$84 Cheap Flights from San Juan (SJU) to Chicago (ORD)

View $84 flight on Sat, May 10, 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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Find available prices by choosing your travel dates.

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

Prices were available within the past 7 days and start at $84 for one-way flights and $175 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Spirit Airlines
Sat, May 3 - Sat, May 10
SJU
San Juan
ORD
Chicago
$175 Roundtrip, found 1 hour ago
$175
Roundtrip
found 1 hour ago
Select Spirit Airlines flight, departing Sat, May 3 from San Juan to Chicago, returning Sat, May 10, priced at $175 found 1 hour ago
Spirit Airlines
Sat, May 10 - Mon, May 12
SJU
San Juan
ORD
Chicago
$190 Roundtrip, found 3 hours ago
$190
Roundtrip
found 3 hours ago
Select Spirit Airlines flight, departing Sat, May 10 from San Juan to Chicago, returning Mon, May 12, priced at $190 found 3 hours ago
Spirit Airlines
Fri, May 9 - Sat, May 10
SJU
San Juan
ORD
Chicago
$195 Roundtrip, found 1 day ago
$195
Roundtrip
found 1 day ago
Select Spirit Airlines flight, departing Fri, May 9 from San Juan to Chicago, returning Sat, May 10, priced at $195 found 1 day ago
Spirit Airlines
Sat, May 3 - Sun, May 11
SJU
San Juan
ORD
Chicago
$198 Roundtrip, found 4 hours ago
$198
Roundtrip
found 4 hours ago
Select Spirit Airlines flight, departing Sat, May 3 from San Juan to Chicago, returning Sun, May 11, priced at $198 found 4 hours ago
Spirit Airlines
Fri, May 9 - Sat, May 10
SJU
San Juan
ORD
Chicago
$198 Roundtrip, found 1 day ago
$198
Roundtrip
found 1 day ago
Select Spirit Airlines flight, departing Fri, May 9 from San Juan to Chicago, returning Sat, May 10, priced at $198 found 1 day ago
Spirit Airlines
Thu, May 8 - Sat, May 10
SJU
San Juan
ORD
Chicago
$205 Roundtrip, found 1 hour ago
$205
Roundtrip
found 1 hour ago
Select Spirit Airlines flight, departing Thu, May 8 from San Juan to Chicago, returning Sat, May 10, priced at $205 found 1 hour ago
Frontier Airlines
Thu, May 8 - Sat, May 10
SJU
San Juan
ORD
Chicago
$240 Roundtrip, found 1 hour ago
$240
Roundtrip
found 1 hour ago
Select Frontier Airlines flight, departing Thu, May 8 from San Juan to Chicago, returning Sat, May 10, priced at $240 found 1 hour ago
American Airlines
Fri, Sep 12 - Sat, Sep 13
SJU
San Juan
ORD
Chicago
$307 Roundtrip, just found
$307
Roundtrip
just found
Select American Airlines flight, departing Fri, Sep 12 from San Juan to Chicago, returning Sat, Sep 13, priced at $307 just found
Delta
Fri, Sep 12 - Sat, Sep 13
SJU
San Juan
ORD
Chicago
$307 Roundtrip, just found
$307
Roundtrip
just found
Select Delta flight, departing Fri, Sep 12 from San Juan to Chicago, returning Sat, Sep 13, priced at $307 just found
JetBlue Airways
Wed, May 28 - Sat, Jun 7
SJU
San Juan
ORD
Chicago
$323 Roundtrip, just found
$323
Roundtrip
just found
Select JetBlue Airways flight, departing Wed, May 28 from San Juan to Chicago, returning Sat, Jun 7, priced at $323 just found

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 $212. 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 May 15 2025 and touching down at ORD. The price was last updated on April 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 $106. This fare is based on the lowest price found on Expedia departing within the next three months. The flight takes off from SJU on May 15 2025. Prices were last updated on April 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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