$97 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.

Sat, Apr 5 - Thu, Apr 10
MDW
Midway Intl.
SJU
Luis Munoz Marin Intl.
$336 Roundtrip, found 20 hours ago
$336
Roundtrip
found 20 hours ago
Select Frontier Airlines flight, departing Sat, Apr 5 from Midway Intl. to Luis Munoz Marin Intl., returning Thu, Apr 10, priced at $336 found 20 hours ago
Sun, Apr 6 - Sun, Apr 13
ORD
O'Hare Intl.
SJU
Luis Munoz Marin Intl.
$380 Roundtrip, found 4 hours ago
$380
Roundtrip
found 4 hours ago
Select Frontier Airlines flight, departing Sun, Apr 6 from O'Hare Intl. to Luis Munoz Marin Intl., returning Sun, Apr 13, priced at $380 found 4 hours ago

Airfares from $97 One Way, $179 Round Trip from Chicago to San Juan

Prices starting at $179 for return flights and $97 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.

Sat, Apr 12 - Wed, Apr 23
ORD
Chicago
SJU
San Juan
$179 Roundtrip, found 1 day ago
$179
Roundtrip
found 1 day ago
Select Spirit Airlines flight, departing Sat, Apr 12 from Chicago to San Juan, returning Wed, Apr 23, priced at $179 found 1 day ago
Tue, Apr 29 - Fri, May 9
ORD
Chicago
SJU
San Juan
$190 Roundtrip, found 2 days ago
$190
Roundtrip
found 2 days ago
Select Spirit Airlines flight, departing Tue, Apr 29 from Chicago to San Juan, returning Fri, May 9, priced at $190 found 2 days ago
Tue, Apr 15 - Thu, Apr 24
ORD
Chicago
SJU
San Juan
$195 Roundtrip, found 1 day ago
$195
Roundtrip
found 1 day ago
Select Spirit Airlines flight, departing Tue, Apr 15 from Chicago to San Juan, returning Thu, Apr 24, priced at $195 found 1 day ago
Mon, May 26 - Mon, Jun 2
ORD
Chicago
SJU
San Juan
$282 Roundtrip, just found
$282
Roundtrip
just found
Select Spirit Airlines flight, departing Mon, May 26 from Chicago to San Juan, returning Mon, Jun 2, priced at $282 just found
Fri, May 2 - Sat, May 3
ORD
Chicago
SJU
San Juan
$290 Roundtrip, found 3 days ago
$290
Roundtrip
found 3 days ago
Select JetBlue Airways flight, departing Fri, May 2 from Chicago to San Juan, returning Sat, May 3, priced at $290 found 3 days ago

San Juan economy flight packages

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

San Agustin Apartments

9/10 Wonderful! (257 reviews)

May 10 - May 16

6 night stay

Chicago (CHI) to San Juan (SJU)

Spirit Airlines • Non-stop roundtrip • Coach
per person
found 1 day ago
We rated the property a 3 because the beds were comfortable and parking was included. Communication was prompt and thorough. We booked the Penthouse, sleeps 6, we did not understand that this was a walk up. Midway in the stay the stairwell smelled of death with huge flys. Really gross. There are only 3 chairs in the living area, very uncomfortable to hang out in. The kitchenette was quite poorly appointed. 2 juice cups, 1 wine glass, no oven, microwave or toaster. No cleaning services were offered during our week long stay. We did get to exchange towels toward the end of the week. There is a loud club located directly across the street. Bass thumping and people yelling all night long. Not recommended for families! *Excellent restaurants in the area.

Reviewed on Mar 23, 2025

Ola Boutique Hotel
4.5-star property

Ola Boutique Hotel

9/10 Wonderful! (310 reviews)

May 10 - May 16

6 night stay

Chicago (CHI) to San Juan (SJU)

Spirit Airlines • Non-stop roundtrip • Coach
per person
found 1 day ago
Excellent accommodations. Room was a little small but convenience & extra courteous staff made up for it. Theyre just genuinely warm. Silk restaurant across is phenomenal & grocery is also just across. Walk to Condado area

Reviewed on Jan 4, 2025

Ciqala Suites Hotel
4.0-star property

Ciqala Suites Hotel

7.4/10 Good! (1,008 reviews)

May 10 - May 16

6 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 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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San Juan first class flight packages

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

San Agustin Apartments

9/10 Wonderful! (257 reviews)

May 19 - May 24

5 night stay

Chicago (ORD) to San Juan (SJU)

United • Roundtrip • FirstClass
per person
found 13 hours ago
We rated the property a 3 because the beds were comfortable and parking was included. Communication was prompt and thorough. We booked the Penthouse, sleeps 6, we did not understand that this was a walk up. Midway in the stay the stairwell smelled of death with huge flys. Really gross. There are only 3 chairs in the living area, very uncomfortable to hang out in. The kitchenette was quite poorly appointed. 2 juice cups, 1 wine glass, no oven, microwave or toaster. No cleaning services were offered during our week long stay. We did get to exchange towels toward the end of the week. There is a loud club located directly across the street. Bass thumping and people yelling all night long. Not recommended for families! *Excellent restaurants in the area.

Reviewed on Mar 23, 2025

Aire de O:live
4.0-star property

Aire de O:live

9.2/10 Wonderful! (91 reviews)

May 23 - May 27

4 night stay

Chicago (ORD) to San Juan (SJU)

United • Roundtrip • FirstClass
per person
found 1 day ago
Everything was good. It was very nice being right next to the beach. The only room for improvement is better mattresses.

Reviewed on Mar 22, 2025

The Condado Plaza Hotel
4.0-star property

The Condado Plaza Hotel

7.6/10 Good! (1,011 reviews)

May 23 - May 27

4 night stay

Chicago (ORD) to San Juan (SJU)

United • Roundtrip • FirstClass
per person
found 1 day ago
Easy access to Old San Juan and major highways. Área is quiet and beach closed by.

Reviewed on Mar 29, 2025

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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
5:45PM UTC
Latest Flight Arrival
3:54AM UTC

Chicago to San Juan

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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.