$111 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.

Sun, Sep 20 - Wed, Sep 23
MDW
Midway Intl.
SJU
Luis Munoz Marin Intl.
$291 Roundtrip, found 3 days ago
$291
Roundtrip
found 3 days ago
Select Frontier Airlines flight, departing Sun, Sep 20 from Midway Intl. to Luis Munoz Marin Intl., returning Wed, Sep 23, priced at $291 found 3 days ago
Sat, Sep 19 - Fri, Sep 25
ORD
O'Hare Intl.
SJU
Luis Munoz Marin Intl.
$312 Roundtrip, found 1 day ago
$312
Roundtrip
found 1 day ago
Select American Airlines flight, departing Sat, Sep 19 from O'Hare Intl. to Luis Munoz Marin Intl., returning Fri, Sep 25, priced at $312 found 1 day ago

Airfares from $111 One Way, $192 Round Trip from Chicago to San Juan

Prices starting at $192 for return flights and $111 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.

Sun, Oct 18 - Thu, Oct 22
MDW
Chicago
SJU
San Juan
$192 Roundtrip, found 4 days ago
$192
Roundtrip
found 4 days ago
Select Frontier Airlines flight, departing Sun, Oct 18 from Chicago to San Juan, returning Thu, Oct 22, priced at $192 found 4 days ago
Wed, Oct 21 - Wed, Oct 28
MDW
Chicago
SJU
San Juan
$209 Roundtrip, found 4 days ago
$209
Roundtrip
found 4 days ago
Select Frontier Airlines flight, departing Wed, Oct 21 from Chicago to San Juan, returning Wed, Oct 28, priced at $209 found 4 days ago
Tue, Oct 27 - Wed, Oct 28
ORD
Chicago
SJU
San Juan
$212 Roundtrip, found 6 days ago
$212
Roundtrip
found 6 days ago
Select United flight, departing Tue, Oct 27 from Chicago to San Juan, returning Wed, Oct 28, priced at $212 found 6 days ago
Wed, Oct 21 - Wed, Oct 28
MDW
Chicago
SJU
San Juan
$212 Roundtrip, found 3 days ago
$212
Roundtrip
found 3 days ago
Select Frontier Airlines flight, departing Wed, Oct 21 from Chicago to San Juan, returning Wed, Oct 28, priced at $212 found 3 days ago
Tue, Nov 3 - Wed, Nov 4
ORD
Chicago
SJU
San Juan
$216 Roundtrip, found 5 days ago
$216
Roundtrip
found 5 days ago
Select American Airlines flight, departing Tue, Nov 3 from Chicago to San Juan, returning Wed, Nov 4, priced at $216 found 5 days ago

San Juan economy flight packages

Price found within the past 48 hours. Click for updated prices.
Lazy Parrot Inn
3.0-star property

Lazy Parrot Inn

9.2/10 Wonderful! (1,003 reviews)

Nov 2 - Nov 6

4 night stay

Chicago (CHI) to San Juan (SJU)

American Airlines • Non-stop • Coach

San Juan (SJU) to Chicago (CHI)

Frontier Airlines • Non-stop • Coach
Save 100% on your flight
Price was $700, price is now $446 per person
$446
per person
found 1 day ago
Beautiful place to stay!! The beds are comfortable

Reviewed on Sep 12, 2026

Isla Verde Beachfront Retreat With Parking
2.0-star property

Isla Verde Beachfront Retreat With Parking

10/10 Exceptional! (4 reviews)

Oct 15 - Oct 19

4 night stay

Chicago (CHI) to San Juan (SJU)

Southwest Airlines • Non-stop roundtrip • Coach
Save 100% on your flight
Price was $1,529, price is now $731 per person
$731
per person
found 1 day ago
This place is convenient, nice and clean. I will definitely revisit.

Reviewed on Sep 9, 2026

Signature Collection at Rio Mar
5.0-star property

Signature Collection at Rio Mar

6/10 (1 review)

Nov 4 - Nov 8

4 night stay

Chicago (CHI) to San Juan (SJU)

Southwest Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $3,895, price is now $2,574 per person
$2,574
per person
found 1 day ago
Everything is 10 times more expensive compare to any other place I visites

Reviewed on Aug 8, 2026

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San Juan packages with premium economy flights

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

Ola Boutique Hotel

9/10 Wonderful! (957 reviews)

Nov 6 - Nov 10

4 night stay

Chicago (ORD) to San Juan (SJU)

Frontier Airlines • Non-stop roundtrip • PremiumEconomy
Price was $1,355, price is now $957 per person
$957
per person
found 1 day ago

Fairmont El San Juan Villa Experience
5.0-star property

Fairmont El San Juan Villa Experience

7.8/10 Good! (156 reviews)

Nov 6 - Nov 10

4 night stay

Chicago (ORD) to San Juan (SJU)

Frontier Airlines • Non-stop roundtrip • PremiumEconomy
Save 100% on your flight
Price was $2,382, price is now $1,689 per person
$1,689
per person
found 1 day ago
Nice.. expensive but nice

Reviewed on Sep 8, 2026

WALD HAUS by DW
4.0-star property

WALD HAUS by DW

9.2/10 Wonderful! (11 reviews)

Nov 6 - Nov 10

4 night stay

Chicago (ORD) to San Juan (SJU)

Frontier Airlines • Non-stop roundtrip • PremiumEconomy
Save 100% on your flight
Price was $3,009, price is now $2,143 per person
$2,143
per person
found 1 day ago
Overall the area and the views were nice. The pool was refreshing. However, it was difficult to get in touch with the management team, and we had issues with the AC, plumbing, and cockroaches. Also make sure you rent an AWH or 4WD as the hill to get in and out is steep. Upon arrival, one of the rooms AC unit was making a very loud grinding noise and was leaking everywhere. It took multiple attempts for them to reach the property managers and their solution was to turn it off. So one of our guests went without AC for a night. I took a video and sent it to management as proof. It eventually worked, but the property said that because their technicians found it working before and after our stay (regardless of the video) they would not provide anything in return for the inconvenience. Then, a surprise $495 charge came. They said we clogged the entire plumbing system within our 4 day stay and a couple of accidental toilet paper flushes. Truly feel scammed as there’s no way we could have been soley responsible for this and had only checked out (and everything was fine) a few hours before. There were also cockroaches in the bathrooms and kitchens. We killed several while on the property. Overall, I would NOT recommend staying here as the hosts were not accommodating or helpful and I feel we got scammed with the surprise charge.

Reviewed on Sep 12, 2026

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San Juan first class flight packages

Price found within the past 48 hours. Click for updated prices.
La Esmeralda PR
3.0-star property

La Esmeralda PR

9.2/10 Wonderful! (295 reviews)

Nov 3 - Nov 10

7 night stay

Chicago (ORD) to San Juan (SJU)

American Airlines • FirstClass

San Juan (SJU) to Chicago (ORD)

Delta • FirstClass
Price was $1,763, price is now $1,428 per person
$1,428
per person
found 19 hours ago

DREAMCATCHER by DW - ADULTS ONLY
3.5-star property

DREAMCATCHER by DW - ADULTS ONLY

9.4/10 Exceptional! (1,001 reviews)

Nov 3 - Nov 10

7 night stay

Chicago (ORD) to San Juan (SJU)

American Airlines • FirstClass

San Juan (SJU) to Chicago (ORD)

Delta • FirstClass
Price was $2,853, price is now $2,141 per person
$2,141
per person
found 19 hours ago
The property is gorgeous and well maintained. The romance suite was such a beautiful space. Also, it is a plus that the location is a few minutes walk to the beach as well as restaurants. The food onsite was delicious and staff lovely to interact with. I can't say enough how special the Dreamcatcher is.

Reviewed on Sep 10, 2026

Olive Boutique Hotel, A Small Luxury Hotel of the World (Adults Only)
4.0-star property

Olive Boutique Hotel, A Small Luxury Hotel of the World (Adults Only)

9/10 Wonderful! (684 reviews)

Nov 3 - Nov 10

7 night stay

Chicago (ORD) to San Juan (SJU)

American Airlines • FirstClass

San Juan (SJU) to Chicago (ORD)

Delta • FirstClass
Price was $3,681, price is now $2,963 per person
$2,963
per person
found 19 hours ago
⭐️⭐️⭐️

Reviewed on Sep 13, 2026

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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
Direct Flight Airlines
Earliest Flight Arrival
Latest Flight Arrival

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!

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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.