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£113 Cheap Flights from Chicago (ORD) to San Juan (SJU)

View £113 flight on Mon, 14 Sept 2026Opens in a new window

Popular airlines from Chicago O'Hare International Airport (ORD) to Luis Munoz Marin Intl. Airport (SJU)

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Cheap Flights from Chicago (ORD) to San Juan (SJU)

Prices were available within the past 7 days and start at £113 for one-way flights and £207 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

American Airlines
Sat, 12 Sept - Tue, 15 Sept
ORD
Chicago
SJU
San Juan
£207 Return, found 4 days ago
£207
Return
found 4 days ago
Select American Airlines flight, departing Sat, 12 Sept from Chicago to San Juan, returning Tue, 15 Sept, priced at £207 found 4 days ago
JetBlue Airways
Wed, 16 Sept - Wed, 23 Sept
ORD
Chicago
SJU
San Juan
£226 Return, found 2 days ago
£226
Return
found 2 days ago
Select JetBlue Airways flight, departing Wed, 16 Sept from Chicago to San Juan, returning Wed, 23 Sept, priced at £226 found 2 days ago
American Airlines
Sat, 12 Sept - Tue, 15 Sept
ORD
Chicago
SJU
San Juan
£233 Return, found 4 days ago
£233
Return
found 4 days ago
Select American Airlines flight, departing Sat, 12 Sept from Chicago to San Juan, returning Tue, 15 Sept, priced at £233 found 4 days ago
Delta
Sat, 12 Sept - Tue, 15 Sept
ORD
Chicago
SJU
San Juan
£246 Return, found 4 days ago
£246
Return
found 4 days ago
Select Delta flight, departing Sat, 12 Sept from Chicago to San Juan, returning Tue, 15 Sept, priced at £246 found 4 days ago
JetBlue Airways
Tue, 3 Nov - Tue, 17 Nov
ORD
Chicago
SJU
San Juan
£246 Return, found 4 days ago
£246
Return
found 4 days ago
Select JetBlue Airways flight, departing Tue, 3 Nov from Chicago to San Juan, returning Tue, 17 Nov, priced at £246 found 4 days ago
JetBlue Airways
Wed, 16 Sept - Wed, 23 Sept
ORD
Chicago
SJU
San Juan
£260 Return, found 2 days ago
£260
Return
found 2 days ago
Select JetBlue Airways flight, departing Wed, 16 Sept from Chicago to San Juan, returning Wed, 23 Sept, priced at £260 found 2 days ago
Delta
Sat, 5 Sept - Thu, 24 Sept
ORD
Chicago
SJU
San Juan
£261 Return, found 4 days ago
£261
Return
found 4 days ago
Select Delta flight, departing Sat, 5 Sept from Chicago to San Juan, returning Thu, 24 Sept, priced at £261 found 4 days ago
American Airlines
Sat, 12 Sept - Tue, 15 Sept
ORD
Chicago
SJU
San Juan
£262 Return, found 4 days ago
£262
Return
found 4 days ago
Select American Airlines flight, departing Sat, 12 Sept from Chicago to San Juan, returning Tue, 15 Sept, priced at £262 found 4 days ago
JetBlue Airways
Mon, 14 Sept - Mon, 21 Sept
ORD
Chicago
SJU
San Juan
£264 Return, found 2 days ago
£264
Return
found 2 days ago
Select JetBlue Airways flight, departing Mon, 14 Sept from Chicago to San Juan, returning Mon, 21 Sept, priced at £264 found 2 days ago
United
Sun, 23 Aug - Wed, 9 Sept
ORD
Chicago
SJU
San Juan
£322 Return, found 4 days ago
£322
Return
found 4 days ago
Select United flight, departing Sun, 23 Aug from Chicago to San Juan, returning Wed, 9 Sept, priced at £322 found 4 days ago

Alternative airports near San Juan

Prices were available within the past 7 days. Prices and availability are subject to change.

Select flight to Luis Munoz Marin Intl. SJU. Cheapest option available. Average driving time to city centre is 16 minutes. Flights from £295
SJU
Luis Munoz Marin Intl.
Cheapest
Average driving time to city centre16 min
Flights from £295

Frequently asked questions

How much does a flight from Chicago, IL (ORD-O'Hare Intl.) to San Juan (SJU-Luis Munoz Marin Intl.) cost?
You can find cheap one-way flights from £113 and cheap return flights from £207 ORD to SJU with Expedia. One-way flights typically cost between £313 and £465. Flight prices vary based on the month and day of the week you want to travel, as well as the airline and how far in advance you book your ticket. Filter your search on Expedia by "Price (lowest to highest)" to see the cheapest fares first, and use the Price Tracking tool to receive alerts when ORD to SJU ticket fares go up or down.
What is the cheapest month to fly from Chicago, IL (ORD-O'Hare Intl.) to San Juan (SJU-Luis Munoz Marin Intl.)?
The cheapest months to fly from ORD to SJU are typically during off-peak season when demand is low. Traveling in off-peak or shoulder months is usually a good way to secure cheap tickets, just remember to avoid flying during holidays if you are able to. Use the calendar view in your search to see which months have low fares on this route.
Which airlines fly direct from Chicago, IL (ORD) to San Juan (SJU)?
Enter ORD to SJU and your travel dates, then apply the 'Nonstop' filter to see only direct flights.
What is the cheapest airline that flies from Chicago, IL (ORD-O'Hare Intl.) to San Juan (SJU-Luis Munoz Marin Intl.)?
Frontier Airlines also offers one of the cheapest connecting return flights on this route, with tickets starting from around £86. Frontier Airlines is one of the cheapest airlines offering nonstop return flights from Chicago, IL (ORD-O'Hare Intl.) to San Juan (SJU-Luis Munoz Marin Intl.), with tickets starting from around £95 for flights that can be booked for departure within the next year. These prices are per adult, for economy/coach class. Use Expedia's search tool to compare the prices and schedules of airlines that fly this route to find the best option for your plans and budget.
How do I find cheap flights from Chicago, IL (ORD) to San Juan (SJU)?
To find a cheap flight from Chicago, IL (ORD) to San Juan (SJU), be flexible with your dates. Traveling outside of peak vacation months and booking a mid-week flight can help you save. Early morning and late night flights are often more affordable, too. Expedia allows you to compare flight times, airlines and routes all in one place to find low fares. You can also set up Price Tracking and receive alerts when fares go up or down.
What is the best time to fly from Chicago, IL (ORD-O'Hare Intl.) to San Juan (SJU-Luis Munoz Marin Intl.)?
The best time to fly is usually mid-week (Tuesday or Wednesday) and during early morning hours as flights tend to be cheaper, less crowded, and generally more on-time. Avoid major holidays and peak vacation seasons for smoother travel. Combining off-peak days and hours often gives the best combination of cost, comfort, and convenience.
What is the earliest flight from Chicago, IL (ORD) to San Juan (SJU)?
Sort flights by "Departure (earliest)" on Expedia to find the earliest flight from Chicago, IL (ORD) to San Juan (SJU). To compare more early flights, use the "Early Morning" and "Morning" filters in your search.
How long does it take to fly from Chicago, IL (ORD-O'Hare Intl.) to San Juan (SJU-Luis Munoz Marin Intl.)?
Flying nonstop from ORD to SJU takes around 4 hours 50 minutes, with the route covering approximately 3,338 kilometers. Flights with a layover typically take 3 hours 30 minutes longer than direct options. Keep in mind that actual flight times can vary due to wind patterns, weather, and air traffic.
Can you fly business or first class from Chicago, IL (ORD) to San Juan (SJU)?
Select the "Business class" and "First class" filters when looking for Chicago, IL (ORD) to San Juan (SJU) flights on Expedia. This is the easiest way to compare prices, routes and flight times for your trip.
How do I earn miles on a Chicago, IL (ORD) to San Juan (SJU) flight with Expedia?
It's easy to earn miles on a Chicago, IL (ORD) to San Juan (SJU) flight when you book with Expedia. Before you confirm your booking, simply select your frequent flyer program and enter your program number. As a member of One Key™, you can also earn OneKeyCash™* on top of your airline miles when you book with Expedia.*Excludes taxes and fees. OneKeyCash is not redeemable for cash and can only be used on Expedia and other participating brands.
Is it cheaper to buy a plane ticket from Chicago, IL (ORD) to San Juan (SJU) at the last minute?
Typically, booking a last minute flight from Chicago, IL (ORD) to San Juan (SJU) will be more expensive than booking in advance. As the departure date approaches, there are usually fewer seats available which can drive up the cost. However, if there's some wiggle room with your travel dates and times, you could bag a cheap last-minute fare.
Is it cheaper to book a Chicago, IL (ORD) to San Juan (SJU) flight and hotel package?
Securing a Chicago, IL (ORD) to San Juan (SJU) flight and hotel package is usually cheaper than booking separately. With Expedia, you can enjoy the ease of organizing your travels all in one place. Select from our extensive range of stays and then add flights, activities and car rentals to your booking. Bundle everything together, and you could save hundreds of dollars.
Can I cancel or change the date of my flight from Chicago, IL (ORD) to San Juan (SJU)?
If you booked your Chicago, IL (ORD) to San Juan (SJU) flight within the last 24 hours, you may be able to modify or cancel it without any fees. Depending on the airline and the type of ticket you have, additional charges may apply for changes beyond this timeframe. Airline policies and contact information can be found in your itinerary or confirmation email. Or, head to our Customer Service portal if you'd like more information.

Travel information

Origin airport
O'Hare Intl.
Destination airport
Luis Munoz Marin Intl.
Airlines serving
JetBlue Airways
Return price
£206
Distance
3317 km
Average flight time
5 hours 56 mins

Book with confidence

Compare flights from Chicago to San Juan easily and book with confidence

For travelling on business or for pleasure, Expedia makes it easy to book your flights from Chicago to San Juan. Operating between them flights per day, 20 airlines cover the route. And fly direct, getting you to Luis Munoz Marin Intl. in just hours. If you have a preferred carrier, use our advanced search tool to find the right flight from O'Hare Intl. to Luis Munoz Marin Intl..  

To make things even better, in the advanced search, you can also choose to fly economy, premium economy, business or first class, select your maximum number of stops, and pick your preferred departure and arrival time. You can also opt for refundable and direct flights. 

Grab a great deal on your flight from O'Hare Intl. (ORD) to Luis Munoz Marin Intl. (SJU)

The easiest way to view the best deals on flights from Chicago to San Juan today is to enter your travel dates and hit search. From here, you can sort your results by price to see the cheapest flights first. Right now, return flights from O'Hare Intl. to Luis Munoz Marin Intl. start at just £207 and range up to £322.  

To find an even better deal, try  

  • being flexible on your dates – midweek flights can be cheaper
  • looking for other airports near Chicago and San Juan
  • booking your flight during September, the cheapest month on this route
  • varying your flight times – early morning and late at night are sometimes cheaper 

Why you should book your Chicago to San Juan flight with Expedia!

We cater for all flight types, cabin classes and airlines. So whether you’re booking flights from O'Hare Intl. to Luis Munoz Marin Intl. for a budget break or a business trip with a bit of pleasure thrown in, we make it easy to secure the seat that’s right for you.  

Thanks to our supersized inventory that offers great choice all in one place, you know you’ll get a great deal with Expedia. Especially if you bundle your flight together with your hotel, you will unlock amazing savings. For added peace of mind, you can choose flexible bookings or filter to find refundable options, so you won’t pay a fee to change your flight.  

Compare flights from Chicago to San Juan easily and book with confidence

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*Available to Expedia members.