A coastal fortification with a large dome, overlooking a calm sea and distant mountains.

$104 Cheap Flights from Chicago (ORD) to San Juan (SJU)

View $104 flight on Mon, Aug 31, 2026Opens in a new window

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

  • Be in the know

    Get alerts if flight prices drop or rise*

  • Book smarter

    Save up to 30% on select hotels after you book a flight*

  • Earn twice

    Earn your airline miles on top of our OneKeyCash
    Learn about One Key

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

Prices were available within the past 7 days and start at $104 for one-way flights and $209 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Frontier Airlines
Mon, Aug 31 - Sat, Sep 5
ORD
Chicago
SJU
San Juan
$209 Roundtrip, found 4 hours ago
$209
Roundtrip
found 4 hours ago
Select Frontier Airlines flight, departing Mon, Aug 31 from Chicago to San Juan, returning Sat, Sep 5, priced at $209 found 4 hours ago
Frontier Airlines
Mon, Aug 31 - Wed, Sep 2
ORD
Chicago
SJU
San Juan
$210 Roundtrip, found 5 hours ago
$210
Roundtrip
found 5 hours ago
Select Frontier Airlines flight, departing Mon, Aug 31 from Chicago to San Juan, returning Wed, Sep 2, priced at $210 found 5 hours ago
Frontier Airlines
Tue, Sep 1 - Wed, Sep 2
ORD
Chicago
SJU
San Juan
$212 Roundtrip, found 4 hours ago
$212
Roundtrip
found 4 hours ago
Select Frontier Airlines flight, departing Tue, Sep 1 from Chicago to San Juan, returning Wed, Sep 2, priced at $212 found 4 hours ago
Frontier Airlines
Mon, Aug 31 - Sat, Sep 5
ORD
Chicago
SJU
San Juan
$218 Roundtrip, found 3 hours ago
$218
Roundtrip
found 3 hours ago
Select Frontier Airlines flight, departing Mon, Aug 31 from Chicago to San Juan, returning Sat, Sep 5, priced at $218 found 3 hours ago
Frontier Airlines
Mon, Aug 24 - Tue, Sep 1
ORD
Chicago
SJU
San Juan
$220 Roundtrip, found 1 hour ago
$220
Roundtrip
found 1 hour ago
Select Frontier Airlines flight, departing Mon, Aug 24 from Chicago to San Juan, returning Tue, Sep 1, priced at $220 found 1 hour ago
Frontier Airlines
Mon, Aug 24 - Sat, Sep 5
ORD
Chicago
SJU
San Juan
$228 Roundtrip, found 1 hour ago
$228
Roundtrip
found 1 hour ago
Select Frontier Airlines flight, departing Mon, Aug 24 from Chicago to San Juan, returning Sat, Sep 5, priced at $228 found 1 hour ago
Frontier Airlines
Mon, Aug 24 - Wed, Sep 2
ORD
Chicago
SJU
San Juan
$230 Roundtrip, found 1 hour ago
$230
Roundtrip
found 1 hour ago
Select Frontier Airlines flight, departing Mon, Aug 24 from Chicago to San Juan, returning Wed, Sep 2, priced at $230 found 1 hour ago
American Airlines
Thu, Aug 27 - Thu, Sep 3
ORD
Chicago
SJU
San Juan
$247 Roundtrip, just found
$247
Roundtrip
just found
Select American Airlines flight, departing Thu, Aug 27 from Chicago to San Juan, returning Thu, Sep 3, priced at $247 just found
JetBlue Airways
Tue, Sep 1 - Wed, Sep 2
ORD
Chicago
SJU
San Juan
$293 Roundtrip, found 4 hours ago
$293
Roundtrip
found 4 hours ago
Select JetBlue Airways flight, departing Tue, Sep 1 from Chicago to San Juan, returning Wed, Sep 2, priced at $293 found 4 hours ago
Delta
Wed, Sep 9 - Wed, Sep 16
ORD
Chicago
SJU
San Juan
$316 Roundtrip, found 3 hours ago
$316
Roundtrip
found 3 hours ago
Select Delta flight, departing Wed, Sep 9 from Chicago to San Juan, returning Wed, Sep 16, priced at $316 found 3 hours 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 center is 16 minutes. Flights from $318
SJU
Luis Munoz Marin Intl.
Cheapest
Average driving time to city center16 min
Flights from $318

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

August is typically the cheapest month to fly

From $148 - $345 per traveler.

What you need to know for your flight from O'Hare Intl. to Luis Munoz Marin Intl.

Chicago (ORD) to San Juan (SJU) at a glance

Embark on your journey from Chicago (ORD) to San Juan (SJU) with a selection of airlines catering to this international long-haul route. You can choose between full-service and budget carriers, allowing you to find flights from Chicago that align with your budget and travel schedule. As you plan your adventure, be sure to discover San Juan's iconic sights and vibrant neighborhoods, and check out the essential details for flying from O'Hare International Airport to Luis Munoz Marin International Airport.

  • Fastest flight duration: around 4h 45m non-stop
  • Route distance: roughly 2,100 miles (3,380 km)
  • Flights per week: around 40+ flights with multiple daily departures on average
  • Typical fares (one-way): economy tickets often range from $115–$430, depending on seasonality and how far ahead you book

Flights from O'Hare International Airport (ORD) to Luis Munoz Marin International Airport (SJU)

According to recent traveler bookings, here are the top airlines favored for flights from Chicago to San Juan, featuring both non-stop and one-stop options. Popular layover airports include John F. Kennedy International Airport (JFK) with approximately a 1 hour and 30 minute layover, Hartsfield-Jackson Atlanta International Airport (ATL) at around 2 hours, and Orlando International Airport (MCO) with a 1 hour and 45 minute layover. This variety allows you to mix and match price, total travel time, and cabin class to create the ideal itinerary.

  • American Airlines: This full-service airline provides non-stop, one-stop, and multi-stop options, with one-way ticket prices generally falling between $130 and $440. It represents about 37% of flights on this route, boasting a standard non-stop travel time of 4 hours and 45 minutes.
  • United: Another full-service option, United Airlines also offers both non-stop and one-stop flights, with one-way fares typically ranging from $135 to $500. Approximately 32% of departures are with United, with a similar non-stop journey time of around 4 hours and 45 minutes.
  • Frontier Airlines: As a low-cost option, Frontier Airlines provides one-stop service, with one-way fares usually between $115 and $330. It accounts for about 10% of flights on this route, featuring an in-flight duration of 6 hours and a total travel time of approximately 7 hours and 45 minutes, including layovers.
  • JetBlue Airways: JetBlue is a budget airline that offers one-stop service, with one-way prices typically ranging from $115 to $265. It holds approximately 9% of departures on this route, with a flight time of 6 hours and a total journey time of around 7 hours and 45 minutes, factoring in a layover.
  • Delta: This full-service carrier provides one-stop flights, with one-way ticket prices typically ranging from $120 to $435. Delta accounts for about 7% of departures on this route, featuring an in-flight duration of 6 hours and a total travel time of around 7 hours and 45 minutes, including layover time.

Travelers flying from Chicago to San Juan can elevate their experience by upgrading their service. United offers First Class, American Airlines provides Business Class, and Delta features Premium Economy for a more comfortable journey.

Best time to fly from Chicago (ORD) to San Juan (SJU)

The most popular months for travelers flying from Chicago to San Juan are January, March, and April, when peak temperatures in San Juan reach up to 78.1°F in April. If you prefer quieter travel, consider October, the least busy and relatively cheaper time to visit with fewer crowds and temperatures around 81.1°F. For better deals, January usually offers the lowest average one-way fare around $228. Flight availability peaks in March, with approximately 62 flights per week, making it easier to find convenient departure times.

  • Cheapest time to fly: January usually offers good deals with average one-way fare around $228, roughly 13% cheaper than the yearly average.
  • More budget-friendly months to fly: April, May, and October typically offer average one-way fares of around $240.
  • Most flight options: March has the highest number of flights from Chicago to San Juan, with approximately 62 flights per week, giving you more flexibility in scheduling your trip.
calendar iconMonthtemperature iconTemperaturecrowd level iconDemandflights iconWeekly Flightsprice iconAverage one-way Fare
January76.5°F (24.7°C)High40$228
February76.5°F (24.7°C)Average44$255
March76.6°F (24.8°C)High62$281
April78.1°F (25.6°C)High41$239
May79.7°F (26.5°C)Average35$239
June81.3°F (27.4°C)Average35$273
July81.9°F (27.7°C)Average34$268
August82.0°F (27.8°C)Average32$271
September82.0°F (27.8°C)Low26$258
October81.1°F (27.3°C)Low25$240
November79.2°F (26.2°C)Low32$261
December77.4°F (25.2°C)Average54$340

*Average one-way fare is based on Expedia flight booking data from January 2025 to April 2026 for the specified route and travel class and may change depending on availability, dates, and demand.

Alternative routes from Chicago (ORD) to San Juan (SJU)

  • Chicago to San Juan (MDW-SJU): Midway International Airport (MDW) lies approximately 16 miles from O'Hare International Airport (ORD). One-way economy prices for this journey typically fall between $90 and $445, influenced by the season and timing of your booking. Travelers can choose from both non-stop and one-stop flights, with common layover points at Hartsfield-Jackson Atlanta International Airport (ATL) and Orlando International Airport (MCO). The leading airlines for this route include Southwest Airlines and Frontier Airlines, both of which are low-cost carriers.
  • Chicago to Aguadilla (ORD-BQN): Rafael Hernandez Airport (BQN) is located about 74 miles from Luis Munoz Marin International Airport (SJU). One-way economy fares on this route generally range from $110 to $490, based on the time of year and your booking schedule. This route typically features one-stop flights, with frequent layovers at Newark Liberty International Airport (EWR) and Orlando International Airport (MCO). Major airlines providing service on this route are United and Frontier Airlines, the latter being a low-cost option.

How to find the best prices for flights from Chicago (ORD) to San Juan (SJU)

Getting some of the best deals on flights from Chicago to San Juan is all about timing and flexibility. Here are some key tips to help you save:

  1. Best times to book and fly: cheaper fares are usually found when booking 2-8 weeks in advance, which aligns with when most travelers make their reservations. Departures in the afternoon (12pm-6pm) tend to offer lower prices, while morning flights (5am-12pm) are the most popular. Additionally, flying on Tuesday generally provides cheaper prices, although Thursday is the busiest travel day.
  2. Set up price alerts: stay updated on price changes by using Expedia's Price Tracker. Receive alerts when fares drop for your selected route.
  3. Bundle and save: bundle your flight and hotel to save on Expedia, or unlock a hotel deal after booking your flight.* Find San Juan hotel and flight deals.
  4. Compare flight options: use Expedia's search tool to compare airlines, routes, direct vs. non-direct flights, and flight times. You can also sort by price to find the most affordable options.
  5. Stay flexible with dates: being open to different travel days can sometimes help you find better prices on flights and hotels.
  6. Think about luggage: nowadays, it's important to check the airline's baggage policies to find the best value. That may be paying for an additional carry-on bag or booking a ticket with checked luggage included. Either way, double-check your allowance before confirming your booking to avoid excess baggage fees at the airport.

*Members only. Savings vary and are not available on all bundles. Select hotels.

Arriving at Luis Munoz Marin International Airport from O'Hare International Airport

San Juan welcomes travelers from Chicago with a range of transport options based on price, convenience, and proximity. San Juan city center is approximately a 15-minute drive (covering about 10 miles) from Luis Munoz Marin International Airport, depending on traffic. Here's how to reach San Juan efficiently:

  • Hotel transfer: Transfers offer a convenient way to reach your hotel in San Juan, with options including free hotel shuttles and private rides, which can be arranged in advance with your hotel.
  • Car rental: Renting a car from Luis Munoz Marin International Airport is a great option if you plan to explore and sightsee beyond the city. Browse cheap car rentals at Luis Munoz Marin International Airport on Expedia.
  • Taxi/ride-hailing: Taxis and ride-hailing services may be available from designated pickup areas outside the terminal, check locally on arrival.
  • Public transportation: From Luis Munoz Marin International Airport, several key transport options are a short drive away. Universidad Station, a metro station, is located about 4.9 miles from the airport, while San Juan Seaport, a seaport, is around 7.1 miles away by car. For ferry travel, San Juan Ferry Dock, a ferry terminal, is approximately 8.9 miles from the airport.

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 $104 and cheap return flights from $209 Chicago, IL (ORD-O'Hare Intl.) to San Juan (SJU-Luis Munoz Marin Intl.) with Expedia. One-way flights usually range from $157 to $832, and return flights typically cost between $283 and $3587. 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 Chicago, IL (ORD-O'Hare Intl.) to San Juan (SJU-Luis Munoz Marin Intl.) ticket fares go up or down.*Typical price ranges based on flights available on Expedia in the last year. Prices include multi-airline options.
What is the cheapest month to fly from Chicago, IL (ORD-O'Hare Intl.) to San Juan (SJU-Luis Munoz Marin Intl.)?
The cheapest month to fly from ORD to SJU is August 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're 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-O'Hare Intl.) to San Juan (SJU-Luis Munoz Marin Intl.)?
There are 3 airlines offering direct flights from ORD to SJU:

  • United operates around 14 direct flights from ORD to SJU every week
  • American Airlines operates around 11 direct flights from ORD to SJU every week
  • Spirit Airlines operates around 10 direct flights from ORD to SJU every week

What is the cheapest airline that flies from Chicago, IL (ORD-O'Hare Intl.) to San Juan (SJU-Luis Munoz Marin Intl.)?
Spirit Airlines is one of the cheapest airlines offering connecting flights from O'Hare Intl. (ORD) to Luis Munoz Marin Intl. (SJU), with round-trip tickets starting from around $310 with a layover in an unspecified location. 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.*Prices based on flights available on Expedia in the last year.
How do I find cheap flights from Chicago, IL (ORD-O'Hare Intl.) to San Juan (SJU-Luis Munoz Marin Intl.)?
To find a cheap flight from Chicago, IL (ORD-O'Hare Intl.) to San Juan (SJU-Luis Munoz Marin 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 Chicago, IL (ORD-O'Hare Intl.) to San Juan (SJU-Luis Munoz Marin Intl.)?
The best airline to fly with from Chicago, IL (ORD-O'Hare Intl.) to San Juan (SJU-Luis Munoz Marin Intl.) will differ from traveler to traveler. If you like to fly early, Spirit Airlines offers early morning flights. If price is the most important factor, Spirit Airlines typically offers the lowest fares. American Airlines offers the most daily flights from ORD to SJU, 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 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.
How many flights per day from Chicago, IL (ORD-O'Hare Intl.) to San Juan (SJU-Luis Munoz Marin Intl.)?
You can find approximately 5 nonstop flights per day from O'Hare Intl. (ORD) to Luis Munoz Marin Intl. (SJU). For more options, look at flights that include layovers.
What is the earliest flight from Chicago, IL (ORD-O'Hare Intl.) to San Juan (SJU-Luis Munoz Marin Intl.)?
The earliest flight from O'Hare International Airport (ORD) to Luis Munoz Marin International Airport (SJU) usually departs at 12:00 AM, operated by American Airlines. This seasonal service is active in December, allowing you to start your trip to San Juan right at midnight. To compare early flights on Expedia, select the "Early Morning" and "Morning" filters in your search.
What are the most popular departure times for flights from Chicago, IL (ORD-O'Hare Intl.) to San Juan (SJU-Luis Munoz Marin Intl.)?
The most popular departure times for flights from Chicago, IL (ORD) to San Juan (SJU) are from 6am to 9am. This accounts for around 40% of total traffic. Many major carriers, including American Airlines, United and American Airlines, offer flights during this window. This timing is favored as it allows travelers to arrive in San Juan with a full day ahead to explore the beautiful island.
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 2,074 miles. 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-O'Hare Intl.) to San Juan (SJU-Luis Munoz Marin Intl.)?
Business class seats are offered on the ORD to SJU route with American Airlines.First class cabins are available on:

  • Spirit Airlines
  • United Airlines
  • Delta Air Lines

How much is a business class flight from Chicago, IL (ORD-O'Hare Intl.) to San Juan (SJU-Luis Munoz Marin Intl.)?
A direct, return business class ticket from Chicago (ORD) to San Juan (SJU) typically costs between $1,597 - $3,907. A non-stop, one-way business class flight is usually around $483 - $608. Prices often fluctuate based on seasonality and how early you book. You may also be able to find a cheaper business class journey between Chicago, IL (ORD-O'Hare Intl.) to San Juan (SJU-Luis Munoz Marin Intl.) if you opt for a connecting flight.*Prices based on flights available on Expedia in the last year.
How do I earn miles on a Chicago, IL (ORD-O'Hare Intl.) to San Juan (SJU-Luis Munoz Marin Intl.) flight with Expedia?
It's easy to earn miles on a Chicago, IL (ORD-O'Hare Intl.) to San Juan (SJU-Luis Munoz Marin 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 San Juan from O'Hare Intl. (ORD)?
If you're planning to travel to San Juan from O'Hare Intl. (ORD), you can fly into Luis Munoz Marin Intl. (SJU) Some flights may connect through major hubs like Ronald Reagan Washington National (DCA), Dallas-Fort Worth Intl. (DFW), Philadelphia Intl. (PHL) before reaching San Juan. 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 Chicago, IL (ORD-O'Hare Intl.) to San Juan (SJU-Luis Munoz Marin Intl.) at the last minute?
Typically, booking a last minute flight from Chicago, IL (ORD-O'Hare Intl.) to San Juan (SJU-Luis Munoz Marin 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 Chicago, IL (ORD-O'Hare Intl.) to San Juan (SJU-Luis Munoz Marin Intl.) flight and hotel package?
Securing a Chicago, IL (ORD-O'Hare Intl.) to San Juan (SJU-Luis Munoz Marin 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 Chicago, IL (ORD-O'Hare Intl.) to San Juan (SJU-Luis Munoz Marin Intl.)?
If you booked your Chicago, IL (ORD-O'Hare Intl.) to San Juan (SJU-Luis Munoz Marin 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
O'Hare Intl.
Destination airport
Luis Munoz Marin Intl.
Airlines serving
American Airlines, Delta, Frontier Airlines, JetBlue Airways, United
Roundtrip price
$209
Distance
2073 mi
Average flight time
5 hours 54 mins

Book with confidence

Chicago to San Juan Flights

The cheapest times to fly from Chicago to San Juan

On average, Thursday can be the cheapest time to fly, according to data from the Airlines Reporting Corporation (ARC), one of the world's biggest databases for global airline sales. The data reveals that you could save up to 16% by flying on a Thursday—the cheapest day to travel on average—instead of a Sunday—the most expensive. Some of the most affordable flights from Chicago to San Juan are during the month of August. You can find some of the cheapest flights from Chicago to San Juan with Expedia's search tool and vast selection of airlines.

 

The best time to book a flight from Chicago to San Juan

Sunday is one of the best days to book for cheap flights from Chicago to San Juan: Tickets reserved on a Sunday cost between 6% and 13% less than those reserved on a Friday, according to ARC data. The data also suggests booking early can also lead to cheaper airfares. You could save 24% by buying your tickets for domestic flights at least a month in advance and 10% by booking international flights 2 months in advance.

 

How to find cheap round-trip tickets from Chicago to San Juan

Being flexible with your dates and using Expedia's Price Drop Protection and Price Tracking features are some of the best ways of finding a cheap ticket from Chicago to San Juan in 2026. You can also book with separate airlines for your outbound and return journeys, from $104 one-way. Expedia also offers Price Drop Protection, so if the cost of your airfare goes down after booking, you'll receive a credit for the difference*. This is available for a small fee, and is free to One Key Gold and Platinum tier members.

 

Expedia's Price Tracking feature means you can stay on top of airfares without manually checking every day. It sends you automated price alerts for cheap Chicago to San Juan flights and uses historical data to indicate when the best time to book is. Download Expedia's free app to activate this handy tool in a few easy taps.

 

You could also save big by booking one of Expedia's vacation packages. Bundling together your Chicago to San Juan airfare with your accommodations and car rental is often cheaper than booking everything separately. There’s also One Key, Expedia's generous rewards program. Join for free and you could earn One Key cash on most bookings to save on future adventures.

 

*Terms apply.

 

Disclaimer: ARC The statistics are based on average round-trip ticket prices between January and August 2023. The percentages you see are averages.

 

Chicago to San Juan Flights

*Flight schedules are subject to change.

*Available to One Key members.

 

Explore a world of travel with Expedia