ORD - SJU

£80 Find Cheap Flights from Chicago to San Juan

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Chicago to San Juan departing on 21/10. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
1 adult, Economy

KAYAK searches hundreds of travel sites at once for deals on flights to San Juan Luis Munoz Marin Intl Airport

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to San Juan, as well as popular online travel agencies
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to San Juan, as well as popular online travel agencies
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Flight Deals

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

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for return flights from Chicago to San Juan that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent return flight deals from Chicago to San Juan

Tue, 11 Nov - Wed, 12 Nov
United Airlines Logo
14:30 - 00:36ORD-SJU
8h 06m1 stop
United Airlines Logo
08:10 - 11:32SJU-ORD
5h 22mdirect
£160United Airlines
Find Deal
Thu, 30 Oct - Wed, 5 Nov
United Airlines Logo
14:20 - 20:00ORD-SJU
4h 40mdirect
United Airlines Logo
08:10 - 11:32SJU-ORD
5h 22mdirect
£160United Airlines
Find Deal
Tue, 11 Nov - Wed, 12 Nov
United Airlines Logo
15:07 - 00:36ORD-SJU
7h 29m1 stop
United Airlines Logo
08:30 - 13:55SJU-ORD
7h 25m1 stop
£163United Airlines
Find Deal
Tue, 28 Oct - Mon, 3 Nov
United Airlines Logo
13:00 - 21:22ORD-SJU
7h 22m1 stop
United Airlines Logo
16:52 - 20:20SJU-ORD
5h 28mdirect
£164United Airlines
Find Deal
Tue, 28 Oct - Tue, 4 Nov
Delta Logo
06:45 - 16:33ORD-SJU
8h 48m1 stop
Delta Logo
07:15 - 16:41SJU-ORD
11h 26m1 stop
£167Delta
Find Deal
Tue, 27 Jan - Wed, 4 Feb
Delta Logo
07:30 - 16:51ORD-SJU
7h 21m1 stop
Delta Logo
18:20 - 23:54SJU-ORD
7h 34m1 stop
£196Delta
Find Deal
Tue, 4 Nov - Sat, 8 Nov
Southwest Logo
06:05 - 23:20ORD-SJU
15h 15m2 stops
Southwest Logo
05:40 - 11:10SJU-ORD
7h 30m1 stop
£215Southwest
Find Deal
Tue, 10 Mar - Wed, 11 Mar
JetBlue Logo
07:00 - 15:25ORD-SJU
7h 25m1 stop
JetBlue Logo
12:15 - 21:33SJU-ORD
10h 18m1 stop
£227JetBlue
Find Deal
Wed, 12 Nov - Sun, 16 Nov
Southwest Logo
15:45 - 00:35ORD-SJU
6h 50m1 stop
Southwest Logo
05:40 - 11:10SJU-ORD
7h 30m1 stop
£251Southwest
Find Deal
Fri, 6 Feb - Fri, 13 Feb
JetBlue Logo
14:20 - 23:55ORD-SJU
7h 35m1 stop
JetBlue Logo
13:15 - 21:33SJU-ORD
10h 18m1 stop
£254JetBlue
Find Deal

Everything you should know

Our travellers' advice
AI-generated summary based on content written by travel experts
United's Economy Plus offers extra legroom on this route.
Expect long security lines at O'Hare during peak times.
Expert advice
Expert advice
Expert advice
Expert advice
When to travel
January
Cheapest • 14% price drop
March
Most popular
Good to know
Good to know
+1
+1
Good to know
Good to know
+1
Cheapest return fare
£160
Overall average: £257
United Airlines
Tue 11/11Wed 12/11
ORD - SJU • 1 stop
Cheapest direct flights
£160
Typical prices: £174-359
United Airlines
Thu 30/10Wed 5/11
ORD - SJU • Direct
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We hope you love your trip to San Juan!
Expert advice

Expert advice for your flight from Chicago to San Juan

 
Snippets provided in this section are AI-generated based on a summarisation of KAYAK-commissioned articles. The articles are presented as-is, for general informational purposes only, and may not be up-to-date. The opinions contained in the articles are original to the author and reflect their authentic experience, which may vary significantly from the experience of others.
KAYAK teamed up with top travel experts to share the best tips for your journey.
Airlines
American Airlines

American's Main Cabin Extra offers early boarding and complimentary drinks for a fee.


Download the American Airlines app for access to inflight entertainment on personal devices.

Read more about American Airlinesby Harriet Baskas
United Airlines

United's Economy Plus offers up to 6 inches more legroom than standard economy seats.


United's Wi-Fi offers free messaging; check coverage before purchasing for surfing or streaming.

Read more about United Airlinesby Stefanie Waldek
Spirit Airlines

Spirit offers low fares with optional add-ons like carry-on or checked bags for flexibility.


Upgrade to Big Front Seat for 20-inch width and 11” extra legroom on Spirit.

Read more about Spirit Airlinesby Joe Cortez
Airports
ORD

Security lines at O'Hare can exceed 30 minutes during peak times. Arrive early to ensure a smooth departure.

Read more about ORDby Stefanie Waldek
SJU

For quick access to San Juan, taxis or Uber are efficient options, taking about 25 minutes to Old San Juan.

Read more about SJUby Gabriel Leigh
Our travel experts
Harriet Baskas

Harriet Baskas

Expert on American Airlines

Harriet Baskas

Harriet Baskas

Harriet is an award-winning journalist who is happiest in an airport or an unusual museum. Her stories about airports, air travel, and the business of travel have appeared on NBC News, CNBC, The Points Guy, and other outlets. She is the creator of the StuckatTheAirport.com blog and the author of nine books. When not out on the road or exploring the latest airport amenities, she’s home in Seattle getting ready for the next adventure.

Read more
Stefanie Waldek

Stefanie Waldek

Expert on United Airlines and ORD

Stefanie Waldek

Stefanie Waldek

Stefanie Waldek is a freelance space, travel, and design writer based in Saratoga Springs, NY. Her words have appeared in Space.com, Travel + Leisure, Condé Nast Traveler, Architectural Digest, and House Beautiful, among other publications. An expert in aviation and expedition cruising, Stefanie is frequently up in the air or out at sea, likely en route to Antarctica or the Arctic.

Read more
Joe Cortez

Joe Cortez

Expert on Spirit Airlines

Joe Cortez

Joe Cortez

Joe Cortez is a seasoned managing editor in aviation with over a decade of industry experience. His work has been featured on prominent platforms such as FlyerTalk and TripSavvy, establishing him as a respected voice in aviation journalism.

Read more
Gabriel Leigh

Gabriel Leigh

Expert on SJU

Gabriel Leigh

Gabriel Leigh

Gabriel is a writer and video creator. As senior content producer for Flightradar24 and Monocle’s transport correspondent, he keeps a close eye on aviation in particular. He has also written travel articles for the likes of The New York Times. Born in New York but raised around the world, he now lives in Sweden. He’s been to 75 countries, flying 2.3 million miles on 113 airlines and through 234 airports in the process.

Read more
Booking Insights

KAYAK's insights & trends for Chicago to San Juan flights

Get data-powered insights and trends into flights from Chicago to San Juan to help you find the cheapest flights, the best time to fly and much more.

What is the cheapest month to fly from Chicago O'Hare Intl Airport to San Juan Luis Munoz Marin Intl Airport?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Chicago O'Hare Intl Airport to San Juan Luis Munoz Marin Intl Airport, removes the top 0.1% to account for outliers, and then takes the median of all values for each month.

The cheapest month for flights from Chicago O'Hare Intl Airport to San Juan Luis Munoz Marin Intl Airport is January, where tickets cost £247 (return) on average. On the other hand, the most expensive months are December and March, where the average cost of round-trip tickets is £389 and £330 respectively.

How far in advance should I book a flight from Chicago O'Hare Intl Airport to San Juan Luis Munoz Marin Intl Airport?

To calculate weekly average prices, KAYAK takes all prices for each week before departure over the last year for round-trip flights from Chicago O'Hare Intl Airport to San Juan Luis Munoz Marin Intl Airport, removes the top 0.1% to account for outliers, and then takes the average of all the values for each week.

To get a below average price on the flight from Chicago O'Hare Intl Airport to San Juan Luis Munoz Marin Intl Airport, you should book around 1 week before departure. For the absolute cheapest price, our data suggests you should book 5 weeks before departure.

Find deals

Good to know - Cheap tickets from Chicago to San Juan

Low seasonSeptember
Cheapest flight£80
Best time to beat the crowds (5% less expensive on average)
Most popular time to fly (14% more expensive on average)
Flight from Chicago to San Juan

When to book flights from Chicago to San Juan

Are your dates flexible? Find out the best times to travel from Chicago to San Juan based on our flight data from the last year. Discover the cheapest month and even day to fly.
Estimated return price
KAYAK looks at all historical flight data for each date to provide a predicted price for one-way trips or returns with a duration up to 40 days. While we try to provide actual minimum prices for each date, some prices are predictions and actual prices may differ.

FAQs for booking Chicago to San Juan flights

  • What is the cheapest flight from Chicago O'Hare Intl Airport to San Juan Luis Munoz Marin Intl Airport?

    In the last 3 days, the lowest price for a flight from Chicago O'Hare Intl Airport to San Juan Luis Munoz Marin Intl Airport was £109 for a one-way ticket and £217 for a return.

  • Which airports will I be using when flying from Chicago to San Juan?

    Chicago and San Juan are both served by 1 main airport. You will leave Chicago from Chicago O'Hare Intl and will be arriving at San Juan Luis Munoz Marin Intl.

  • Which airlines offer Wi-Fi service onboard planes from Chicago to San Juan?

    American Airlines, Delta, Alaska Airlines, and JetBlue offer inflight Wi-Fi service on the Chicago to San Juan flight route.

  • Which aircraft models fly most regularly from Chicago to San Juan?

    The Airbus A321neo is the aircraft model that flies most regularly on the Chicago to San Juan flight route.

  • Which airline alliances offer flights from Chicago to San Juan?

    oneworld, and Star Alliance are the airline alliances operating flights between Chicago and San Juan, with Star Alliance being the most commonly used for this route.

  • On which days can I fly direct from Chicago to San Juan?

    There are direct flights from Chicago to San Juan on a daily basis.

  • How does KAYAK find such low prices on flights from Chicago to San Juan?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Chicago to San Juan.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Chicago to San Juan?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to San Juan from Chicago is likely to change within 7 days, so travellers know whether to wait or book now.

  • What is the Hacker Fare option on flights from Chicago to San Juan?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional return ticket. You could then fly to San Juan with an airline and back to Chicago with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Chicago to San Juan?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying to San Juan from Chicago up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

Prefer to fly direct from Chicago to San Juan?

 
Direct data is based off flight results for the next 60 days. Find direct flights from all airlines flying direct from Chicago O'Hare Intl to San Juan Luis Munoz Marin Intl.
Find which airlines fly direct from Chicago O'Hare Intl Airport to San Juan Luis Munoz Marin Intl Airport, which days they fly and book direct flights.

Direct departures

Chicago O'Hare Intl to San Juan Luis Munoz Marin Intl

Monday

American Airlines, Spirit Airlines, United Airlines

American Airlines, Spirit Airlines, +1 more

Tuesday

American Airlines, United Airlines, Spirit Airlines

American Airlines, United Airlines, +1 more

Wednesday

American Airlines, United Airlines, Spirit Airlines

American Airlines, United Airlines, +1 more

Thursday

American Airlines, Spirit Airlines, United Airlines

American Airlines, Spirit Airlines, +1 more

Friday

American Airlines, Spirit Airlines, United Airlines

American Airlines, Spirit Airlines, +1 more

Saturday

American Airlines, Spirit Airlines, United Airlines

American Airlines, Spirit Airlines, +1 more

Sunday

American Airlines, Spirit Airlines, United Airlines

American Airlines, Spirit Airlines, +1 more

See more direct flights

Direct returns

San Juan Luis Munoz Marin Intl to Chicago O'Hare Intl

Monday

American Airlines, Spirit Airlines, United Airlines

American Airlines, Spirit Airlines, +1 more

Tuesday

American Airlines, United Airlines, Spirit Airlines

American Airlines, United Airlines, +1 more

Wednesday

American Airlines, United Airlines, Spirit Airlines

American Airlines, United Airlines, +1 more

Thursday

American Airlines, Spirit Airlines, United Airlines

American Airlines, Spirit Airlines, +1 more

Friday

American Airlines, Spirit Airlines, United Airlines

American Airlines, Spirit Airlines, +1 more

Saturday

American Airlines, Spirit Airlines, United Airlines

American Airlines, Spirit Airlines, +1 more

Sunday

American Airlines, Spirit Airlines, United Airlines

American Airlines, Spirit Airlines, +1 more

See more direct flights

Everything you need to know for your flight from Chicago to San Juan

Information on your arrival and departure airports

Chicago (ORD)
Luis Munoz Marin Intl (SJU)

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