$70 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, Feb 2 - Sat, Feb 8
ORD
O'Hare Intl.
SJU
Luis Munoz Marin Intl.
$199 Roundtrip, just found
$199
Roundtrip
just found
Select Spirit Airlines flight, departing Sun, Feb 2 from O'Hare Intl. to Luis Munoz Marin Intl., returning Sat, Feb 8, priced at $199 just found
Sun, Feb 2 - Wed, Feb 12
MDW
Midway Intl.
SJU
Luis Munoz Marin Intl.
$263 Roundtrip, found 2 days ago
$263
Roundtrip
found 2 days ago
Select Frontier Airlines flight, departing Sun, Feb 2 from Midway Intl. to Luis Munoz Marin Intl., returning Wed, Feb 12, priced at $263 found 2 days ago

Airfares from $70 One Way, $131 Round Trip from Chicago to San Juan

Prices starting at $131 for return flights and $70 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, Feb 9 - Wed, Feb 19
ORD
Chicago
SJU
San Juan
$131 Roundtrip, found 1 day ago
$131
Roundtrip
found 1 day ago
Select Spirit Airlines flight, departing Sun, Feb 9 from Chicago to San Juan, returning Wed, Feb 19, priced at $131 found 1 day ago
Tue, Mar 4 - Wed, Mar 5
ORD
Chicago
SJU
San Juan
$133 Roundtrip, found 9 hours ago
$133
Roundtrip
found 9 hours ago
Select Spirit Airlines flight, departing Tue, Mar 4 from Chicago to San Juan, returning Wed, Mar 5, priced at $133 found 9 hours ago
Tue, Mar 4 - Wed, Mar 5
ORD
Chicago
SJU
San Juan
$140 Roundtrip, found 9 hours ago
$140
Roundtrip
found 9 hours ago
Select Spirit Airlines flight, departing Tue, Mar 4 from Chicago to San Juan, returning Wed, Mar 5, priced at $140 found 9 hours ago
Mon, Mar 3 - Tue, Mar 11
MDW
Chicago
SJU
San Juan
$140 Roundtrip, found 3 hours ago
$140
Roundtrip
found 3 hours ago
Select Frontier Airlines flight, departing Mon, Mar 3 from Chicago to San Juan, returning Tue, Mar 11, priced at $140 found 3 hours ago
Sat, Feb 15 - Thu, Feb 20
ORD
Chicago
SJU
San Juan
$140 Roundtrip, found 1 hour ago
$140
Roundtrip
found 1 hour ago
Select Frontier Airlines flight, departing Sat, Feb 15 from Chicago to San Juan, returning Thu, Feb 20, priced at $140 found 1 hour ago

San Juan economy flight packages

Price found within the past 48 hours. Click for updated prices.
The Condado Plaza Hotel
4.0-star property

The Condado Plaza Hotel

7.4/10 Good! (1,007 reviews)

Mar 12 - Mar 16

4 night stay

Chicago (CHI) to San Juan (SJU)

Spirit Airlines • Roundtrip • Coach
Save 100% on your flight
per person
found 1 day ago
Elevator didn’t work, staff wasn’t always friendly. Nice location

Reviewed on Jan 3, 2025

Ola Boutique Hotel
4.5-star property

Ola Boutique Hotel

8.8/10 Excellent! (253 reviews)

Mar 12 - Mar 16

4 night stay

Chicago (CHI) to San Juan (SJU)

Spirit Airlines • 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

Aire de O:live
4.0-star property

Aire de O:live

9.2/10 Wonderful! (39 reviews)

Mar 12 - Mar 16

4 night stay

Chicago (CHI) to San Juan (SJU)

Spirit Airlines • Roundtrip • Coach
Save 100% on your flight
per person
found 1 day ago
This was a pure oasis. The rooms are clean and zen-like (which means no desk to do work at, which I could have used), but lovely natural materials for the furniture, quiet, there’s no lobby area to hang out in but the use of wood and stone throughout, the 2nd floor pool (which is small and shady in the afternoon but similarly relaxing and oasis like), and the convenience to the beach-across a small street and off the busy main strip in Isla Verde was wonderful.

Reviewed on Jan 6, 2025

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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

8.8/10 Excellent! (253 reviews)

Mar 26 - Mar 30

4 night stay

Chicago (ORD) to San Juan (SJU)

Delta • Non-stop roundtrip • PremiumEconomy
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

The St. Regis Bahia Beach Resort, Puerto Rico
5.0-star property

The St. Regis Bahia Beach Resort, Puerto Rico

9.4/10 Exceptional! (423 reviews)

Mar 26 - Mar 30

4 night stay

Chicago (ORD) to San Juan (SJU)

Delta • Non-stop roundtrip • PremiumEconomy
Save 100% on your flight
per person
found 1 day ago
Gorgeous resort property on a nature preserve/compound with private homes, bike paths, animal shelter, golf course, restaurants. We did not leave the compound our entire stay. Excellent service and bikes are provided to explore the property. Tours and transportation available on golf carts. Only warnings are: Can't wear heals or ride bikes on the wooden paths to the rooms so ladies bring flats. Iguanas roam the property freely and jumped in the pool. Stray cats and birds harass you when eating in the outdoor cafe.

Reviewed on Feb 27, 2024

Aire de O:live
4.0-star property

Aire de O:live

9.2/10 Wonderful! (39 reviews)

Mar 26 - Mar 30

4 night stay

Chicago (ORD) to San Juan (SJU)

Delta • Non-stop roundtrip • PremiumEconomy
per person
found 1 day ago
This was a pure oasis. The rooms are clean and zen-like (which means no desk to do work at, which I could have used), but lovely natural materials for the furniture, quiet, there’s no lobby area to hang out in but the use of wood and stone throughout, the 2nd floor pool (which is small and shady in the afternoon but similarly relaxing and oasis like), and the convenience to the beach-across a small street and off the busy main strip in Isla Verde was wonderful.

Reviewed on Jan 6, 2025

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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! (154 reviews)

Mar 23 - Mar 30

7 night stay

Chicago (ORD) to San Juan (SJU)

Delta • Non-stop roundtrip • FirstClass
per person
found 12 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

Ola Boutique Hotel
4.5-star property

Ola Boutique Hotel

8.8/10 Excellent! (253 reviews)

Mar 22 - Mar 29

7 night stay

Chicago (ORD) to San Juan (SJU)

United • Roundtrip • FirstClass
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

Hotel Puerto Valdes
4.0-star property

Hotel Puerto Valdes

9/10 Wonderful! (364 reviews)

Mar 23 - Mar 30

7 night stay

Chicago (ORD) to San Juan (SJU)

Delta • Non-stop roundtrip • FirstClass
per person
found 12 hours ago
The staff is what made this stay a win win! Thanks to Alex and his recommendations we had a great time. He definitely made up for the construction noise and the roof top being closed. To the owner or owners if it was not for your staff we would have left after the first day due to not being told about the construction.

Reviewed on Sep 3, 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, Spirit Airlines
Earliest Flight Arrival
6:45PM UTC
Latest Flight Arrival
12:21AM UTC

Chicago to San Juan

For the best travel experience from Chicago to San Juan domestic and international travelers everywhere choose Orbitz for guaranteed low prices and cutting-edge mobile tools.

Convenient Low-Cost Travel

Orbitz makes it simple to book discount flights from Chicago to {destination.name} without compromising your schedule. You can always find deals on domestic flights from a location near you. You may find the best deals to fit your schedule by mixing and matching airlines to get you from Chicago to San Juan.

Access Orbitz On The Move

You can access Orbitz anywhere at anytime for travel from Chicago to San Juan using the latest technology. Via your mobile phone you can track any changes to your flight status, gate and baggage claim details, and with Orbitz’s full-service mobile apps for iPhone and Android you can view these trip details anytime anywhere. You can also get fare alerts and travel updates to keep you informed of the cheapest flights from Chicago to San Juan.

Earn Rewards on Your Chicago to San Juan Flights

At Orbitz you can benefit from low cost travel and have your loyalty rewarded on certain types of Chicago to San Juan flights. All you need to do is enter you frequent flyer number when booking and rack up your rewards through Orbitz online on the Traveler Information page for use on future flights. You can even add your frequent flyer number to an existing reservation to start the ball rolling.

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.