$94 Cheap Flights from San Juan (SJU) to Chicago (ORD)

View $94 flight on Fri, Aug 15, 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 $94 for one-way flights and $189 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Spirit Airlines
Fri, Aug 15 - Mon, Aug 18
SJU
San Juan
ORD
Chicago
$189 Roundtrip, just found
$189
Roundtrip
just found
Select Spirit Airlines flight, departing Fri, Aug 15 from San Juan to Chicago, returning Mon, Aug 18, priced at $189 just found
Spirit Airlines
Fri, Aug 15 - Sun, Aug 17
SJU
San Juan
ORD
Chicago
$202 Roundtrip, just found
$202
Roundtrip
just found
Select Spirit Airlines flight, departing Fri, Aug 15 from San Juan to Chicago, returning Sun, Aug 17, priced at $202 just found
Spirit Airlines
Fri, Aug 15 - Sat, Sep 6
SJU
San Juan
ORD
Chicago
$213 Roundtrip, found 10 hours ago
$213
Roundtrip
found 10 hours ago
Select Spirit Airlines flight, departing Fri, Aug 15 from San Juan to Chicago, returning Sat, Sep 6, priced at $213 found 10 hours ago
Spirit Airlines
Fri, Aug 15 - Sun, Aug 17
SJU
San Juan
ORD
Chicago
$215 Roundtrip, just found
$215
Roundtrip
just found
Select Spirit Airlines flight, departing Fri, Aug 15 from San Juan to Chicago, returning Sun, Aug 17, priced at $215 just found
Spirit Airlines
Fri, Aug 15 - Sat, Aug 23
SJU
San Juan
ORD
Chicago
$220 Roundtrip, found 12 hours ago
$220
Roundtrip
found 12 hours ago
Select Spirit Airlines flight, departing Fri, Aug 15 from San Juan to Chicago, returning Sat, Aug 23, priced at $220 found 12 hours ago
Frontier Airlines
Wed, Aug 13 - Mon, Aug 18
SJU
San Juan
ORD
Chicago
$222 Roundtrip, just found
$222
Roundtrip
just found
Select Frontier Airlines flight, departing Wed, Aug 13 from San Juan to Chicago, returning Mon, Aug 18, priced at $222 just found
Spirit Airlines
Fri, Aug 15 - Mon, Aug 18
SJU
San Juan
ORD
Chicago
$223 Roundtrip, just found
$223
Roundtrip
just found
Select Spirit Airlines flight, departing Fri, Aug 15 from San Juan to Chicago, returning Mon, Aug 18, priced at $223 just found
JetBlue Airways
Sat, Sep 13 - Tue, Sep 16
SJU
San Juan
ORD
Chicago
$334 Roundtrip, found 1 hour ago
$334
Roundtrip
found 1 hour ago
Select JetBlue Airways flight, departing Sat, Sep 13 from San Juan to Chicago, returning Tue, Sep 16, priced at $334 found 1 hour ago
American Airlines
Thu, Nov 6 - Mon, Nov 10
SJU
San Juan
ORD
Chicago
$342 Roundtrip, found 2 hours ago
$342
Roundtrip
found 2 hours ago
Select American Airlines flight, departing Thu, Nov 6 from San Juan to Chicago, returning Mon, Nov 10, priced at $342 found 2 hours ago
Delta
Sat, Nov 1 - Sat, Nov 8
SJU
San Juan
ORD
Chicago
$351 Roundtrip, found 15 hours ago
$351
Roundtrip
found 15 hours ago
Select Delta flight, departing Sat, Nov 1 from San Juan to Chicago, returning Sat, Nov 8, priced at $351 found 15 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 - $554 per traveler.

Graph displaying average flight prices per month

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 $268
MDW
Midway Intl.
Closest
Average driving time to city center16 min
Flights from $268
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
$189
Distance
2073 mi
Average flight time
4 hours 15 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 August. 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 $94 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?
You'll find affordable return tickets from Luis Munoz Marin Intl. Airport (SJU) to O'Hare Intl. Airport (ORD) starting from $238. Book a seat and take off on your trip. This information is based on the cheapest price found on Expedia for this return journey departing within the next three months. This airfare is for a Spirit Airlines flight leaving SJU on July 27 2025 and touching down at ORD. The price was last updated on July 23 2025 and has not changed since.
What is the cheapest month to fly from SJU to ORD?
The cheapest flights from SJU to ORD are usually during off-peak season, when demand is lower. To save money, avoid flying during public holidays, school breaks and major local events.
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 SJU to ORD?
Journey from SJU to ORD with Spirit Airlines. This carrier currently has the cheapest one-way ticket for this route, starting at $119. This fare is based on the lowest price found on Expedia departing within the next three months. The flight takes off from SJU on July 31 2025. Prices were last updated on July 23 2025 and have not changed since.
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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