$110 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, May 30 - Thu, Jun 5
MDW
Midway Intl.
SJU
Luis Munoz Marin Intl.
$259 Roundtrip, found 9 hours ago
$259
Roundtrip
found 9 hours ago
Select Frontier Airlines flight, departing Fri, May 30 from Midway Intl. to Luis Munoz Marin Intl., returning Thu, Jun 5, priced at $259 found 9 hours ago
Fri, May 30 - Fri, Jun 6
ORD
O'Hare Intl.
SJU
Luis Munoz Marin Intl.
$289 Roundtrip, just found
$289
Roundtrip
just found
Select Frontier Airlines flight, departing Fri, May 30 from O'Hare Intl. to Luis Munoz Marin Intl., returning Fri, Jun 6, priced at $289 just found

Airfares from $110 One Way, $230 Round Trip from Chicago to San Juan

Prices starting at $230 for return flights and $110 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, Jul 8 - Thu, Jul 31
ORD
Chicago
SJU
San Juan
$230 Roundtrip, found 4 days ago
$230
Roundtrip
found 4 days ago
Select Spirit Airlines flight, departing Tue, Jul 8 from Chicago to San Juan, returning Thu, Jul 31, priced at $230 found 4 days ago
Tue, Jul 8 - Thu, Jul 17
ORD
Chicago
SJU
San Juan
$231 Roundtrip, found 1 day ago
$231
Roundtrip
found 1 day ago
Select Spirit Airlines flight, departing Tue, Jul 8 from Chicago to San Juan, returning Thu, Jul 17, priced at $231 found 1 day ago
Thu, Jul 10 - Sun, Jul 13
ORD
Chicago
SJU
San Juan
$242 Roundtrip, just found
$242
Roundtrip
just found
Select Spirit Airlines flight, departing Thu, Jul 10 from Chicago to San Juan, returning Sun, Jul 13, priced at $242 just found
Sat, Sep 6 - Sun, Sep 7
ORD
Chicago
SJU
San Juan
$243 Roundtrip, found 1 hour ago
$243
Roundtrip
found 1 hour ago
Select Frontier Airlines flight, departing Sat, Sep 6 from Chicago to San Juan, returning Sun, Sep 7, priced at $243 found 1 hour ago
Sat, Jul 5 - Tue, Jul 8
ORD
Chicago
SJU
San Juan
$307 Roundtrip, found 11 hours ago
$307
Roundtrip
found 11 hours ago
Select United flight, departing Sat, Jul 5 from Chicago to San Juan, returning Tue, Jul 8, priced at $307 found 11 hours ago

San Juan economy flight packages

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

Urbana Hotel

8.4/10 Very Good! (255 reviews)

Jun 29 - Jul 3

4 night stay

Chicago (CHI) to San Juan (SJU)

Spirit Airlines • Non-stop roundtrip • Coach
Save 100% on your flight
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

El Colonial - Adults Only
3.5-star property

El Colonial - Adults Only

9.4/10 Exceptional! (1,189 reviews)

Jun 29 - Jul 3

4 night stay

Chicago (CHI) to San Juan (SJU)

Spirit Airlines • Non-stop roundtrip • Coach
Save 100% on your flight
per person
found 1 day ago
This was the perfect spot the night before our cruise. Extremely convenient to all of the highlights of San Juan and the cruise port. The staff was excellent and very welcoming

Reviewed on Feb 15, 2025

The Oliver Hotel
3.0-star property

The Oliver Hotel

9/10 Wonderful! (22 reviews)

Jun 29 - Jul 3

4 night stay

Chicago (CHI) to San Juan (SJU)

Spirit Airlines • Non-stop roundtrip • Coach
Save 100% on your flight
per person
found 1 day ago
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San Juan first class flight packages

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

Urbana Hotel

8.4/10 Very Good! (255 reviews)

Jul 16 - Jul 19

3 night stay

Chicago (CHI) to San Juan (SJU)

United • Non-stop roundtrip • FirstClass
per person
found 13 hours 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

El Colonial - Adults Only
3.5-star property

El Colonial - Adults Only

9.4/10 Exceptional! (1,189 reviews)

Jul 16 - Jul 19

3 night stay

Chicago (CHI) to San Juan (SJU)

United • Non-stop roundtrip • FirstClass
per person
found 13 hours ago
This was the perfect spot the night before our cruise. Extremely convenient to all of the highlights of San Juan and the cruise port. The staff was excellent and very welcoming

Reviewed on Feb 15, 2025

Ciqala Suites Hotel
4.0-star property

Ciqala Suites Hotel

7.4/10 Good! (1,013 reviews)

Jul 16 - Jul 19

3 night stay

Chicago (CHI) to San Juan (SJU)

United • Non-stop roundtrip • FirstClass
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, Air Canada, Alaska Airlines, Air New Zealand, United Airlines
Earliest Flight Arrival
6:00PM UTC
Latest Flight Arrival
3:54AM UTC

Chicago to San Juan

When you’re ready to take your next trip, get the most affordable prices on flights from Chicago to San Juan with Orbitz! The guaranteed low prices and cutting-edge mobile tools on Orbits make it easy for you to plan your next great vacation.

Keep Up With Sudden Flight Changes

As any traveler knows, air travel can suddenly be temporarily halted due to service disruptions. Along with offering the best fares for flights from Chicago to San Juan, Orbitz also offers free mobile phone and email alerts that help you keep up with sudden changes to your flight plans. Choose from email, text, or voice message alerts.

Get Great Prices for Chicago to San Juan Flights

Orbitz features both an Android app and an iPhone app to give you the lowest prices for Chicago to San Juan flights. Use these mobile apps to get updates on your flight, the details of your itinerary, and to learn about available hotel deals in the area.

Fly for Less and Earn Miles

Did you know you can earn miles and points for your frequent flyer program with Orbitz? To do this with specific flights from Chicago to San Juan, enter your frequent flyer account number when you book your ticket online. For even more convenience, keep a record of your loyalty travel program numbers directly with Orbitz by storing them in your account profile. This way, you can add your account numbers to your next reservation for Chicago to San Juan flights automatically without the annoying hassle of having to look them up.

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.