ORD - SJU

£101 Find Cheap Flights from Chicago to San Juan – Compare and Save

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1 adult, Economy, 0 bags

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Everything you should know

Cheapest return fare
£202
Typical prices: £191-£391
United Airlines
Mon 18/1Thu 21/1
ORD - SJU • Direct
Cheapest one-way flight
£101
Typical prices: £154-£283
United Airlines
Tue 8/12
ORD - SJU • Direct
Direct flights
You can fly direct with American Airlines, Frontier, and United Airlines. Average duration is 4h 42m
Direct flights
Direct flights
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Direct flights
Direct flights
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Avoid delays
Most punctual • 82% on-time
Best time • Fewest delays
Insights
Insights
Insights
Insights
When to travel
Cheapest • 18% price drop
Most popular
Good to know
Good to know
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Flight Deals

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

 
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent return flight deals from Chicago to San Juan

Mon, 18 Jan - Thu, 21 Jan
United Airlines Logo
08:52 - 15:40ORD  Chicago O'Hare Intl-SJU San Juan Luis Munoz Marin Intl
4h 48mdirect
United Airlines Logo
08:25 - 11:49SJU  San Juan Luis Munoz Marin Intl-ORD Chicago O'Hare Intl
5h 24mdirect
£202United Airlines
Sat, 5 Dec - Thu, 10 Dec
American Airlines Logo
17:59 - 09:36ORD  Chicago O'Hare Intl-SJU San Juan Luis Munoz Marin Intl
13h 37m1 stop Miami
American Airlines Logo
15:50 - 19:29SJU  San Juan Luis Munoz Marin Intl-ORD Chicago O'Hare Intl
5h 39mdirect
£204American Airlines
Tue, 2 Mar - Tue, 2 Mar
United Airlines Logo
10:25 - 21:24ORD  Chicago O'Hare Intl-SJU San Juan Luis Munoz Marin Intl
8h 59m1 stop Houston George Bush Intcntl
United Airlines Logo
02:05 - 11:02SJU  San Juan Luis Munoz Marin Intl-ORD Chicago O'Hare Intl
10h 57m1 stop Newark
£205United Airlines
Wed, 9 Dec - Wed, 16 Dec
United Airlines Logo
12:55 - 00:36ORD  Chicago O'Hare Intl-SJU San Juan Luis Munoz Marin Intl
9h 41m1 stop Newark
United Airlines Logo
08:25 - 11:49SJU  San Juan Luis Munoz Marin Intl-ORD Chicago O'Hare Intl
5h 24mdirect
£206United Airlines
Sat, 5 Dec - Thu, 10 Dec
American Airlines Logo
19:50 - 10:44ORD  Chicago O'Hare Intl-SJU San Juan Luis Munoz Marin Intl
12h 54m1 stop Miami
American Airlines Logo
10:26 - 18:25SJU  San Juan Luis Munoz Marin Intl-ORD Chicago O'Hare Intl
9h 59m1 stop Miami
£207American Airlines
Tue, 26 Jan - Tue, 2 Feb
JetBlue Logo
07:00 - 16:23ORD  Chicago O'Hare Intl-SJU San Juan Luis Munoz Marin Intl
7h 23m1 stop Fort Lauderdale
JetBlue Logo
18:08 - 23:47SJU  San Juan Luis Munoz Marin Intl-ORD Chicago O'Hare Intl
7h 39m1 stop Fort Lauderdale
£208JetBlue
Wed, 17 Feb - Tue, 23 Feb
United Airlines Logo
05:46 - 16:36ORD  Chicago O'Hare Intl-SJU San Juan Luis Munoz Marin Intl
8h 50m1 stop Houston George Bush Intcntl
United Airlines Logo
02:05 - 11:02SJU  San Juan Luis Munoz Marin Intl-ORD Chicago O'Hare Intl
10h 57m1 stop Newark
£209United Airlines
Sat, 5 Dec - Tue, 15 Dec
United Airlines Logo
10:30 - 22:22ORD  Chicago O'Hare Intl-SJU San Juan Luis Munoz Marin Intl
9h 52m1 stop Washington, D.C. Dulles Intl
United Airlines Logo
08:25 - 11:49SJU  San Juan Luis Munoz Marin Intl-ORD Chicago O'Hare Intl
5h 24mdirect
£213United Airlines
Mon, 14 Dec - Wed, 16 Dec
United Airlines Logo
12:55 - 00:36ORD  Chicago O'Hare Intl-SJU San Juan Luis Munoz Marin Intl
9h 41m1 stop Newark
United Airlines Logo
16:55 - 20:26SJU  San Juan Luis Munoz Marin Intl-ORD Chicago O'Hare Intl
5h 31mdirect
£214United Airlines
Fri, 19 Feb - Tue, 23 Feb
United Airlines Logo
17:59 - 06:15ORD  Chicago O'Hare Intl-SJU San Juan Luis Munoz Marin Intl
10h 16m1 stop Houston George Bush Intcntl
United Airlines Logo
17:50 - 23:25SJU  San Juan Luis Munoz Marin Intl-ORD Chicago O'Hare Intl
7h 35m1 stop Washington, D.C. Dulles Intl
£216United Airlines
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.

How much is a return flight from Chicago O'Hare Intl Airport to San Juan Luis Munoz Marin Intl Airport?

Flight prices are below average for this route right now.

Flights to San Juan Luis Munoz Marin Intl Airport from Chicago O'Hare Intl Airport usually cost between £277 and £446 in January.
The lowest price found in the past 5 days was £202 on United Airlines (18 Jan–21 Jan).

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

The cheapest month for flights from Chicago O'Hare Intl Airport to San Juan Luis Munoz Marin Intl Airport is August, where tickets cost £256 (return) on average. On the other hand, the most expensive months are December and June, where the average cost of round-trip tickets is £403 and £351 respectively.

Can I save money by flying with a stopover from Chicago O'Hare Intl Airport to San Juan Luis Munoz Marin Intl Airport?

Yes, flying with a stopover may cost you more time, but you can also save money on the route, with a 1 stop stopover the cheapest option at £368 on average.

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

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 9 weeks before departure.

Good to know - Cheap tickets from Chicago to San Juan

Low season

October

Cheapest flight

£101
Best time to beat the crowds but there is an average 9% increase in price.
Most popular time to fly (10% 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

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 5 days, the lowest price for a flight from Chicago O'Hare Intl Airport to San Juan Luis Munoz Marin Intl Airport was £101 for a one-way ticket and £202 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, Alaska Airlines, JetBlue, Alaska Airlines, and Delta 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.

  • 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?

 
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,Frontier,United Airlines

American Airlines,Frontier, +1 more

Tuesday

American Airlines,Frontier,United Airlines

American Airlines,Frontier, +1 more

Wednesday

American Airlines,Frontier,United Airlines

American Airlines,Frontier, +1 more

Thursday

American Airlines,Frontier,United Airlines

American Airlines,Frontier, +1 more

Friday

American Airlines,Frontier,United Airlines

American Airlines,Frontier, +1 more

Saturday

American Airlines,Frontier,United Airlines

American Airlines,Frontier, +1 more

Sunday

American Airlines,Frontier,United Airlines

American Airlines,Frontier, +1 more

See more direct flights

Direct returns

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

Monday

American Airlines,Frontier,United Airlines

American Airlines,Frontier, +1 more

Tuesday

American Airlines,Frontier,United Airlines

American Airlines,Frontier, +1 more

Wednesday

American Airlines,Frontier,United Airlines

American Airlines,Frontier, +1 more

Thursday

American Airlines,Frontier,United Airlines

American Airlines,Frontier, +1 more

Friday

American Airlines,Frontier,United Airlines

American Airlines,Frontier, +1 more

Saturday

American Airlines,Frontier,United Airlines

American Airlines,Frontier, +1 more

Sunday

American Airlines,Frontier,United Airlines

American Airlines,Frontier, +1 more

See more direct flights

More options for your flight from Chicago to San Juan

Complete your trip to San Juan with a hotel stay or car hire