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O'Hare Intl

$115+ 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 5/4. Fares are subject to change and may not be available on all flights or dates of travel.
SJU — ORD
Apr 21 — Apr 281
Tue 4/21
Tue 4/28
1 adult, Economy
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1. Tell us where you want to go

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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 82 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 March 22, 2026.

This eDestinos deal was found by Cheapflights users on 3/20. 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/96:07 pm
SJU
-
ORD
1 stop22h 50m
Frontier
Sun 4/124:21 pm
ORD
-
SJU
1 stop26h 39m
Frontier
Deal found 3/20$168
This Expedia deal was found by Cheapflights users on 3/22. 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.
Fri 4/173:23 pm
SJU
-
ORD
1 stop8h 16m
Frontier
Mon 4/204:58 pm
ORD
-
SJU
1 stop24h 01m
Frontier
Deal found 3/22$176
This eDestinos deal was found by Cheapflights users on 3/20. 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/233:31 pm
SJU
-
ORD
1 stop27h 43m
Frontier
Sun 4/2612:38 pm
ORD
-
SJU
1 stop10h 21m
Frontier
Deal found 3/20$178
This Kiwi.com deal was found by Cheapflights users on 3/21. 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 4/163:31 pm
SJU
-
ORD
1 stop9h 13m
Frontier
Sun 4/193:52 pm
ORD
-
SJU
1 stop25h 07m
Frontier
Deal found 3/21$183
This Frontier deal was found by Cheapflights users on 3/20. 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.
Thu 4/163:31 pm
SJU
-
ORD
1 stop9h 13m
Frontier
Thu 4/232:05 pm
ORD
-
SJU
1 stop10h 56m
Frontier
Deal found 3/20$186
This eDestinos deal was found by Cheapflights users on 3/21. 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/1511:05 am
SJU
-
ORD
1 stop27h 48m
Frontier
Sun 4/193:52 pm
ORD
-
SJU
1 stop25h 07m
Frontier
Deal found 3/21$191
This Frontier deal was found by Cheapflights users on 3/20. 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.
Fri 4/243:23 pm
SJU
-
ORD
1 stop8h 16m
Frontier
Sun 4/2612:38 pm
ORD
-
SJU
1 stop10h 21m
Frontier
Deal found 3/20$196
This Gotogate deal was found by Cheapflights users on 3/22. 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 Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/176:00 am
SJU
-
ORD
1 stop17h 54m
Frontier
Sun 4/262:20 pm
ORD
-
SJU
1 stop9h 09m
Frontier
Deal found 3/22$198
This eDestinos deal was found by Cheapflights users on 3/20. 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/181:59 am
SJU
-
ORD
1 stop12h 33m
Frontier
Sun 4/2612:38 pm
ORD
-
SJU
1 stop10h 21m
Frontier
Deal found 3/20$200
This eDestinos deal was found by Cheapflights users on 3/19. 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/166:00 am
SJU
-
ORD
1 stop16h 17m
Frontier
Sat 4/188:00 am
ORD
-
SJU
1 stop17h 01m
Frontier
Deal found 3/19$201
This Cheapflightsfares deal was found by Cheapflights users on 3/18. 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.
Tue 4/71:29 am
SJU
-
ORD
Nonstop5h 16m
Spirit Airlines
Sun 4/127:17 am
ORD
-
SJU
1 stop10h 38m
Spirit Airlines
Deal found 3/18$202
This CheapOair deal was found by Cheapflights users on 3/18. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/81:29 am
SJU
-
ORD
Nonstop5h 16m
Spirit Airlines
Mon 4/135:05 am
ORD
-
SJU
1 stop12h 50m
Spirit Airlines
Deal found 3/18$203

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 March 22, 2026.

Round-trip from

$168
(eDestinos)

One-way from

$115
(Super.com)

Popular in

November

Cheapest in

February

Average price

$379
From San Juan to Chicago O'Hare Intl
Search Deals
One-way flight from San Juan to Chicago O'Hare Intl
Search Deals
Highest demand for flights based on searches. 10% potential increase in price ($37 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($5 potential savings vs. average RT price).
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Average for round-trip flights in March 2026
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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 March 22, 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

Fly to

Route

Depart

Return

Price

Cheapest round-trip
Quickest round-trip

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Mon 4/13

1:29 am-5:45 am

Nonstop5h 16m

Chicago O'Hare Intl

Tue 4/21

10:00 am-3:39 pm

Nonstop4h 39m

$233

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Tue 4/21

2:00 pm-8:05 am

1 stop19h 05m

Chicago O'Hare Intl

Tue 4/28

10:00 am-3:39 pm

Nonstop4h 39m

$307

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Fri 4/24

3:37 pm-10:39 pm

2 stops32h 02m

Chicago O'Hare Intl

Mon 4/27

5:50 am-9:54 am

2 stops51h 04m

$321

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Wed 5/6

3:56 pm-8:15 pm

Nonstop5h 19m

Chicago O'Hare Intl

Wed 5/13

2:38 pm-8:34 pm

Nonstop4h 56m

$327

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Thu 4/30

7:40 am-11:53 am

Nonstop5h 13m

Chicago O'Hare Intl

Wed 5/6

2:38 pm-8:34 pm

Nonstop4h 56m

$327

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Wed 4/15

7:40 am-11:53 am

Nonstop5h 13m

Chicago O'Hare Intl

Thu 4/23

2:38 pm-8:34 pm

Nonstop4h 56m

$377

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Fri 4/24

7:40 am-11:53 am

Nonstop5h 13m

Chicago O'Hare Intl

Sun 4/26

2:38 pm-8:34 pm

Nonstop4h 56m

$437

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Sun 5/17

9:45 pm-12:50 pm

2 stops16h 05m

Chicago O'Hare Intl

Sun 5/31

1:35 pm-11:45 pm

1 stop9h 10m

$449

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Tue 4/21

7:40 am-11:53 am

Nonstop5h 13m

Chicago O'Hare Intl

Tue 4/28

2:38 pm-8:34 pm

Nonstop4h 56m

$477
Cheapest one-way

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Tue 5/19

1:14 pm-10:27 pm

1 stop10h 13m

$158

Flights are sorted by cheapest round-trip flights first.

Deals found on 3/18

Showing 1-10 of 18 resultsSorted by cheapest first
1
2

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 March 13, 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 82 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, May is the cheapest month in which you can book a flight from San Juan to Chicago O'Hare Intl Airport (average of $113). 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 March 22, 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 43% 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 March 14, 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 March 22, 2026.

The most flights from PR1 to ORD are scheduled on a Saturday (16 on average). You will have fewer flight options on Wednesday, which is when the least amount of flights are scheduled (10 on average).

How much does it cost to fly round-trip from San Juan to Chicago O'Hare Intl Airport?

How often are flights from San Juan to Chicago delayed?

About 8% of weekly flights between San Juan and Chicago have experienced delays in the past year, with the average delay time being 185 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 4% 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 March 22, 2026.
Get a feel of what it's like to fly with United Airlines,JetBlue, andAmerican Airlines 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
9,459 reviews

Overall

7.4

Crew

8.1

Comfort

7.3

Boarding

7.7

Food

6.6

Entertainment

7.1

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.
United Airlines
7.4
Good
9,459 reviews
United Airlines
7.4
Good
9,459 reviews

Overall

7.4

Crew

8.1

Comfort

7.3

Boarding

7.7

Food

6.6

Entertainment

7.1

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.
JetBlue
7.2
Good
2,911 reviews
United Airlines
7.4
Good
9,459 reviews

Overall

7.4

Crew

8.1

Comfort

7.3

Boarding

7.7

Food

6.6

Entertainment

7.1

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.
American Airlines
7.1
Good
11,485 reviews
United Airlines
7.4
Good
9,459 reviews

Overall

7.4

Crew

8.1

Comfort

7.3

Boarding

7.7

Food

6.6

Entertainment

7.1

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.
Spirit Airlines
6.3
Okay
8,533 reviews
United Airlines
7.4
Good
9,459 reviews

Overall

7.4

Crew

8.1

Comfort

7.3

Boarding

7.7

Food

6.6

Entertainment

7.1

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.
Frontier
5.7
Fair
3,020 reviews
United Airlines
7.4
Good
9,459 reviews

Overall

7.4

Crew

8.1

Comfort

7.3

Boarding

7.7

Food

6.6

Entertainment

7.1

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 5h 16m. 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, Frontier ($64), Spirit Airlines ($122), 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 80% 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 $95 while deals on Frontier start at $103 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 (88%), United Airlines (88%), Air New Zealand (88%).

  • 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 $132. On average you can expect to pay $679. The most popular route, (San Juan Luis Munoz Marin Intl - Chicago O'Hare Intl), can usually be booked for $202.

  • 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, May is the cheapest month in which you can book a flight from San Juan to Chicago O'Hare Intl Airport (average of $113). 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
Gurnee
Naperville
Lake Geneva
Hoffman Estates
Delavan
Downers Grove
Des Plaines
Elgin
Oak Brook
South Holland
Elk Grove Village
Libertyville
Waukegan
Beloit
Warrenville
Oakbrook Terrace
Bridgeview
Great Lakes

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Alternative routes for San Juan to O'Hare Intl

See prices for flight routes from nearby airports that may be better suited for you.
Luis Munoz Marin Intl to O'Hare Intl flights
Aguadilla to O'Hare Intl flights

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 March 22, 2026.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$64Average$259FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$122Average$268FlexibilityNo cancel feeOn-time65%
JetBlueCheapest$131Average$201FlexibilityNo cancel feeOn-time62%
United AirlinesCheapest$256Average$483FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$257Average$446FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$292Average$439FlexibilityNo cancel feeOn-time63%

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