O'Hare Intl

$96+ Cheap flights from San Juan to O'Hare Intl (ORD)

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 5/7. Fares are subject to change and may not be available on all flights or dates of travel.
SJU — ORD
Mar 4 — Mar 111
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Cheapflights Tip: The best prices from San Juan to Chicago O'Hare Intl are usually found in February or January, booked 67 days in advance, depart on a Friday or Thursday and return on a Monday

Cheap flight deals from San Juan to O'Hare Intl

Cheapest flights from San Juan to O'Hare Intl
Explore the most affordable flight options available from San Juan to O'Hare Intl. Find the lowest fares from popular airlines and budget airlines, with prices last updated on February 2, 2026.

This Travelocity deal was found by Cheapflights users on 1/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Travelocity is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/512:32 pm
SJU
-
ORD
Nonstop5h 16m
Spirit Airlines
Mon 3/98:16 pm
ORD
-
SJU
1 stop17h 15m
Spirit Airlines
Deal found 1/30$134
This Orbitz deal was found by Cheapflights users on 1/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 2/2711:52 am
SJU
-
ORD
1 stop8h 26m
Spirit Airlines
Mon 3/28:16 pm
ORD
-
SJU
1 stop17h 15m
Spirit Airlines
Deal found 1/31$144
This Orbitz deal was found by Cheapflights users on 2/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/512:32 pm
SJU
-
ORD
Nonstop5h 16m
Spirit Airlines
Sat 3/78:16 pm
ORD
-
SJU
1 stop16h 15m
Spirit Airlines
Deal found 2/1$146
This Orbitz deal was found by Cheapflights users on 1/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/1912:32 pm
SJU
-
ORD
Nonstop5h 16m
Spirit Airlines
Mon 2/2312:17 pm
ORD
-
SJU
Nonstop4h 32m
Spirit Airlines
Deal found 1/31$147
This Expedia deal was found by Cheapflights users on 2/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/51:22 pm
SJU
-
ORD
Nonstop5h 15m
Spirit Airlines
Sat 2/712:17 pm
ORD
-
SJU
Nonstop4h 32m
Spirit Airlines
Deal found 2/1$149
This Orbitz deal was found by Cheapflights users on 1/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/1111:32 am
SJU
-
ORD
Nonstop5h 16m
Spirit Airlines
Wed 3/1810:55 am
ORD
-
SJU
1 stop12h 03m
Spirit Airlines
Deal found 1/31$156
This Cheapflightsfares deal was found by Cheapflights users on 2/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/2611:52 am
SJU
-
ORD
1 stop8h 26m
Spirit Airlines
Tue 3/38:16 pm
ORD
-
SJU
1 stop17h 15m
Spirit Airlines
Deal found 2/1$157

Find flight deals from San Juan to O'Hare Intl

Discover tips and strategies to find the most affordable flight options for your journey from San Juan (PR1) to O'Hare Intl (ORD). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated February 2, 2026.

Round-trip from

$134
(Travelocity)

One-way from

$96
(Trip.com)

Popular in

November

Cheapest in

February

Average price

$210
From San Juan to Chicago O'Hare Intl
One-way flight from San Juan to Chicago O'Hare Intl
Highest demand for flights based on searches. 11% potential increase in price ($41 potential increase over avg. RT price).
Cheapest flight prices on average. 1% potential price decrease ($6 potential savings vs. average RT price).
Average for round-trip flights in February 2026

Cheapflights Fare Finder

 
Customize your flight search to find flights from San Juan to O'Hare Intl that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated February 2, 2026.
Use the filters below to find and compare flights from San Juan to Chicago O'Hare Intl Airport that are best for you.

Fly from

San Juan

Fly to

O'Hare Intl

Route

Depart

Return

Price

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Tue 3/10

6:39 pm-9:39 am

1 stop16h 00m

Chicago O'Hare Intl

Wed 3/18

10:55 am-11:58 pm

1 stop12h 03m

$182

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Fri 2/27

11:52 am-6:18 pm

1 stop8h 26m

Chicago O'Hare Intl

Sun 3/1

9:18 am-2:09 am

1 stop14h 51m

$188

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Tue 4/7

11:03 am-9:50 am

1 stop23h 47m

Chicago O'Hare Intl

Mon 4/13

10:55 am-11:58 pm

1 stop12h 03m

$196

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Fri 2/27

11:52 am-6:18 pm

1 stop8h 26m

Chicago O'Hare Intl

Mon 3/2

8:42 pm-3:31 pm

2 stops16h 49m

$205

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Thu 2/26

11:52 am-6:18 pm

1 stop8h 26m

Chicago O'Hare Intl

Tue 3/3

8:42 pm-3:31 pm

2 stops16h 49m

$205

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Wed 4/22

11:07 am-6:15 pm

1 stop8h 08m

Chicago O'Hare Intl

Sat 4/25

6:34 pm-1:20 am

1 stop29h 46m

$209

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Thu 2/26

11:52 am-9:39 am

1 stop23h 47m

Chicago O'Hare Intl

Sun 3/1

12:17 pm-6:49 pm

Nonstop4h 32m

$210

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Tue 3/31

11:03 am-9:50 am

1 stop23h 47m

Chicago O'Hare Intl

Tue 4/7

8:56 pm-2:29 am

Nonstop4h 33m

$223

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Wed 3/18

11:03 am-6:31 pm

1 stop8h 28m

Chicago O'Hare Intl

Mon 3/23

8:58 pm-11:49 am

2 stops13h 51m

$228

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Tue 2/17

12:32 pm-3:48 pm

Nonstop5h 16m

Chicago O'Hare Intl

Sat 2/21

8:15 am-6:59 pm

1 stop8h 44m

$236

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/31

Showing 1-10 of 21 results
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Best time to book a flight from San Juan to O'Hare Intl

Have a flexible travel schedule? Discover the best time to fly to O'Hare Intl from San Juan with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

Everything you need to know about your flight from San Juan to Chicago O'Hare Intl Airport

How far ahead should I book a flight from San Juan to Chicago O'Hare Intl Airport?

Use this chart to determine the optimal time to book a round-trip flight from San Juan to O'Hare Intl. Price data was last updated on January 30, 2026.

To ensure you get the cheapest price possible for a flight from San Juan to Chicago O'Hare Intl Airport, you should look to book at least 67 days in advance of your intended travel date. The price of your flight may increase if you delay and leave booking until a week or so before departure.

What is the cheapest month to book a flight from San Juan to Chicago O'Hare Intl Airport?

Currently, February is the cheapest month in which you can book a flight from San Juan to Chicago O'Hare Intl Airport (average of $120). Flying from San Juan to Chicago O'Hare Intl Airport in December is currently the most expensive (average of $157). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

What is the cheapest time of day to fly from SJU to ORD?

Find hourly flight availability from San Juan to O'Hare Intl. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated February 2, 2026.

It’s typically best to fly out from San Juan to Chicago O'Hare Intl Airport in the evening. Doing so could potentially save you 47% on the flight price compared to flying in the afternoon, which is usually more expensive.

What is the cheapest day to fly from San Juan to Chicago O'Hare Intl Airport?

Use this chart to determine the cheapest time to fly round-trip from San Juan to O'Hare Intl. Price data was last updated on January 31, 2026.

Travelers seeking maximum savings on their San Juan to Chicago O'Hare Intl Airport flight should consider departing on Sunday at noon when fares are most often at their lowest. Sunday afternoons flights should be avoided if possible as fares are typically the most expensive at this time.

Weekly flight availability from San Juan to Chicago O'Hare Intl Airport

Explore weekly flight availability from San Juan to O'Hare Intl. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated February 2, 2026.

The most flights from PR1 to ORD are scheduled on a Monday (12 on average). You will have fewer flight options on Wednesday, which is when the least amount of flights are scheduled (7 on average).

How often are flights from San Juan to Chicago delayed?

About 9% of weekly flights between San Juan and Chicago have experienced delays in the past year, with the average delay time being 171 minutes.

What is the most punctual flight time for San Juan to Chicago flights?

Historically, flights departing in the morning are less likely to be delayed, whereas flights leaving in the evening tend to experience delays more often.

What day of the week experiences the fewest flight delays on this route?

Thursday tends to have the lowest number of delays on this route, whereas Sunday has historically faced a higher average of delays compared to other days of the week.

Which airline has the best punctuality record on San Juan to Chicago flights?

Over the last year, United Airlines have had the lowest number of delays on this route, with just 5% of flights being delayed.

Reviews of airlines servicing O'Hare Intl

Get insights into the airlines that provide service to O'Hare Intl. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to O'Hare Intl. Reviews last updated February 2, 2026.
Get a feel of what it's like to fly with United Airlines, American Airlines, and JetBlue from San Juan to Chicago O'Hare Intl Airport by reading reviews from past customers. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.

Boarding

7.7

Comfort

7.3

Crew

8.1

Overall

7.4

Entertainment

7.1

Food

6.6

Reviews

1 / 20
8.0
Excellent

Anonymous,Oct 2025

YUL - ORD

Crew and customer service are 5 stars. I had a lot of luggage for a very long trip and they were nothing but helpful and found solutions to every problem. It was my first time flying with United, and they really are the friendly skies. Leg room however, on 2/3 flights was terrible. Same for entertainment: There was only a seat-mounted screen on 1/3 flights. It would have been nice to have on the longest leg of the journey.

Boarding

7.7

Comfort

7.3

Crew

8.1

Overall

7.4

Entertainment

7.1

Food

6.6

Reviews

1 / 20
8.0
Excellent

Anonymous,Oct 2025

YUL - ORD

Crew and customer service are 5 stars. I had a lot of luggage for a very long trip and they were nothing but helpful and found solutions to every problem. It was my first time flying with United, and they really are the friendly skies. Leg room however, on 2/3 flights was terrible. Same for entertainment: There was only a seat-mounted screen on 1/3 flights. It would have been nice to have on the longest leg of the journey.

Boarding

7.7

Comfort

7.3

Crew

8.1

Overall

7.4

Entertainment

7.1

Food

6.6

Reviews

1 / 20
8.0
Excellent

Anonymous,Oct 2025

YUL - ORD

Crew and customer service are 5 stars. I had a lot of luggage for a very long trip and they were nothing but helpful and found solutions to every problem. It was my first time flying with United, and they really are the friendly skies. Leg room however, on 2/3 flights was terrible. Same for entertainment: There was only a seat-mounted screen on 1/3 flights. It would have been nice to have on the longest leg of the journey.

Boarding

7.7

Comfort

7.3

Crew

8.1

Overall

7.4

Entertainment

7.1

Food

6.6

Reviews

1 / 20
8.0
Excellent

Anonymous,Oct 2025

YUL - ORD

Crew and customer service are 5 stars. I had a lot of luggage for a very long trip and they were nothing but helpful and found solutions to every problem. It was my first time flying with United, and they really are the friendly skies. Leg room however, on 2/3 flights was terrible. Same for entertainment: There was only a seat-mounted screen on 1/3 flights. It would have been nice to have on the longest leg of the journey.

Boarding

7.7

Comfort

7.3

Crew

8.1

Overall

7.4

Entertainment

7.1

Food

6.6

Reviews

1 / 20
8.0
Excellent

Anonymous,Oct 2025

YUL - ORD

Crew and customer service are 5 stars. I had a lot of luggage for a very long trip and they were nothing but helpful and found solutions to every problem. It was my first time flying with United, and they really are the friendly skies. Leg room however, on 2/3 flights was terrible. Same for entertainment: There was only a seat-mounted screen on 1/3 flights. It would have been nice to have on the longest leg of the journey.

Boarding

7.7

Comfort

7.3

Crew

8.1

Overall

7.4

Entertainment

7.1

Food

6.6

Reviews

1 / 20
8.0
Excellent

Anonymous,Oct 2025

YUL - ORD

Crew and customer service are 5 stars. I had a lot of luggage for a very long trip and they were nothing but helpful and found solutions to every problem. It was my first time flying with United, and they really are the friendly skies. Leg room however, on 2/3 flights was terrible. Same for entertainment: There was only a seat-mounted screen on 1/3 flights. It would have been nice to have on the longest leg of the journey.

Related info for your journey

Find useful and relevant information for your journey from San Juan to O'Hare Intl. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
  • How long is the flight from San Juan to Chicago O'Hare Intl Airport?

    Departing from San Juan to Chicago O'Hare Intl Airport will take you 23h 47m. Airlines will cover a distance of 2073 mi.

  • What are the cheapest airlines flying from San Juan to Chicago O'Hare Intl Airport round-trip?

    According to our current data, Delta ($116), Spirit Airlines ($120), and JetBlue ($131) offers the cheapest pricing from San Juan to Chicago O'Hare Intl Airport. You may be able to fly from San Juan to Chicago O'Hare Intl Airport for 64% less than the average price by searching for these airlines.

  • What are the cheapest airlines to fly from San Juan to Chicago O'Hare Intl Airport one-way?

    To fly one-way, consider booking your trip with JetBlue, which is currently one of the cheapest options available, starting at $74. Spirit Airlines flights start at $93 while deals on Frontier start at $102 one-way.

  • What are the most reliable airlines from San Juan to Chicago O'Hare Intl Airport?

    Looking for the most reliable airlines to get you to your destination on time? Our data shows these are most likely to get you from San Juan to Chicago O'Hare Intl Airport on time: Air Canada (83%), United Airlines (83%), Air New Zealand (83%).

  • What are the cheapest flights from San Juan to Chicago O'Hare Intl Airport?

    The cheapest flight price from San Juan to Chicago O'Hare Intl Airport is $119. On average you can expect to pay $474. The most popular route, (San Juan Luis Munoz Marin Intl - Chicago O'Hare Intl), can usually be booked for $144.

  • Can I find deals for flights from San Juan to O'Hare Intl that include hotel bookings?

    Yes. In addition to deals on San Juan to O'Hare Intl flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from San Juan to O'Hare Intl?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from San Juan to O'Hare Intl.

  • Can I find deals for business class flights from San Juan to O'Hare Intl?

    Yes. Cheapflights offers flight deals from San Juan to O'Hare Intl by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from San Juan to Chicago O'Hare Intl Airport?

    Currently, February is the cheapest month in which you can book a flight from San Juan to Chicago O'Hare Intl Airport (average of $120). Flying from San Juan to Chicago O'Hare Intl Airport in December is currently the most expensive (average of $157). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

Traveling to a place near Chicago O'Hare Intl Airport?

Book flights to Chicago O'Hare Intl Airport if you plan to visit one of these locations
Schaumburg
Rosemont
Naperville
Gurnee
Elgin
Hoffman Estates
Beloit
Delavan
Oak Brook
Des Plaines
Downers Grove
Elk Grove Village
Skokie
Libertyville
Lake Geneva
Waukegan
Bridgeview
Kenosha
Warrenville
Aurora

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Top 6 airlines flying from San Juan to O'Hare Intl

Discover the top 6 airlines that operate flights from San Juan to O'Hare Intl. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated February 2, 2026.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$116Average$538FlexibilityNo cancel feeOn-timeN/A
Spirit AirlinesCheapest$120Average$266FlexibilityNo cancel feeOn-time65%
JetBlueCheapest$131Average$201FlexibilityNo cancel feeOn-time62%
FrontierCheapest$137Average$258FlexibilityNo cancel feeOn-time62%
United AirlinesCheapest$256Average$481FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$258Average$483FlexibilityNo cancel feeOn-time71%

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