$64 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, Mar 9 - Tue, Mar 25
MDW
Midway Intl.
SJU
Luis Munoz Marin Intl.
$317 Roundtrip, found 1 day ago
$317
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Sun, Mar 9 from Midway Intl. to Luis Munoz Marin Intl., returning Tue, Mar 25, priced at $317 found 1 day ago
Sat, Mar 8 - Mon, Mar 17
ORD
O'Hare Intl.
SJU
Luis Munoz Marin Intl.
$336 Roundtrip, just found
$336
Roundtrip
just found
Select Frontier Airlines flight, departing Sat, Mar 8 from O'Hare Intl. to Luis Munoz Marin Intl., returning Mon, Mar 17, priced at $336 just found

Airfares from $64 One Way, $135 Round Trip from Chicago to San Juan

Prices starting at $135 for return flights and $64 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, May 13 - Tue, May 20
ORD
Chicago
SJU
San Juan
$135 Roundtrip, found 1 hour ago
$135
Roundtrip
found 1 hour ago
Select Spirit Airlines flight, departing Tue, May 13 from Chicago to San Juan, returning Tue, May 20, priced at $135 found 1 hour ago
Sat, May 10 - Mon, May 12
ORD
Chicago
SJU
San Juan
$139 Roundtrip, found 1 hour ago
$139
Roundtrip
found 1 hour ago
Select Spirit Airlines flight, departing Sat, May 10 from Chicago to San Juan, returning Mon, May 12, priced at $139 found 1 hour ago
Fri, May 9 - Tue, May 13
ORD
Chicago
SJU
San Juan
$142 Roundtrip, just found
$142
Roundtrip
just found
Select Spirit Airlines flight, departing Fri, May 9 from Chicago to San Juan, returning Tue, May 13, priced at $142 just found
Tue, Apr 1 - Wed, Apr 2
MDW
Chicago
SJU
San Juan
$173 Roundtrip, found 11 hours ago
$173
Roundtrip
found 11 hours ago
Select Frontier Airlines flight, departing Tue, Apr 1 from Chicago to San Juan, returning Wed, Apr 2, priced at $173 found 11 hours ago
Tue, Apr 1 - Wed, Apr 2
ORD
Chicago
SJU
San Juan
$173 Roundtrip, found 1 day ago
$173
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Tue, Apr 1 from Chicago to San Juan, returning Wed, Apr 2, priced at $173 found 1 day 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

9.2/10 Wonderful! (212 reviews)

Apr 12 - Apr 14

2 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
Nice staff, Morning construction is bothersome.

Reviewed on Feb 25, 2025

Ola Boutique Hotel
4.5-star property

Ola Boutique Hotel

8.8/10 Excellent! (253 reviews)

Apr 24 - Apr 28

4 night stay

Chicago (CHI) to San Juan (SJU)

United • Coach

San Juan (SJU) to Chicago (CHI)

Delta • 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

Urbana Hotel
2.0-star property

Urbana Hotel

8.4/10 Very Good! (154 reviews)

Apr 12 - Apr 14

2 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

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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
5:40PM UTC
Latest Flight Arrival
6:27AM UTC

Chicago to San Juan

The perfect trip begins with Orbitz. From booking your flights from Chicago to San Juan to finding the best hotels, Orbitz has got it covered.

Stress-free Searching

With an easy to use system, Orbitz takes the stress and expense out of travel. Not only does Orbitz match your Chicago to San Juan flights to your ideal hotel, the Display Matrix shows your deals and discounts, including free nights and other savings.

Be One Step Ahead

Need to know what is going on at the airport before you get there? With Orbitz’s free alerts service, you can quickly find out about any booking changes, or flight from Chicago to San Juan disruptions, saving you hours of wasted time. And if you are being picked up at the airport after your Chicago to San Juan flights, have alerts sent straight to your contact’s mobile phone or email.

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Find the best price on flights from Chicago to San Juan with Orbitz’s mobile apps for iPhone and Android. Use m.orbitz.com on your mobile browser to check your gate, baggage allowance and delays, or find exclusive deals on hotels only available to mobile users.

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Not only does booking with us ensure guaranteed low prices, but Orbitz does the hard work, leaving you to relax. Just tell us what you want, from Chicago to San Juan flights, to great deals on hotels and car rental, and activities and tours, and we will do all the rest.

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.