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$113+ 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 1/27. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — SJU
Dec 13 — Dec 201
Sat 12/13
Sat 12/20
1 adult, Economy
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Cheapflights Tip: The best prices from Chicago to San Juan are usually found in April or May, booked 28 days in advance, depart on a Tuesday or Monday and return on a Friday

Find 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 November 13, 2025.

This Kiwi.com deal was found by Cheapflights users on 11/12. 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 12/159:14 pmORD - SJU
1 stop24h 11mMultiple Airlines
Sat 12/204:02 pmSJU - ORD
1 stop8h 44mMultiple Airlines
Deal found 11/12$211
This FlightHub deal was found by Cheapflights users on 11/12. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/52:00 pmORD - SJU
1 stop8h 49mMultiple Airlines
Sun 12/148:45 pmSJU - ORD
Nonstop5h 14mMultiple Airlines
Deal found 11/12$212
This Mytrip deal was found by Cheapflights users on 11/12. 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.
Fri 11/285:00 amORD - SJU
1 stop13h 27mSpirit Airlines
Sat 12/61:32 pmSJU - ORD
2 stops12h 37mSpirit Airlines
Deal found 11/12$213
This Kiwi.com deal was found by Cheapflights users on 11/11. 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 11/276:23 pmORD - SJU
2 stops24h 04mMultiple Airlines
Fri 12/53:06 pmSJU - ORD
1 stop7h 36mMultiple Airlines
Deal found 11/11$214
This Mytrip deal was found by Cheapflights users on 11/12. 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.
Thu 11/206:48 amORD - SJU
1 stop15h 36mSpirit Airlines
Sun 11/2311:55 amSJU - ORD
2 stops21h 48mSpirit Airlines
Deal found 11/12$215
This Frontier deal was found by Cheapflights users on 11/11. 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.
Sun 12/76:37 pmMDW - SJU
1 stop13h 18mFrontier
Sat 12/204:02 pmSJU - MDW
1 stop8h 10mFrontier
Deal found 11/11$216
This Cheapflightsfares deal was found by Cheapflights users on 11/11. 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.
Wed 12/35:00 amORD - SJU
1 stop13h 27mSpirit Airlines
Tue 12/96:00 amSJU - ORD
1 stop16h 09mSpirit Airlines
Deal found 11/11$217
This Kiwi.com deal was found by Cheapflights users on 11/12. 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.
Sun 12/145:40 amORD - SJU
Nonstop4h 41mSpirit Airlines
Sat 12/208:08 pmSJU - ORD
Nonstop5h 17mSpirit Airlines
Deal found 11/12$218
This Kiwi.com deal was found by Cheapflights users on 11/12. 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.
Fri 11/284:46 pmMDW - SJU
1 stop8h 08mFrontier
Wed 12/39:15 amSJU - MDW
1 stop29h 46mFrontier
Deal found 11/12$219
This Kiwi.com deal was found by Cheapflights users on 11/12. 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 11/295:20 amORD - SJU
1 stop8h 30mMultiple Airlines
Fri 12/128:45 pmSJU - ORD
Nonstop5h 14mMultiple Airlines
Deal found 11/12$220
This Kiwi.com deal was found by Cheapflights users on 11/12. 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 12/47:23 pmMDW - SJU
2 stops27h 22mMultiple Airlines
Thu 12/1110:42 amSJU - MDW
1 stop13h 11mMultiple Airlines
Deal found 11/12$220
This American Airlines deal was found by Cheapflights users on 11/12. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/317:26 pmORD - SJU
1 stop12h 09mAmerican Airlines
Thu 1/154:28 pmSJU - ORD
Nonstop5h 32mAmerican Airlines
Deal found 11/12$221

Cheap 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 November 13, 2025.

Round-trip from

$211
(Kiwi.com)

One-way from

$113
(American Airlines)

Popular in

December

Cheapest in

April

Average price

$432
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. 11% potential increase in price ($50 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($16 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in November 2025
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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 November 13, 2025.
Use the filters below to find and compare flights from Chicago to San Juan that are best for you.

Fly from

Chicago

Fly to

San Juan

Route

Depart

Return

Price

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Sun 2/1

2:20 pm-9:00 pm

Nonstop4h 40m

San Juan Luis Munoz Marin Intl

Tue 2/3

2:05 am-10:53 am

1 stop10h 48m

$223

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Thu 1/29

3:15 pm-12:35 am

1 stop7h 20m

San Juan Luis Munoz Marin Intl

Tue 2/3

6:10 am-1:55 pm

2 stops9h 45m

$226

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Sat 1/31

6:20 pm-6:11 am

1 stop9h 51m

San Juan Luis Munoz Marin Intl

Mon 2/2

2:05 am-9:40 am

1 stop9h 35m

$227

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Tue 2/3

8:25 am-5:05 pm

1 stop6h 40m

San Juan Luis Munoz Marin Intl

Tue 2/10

6:10 am-11:35 am

1 stop7h 25m

$227

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Sun 2/1

8:54 am-9:26 pm

1 stop10h 32m

San Juan Luis Munoz Marin Intl

Fri 2/27

2:05 am-9:36 am

1 stop9h 31m

$227

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Mon 1/26

1:50 pm-12:35 am

2 stops8h 45m

San Juan Luis Munoz Marin Intl

Fri 1/30

6:10 am-1:55 pm

2 stops9h 45m

$245

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Sun 2/15

8:10 pm-6:11 am

1 stop8h 01m

San Juan Luis Munoz Marin Intl

Tue 2/17

2:05 am-9:36 am

1 stop9h 31m

$257

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Sun 2/15

8:10 pm-6:11 am

1 stop8h 01m

San Juan Luis Munoz Marin Intl

Thu 2/19

8:10 am-2:20 pm

1 stop8h 10m

$257

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Tue 1/27

8:10 am-7:05 pm

2 stops8h 55m

San Juan Luis Munoz Marin Intl

Sat 1/31

5:30 am-12:10 pm

1 stop8h 40m

$265

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Wed 1/21

2:20 pm-9:00 pm

Nonstop4h 40m

San Juan Luis Munoz Marin Intl

Fri 1/23

2:05 am-9:40 am

1 stop9h 35m

$279

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/11

Showing 1-10 of 40 results
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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 November 7, 2025.

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, January is the cheapest month in which you can book a flight from Chicago to San Juan (average of $126). Flying from Chicago to San Juan in December is currently the most expensive (average of $188). 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 November 13, 2025.

It’s typically best to fly out from Chicago to San Juan in the afternoon. Doing so could potentially save you 39% 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 December 16, 2024.

Travelers seeking maximum savings on their Chicago to San Juan flight should consider departing on Tuesday mornings when fares are most often at their lowest. Sunday mornings 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 November 13, 2025.

The most flights from CHI to PR1 are scheduled on a Monday (8 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (6 on average).

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

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 November 13, 2025.
Read through reviews of airlines operating flights from Chicago to San Juan, such as Southwest, United Airlines, and American Airlines. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,242 reviews

Boarding

8.1

Comfort

8.0

Food

7.0

Overall

8.0

Entertainment

7.5

Crew

8.6

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Southwest
8.0
Very good
4,242 reviews
Southwest
8.0
Very good
4,242 reviews

Boarding

8.1

Comfort

8.0

Food

7.0

Overall

8.0

Entertainment

7.5

Crew

8.6

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
United Airlines
7.4
Good
9,017 reviews
Southwest
8.0
Very good
4,242 reviews

Boarding

8.1

Comfort

8.0

Food

7.0

Overall

8.0

Entertainment

7.5

Crew

8.6

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
American Airlines
7.2
Good
11,051 reviews
Southwest
8.0
Very good
4,242 reviews

Boarding

8.1

Comfort

8.0

Food

7.0

Overall

8.0

Entertainment

7.5

Crew

8.6

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Spirit Airlines
6.3
Okay
8,139 reviews
Southwest
8.0
Very good
4,242 reviews

Boarding

8.1

Comfort

8.0

Food

7.0

Overall

8.0

Entertainment

7.5

Crew

8.6

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Frontier
5.8
Fair
3,109 reviews
Southwest
8.0
Very good
4,242 reviews

Boarding

8.1

Comfort

8.0

Food

7.0

Overall

8.0

Entertainment

7.5

Crew

8.6

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines

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 40m. Fly via 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 $106. Other airlines that can offer you cheap pricing are Spirit Airlines, from $139, and Delta, from $196. Frontier is priced at 73% 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?

    $113 is the cheapest one-way deal found within the past few days, from Delta. You may also be able to find cheap deals on Southwest and United Airlines, with prices starting from $113 and $114, 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: American Airlines (94%), Alaska Airlines (89%), Spirit Airlines (72%).

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

    Looking at all options, your cheapest flight can be booked for $113. While the most popular route (Chicago O'Hare Intl - San Juan Luis Munoz Marin Intl) can be booked for $165 on average, our data indicates $680 when flying from Chicago to San Juan.

  • 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, January is the cheapest month in which you can book a flight from Chicago to San Juan (average of $126). Flying from Chicago to San Juan in December is currently the most expensive (average of $188). 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 November 13, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$106Average$288FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$139Average$318FlexibilityNo cancel feeOn-time65%
DeltaCheapest$196Average$400FlexibilityNo cancel feeOn-timeN/A
JetBlueCheapest$271Average$406FlexibilityNo cancel feeOn-time62%
United AirlinesCheapest$276Average$489FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$358Average$526FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$380Average$490FlexibilityNo cancel feeOn-time63%

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