$109 Cheap Flights from San Juan (SJU) to Chicago (ORD)

View $109 flight on Tue, Nov 25, 2025Opens in a new window

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

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

Prices were available within the past 7 days and start at $109 for one-way flights and $203 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Spirit Airlines
Thu, Nov 6 - Mon, Nov 17
SJU
San Juan
ORD
Chicago
$203 Roundtrip, found 1 day ago
$203
Roundtrip
found 1 day ago
Select Spirit Airlines flight, departing Thu, Nov 6 from San Juan to Chicago, returning Mon, Nov 17, priced at $203 found 1 day ago
United
Sat, Nov 15 - Sat, Nov 15
SJU
San Juan
ORD
Chicago
$205 Roundtrip, found 4 days ago
$205
Roundtrip
found 4 days ago
Select United flight, departing Sat, Nov 15 from San Juan to Chicago, returning Sat, Nov 15, priced at $205 found 4 days ago
Frontier Airlines
Wed, Dec 24 - Mon, Jan 5
SJU
San Juan
ORD
Chicago
$215 Roundtrip, found 2 hours ago
$215
Roundtrip
found 2 hours ago
Select Frontier Airlines flight, departing Wed, Dec 24 from San Juan to Chicago, returning Mon, Jan 5, priced at $215 found 2 hours ago
Spirit Airlines
Fri, Dec 5 - Mon, Dec 8
SJU
San Juan
ORD
Chicago
$218 Roundtrip, just found
$218
Roundtrip
just found
Select Spirit Airlines flight, departing Fri, Dec 5 from San Juan to Chicago, returning Mon, Dec 8, priced at $218 just found
American Airlines
Wed, Jan 14 - Mon, Jan 19
SJU
San Juan
ORD
Chicago
$218 Roundtrip, found 2 hours ago
$218
Roundtrip
found 2 hours ago
Select American Airlines flight, departing Wed, Jan 14 from San Juan to Chicago, returning Mon, Jan 19, priced at $218 found 2 hours ago
Frontier Airlines
Fri, Dec 12 - Thu, Jan 8
SJU
San Juan
ORD
Chicago
$222 Roundtrip, found 3 days ago
$222
Roundtrip
found 3 days ago
Select Frontier Airlines flight, departing Fri, Dec 12 from San Juan to Chicago, returning Thu, Jan 8, priced at $222 found 3 days ago
United
Fri, Jan 16 - Wed, Jan 21
SJU
San Juan
ORD
Chicago
$223 Roundtrip, just found
$223
Roundtrip
just found
Select United flight, departing Fri, Jan 16 from San Juan to Chicago, returning Wed, Jan 21, priced at $223 just found
Frontier Airlines
Wed, Dec 24 - Thu, Jan 1
SJU
San Juan
ORD
Chicago
$225 Roundtrip, found 4 hours ago
$225
Roundtrip
found 4 hours ago
Select Frontier Airlines flight, departing Wed, Dec 24 from San Juan to Chicago, returning Thu, Jan 1, priced at $225 found 4 hours ago
Frontier Airlines
Thu, Jan 22 - Sun, Feb 1
SJU
San Juan
ORD
Chicago
$225 Roundtrip, found 2 hours ago
$225
Roundtrip
found 2 hours ago
Select Frontier Airlines flight, departing Thu, Jan 22 from San Juan to Chicago, returning Sun, Feb 1, priced at $225 found 2 hours ago
Delta
Fri, Jan 23 - Mon, Feb 2
SJU
San Juan
ORD
Chicago
$227 Roundtrip, found 2 hours ago
$227
Roundtrip
found 2 hours ago
Select Delta flight, departing Fri, Jan 23 from San Juan to Chicago, returning Mon, Feb 2, priced at $227 found 2 hours ago

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

January is typically the cheapest month to fly

From $118 - $495 per traveler.

Alternative airports near Chicago

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

Select flight to Midway Intl. MDW. Closest option available. Average driving time to city center is 16 minutes. Flights from $470
MDW
Midway Intl.
Closest
Average driving time to city center16 min
Flights from $470
Flights from San Juan (SJU) to Chicago (ORD)
Origin airport
Luis Munoz Marin Intl.
Destination airport
O'Hare Intl.
Airlines serving
American Airlines, Delta, Frontier Airlines, JetBlue Airways, Southwest Airlines, Spirit Airlines, United
Roundtrip price
$202
Distance
2073 mi
Average flight time
3 hours 59 mins

San Juan to Chicago Flights

The cheapest times to fly from San Juan to Chicago

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 San Juan to Chicago are during the month of November. You can find some of the cheapest flights from San Juan to Chicago with Expedia's search tool and vast selection of airlines.

 

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

Sunday is one of the best days to book for cheap flights from San Juan to Chicago: 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 San Juan to Chicago

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 San Juan to Chicago in 2025. You can also book with separate airlines for your outbound and return journeys, from $109 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 San Juan to Chicago 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 San Juan to Chicago 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.

 

Frequently asked questions

How much does a flight from Luis Munoz Marin Intl. Airport (SJU) to O'Hare Intl. Airport (ORD) cost?
Get a cheap one-way flight from $109 or cheap return flight from $203 from Luis Munoz Marin Intl. Airport (SJU) to O'Hare Intl. Airport (ORD) with Expedia. Enter your travel dates and sort by "Price (lowest to highest)" to see our cheapest flight offers on this route.
What is the cheapest month to fly from Luis Munoz Marin Intl. Airport (SJU) to O'Hare Intl. Airport (ORD)?
The cheapest month to fly from SJU to ORD is November, when demand is low. Off-peak months are typically when you'll find lower airfares between these airports.
Which airlines fly direct from Luis Munoz Marin Intl. Airport (SJU) to O'Hare Intl. Airport (ORD)?
Skip the layovers and travel straight from Luis Munoz Marin Intl. Airport (SJU) to O'Hare Intl. Airport (ORD) with 3 airlines, including:

  • United Airlines
  • Spirit Airlines
  • American Airlines

What is the cheapest airline that flies from Luis Munoz Marin Intl. Airport (SJU) to O'Hare Intl. Airport (ORD)?
The cheapest airline to offer flights between Luis Munoz Marin Intl. Airport (SJU) and O'Hare Intl. Airport (ORD) will change depending on your travel plans. Spirit Airlines and American Airlines are just some of the choices offering competitive fares. Use Expedia's filter tool to compare airlines in one place and find the right SJU to ORD flight that fits your budget.
How many flights per day from Luis Munoz Marin Intl. Airport (SJU) to O'Hare Intl. Airport (ORD)?
When taking off from Luis Munoz Marin Intl. Airport (SJU), you can pick from an average of 3 daily direct flights to O'Hare Intl. Airport (ORD).
What are the most popular departure times for flights from Luis Munoz Marin Intl. Airport (SJU) to O'Hare Intl. Airport (ORD)?
More passengers fly between SJU and ORD at 3 PM than at any other point in the day. Looking for a quieter experience? Try choosing a quieter departure window and it's possible you'll save on your ticket as well.
What day of the week has the most flights from SJU to ORD?
Fly on a Sunday if you're looking for the best choice of flights from Luis Munoz Marin Intl. Airport (SJU) to O'Hare Intl. Airport (ORD).
What is the earliest flight from Luis Munoz Marin Intl. Airport (SJU) to O'Hare Intl. Airport (ORD)?
Luis Munoz Marin Intl. Airport (SJU)'s earliest flight to O'Hare Intl. Airport (ORD) leaves at approximately 8:35AM UTC-4. With a total flight time of 5h 19m, you'll touch down at around 11:54AM UTC-6.
How long does it take to fly from Luis Munoz Marin Intl. Airport (SJU) to O'Hare Intl. Airport (ORD)?
It usually takes 5 hours and 24 minutes to cover the 2,100 mi from SJU to ORD.
What airline has the least delays from SJU to ORD?
United Airlines has the best track record for on-time direct flights from Luis Munoz Marin Intl. Airport (SJU) to O'Hare Intl. Airport (ORD), with an on-time rating of 87%. Use the Expedia App to look up your journey status before you head off and get notified of any trip changes.
What is the best time to fly from Luis Munoz Marin Intl. Airport (SJU) to O'Hare Intl. Airport (ORD)?
To land at O'Hare Intl. Airport (ORD) on schedule, select a flight that leaves Luis Munoz Marin Intl. Airport (SJU) before 3 PM. The likelihood of cancellations is 22% higher, on average, for departures after this hour.**Most reliable time of the day and month to travel recommendation is based on January through August 2024 flight status data sourced from OAG's global flight data platform.
What airports do you fly into for Chicago from Luis Munoz Marin Intl. Airport (SJU)?
If you're taking a direct flight from Luis Munoz Marin Intl. Airport (SJU) to Chicago, you can land at either O'Hare Intl. Airport (ORD) or Midway Intl. Airport (MDW).
Is it cheaper to buy a plane ticket from Luis Munoz Marin Intl. Airport (SJU) to O'Hare Intl. Airport (ORD) last-minute?
Last-minute fares from SJU to ORD are generally more expensive. For the cheapest rates, start looking for flights as soon as possible. That said, if your travel plans are flexible, you may score a cheap ticket right before your journey.
Is it cheaper to book a SJU to ORD flight and hotel package?
You'll typically save money by booking a SJU to ORD flight and hotel package compared to booking separately. In fact, travelers could save hundreds of dollars by bundling with Expedia. And it's simple to manage it all in one place. After choosing your preferred accommodations and flights, consider other add-ons like car rentals, activities and tours.
Can I cancel or change the date of my flight from Luis Munoz Marin Intl. Airport (SJU) to O'Hare Intl. Airport (ORD)?
It's generally possible to reschedule or cancel your SJU to ORD flight. However, if the booking was made more than 24 hours ago, additional fees may apply. Check your airline's policies in your itinerary to see what changes are allowed and if any costs are involved. You'll also find more information on our Customer Service portal.

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