$105 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, Apr 27 - Wed, Apr 30
ORD
O'Hare Intl.
SJU
Luis Munoz Marin Intl.
$282 Roundtrip, found 6 hours ago
$282
Roundtrip
found 6 hours ago
Select Spirit Airlines flight, departing Sun, Apr 27 from O'Hare Intl. to Luis Munoz Marin Intl., returning Wed, Apr 30, priced at $282 found 6 hours ago
Sun, Apr 27 - Thu, May 1
MDW
Midway Intl.
SJU
Luis Munoz Marin Intl.
$308 Roundtrip, found 17 hours ago
$308
Roundtrip
found 17 hours ago
Select Frontier Airlines flight, departing Sun, Apr 27 from Midway Intl. to Luis Munoz Marin Intl., returning Thu, May 1, priced at $308 found 17 hours ago

Airfares from $105 One Way, $182 Round Trip from Chicago to San Juan

Prices starting at $182 for return flights and $105 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, Apr 29 - Thu, May 1
ORD
Chicago
SJU
San Juan
$182 Roundtrip, found 15 hours ago
$182
Roundtrip
found 15 hours ago
Select Spirit Airlines flight, departing Tue, Apr 29 from Chicago to San Juan, returning Thu, May 1, priced at $182 found 15 hours ago
Tue, Apr 29 - Sat, May 3
ORD
Chicago
SJU
San Juan
$193 Roundtrip, found 17 hours ago
$193
Roundtrip
found 17 hours ago
Select Spirit Airlines flight, departing Tue, Apr 29 from Chicago to San Juan, returning Sat, May 3, priced at $193 found 17 hours ago
Sun, May 11 - Thu, May 15
ORD
Chicago
SJU
San Juan
$212 Roundtrip, just found
$212
Roundtrip
just found
Select Spirit Airlines flight, departing Sun, May 11 from Chicago to San Juan, returning Thu, May 15, priced at $212 just found
Tue, Sep 23 - Mon, Sep 29
ORD
Chicago
SJU
San Juan
$298 Roundtrip, found 5 hours ago
$298
Roundtrip
found 5 hours ago
Select United flight, departing Tue, Sep 23 from Chicago to San Juan, returning Mon, Sep 29, priced at $298 found 5 hours ago
Sun, May 4 - Mon, May 5
MDW
Chicago
SJU
San Juan
$303 Roundtrip, found 4 days ago
$303
Roundtrip
found 4 days ago
Select Frontier Airlines flight, departing Sun, May 4 from Chicago to San Juan, returning Mon, May 5, priced at $303 found 4 days ago

San Juan economy flight packages

Price found within the past 48 hours. Click for updated prices.
Old San Juan Rentals
3.5-star property

Old San Juan Rentals

8.6/10 Excellent! (562 reviews)

May 22 - May 25

3 night stay

Chicago (CHI) to San Juan (SJU)

Frontier Airlines • Non-stop • Coach

San Juan (SJU) to Chicago (CHI)

Spirit Airlines • Non-stop • Coach
per person
found 11 hours ago
Great location. Lots toDo Within walking distance. Easy pick up for Uber in the plaza two blocks away. Can get quite noisy at night but that’s to be expected given the location. Property itself needs lots of care. Hot water was scarce. Ants in the kitchen. Micro wave and shower dispensers were broken. Linen meeds to be updated. Poor lighting unless the shutters are open. Great deck with nice views, but it needs to be renovated.

Reviewed on Mar 22, 2025

Ola Boutique Hotel
4.5-star property

Ola Boutique Hotel

9/10 Wonderful! (310 reviews)

Jun 6 - Jun 13

7 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

Ciqala Suites Hotel
4.0-star property

Ciqala Suites Hotel

7.4/10 Good! (1,008 reviews)

Jun 15 - Jun 19

4 night stay

Chicago (CHI) to San Juan (SJU)

United • Coach

San Juan (SJU) to Chicago (CHI)

Spirit Airlines • Coach
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 packages with premium economy flights

Price found within the past 48 hours. Click for updated prices.
3 Bedroom Oceanfront Beach House
3.5-star property

3 Bedroom Oceanfront Beach House

9.8/10 Exceptional! (26 reviews)

Jun 4 - Jun 7

3 night stay

Chicago (MDW) to San Juan (SJU)

Delta • PremiumEconomy

San Juan (SJU) to Chicago (MDW)

United • PremiumEconomy
per person
found 1 day ago
THE VIEW LUXE HOTEL
2.0-star property

THE VIEW LUXE HOTEL

10/10 Exceptional! (4 reviews)

Jun 4 - Jun 7

3 night stay

Chicago (MDW) to San Juan (SJU)

Delta • PremiumEconomy

San Juan (SJU) to Chicago (MDW)

United • PremiumEconomy
per person
found 1 day ago
BOHO by THE VIEW LUXE HOTEL
2.0-star property

BOHO by THE VIEW LUXE HOTEL

No reviews

Jun 4 - Jun 7

3 night stay

Chicago (MDW) to San Juan (SJU)

Delta • PremiumEconomy

San Juan (SJU) to Chicago (MDW)

United • PremiumEconomy
per person
found 1 day ago
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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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If value is what you are after, let Orbitz take care of you. Your low cost Chicago to San Juan flights along with our great bargains on hotels and car rentals will make your trip all the more memorable.

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.