£89 Cheap Flights from San Juan (SJU) to Chicago (ORD)

View £89 flight on Tue, 18 Aug 2026Opens in a new window

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

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

Prices were available within the past 7 days and start at £89 for one-way flights and £323 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

JetBlue Airways
Wed, 16 Sept - Tue, 22 Sept
SJU
San Juan
ORD
Chicago
£323 Return, found 1 day ago
£323
Return
found 1 day ago
Select JetBlue Airways flight, departing Wed, 16 Sept from San Juan to Chicago, returning Tue, 22 Sept, priced at £323 found 1 day ago
JetBlue Airways
Fri, 17 Jul - Mon, 20 Jul
SJU
San Juan
ORD
Chicago
£335 Return, found 2 days ago
£335
Return
found 2 days ago
Select JetBlue Airways flight, departing Fri, 17 Jul from San Juan to Chicago, returning Mon, 20 Jul, priced at £335 found 2 days ago
JetBlue Airways
Wed, 16 Sept - Tue, 22 Sept
SJU
San Juan
ORD
Chicago
£336 Return, found 1 day ago
£336
Return
found 1 day ago
Select JetBlue Airways flight, departing Wed, 16 Sept from San Juan to Chicago, returning Tue, 22 Sept, priced at £336 found 1 day ago
JetBlue Airways
Fri, 17 Jul - Mon, 20 Jul
SJU
San Juan
ORD
Chicago
£344 Return, found 2 days ago
£344
Return
found 2 days ago
Select JetBlue Airways flight, departing Fri, 17 Jul from San Juan to Chicago, returning Mon, 20 Jul, priced at £344 found 2 days ago
JetBlue Airways
Wed, 8 Jul - Mon, 13 Jul
SJU
San Juan
ORD
Chicago
£345 Return, found 4 days ago
£345
Return
found 4 days ago
Select JetBlue Airways flight, departing Wed, 8 Jul from San Juan to Chicago, returning Mon, 13 Jul, priced at £345 found 4 days ago
JetBlue Airways
Fri, 17 Jul - Mon, 20 Jul
SJU
San Juan
ORD
Chicago
£355 Return, found 5 days ago
£355
Return
found 5 days ago
Select JetBlue Airways flight, departing Fri, 17 Jul from San Juan to Chicago, returning Mon, 20 Jul, priced at £355 found 5 days ago
JetBlue Airways
Fri, 17 Jul - Mon, 20 Jul
SJU
San Juan
ORD
Chicago
£357 Return, found 3 days ago
£357
Return
found 3 days ago
Select JetBlue Airways flight, departing Fri, 17 Jul from San Juan to Chicago, returning Mon, 20 Jul, priced at £357 found 3 days ago
JetBlue Airways
Thu, 3 Sept - Wed, 9 Sept
SJU
San Juan
ORD
Chicago
£358 Return, found 23 hours ago
£358
Return
found 23 hours ago
Select JetBlue Airways flight, departing Thu, 3 Sept from San Juan to Chicago, returning Wed, 9 Sept, priced at £358 found 23 hours ago
JetBlue Airways
Wed, 8 Jul - Mon, 13 Jul
SJU
San Juan
ORD
Chicago
£363 Return, found 4 days ago
£363
Return
found 4 days ago
Select JetBlue Airways flight, departing Wed, 8 Jul from San Juan to Chicago, returning Mon, 13 Jul, priced at £363 found 4 days ago
JetBlue Airways
Wed, 8 Jul - Mon, 13 Jul
SJU
San Juan
ORD
Chicago
£365 Return, found 4 days ago
£365
Return
found 4 days ago
Select JetBlue Airways flight, departing Wed, 8 Jul from San Juan to Chicago, returning Mon, 13 Jul, priced at £365 found 4 days ago

Find the cheapest month to fly from San Juan (SJU) to Chicago (ORD)

May is typically the cheapest month to fly

From £115 - £225 per traveller.

Frequently asked questions

Which airlines fly direct from San Juan (SJU-Luis Munoz Marin Intl.) to Chicago, IL (ORD-O'Hare Intl.)?
Enter SJU to ORD and your travel dates, then apply the 'Nonstop' filter to see only direct flights.
How do I find cheap flights from San Juan (SJU-Luis Munoz Marin Intl.) to Chicago, IL (ORD-O'Hare Intl.)?
To find a cheap flight from San Juan (SJU-Luis Munoz Marin Intl.) to Chicago, IL (ORD-O'Hare Intl.), 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 airline to fly with from San Juan (SJU-Luis Munoz Marin Intl.) to Chicago, IL (ORD-O'Hare Intl.)?
The best airline to fly with from San Juan (SJU-Luis Munoz Marin Intl.) to Chicago, IL (ORD-O'Hare Intl.) will differ from traveler to traveler. If you like to fly early, NK offers early morning flights. If price is the most important factor, F9 typically offers the lowest fares. AA offers the most daily flights from San Juan (SJU-Luis Munoz Marin Intl.) to Chicago, IL (ORD-O'Hare Intl.), which is great if flexibility is what you value most. The best carrier for this journey could also be the one you have a loyalty membership with, as flying with that airline or another airline within the same alliance could help you collect points or enjoy lounge access.
What is the best time to fly from San Juan (SJU-Luis Munoz Marin Intl.) to Chicago, IL (ORD-O'Hare 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.
How many flights per day from San Juan (SJU-Luis Munoz Marin Intl.) to Chicago, IL (ORD-O'Hare Intl.)?
When flying from San Juan (SJU-Luis Munoz Marin Intl.) to Chicago, IL (ORD-O'Hare Intl.), you'll find approximately 6 nonstop flights per day. For even more choice, look at flights that include layovers, as there are around 84 connecting flights daily. Some common connection points include Miami Intl. (MIA), Charlotte-Douglas Intl. (CLT), and Liberty Intl. (EWR).
What is the earliest flight from San Juan (SJU-Luis Munoz Marin Intl.) to Chicago, IL (ORD-O'Hare Intl.)?
The earliest flight from San Juan (SJU-Luis Munoz Marin Intl.) to Chicago, IL (ORD-O'Hare Intl.) typically departs at approximately 12:10 AM local time, operated by NK. This is a seasonal service active in March. An early departure like this can help you maximize your time at your destination. To compare early flights on Expedia, select the "Early Morning" and "Morning" filters in your search.
What day of the week has the most flights from San Juan (SJU-Luis Munoz Marin Intl.) to Chicago, IL (ORD-O'Hare Intl.)?
If you're flying from San Juan (SJU-Luis Munoz Marin Intl.) to Chicago, IL (ORD-O'Hare Intl.), you'll generally find the most flights on a Thursday, with around 58 flights available. This gives you plenty of options to choose from. Major airlines on this route include American Airlines, United Airlines, and Frontier Airlines. Thursday offers notably more flight options compared to other days of the week, making it a great day to plan your travel.
What are the most popular departure times for flights from San Juan (SJU-Luis Munoz Marin Intl.) to Chicago, IL (ORD-O'Hare Intl.)?
The most popular departure times for flights from San Juan (SJU-Luis Munoz Marin Intl.) to Chicago, IL (ORD-O'Hare Intl.) are in the early morning, from 6am to 9am. About 33% of passengers prefer this time. Many major carriers, including American Airlines and United Airlines, offer flights during this window. This timing works well because it allows you to start your travel day early and arrive in Chicago with plenty of time for your plans.
How long does it take to fly from San Juan (SJU-Luis Munoz Marin Intl.) to Chicago, IL (ORD-O'Hare Intl.)?
A nonstop flight from SJU to ORD typically takes around 5 hours 20 minutes, covering approximately 2,074 miles. Connecting flights on this route usually add 4 hours to your travel time. 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 San Juan (SJU-Luis Munoz Marin Intl.) to Chicago, IL (ORD-O'Hare Intl.)?
Select the "Business class" and "First class" filters when looking for SJU to ORD 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 San Juan (SJU-Luis Munoz Marin Intl.) to Chicago, IL (ORD-O'Hare Intl.) flight with Expedia?
It's easy to earn miles on a San Juan (SJU-Luis Munoz Marin Intl.) to Chicago, IL (ORD-O'Hare Intl.) 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.
What airports do you fly into for Chicago from Luis Munoz Marin Intl. (SJU)?
From Luis Munoz Marin Intl. (SJU), you can fly into Midway Intl. (MDW) and O'Hare Intl. (ORD) in Chicago. Some flights may connect through major hubs like Orlando Intl. (MCO), Baltimore Washington Intl. Thurgood Marshall (BWI), Liberty Intl. (EWR) before reaching Chicago. Compare routes and airports on Expedia to find the best flight options for your travel plans.
Is it cheaper to buy a plane ticket from San Juan (SJU-Luis Munoz Marin Intl.) to Chicago, IL (ORD-O'Hare Intl.) at the last minute?
Typically, booking a last minute flight from San Juan (SJU-Luis Munoz Marin Intl.) to Chicago, IL (ORD-O'Hare Intl.) 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 San Juan (SJU-Luis Munoz Marin Intl.) to Chicago, IL (ORD-O'Hare Intl.) flight and hotel package?
Securing a San Juan (SJU-Luis Munoz Marin Intl.) to Chicago, IL (ORD-O'Hare Intl.) 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 San Juan (SJU-Luis Munoz Marin Intl.) to Chicago, IL (ORD-O'Hare Intl.)?
If you booked your San Juan (SJU-Luis Munoz Marin Intl.) to Chicago, IL (ORD-O'Hare Intl.) 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
Luis Munoz Marin Intl.
Destination airport
O'Hare Intl.
Return price
£323
Distance
3317 km
Average flight time
4 hours 12 mins

Book with confidence

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

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

The easiest way to view the best deals on flights from San Juan to Chicago 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 Luis Munoz Marin Intl. to O'Hare Intl. start at just £323 and range up to £365.  

To find an even better deal, try  

  • being flexible on your dates – midweek flights can be cheaper
  • looking for other airports near San Juan and Chicago
  • 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 San Juan to Chicago flight with Expedia!

We cater for all flight types, cabin classes and airlines. So whether you’re booking flights from Luis Munoz Marin Intl. to O'Hare 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 San Juan to Chicago easily and book with confidence

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*Available to Expedia members.