SJU
San Juan
$138 Roundtrip, found 4 days ago
$138
Roundtrip
found 4 days ago
Select Frontier Airlines flight, departing Mon, Jan 13 from Chicago to San Juan, returning Mon, Jan 27, priced at $138 found 4 days ago
Mon, Jan 6 - Wed, Jan 22
ORD
Chicago
SJU
San Juan
$141 Roundtrip, just found
$141
Roundtrip
just found
Select Spirit Airlines flight, departing Mon, Jan 6 from Chicago to San Juan, returning Wed, Jan 22, priced at $141 just found

San Juan economy flight packages

Price found within the past 48 hours. Click for updated prices.
Urbana Hotel
2.0-star property

Urbana Hotel

8.8/10 Excellent! (76 reviews)

Jan 12 - Jan 17

5 night stay

Chicago (CHI) to San Juan (SJU)

Spirit Airlines • Roundtrip • Coach
per person
found 1 day ago
The Urbana is carved out of newly renovated historic buildings, making for a unique and centrally-located stay. The staff is friendly an helpful, and a bar across the street offers drinks and music. While I stayed there, a couple big music/dance events happened at an events venue also on the block, so the whole street felt alive and energetic. It is about a mile walk to the center of Old San Juan, and you pass lots of plazas and sites of interest on the way. A bakery is just down the block offering breakfast and lunch options, and a co-working space next door is available for guests who need to be on the clock while in town. The rooms are small, but with the beach only 10-15 minutes away on foot, and with San Juan all around you, who needs to be in the room? Even so, the hotel was meticulously clean and comfortable. Depending on the time of day, the water might be more warm than hot, but the in-room AC makes climate control easy. I will definitely seek to stay here again!

Reviewed on Mar 13, 2023

Ola Boutique Hotel
4.5-star property

Ola Boutique Hotel

8.6/10 Excellent! (139 reviews)

Jan 13 - Jan 16

3 night stay

Chicago (CHI) to San Juan (SJU)

Frontier Airlines • Non-stop • Coach

San Juan (SJU) to Chicago (CHI)

Spirit Airlines • Non-stop • Coach
per person
found 1 day ago
Ola Boutique was charming with aesthetic vibes! The staff was wonderful and super accommodating. Clean and nice rooms at a great location! Me and my family were delighted :) Thank You!

Reviewed on Nov 15, 2024

San Agustin Apartments
3.0-star property

San Agustin Apartments

9.2/10 Wonderful! (179 reviews)

Jan 11 - Jan 18

7 night stay

Chicago (CHI) to San Juan (SJU)

United • Roundtrip • Coach
per person
found 1 day ago
We have no complaints! The apartment was equipped with everything we needed. It was HOT the days we were here so while the bedrooms have an excellent AC; be warned that the living area doesn't. However, despite how hot it was outside; the AC from the bedrooms kept the entire space quite livable. The staff was SO friendly and accommodating. They were quick to respond and deliver at all hours. This location is quite close to everything! including being walking distance and 4 minutes drive from Old San Juan. They had a co-working space which provided tea and coffee which I LOVED and found myself in often. The area was quiet, and there's bakery, breakfast spot, juice bar, pizza spot all within walking distance. The beach is also within walking distance. THANK YOU San Agustin. Will definitely consider staying here again and referring to friends. <3

Reviewed on Oct 6, 2024

Don't see what you're looking for?
See all available trips from Chicago to San Juan
View all trips

San Juan business class flight packages

Price found within the past 48 hours. Click for updated prices.
San Agustin Apartments
3.0-star property

San Agustin Apartments

9.2/10 Wonderful! (179 reviews)

Jan 12 - Jan 18

6 night stay

Chicago (CHI) to San Juan (SJU)

American Airlines • Non-stop roundtrip • BusinessClass
Save 100% on your flight
per person
found 15 hours ago
We have no complaints! The apartment was equipped with everything we needed. It was HOT the days we were here so while the bedrooms have an excellent AC; be warned that the living area doesn't. However, despite how hot it was outside; the AC from the bedrooms kept the entire space quite livable. The staff was SO friendly and accommodating. They were quick to respond and deliver at all hours. This location is quite close to everything! including being walking distance and 4 minutes drive from Old San Juan. They had a co-working space which provided tea and coffee which I LOVED and found myself in often. The area was quiet, and there's bakery, breakfast spot, juice bar, pizza spot all within walking distance. The beach is also within walking distance. THANK YOU San Agustin. Will definitely consider staying here again and referring to friends. <3

Reviewed on Oct 6, 2024

Bali Poshtel PR
3.0-star property

Bali Poshtel PR

8.6/10 Excellent! (50 reviews)

Jan 12 - Jan 18

6 night stay

Chicago (CHI) to San Juan (SJU)

American Airlines • Non-stop roundtrip • BusinessClass
per person
found 15 hours ago
Wonderful hotel! It looks just like the pictures. Could relax in that pool all day! Staff were very attentive and helpful. The hotel was a short walk to the beach. Lots of dining options nearby too. Go to the Paneria nearby. This is a new hotel and they’re still working some things out—eg I had issues w the water temperature in my room. But they were responsive and handled it very quickly. I would definitely stay here again!

Reviewed on Oct 20, 2024

Condado Vanderbilt Hotel
5.0-star property

Condado Vanderbilt Hotel

9.2/10 Wonderful! (1,471 reviews)

Jan 12 - Jan 18

6 night stay

Chicago (CHI) to San Juan (SJU)

American Airlines • Non-stop roundtrip • BusinessClass
per person
found 22 hours ago
Staff was professional and helpful. The room were clean and the overall ambiance was great.

Reviewed on Nov 18, 2024

Don't see what you're looking for?
See all available trips from Chicago to San Juan
View all trips

San Juan first class flight packages

Price found within the past 48 hours. Click for updated prices.
Ola Boutique Hotel
4.5-star property

Ola Boutique Hotel

8.6/10 Excellent! (139 reviews)

Jan 11 - Jan 13

2 night stay

Chicago (MDW) to San Juan (SJU)

Delta • Roundtrip • FirstClass
per person
found 10 hours ago
Ola Boutique was charming with aesthetic vibes! The staff was wonderful and super accommodating. Clean and nice rooms at a great location! Me and my family were delighted :) Thank You!

Reviewed on Nov 15, 2024

Bali Poshtel PR
3.0-star property

Bali Poshtel PR

8.6/10 Excellent! (50 reviews)

Jan 11 - Jan 13

2 night stay

Chicago (MDW) to San Juan (SJU)

Delta • Roundtrip • FirstClass
per person
found 10 hours ago
Wonderful hotel! It looks just like the pictures. Could relax in that pool all day! Staff were very attentive and helpful. The hotel was a short walk to the beach. Lots of dining options nearby too. Go to the Paneria nearby. This is a new hotel and they’re still working some things out—eg I had issues w the water temperature in my room. But they were responsive and handled it very quickly. I would definitely stay here again!

Reviewed on Oct 20, 2024

The Weekender by Otium
4.0-star property

The Weekender by Otium

8.4/10 Very Good! (5 reviews)

Jan 11 - Jan 13

2 night stay

Chicago (MDW) to San Juan (SJU)

Delta • Roundtrip • FirstClass
per person
found 10 hours ago
Don't see what you're looking for?
See all available trips from Chicago to San Juan
View all trips

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
Direct Flight Airlines
Earliest Flight Arrival
Latest Flight Arrival

Chicago to San Juan

It can be tedious to sift through pages of Internet search results to find those bargain fares on flights from Chicago to San Juan and hotels, but at Orbitz, everything you need is in one place. Our guaranteed low prices on Chicago to San Juan flights mean we are a leader when it comes to giving you great online deals on air fare and hotels.

Huge savings with little effort

Whether you are traveling for pleasure or business, you can use Orbitz to find cheap Chicago to San Juan flights, together with low-cost accommodations. We pride ourselves on offering you excellent deals that fit your schedule and budget needs.

Unbeatable low fare flights from Chicago to San Juan

Domestic or international travel presents no obstacles to us. We give you unbeatable bargains on flights from Chicago to San Juan. Enjoy huge savings on your flight, which can be better used elsewhere on your trip.

Grab that cheap deal on the move

Our innovative and cutting-edge mobile tools make it easy to search or booking cheap flights from Chicago to San Juan while on the move, via our app for the iPhone, iPad, or Android-based devices. We can also send you instant alerts through email or text messaging if there any delays to your flight.

Orbitz means low-cost trip-planning made easy

Low-cost Chicago to San Juan flights can be booked with total confidence through Orbitz every time. We also make it very easy to cancel flights or other travel arrangements online should you need to. You can also add activities and car rentals to your flight or hotel reservation for a hassle-free trip.

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.