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ORD - SJU

Find cheap flights from Chicago to San Juan from £165

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 12/6. 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
0 bags
Fri 24/5
Fri 31/5

Search hundreds of travel sites at once for deals on flights to San Juan

 
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
In the last 7 days, travellers have searched 45,119,101 times on KAYAK, and here's why:

Save 28% or moreCompare multiple travel sites with one search.

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Filter your dealsChoose cabin class, free Wi-Fi and more.

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Cheap flight deals from Chicago to San Juan (ORD-SJU)

Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip 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 and deals for you by selecting your travel dates.
Choose your dates
11:25 - 20:05ORD-SJU
7h 40m1 stop
11:05 - 19:47SJU-ORD
9h 42m1 stop
£206JetBlue
Find Deal
Sat, 22 Jun - Tue, 25 Jun
08:52 - 14:42ORD-SJU
4h 50mdirect
01:05 - 08:39SJU-ORD
8h 34m1 stop
£252United Airlines
Find Deal
Sat, 11 May - Tue, 14 May
08:40 - 17:27ORD-SJU
7h 47m1 stop
10:58 - 18:20SJU-ORD
8h 22m1 stop
£266JetBlue
Find Deal
Sat, 1 Jun - Tue, 4 Jun
07:00 - 16:13ORD-SJU
8h 13m1 stop
08:15 - 14:36SJU-ORD
7h 21m1 stop
£286Delta
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Tue, 30 Jul - Sat, 3 Aug
09:00 - 20:59ORD-SJU
10h 59m1 stop
22:35 - 07:54SJU-ORD
10h 19m1 stop
£294JetBlue
Find Deal
Wed, 12 Jun - Sun, 16 Jun
07:00 - 19:39ORD-SJU
11h 39m1 stop
17:07 - 23:59SJU-ORD
7h 52m1 stop
£298Delta
Find Deal
Sun, 4 Aug - Thu, 8 Aug
21:15 - 13:45ORD-SJU
15h 30m2 stops
01:05 - 08:34SJU-ORD
8h 29m1 stop
£303United Airlines
Find Deal
Sat, 28 Sep - Mon, 30 Sep
17:58 - 02:00ORD-SJU
7h 02m1 stop
20:05 - 18:18SJU-ORD
23h 13m1 stop
£482Frontier
Find Deal
Fri, 14 Jun - Sat, 22 Jun
09:23 - 15:11ORD-SJU
4h 48mdirect
06:09 - 10:18SJU-ORD
5h 09mdirect
£486Spirit Airlines
Find Deal
Fri, 14 Jun - Sat, 22 Jun
17:58 - 02:00ORD-SJU
7h 02m1 stop
03:08 - 16:39SJU-ORD
14h 31m1 stop
£599Frontier
Find Deal
Fri, 14 Jun - Fri, 21 Jun

Flights from Chicago to San Juan - Travel Insights & Trends

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’s the cheapest day of the week to fly from Chicago to San Juan?

The average price of all flights from Chicago O'Hare Intl Airport to San Juan Luis Munoz Marin Intl Airport clicked on KAYAK for each day over the last 12 months.
Your flight ticket price will generally be cheaper if you fly to San Juan on a Monday and more expensive on a Wednesday. On your return trip to Chicago, you should consider flying back on a Sunday, and avoid Fridays for better deals.

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 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 September, where tickets cost £192 on average. On the other hand, the most expensive months are March and December, where the average cost of tickets is £448 and £422 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 daily average prices, KAYAK takes all prices for each day before departure over the last year for 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 month.
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 2 days before departure. For the absolute cheapest price, our data suggests you should book 70 days before departure.

Which airlines provide the cheapest flights from Chicago to San Juan?

The cheapest price for the route for each airline clicked by KAYAK users in the last 72 hours.
The cheapest return flight ticket from Chicago to San Juan found by KAYAK users in the last 72 hours was for £206 on JetBlue, followed by United Airlines (£252). One-way flight deals have also been found from as low as £165 on JetBlue and from £181 on Southwest.

Which airlines fly most frequently between Chicago and San Juan?

American Airlines connects Chicago to San Juan with up to 2 flights per day. Spirit Airlines also offers 1 flight per day, while United Airlines follows with 1 flight per day.

How many flights are there between Chicago O'Hare Intl Airport and San Juan Luis Munoz Marin Intl Airport per day?

Each day, there are between 4 and 5 nonstop flights that take off from Chicago O'Hare Intl Airport and land in San Juan Luis Munoz Marin Intl Airport, with an average flight time of 4h 46m. The most common departure time is 08:00 and most flights take off in the morning. Each week, there are 29 flights. The most frequent day of departure is Saturday, when 17% of all weekly flights depart. The fewest flights depart on a Thursday.

Which cabin class options are there for flights between Chicago O'Hare Intl Airport and San Juan Luis Munoz Marin Intl Airport?

The average price of flights for each cabin class for the route found by users searching on KAYAK over the last 2 weeks.
There is only one cabin class option available for the route, which is Economy. Perform a search on KAYAK to find the latest prices and availability for all cabin fares, which differ across airlines.

How long does a flight from Chicago to San Juan take?

Direct flights cover the 2,073 miles separating Chicago and San Juan in about 4h 47m.

What’s the earliest departure time from Chicago to San Juan?

Early birds can take the earliest flight from Chicago O'Hare Intl Airport at 08:20 and will be landing in San Juan Luis Munoz Marin Intl Airport at 14:00.

What’s the latest departure time from Chicago to San Juan?

If you prefer to fly at night, the latest flight from Chicago O'Hare Intl Airport to San Juan Luis Munoz Marin Intl Airport jets off at 18:07 and lands at 23:54.

Good to know - Cheap tickets from Chicago to San Juan

Low season

October

High season

December

Cheapest flight

£165
Best time to beat the crowds (38% less expensive on average)
Most popular time to fly (57% 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 £204 for a one-way ticket and £256 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, Breeze Airways, 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 A320neo 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.

See more FAQs

Top tips for finding a cheap flight from Chicago to San Juan

  • Looking for a cheap flight from San Juan to Chicago? 25% of our users found flights on this route for San Juan or less round-trip.

Prefer to fly direct from Chicago to San Juan?

Find which airlines fly direct from O'Hare Intl to Luis Munoz Marin Intl, which days they fly and book direct flights.

Direct departures

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

Monday

Air Canada, Air New Zealand, Alaska Airlines, +3 more

Air Canada, Air New Zealand, +4 more

Tuesday

Air Canada, Air New Zealand, Alaska Airlines, +3 more

Air Canada, Air New Zealand, +4 more

Wednesday

Air Canada, Air New Zealand, Alaska Airlines, +3 more

Air Canada, Air New Zealand, +4 more

Thursday

Air Canada, Air New Zealand, Alaska Airlines, +3 more

Air Canada, Air New Zealand, +4 more

Friday

Air Canada, Air New Zealand, Alaska Airlines, +3 more

Air Canada, Air New Zealand, +4 more

Saturday

Air Canada, Air New Zealand, Alaska Airlines, +3 more

Air Canada, Air New Zealand, +4 more

Sunday

Air Canada, Air New Zealand, Alaska Airlines, +3 more

Air Canada, Air New Zealand, +4 more

See more direct flights

Direct returns

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

Monday

Air Canada, Air New Zealand, Alaska Airlines, +3 more

Air Canada, Air New Zealand, +4 more

Tuesday

Air Canada, Air New Zealand, Alaska Airlines, +3 more

Air Canada, Air New Zealand, +4 more

Wednesday

Air Canada, Air New Zealand, Alaska Airlines, +3 more

Air Canada, Air New Zealand, +4 more

Thursday

Air Canada, Air New Zealand, Alaska Airlines, +3 more

Air Canada, Air New Zealand, +4 more

Friday

Air Canada, Air New Zealand, Alaska Airlines, +3 more

Air Canada, Air New Zealand, +4 more

Saturday

Air Canada, Air New Zealand, Alaska Airlines, +3 more

Air Canada, Air New Zealand, +4 more

Sunday

Air Canada, Air New Zealand, Alaska Airlines, +3 more

Air Canada, Air New Zealand, +4 more

See more direct flights
See more direct flights

Book cheap flights from Chicago to San Juan

Cheapest flights to San Juan from Chicago found in 2024

Recent one-way flight deals

 
Only flying one-way? Below are some of the best one-way flight deals from Chicago to San Juan found on KAYAK in the last 72 hours.
12/6Wed
1 stopJetBlue
8h 28mORD-SJU
£165
12/6Wed
2 stopsSouthwest
17h 00mORD-SJU
£181
12/6Wed
3 stopsSouthwest
29h 55mORD-SJU
£213
12/6Wed
directUnited Airlines
4h 50mORD-SJU
£267
8/5Wed
1 stopUnited Airlines
12h 08mORD-SJU
£306
8/5Wed
2 stopsAmerican Airlines
15h 00mORD-SJU
£365
8/5Wed
directUnited Airlines
4h 50mORD-SJU
£406

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Last minute flights from Chicago to San Juan

Last minute flight, train and bus deals

 
These last-minute flight deals are the cheapest flights found on KAYAK in the last 72 hours for flights from Chicago to San Juan that are departing in the next 10 days.
27/4Sat
directUnited Airlines
4h 47mORD-SJU
28/4Sun
directUnited Airlines
5h 11mSJU-ORD
£275
27/4Sat
multi-stopUnited Airlines
11h 39mORD-SJU
28/4Sun
multi-stopUnited Airlines
8h 42mSJU-ORD
£282
27/4Sat
directUnited Airlines
4h 47mORD-SJU
2/5Thu
multi-stopUnited Airlines
10h 35mSJU-ORD
£284
27/4Sat
multi-stopUnited Airlines
11h 39mORD-SJU
27/4Sat
multi-stopUnited Airlines
9h 30mSJU-ORD
£639
26/4Fri
multi-stopUnited Airlines
10h 12mORD-SJU
28/4Sun
multi-stopUnited Airlines
10h 35mSJU-ORD
£672
26/4Fri
multi-stopUnited Airlines
10h 12mORD-SJU
28/4Sun
multi-stopUnited Airlines
9h 32mSJU-ORD
£860
25/4Thu
multi-stopUnited Airlines
9h 37mORD-SJU
27/4Sat
multi-stopUnited Airlines
9h 30mSJU-ORD
£878
25/4Thu
multi-stopDelta
13h 44mORD-SJU
28/4Sun
multi-stopDelta
7h 28mSJU-ORD
£2,658

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Chicago - San Juan Flights

Departure:

Chicago (ORD)United States

Destination:

San Juan (SJU)Puerto Rico

Return flight deals:

San Juan - Chicago

Cabin classes:

£121

Browse origins:

  • Flights » 
  • Chicago O'Hare Airport

Browse destinations:

  • Flights » 
  • Worldwide » 
  • San Juan Airport