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O'Hare Intl

$101+ 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 1/12. Fares are subject to change and may not be available on all flights or dates of travel.
SJU — ORD
Jan 17 — Jan 241
Sat 1/17
Sat 1/24
1 adult, Economy
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Cheapflights Tip: The best prices from San Juan to Chicago O'Hare Intl are usually found in February or September, 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 December 18, 2025.

This Mytrip deal was found by Cheapflights users on 12/16. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/238:08 pmSJU - ORD
Nonstop5h 17mMultiple Airlines
Mon 1/51:44 pmORD - SJU
1 stop9h 22mMultiple Airlines
Deal found 12/16$184
This Kiwi.com deal was found by Cheapflights users on 12/16. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/256:28 pmSJU - ORD
1 stop8h 02mMultiple Airlines
Sat 1/108:27 pmORD - SJU
1 stop10h 27mMultiple Airlines
Deal found 12/16$185
This Kiwi.com deal was found by Cheapflights users on 12/16. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/248:08 pmSJU - ORD
Nonstop5h 17mMultiple Airlines
Thu 1/88:27 pmORD - SJU
1 stop10h 27mMultiple Airlines
Deal found 12/16$186
This Cheapflightsfares deal was found by Cheapflights users on 12/15. 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.
Mon 12/228:08 pmSJU - ORD
Nonstop5h 17mSpirit Airlines
Mon 1/55:45 amORD - SJU
Nonstop4h 41mSpirit Airlines
Deal found 12/15$187
This Kiwi.com deal was found by Cheapflights users on 12/16. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/256:28 pmSJU - ORD
1 stop8h 02mMultiple Airlines
Tue 1/65:00 amORD - SJU
1 stop16h 44mMultiple Airlines
Deal found 12/16$188
This Frontier deal was found by Cheapflights users on 12/16. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/234:19 pmSJU - ORD
1 stop8h 05mFrontier
Thu 1/83:32 pmORD - SJU
1 stop7h 27mFrontier
Deal found 12/16$192
This Kiwi.com deal was found by Cheapflights users on 12/15. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/228:08 pmSJU - ORD
Nonstop5h 17mMultiple Airlines
Thu 1/16:00 amORD - SJU
1 stop7h 01mMultiple Airlines
Deal found 12/15$193
This Kiwi.com deal was found by Cheapflights users on 12/17. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/248:08 pmSJU - ORD
Nonstop5h 17mMultiple Airlines
Thu 1/112:39 pmORD - SJU
1 stop9h 58mMultiple Airlines
Deal found 12/17$196
This Kiwi.com deal was found by Cheapflights users on 12/16. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/236:25 amSJU - ORD
1 stop7h 40mMultiple Airlines
Fri 1/912:17 pmORD - SJU
Nonstop4h 32mMultiple Airlines
Deal found 12/16$198
This Kiwi.com deal was found by Cheapflights users on 12/16. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/248:08 pmSJU - ORD
Nonstop5h 17mSpirit Airlines
Fri 1/912:17 pmORD - SJU
Nonstop4h 32mSpirit Airlines
Deal found 12/16$199
This Kiwi.com deal was found by Cheapflights users on 12/16. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/2411:57 amSJU - ORD
1 stop10h 09mMultiple Airlines
Wed 1/79:34 amORD - SJU
1 stop7h 21mMultiple Airlines
Deal found 12/16$200

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 December 18, 2025.

Round-trip from

$169
(CheapOair)

One-way from

$101
(eDestinos)

Popular in

June

Cheapest in

February

Average price

$357
From San Juan to Chicago O'Hare Intl
Search Deals
One-way flight from San Juan to Chicago O'Hare Intl
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Highest demand for flights based on searches. 4% potential increase in price ($16 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease ($6 potential savings vs. average RT price).
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Average for round-trip flights in December 2025
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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 December 18, 2025.
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

Thu 2/5

11:06 am-7:31 pm

1 stop10h 25m

Chicago O'Hare Intl

Sun 2/8

7:45 am-6:02 pm

1 stop8h 17m

$179

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Tue 4/7

1:00 pm-9:33 pm

1 stop9h 33m

Chicago O'Hare Intl

Tue 4/14

1:45 pm-1:47 am

1 stop11h 02m

$211

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Wed 2/25

8:35 am-11:57 am

Nonstop5h 22m

Chicago O'Hare Intl

Mon 3/9

2:20 pm-8:00 pm

Nonstop4h 40m

$216

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Tue 3/24

1:30 am-10:05 am

1 stop9h 35m

Chicago O'Hare Intl

Sun 3/29

10:56 am-11:23 pm

1 stop11h 27m

$220

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Thu 1/22

1:22 pm-4:37 pm

Nonstop5h 15m

Chicago O'Hare Intl

Thu 1/29

12:17 pm-6:49 pm

Nonstop4h 32m

$222

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Wed 5/13

12:30 pm-7:26 pm

1 stop7h 56m

Chicago O'Hare Intl

Tue 5/26

3:15 pm-1:59 am

1 stop9h 44m

$248

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Wed 1/21

4:52 pm-8:20 pm

Nonstop5h 28m

Chicago O'Hare Intl

Sat 1/24

2:20 pm-9:00 pm

Nonstop4h 40m

$256

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Fri 2/27

12:32 pm-3:48 pm

Nonstop5h 16m

Chicago O'Hare Intl

Mon 3/2

12:22 pm-6:54 pm

Nonstop4h 32m

$257

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Tue 4/21

2:15 am-6:15 pm

1 stop17h 00m

Chicago O'Hare Intl

Sun 4/26

12:22 pm-5:54 pm

Nonstop4h 32m

$273

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Tue 2/17

3:10 pm-11:10 pm

1 stop10h 00m

$107

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/17

Showing 1-10 of 18 results
1
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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 December 12, 2025.

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, August is the cheapest month in which you can book a flight from San Juan to Chicago O'Hare Intl Airport (average of $121). Flying from San Juan to Chicago O'Hare Intl Airport in June is currently the most expensive (average of $175). 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 December 18, 2025.

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 52% on the flight price compared to flying in the morning, 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 December 16, 2024.

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. Monday at noon 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 December 18, 2025.

The most flights from PR1 to ORD are scheduled on a Monday (6 on average). You will have fewer flight options on Monday, which is when the least amount of flights are scheduled (6 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 169 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 Saturday 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 6% 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 December 18, 2025.
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.
United Airlines
7.4
Good
9,093 reviews

Entertainment

7.1

Food

6.6

Boarding

7.7

Comfort

7.3

Crew

8.1

Overall

7.4

Reviews

1 / 20
4.0
Okay

Kevin,Dec 2025

BOS - EWR

Seems like every United flight has a delay and it’s always someone else’s fault. Step up and take some accountability
United Airlines
7.4
Good
9,093 reviews
United Airlines
7.4
Good
9,093 reviews

Entertainment

7.1

Food

6.6

Boarding

7.7

Comfort

7.3

Crew

8.1

Overall

7.4

Reviews

1 / 20
4.0
Okay

Kevin,Dec 2025

BOS - EWR

Seems like every United flight has a delay and it’s always someone else’s fault. Step up and take some accountability
American Airlines
7.2
Good
11,055 reviews
United Airlines
7.4
Good
9,093 reviews

Entertainment

7.1

Food

6.6

Boarding

7.7

Comfort

7.3

Crew

8.1

Overall

7.4

Reviews

1 / 20
4.0
Okay

Kevin,Dec 2025

BOS - EWR

Seems like every United flight has a delay and it’s always someone else’s fault. Step up and take some accountability
JetBlue
7.2
Good
2,897 reviews
United Airlines
7.4
Good
9,093 reviews

Entertainment

7.1

Food

6.6

Boarding

7.7

Comfort

7.3

Crew

8.1

Overall

7.4

Reviews

1 / 20
4.0
Okay

Kevin,Dec 2025

BOS - EWR

Seems like every United flight has a delay and it’s always someone else’s fault. Step up and take some accountability
Spirit Airlines
6.3
Okay
8,190 reviews
United Airlines
7.4
Good
9,093 reviews

Entertainment

7.1

Food

6.6

Boarding

7.7

Comfort

7.3

Crew

8.1

Overall

7.4

Reviews

1 / 20
4.0
Okay

Kevin,Dec 2025

BOS - EWR

Seems like every United flight has a delay and it’s always someone else’s fault. Step up and take some accountability
Frontier
5.8
Fair
3,081 reviews
United Airlines
7.4
Good
9,093 reviews

Entertainment

7.1

Food

6.6

Boarding

7.7

Comfort

7.3

Crew

8.1

Overall

7.4

Reviews

1 / 20
4.0
Okay

Kevin,Dec 2025

BOS - EWR

Seems like every United flight has a delay and it’s always someone else’s fault. Step up and take some accountability

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 5h 22m. Airlines will cover a distance of 2073 mi. Both multi-stop and nonstop flights can be found to your destination and back.

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

    According to our current data, Delta ($116), JetBlue ($120), and Spirit Airlines ($123) 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 65% 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 $71. Frontier flights start at $91 while deals on Spirit Airlines start at $94 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: Spirit Airlines (87%), Air Canada (82%), United Airlines (82%).

  • 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 $108. On average you can expect to pay $821. The most popular route, (San Juan Luis Munoz Marin Intl - Chicago O'Hare Intl), can usually be booked for $159.

  • 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, August is the cheapest month in which you can book a flight from San Juan to Chicago O'Hare Intl Airport (average of $121). Flying from San Juan to Chicago O'Hare Intl Airport in June is currently the most expensive (average of $175). 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
Gurnee
Elgin
Naperville
Hoffman Estates
Beloit
Delavan
Oak Brook
Downers Grove
Des Plaines
Elk Grove Village
Skokie
Lake Geneva
Bridgeview
Warrenville
Waukegan
Aurora
Kenosha
Evanston

Browse thousands of different options on Cheapflights for your next trip

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Top 7 airlines flying from San Juan to O'Hare Intl

Discover the top 7 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 December 18, 2025.
AirlineCheapestAverageFlexibilityOn-time
JetBlueCheapest$120Average$236FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$138Average$280FlexibilityNo cancel feeOn-time65%
FrontierCheapest$138Average$259FlexibilityNo cancel feeOn-time62%
DeltaCheapest$162Average$538FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$259Average$482FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$271Average$484FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$341Average$479FlexibilityNo cancel feeOn-time63%

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