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San Juan

$98+ Cheap flights from Chicago (CHI) to San Juan

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 4/19. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — SJU
Apr 27 — May 41
Mon 4/27
Mon 5/4
1 adult, Economy
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Cheapflights Tip: The best prices from Chicago to San Juan are usually found in October or January, booked 28 days in advance, depart on a Monday or Tuesday and return on a Friday

Cheap flight deals from Chicago to San Juan

Cheapest flights from Chicago to San Juan
Explore the most affordable flight options available from Chicago to San Juan. Find the lowest fares from popular airlines and budget airlines, with prices last updated on March 28, 2026.

This Kiwi.com deal was found by Cheapflights users on 3/23. 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 8/2412:29 am
ORD
-
SJU
Nonstop4h 57m
Frontier
Thu 9/36:11 pm
SJU
-
ORD
Nonstop5h 15m
Frontier
Deal found 3/23$206
This CheapOair deal was found by Cheapflights users on 3/23. 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.
Fri 4/176:04 pm
ORD
-
SJU
1 stop14h 50m
Frontier
Thu 4/2311:30 am
SJU
-
ORD
1 stop13h 29m
Frontier
Deal found 3/23$207
This Frontier deal was found by Cheapflights users on 3/25. 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 4/162:20 pm
ORD
-
SJU
1 stop9h 09m
Frontier
Mon 4/203:37 pm
SJU
-
ORD
1 stop8h 29m
Frontier
Deal found 3/25$211
This Priceline deal was found by Cheapflights users on 3/25. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/179:14 am
MDW
-
SJU
1 stop29h 23m
Frontier
Sat 4/183:21 am
SJU
-
MDW
1 stop29h 43m
Frontier
Deal found 3/25$211
This eDestinos deal was found by Cheapflights users on 3/27. 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.
Tue 5/2612:40 pm
ORD
-
SJU
1 stop15h 09m
Frontier
Fri 5/296:00 am
SJU
-
ORD
1 stop7h 37m
Frontier
Deal found 3/27$212
This Kiwi.com deal was found by Cheapflights users on 3/27. 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.
Sat 5/28:00 am
ORD
-
SJU
1 stop17h 01m
Frontier
Sat 5/166:41 pm
SJU
-
ORD
1 stop15h 56m
Frontier
Deal found 3/27$213
This Mytrip deal was found by Cheapflights users on 3/27. 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.
Mon 4/68:56 pm
ORD
-
SJU
Nonstop4h 33m
Spirit Airlines
Tue 4/147:54 pm
SJU
-
ORD
1 stop14h 42m
Spirit Airlines
Deal found 3/27$214
This Kiwi.com deal was found by Cheapflights users on 3/23. 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 5/58:00 am
ORD
-
SJU
Nonstop4h 42m
Multiple Airlines
Wed 5/136:41 pm
SJU
-
ORD
1 stop15h 56m
Multiple Airlines
Deal found 3/23$215
This Frontier deal was found by Cheapflights users on 3/25. 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 4/74:34 pm
ORD
-
SJU
1 stop7h 18m
Frontier
Fri 4/173:37 pm
SJU
-
ORD
1 stop8h 29m
Frontier
Deal found 3/25$216
This Frontier deal was found by Cheapflights users on 3/27. 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.
Wed 4/82:56 pm
MDW
-
SJU
1 stop8h 56m
Frontier
Sat 4/188:00 am
SJU
-
MDW
1 stop9h 00m
Frontier
Deal found 3/27$216
This CheapOair deal was found by Cheapflights users on 3/27. 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.
Sat 4/48:56 pm
ORD
-
SJU
Nonstop4h 33m
Multiple Airlines
Thu 4/96:00 am
SJU
-
ORD
1 stop9h 42m
Multiple Airlines
Deal found 3/27$217
This Cheapflightsfares deal was found by Cheapflights users on 3/25. 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 5/48:00 am
ORD
-
SJU
Nonstop4h 42m
Spirit Airlines
Sat 5/92:37 pm
SJU
-
ORD
Nonstop5h 13m
Spirit Airlines
Deal found 3/25$218

Find flight deals from Chicago to San Juan

Discover tips and strategies to find the most affordable flight options for your journey from Chicago (CHI) to San Juan (PR1). 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 28, 2026.

Round-trip from

$206
(Kiwi.com)

One-way from

$98
(Frontier)

Popular in

December

Cheapest in

October

Average price

$416
From Chicago (CHI) to San Juan
Search Deals
One-way flight from Chicago (CHI) to San Juan
Search Deals
Highest demand for flights based on searches. 10% potential increase in price ($45 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($13 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in March 2026
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Cheapflights Fare Finder

 
Customize your flight search to find flights from Chicago to San Juan 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 28, 2026.
Use the filters below to find and compare flights from Chicago to San Juan that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip
Quickest round-trip

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Mon 5/11

8:00 am-1:42 pm

Nonstop4h 42m

San Juan Luis Munoz Marin Intl

Fri 5/15

2:37 pm-6:50 pm

Nonstop5h 13m

$274

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Sat 5/2

2:38 pm-8:34 pm

Nonstop4h 56m

San Juan Luis Munoz Marin Intl

Wed 5/6

3:56 pm-8:15 pm

Nonstop5h 19m

$327

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Tue 5/5

2:38 pm-8:34 pm

Nonstop4h 56m

San Juan Luis Munoz Marin Intl

Tue 5/12

7:40 am-11:53 am

Nonstop5h 13m

$327

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Sat 5/2

12:55 pm-9:24 pm

1 stop7h 29m

San Juan Luis Munoz Marin Intl

Sat 5/16

3:56 pm-8:15 pm

Nonstop5h 19m

$354

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Thu 4/23

2:38 pm-8:34 pm

Nonstop4h 56m

San Juan Luis Munoz Marin Intl

Thu 4/30

3:56 pm-8:15 pm

Nonstop5h 19m

$361

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Tue 5/5

5:55 am-10:40 pm

2 stops15h 45m

San Juan Luis Munoz Marin Intl

Tue 5/12

5:05 am-9:55 pm

2 stops17h 50m

$386

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Sat 5/16

12:45 pm-11:45 pm

2 stops10h 00m

San Juan Luis Munoz Marin Intl

Sat 5/23

1:10 pm-5:20 pm

Nonstop5h 10m

$392

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Thu 4/30

2:38 pm-8:34 pm

Nonstop4h 56m

San Juan Luis Munoz Marin Intl

Tue 5/5

3:56 pm-8:15 pm

Nonstop5h 19m

$397

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Sun 4/19

5:48 am-3:42 pm

1 stop8h 54m

San Juan Luis Munoz Marin Intl

Thu 4/30

1:00 am-7:44 am

1 stop7h 44m

$406

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Tue 6/23

11:23 am-10:27 pm

1 stop10h 04m

San Juan Luis Munoz Marin Intl

Tue 6/30

2:04 pm-8:31 pm

1 stop7h 27m

$416

Flights are sorted by cheapest round-trip flights first.

Deals found on 3/27

Showing 1-10 of 44 resultsSorted by cheapest first
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Best time to book a flight from Chicago to San Juan

Have a flexible travel schedule? Discover the best time to fly to San Juan from Chicago 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 Chicago to San Juan

How far ahead should I book a flight from Chicago to San Juan?

Use this chart to determine the optimal time to book a round-trip flight from Chicago to San Juan. Price data was last updated on March 13, 2026.

To ensure you get the cheapest price possible for a flight from Chicago to San Juan, you should look to book at least 28 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 Chicago to San Juan?

Currently, April is the cheapest month in which you can book a flight from Chicago to San Juan (average of $91). Flying from Chicago to San Juan in December is currently the most expensive (average of $224). 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 CHI to SJU?

Find hourly flight availability from Chicago to San Juan. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated March 28, 2026.

It’s typically best to fly out from Chicago to San Juan in the evening. Doing so could potentially save you 22% on the flight price compared to flying at noon, which is usually more expensive.

What is the cheapest day to fly from Chicago to San Juan?

Use this chart to determine the cheapest time to fly round-trip from Chicago to San Juan. Price data was last updated on March 28, 2026.

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

Weekly flight availability from Chicago to San Juan

Explore weekly flight availability from Chicago to San Juan. 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 28, 2026.

The most flights from CHI to PR1 are scheduled on a Saturday (16 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (2 on average).

How much does it cost to fly round-trip from Chicago to San Juan?

How often are flights from Chicago to San Juan delayed?

About 19% of weekly flights between Chicago and San Juan have experienced delays in the past year, with the average delay time being 142 minutes.

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

Over the last year, American Airlines have had the lowest number of delays on this route, with just 17% of flights being delayed.

Reviews of airlines servicing San Juan

Get insights into the airlines that provide service to San Juan. 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 San Juan. Reviews last updated March 28, 2026.
Read through reviews of airlines operating flights from Chicago to San Juan, such as United Airlines,JetBlue, andAmerican Airlines. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
United Airlines
7.4
Good
9,504 reviews

Food

6.6

Overall

7.4

Entertainment

7.1

Boarding

7.7

Crew

8.1

Comfort

7.3

Reviews

1 / 20
10.0
Excellent

Dane,Jan 2026

TYS - IAD

It was a short flight, so no time for amenities. Just glad everything was quick and easy from boarding to arriving at my destination with my family
United Airlines
7.4
Good
9,504 reviews
United Airlines
7.4
Good
9,504 reviews

Food

6.6

Overall

7.4

Entertainment

7.1

Boarding

7.7

Crew

8.1

Comfort

7.3

Reviews

1 / 20
10.0
Excellent

Dane,Jan 2026

TYS - IAD

It was a short flight, so no time for amenities. Just glad everything was quick and easy from boarding to arriving at my destination with my family
JetBlue
7.2
Good
2,910 reviews
United Airlines
7.4
Good
9,504 reviews

Food

6.6

Overall

7.4

Entertainment

7.1

Boarding

7.7

Crew

8.1

Comfort

7.3

Reviews

1 / 20
10.0
Excellent

Dane,Jan 2026

TYS - IAD

It was a short flight, so no time for amenities. Just glad everything was quick and easy from boarding to arriving at my destination with my family
American Airlines
7.1
Good
11,519 reviews
United Airlines
7.4
Good
9,504 reviews

Food

6.6

Overall

7.4

Entertainment

7.1

Boarding

7.7

Crew

8.1

Comfort

7.3

Reviews

1 / 20
10.0
Excellent

Dane,Jan 2026

TYS - IAD

It was a short flight, so no time for amenities. Just glad everything was quick and easy from boarding to arriving at my destination with my family
Spirit Airlines
6.3
Okay
8,551 reviews
United Airlines
7.4
Good
9,504 reviews

Food

6.6

Overall

7.4

Entertainment

7.1

Boarding

7.7

Crew

8.1

Comfort

7.3

Reviews

1 / 20
10.0
Excellent

Dane,Jan 2026

TYS - IAD

It was a short flight, so no time for amenities. Just glad everything was quick and easy from boarding to arriving at my destination with my family
Frontier
5.7
Fair
3,013 reviews
United Airlines
7.4
Good
9,504 reviews

Food

6.6

Overall

7.4

Entertainment

7.1

Boarding

7.7

Crew

8.1

Comfort

7.3

Reviews

1 / 20
10.0
Excellent

Dane,Jan 2026

TYS - IAD

It was a short flight, so no time for amenities. Just glad everything was quick and easy from boarding to arriving at my destination with my family

Related info for your journey

Find useful and relevant information for your journey from Chicago to San Juan. 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 Chicago to San Juan?

    There are many flights that can get you from Chicago to San Juan in 4h 42m. Fly via Spirit Airlines, United Airlines, or Southwest to get the fastest option. The distance between Chicago and San Juan is about 2073 mi. This flight may include one or multiple stops.

  • What are the cheapest airlines flying from Chicago to San Juan round-trip?

    Cheapflights users have booked flights from Chicago to San Juan round-trip from $114. Other airlines that can offer you cheap pricing are JetBlue, from $119, and Delta, from $132. Frontier is priced at 71% lower than the current average price of a flight leaving 3 months from now.

  • What are the cheapest airlines to fly from Chicago to San Juan one-way?

    $75 is the cheapest one-way deal found within the past few days, from JetBlue. You may also be able to find cheap deals on Spirit Airlines and Frontier, with prices starting from $91 and $98, respectively.

  • What are the most reliable airlines from Chicago to San Juan?

    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 Chicago to San Juan on time: Qatar Airways (92%), Alaska Airlines (88%), American Airlines (87%).

  • What are the cheapest flights from Chicago to San Juan?

    Looking at all options, your cheapest flight can be booked for $118. While the most popular route (Chicago O'Hare Intl - San Juan Luis Munoz Marin Intl) can be booked for $178 on average, our data indicates $683 when flying from Chicago to San Juan.

  • Where are the most common layover locations when flying from Chicago to San Juan?

    Chicago to San Juan flights have a layover in New York most of the time.

  • What are some popular things to do or see while on a layover in New York?

    Times Square, New York City Center, and Madison Square Garden are the most popular attractions in New York if you're in need of something to do during your layover. Times Square, New York City Center, and Madison Square Garden are located about 13.6 mi, 13.6 mi, and 13.6 mi, respectively from New York John F Kennedy Intl. Those landing in New York looking to spend some time exploring during their layover can rent a car for about $64 per day.

  • Where are the least popular layover locations for Chicago to San Juan flights?

    Of the flights from Chicago to San Juan that have layovers, the fewest flights stop in Orlando.

  • Can I find deals for flights from Chicago to San Juan that include hotel bookings?

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

  • How can I find direct flights from Chicago to San Juan?

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

  • Can I find deals for business class flights from Chicago to San Juan?

    Yes. Cheapflights offers flight deals from Chicago to San Juan 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 Chicago to San Juan?

    Currently, April is the cheapest month in which you can book a flight from Chicago to San Juan (average of $91). Flying from Chicago to San Juan in December is currently the most expensive (average of $224). 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

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Top 7 airlines flying from Chicago to San Juan

Discover the top 7 airlines that operate flights from Chicago to San Juan. 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 28, 2026.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$114Average$291FlexibilityNo cancel feeOn-time62%
JetBlueCheapest$119Average$236FlexibilityNo cancel feeOn-time62%
DeltaCheapest$132Average$420FlexibilityNo cancel feeOn-timeN/A
Spirit AirlinesCheapest$139Average$315FlexibilityNo cancel feeOn-time65%
United AirlinesCheapest$254Average$500FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$311Average$520FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$377Average$488FlexibilityNo cancel feeOn-time63%

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