$94 Cheap flight deals from Chicago (CHI) to Puerto Rico Island (SJU)

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This Weekend's Flight Deals from Chicago to Puerto Rico Island

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, Aug 16 - Sat, Aug 23
ORD
O'Hare Intl.
BQN
Rafael Hernandez
$248 Roundtrip, found 4 days ago
$248
Roundtrip
found 4 days ago
Select Frontier Airlines flight, departing Sat, Aug 16 from O'Hare Intl. to Rafael Hernandez, returning Sat, Aug 23, priced at $248 found 4 days ago
Sun, Aug 17 - Sat, Aug 23
MDW
Midway Intl.
SJU
Luis Munoz Marin Intl.
$277 Roundtrip, found 4 days ago
$277
Roundtrip
found 4 days ago
Select Frontier Airlines flight, departing Sun, Aug 17 from Midway Intl. to Luis Munoz Marin Intl., returning Sat, Aug 23, priced at $277 found 4 days ago
Fri, Aug 15 - Sat, Aug 23
ORD
O'Hare Intl.
SJU
Luis Munoz Marin Intl.
$307 Roundtrip, found 1 hour ago
$307
Roundtrip
found 1 hour ago
Select Frontier Airlines flight, departing Fri, Aug 15 from O'Hare Intl. to Luis Munoz Marin Intl., returning Sat, Aug 23, priced at $307 found 1 hour ago
Fri, Aug 15 - Mon, Aug 18
ORD
O'Hare Intl.
PSE
Mercedita
$672 Roundtrip, found 1 day ago
$672
Roundtrip
found 1 day ago
Select JetBlue Airways flight, departing Fri, Aug 15 from O'Hare Intl. to Mercedita, returning Mon, Aug 18, priced at $672 found 1 day ago

Airfares from $94 One Way, $205 Round Trip from Chicago to Puerto Rico Island

Prices starting at $205 for return flights and $94 for one-way flights to Puerto Rico Island 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, Aug 24 - Sat, Sep 13
ORD
Chicago
SJU
San Juan
$205 Roundtrip, found 6 days ago
$205
Roundtrip
found 6 days ago
Select Spirit Airlines flight, departing Sun, Aug 24 from Chicago to San Juan, returning Sat, Sep 13, priced at $205 found 6 days ago
Sat, Aug 16 - Sat, Aug 23
ORD
Chicago
BQN
Aguadilla
$248 Roundtrip, found 4 days ago
$248
Roundtrip
found 4 days ago
Select Frontier Airlines flight, departing Sat, Aug 16 from Chicago to Aguadilla, returning Sat, Aug 23, priced at $248 found 4 days ago
Mon, Oct 20 - Fri, Oct 24
ORD
Chicago
SJU
San Juan
$254 Roundtrip, found 7 hours ago
$254
Roundtrip
found 7 hours ago
Select American Airlines flight, departing Mon, Oct 20 from Chicago to San Juan, returning Fri, Oct 24, priced at $254 found 7 hours ago
Sat, Sep 13 - Thu, Sep 18
ORD
Chicago
PSE
Ponce
$277 Roundtrip, found 4 days ago
$277
Roundtrip
found 4 days ago
Select Frontier Airlines flight, departing Sat, Sep 13 from Chicago to Ponce, returning Thu, Sep 18, priced at $277 found 4 days ago
Fri, Oct 17 - Sun, Oct 19
MDW
Chicago
BQN
Aguadilla
$298 Roundtrip, found 1 day ago
$298
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Fri, Oct 17 from Chicago to Aguadilla, returning Sun, Oct 19, priced at $298 found 1 day ago

Puerto Rico Island economy flight packages

Price found within the past 48 hours. Click for updated prices.
The Wave Hotel at Condado
3.0-star property

The Wave Hotel at Condado

7.6/10 Good! (1,235 reviews)

Sep 18 - Sep 24

6 night stay

Chicago (CHI) to San Juan (SJU)

Spirit Airlines • Non-stop • Coach

San Juan (SJU) to Chicago (CHI)

American Airlines • Non-stop • Coach
per person
found 1 day ago
Great location that feels like a midway point between the more touristy aspects of Condado and the beach, and more traditional city vibes of places like Calle Cerra. Excellent staff, everyone is nice, personable and helpful, especially NInoshka at the front desk. Nice rooftop with a 360 view that gives you a long view towards the beach on one side, and the mountains on the other, with all sorts of highrise architecture and cityscape in between. My room was a good size with a comfortable bed, standard furnishings, comfortable use-of-space bathroom and a good view of the city area around Condado Beach (before you hit the beach itself). Housekeeping is consistent with the quality of cleaning, and of course if you want to sleep in after a night out you can put up the sign to skip your room for the day. I'd stay again👏

Reviewed on Apr 5, 2025

Fairmont El San Juan Hotel
5.0-star property

Fairmont El San Juan Hotel

8.4/10 Very Good! (1,894 reviews)

Sep 18 - Sep 24

6 night stay

Chicago (CHI) to San Juan (SJU)

Spirit Airlines • Non-stop • Coach

San Juan (SJU) to Chicago (CHI)

American Airlines • Non-stop • Coach
Save 100% on your flight
per person
found 1 day ago
Great pool and beach.

Reviewed on Aug 8, 2025

DoubleTree by Hilton San Juan
4.0-star property

DoubleTree by Hilton San Juan

8.8/10 Excellent! (1,013 reviews)

Sep 18 - Sep 24

6 night stay

Chicago (CHI) to San Juan (SJU)

Spirit Airlines • Non-stop • Coach

San Juan (SJU) to Chicago (CHI)

American Airlines • Non-stop • Coach
Save 100% on your flight
per person
found 1 day ago
Staff was great. Room was clean. Would Definitely stay here again. Right across from supermarket. Beach shuttle was reliable. Cafe downstairs served a good brunch.

Reviewed on May 12, 2025

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Puerto Rico Island packages with premium economy flights

Price found within the past 48 hours. Click for updated prices.
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! (629 reviews)

Oct 7 - Oct 10

3 night stay

Chicago (ORD) to San Juan (SJU)

Delta • Non-stop roundtrip • PremiumEconomy
per person
found 1 day ago
Gorgeous, unique property. If you cannot stand the chain hotels and need a little character in your hotel, you will LOVE Olive. The rest is also amazing 5 star all the way.

Reviewed on Aug 9, 2025

The Tryst Beachfront Hotel
3.5-star property

The Tryst Beachfront Hotel

8/10 Very Good! (528 reviews)

Sep 11 - Sep 14

3 night stay

Chicago (ORD) to San Juan (SJU)

Delta • Non-stop roundtrip • PremiumEconomy
per person
found 1 day ago
Love that this property is beachfront. Also I felt very safe as a woman who traveled solo with their 24-hour front desk and security. The food is amazing! Only thing I wish the room doors were more soundproof. I was able to hear the movie that the guest across the hall from me was a watching. Nonetheless, I will still be back to visit!

Reviewed on May 13, 2025

Romeo Gay Hotel
4.0-star property

Romeo Gay Hotel

8.6/10 Excellent! (53 reviews)

Sep 11 - Sep 14

3 night stay

Chicago (ORD) to San Juan (SJU)

Delta • Non-stop roundtrip • PremiumEconomy
per person
found 1 day ago
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More About Flying To Puerto Rico Island from Chicago

Route Information for Flights from Chicago to Puerto Rico Island

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
6:05PM UTC
Latest Flight Arrival
3:54AM UTC

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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.