HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
San Juan

$69+ Cheap flights from Illinois 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 1/11. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — SJU
Dec 3 — Dec 101
Wed 12/3
Wed 12/10
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Illinois to San Juan with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

Find flight deals from Illinois to San Juan

Cheapest flights from Illinois to San Juan
Explore the most affordable flight options available from Illinois to San Juan. Find the lowest fares from popular airlines and budget airlines, with prices last updated on November 3, 2025.

This Frontier deal was found by Cheapflights users on 11/1. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/162:12 pmSTL - SJU
1 stop10h 42mFrontier
Thu 11/206:01 amSJU - STL
1 stop10h 28mFrontier
Deal found 11/1$168
This Kiwi.com deal was found by Cheapflights users on 11/1. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/2010:12 amORD - SJU
1 stop8h 15mSpirit Airlines
Tue 11/254:12 pmSJU - ORD
Nonstop5h 11mSpirit Airlines
Deal found 11/1$210
This Priceline deal was found by Cheapflights users on 11/2. 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.
Wed 12/1012:09 pmORD - SJU
1 stop10h 07mMultiple Airlines
Sun 12/141:59 amSJU - ORD
1 stop14h 04mMultiple Airlines
Deal found 11/2$211
This Frontier deal was found by Cheapflights users on 10/31. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/176:15 amMDW - SJU
1 stop7h 04mFrontier
Mon 11/247:11 amSJU - MDW
2 stops17h 32mFrontier
Deal found 10/31$212
This Kiwi.com deal was found by Cheapflights users on 11/2. 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 12/14:58 pmORD - SJU
1 stop15h 51mMultiple Airlines
Fri 12/53:06 pmSJU - ORD
1 stop7h 36mMultiple Airlines
Deal found 11/2$213
This Priceline deal was found by Cheapflights users on 11/2. 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 12/52:00 pmORD - SJU
1 stop8h 49mFrontier
Sun 12/71:59 amSJU - ORD
1 stop14h 04mFrontier
Deal found 11/2$216
This Booking.com deal was found by Cheapflights users on 10/31. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/146:15 amMDW - SJU
1 stop7h 04mFrontier
Wed 11/196:17 pmSJU - MDW
1 stop19h 25mFrontier
Deal found 10/31$217
This CheapOair deal was found by Cheapflights users on 11/2. 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.
Tue 12/28:41 amORD - SJU
Nonstop4h 36mSpirit Airlines
Mon 12/88:45 pmSJU - ORD
Nonstop5h 14mSpirit Airlines
Deal found 11/2$218
This Cheapflightsfares deal was found by Cheapflights users on 11/2. 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 12/28:41 amORD - SJU
Nonstop4h 36mSpirit Airlines
Tue 12/96:00 amSJU - ORD
1 stop16h 09mSpirit Airlines
Deal found 11/2$219
This Kiwi.com deal was found by Cheapflights users on 11/2. 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 12/42:16 pmMDW - SJU
1 stop18h 16mMultiple Airlines
Tue 12/95:00 pmSJU - MDW
2 stops17h 46mMultiple Airlines
Deal found 11/2$220
This Kiwi.com deal was found by Cheapflights users on 11/1. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/186:40 amORD - SJU
1 stop9h 14mFrontier
Mon 11/247:11 amSJU - ORD
1 stop12h 48mFrontier
Deal found 11/1$221
This Cheapflightsfares deal was found by Cheapflights users on 11/2. 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.
Sun 11/165:10 amORD - SJU
1 stop10h 09mSpirit Airlines
Sat 11/224:12 pmSJU - ORD
Nonstop5h 11mSpirit Airlines
Deal found 11/2$222

Cheap flight deals from Illinois to San Juan

Keep the following information in mind while searching for Illinois to San Juan flight deals. Data was last updated November 3, 2025.

Round-trip from

$153
(CheapOair)

One-way from

$69
(CheapOair)

Popular in

December

Cheapest in

April

Average price

$381
From Illinois to San Juan
Search Deals
One-way flight from Illinois to San Juan
Search Deals
Highest demand for flights based on searches. 7% potential increase in price ($33 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($15 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in November 2025
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Illinois 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 3, 2025.
Use the filters below to find and compare flights from Illinois to San Juan that are best for you.

Fly from

Illinois

Fly to

San Juan

Route

Depart

Return

Price

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Mon 2/23

8:55 am-3:40 pm

Nonstop4h 45m

San Juan Luis Munoz Marin Intl

Wed 2/25

2:05 am-9:36 am

1 stop9h 31m

$223

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Sun 1/25

11:18 am-8:57 pm

1 stop7h 39m

San Juan Luis Munoz Marin Intl

Wed 2/11

7:00 am-5:45 pm

1 stop12h 45m

$227

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Mon 1/26

3:15 pm-12:35 am

1 stop7h 20m

San Juan Luis Munoz Marin Intl

Thu 1/29

6:10 am-1:55 pm

2 stops9h 45m

$227

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Sun 1/25

5:40 am-4:36 pm

1 stop8h 56m

San Juan Luis Munoz Marin Intl

Wed 1/28

5:50 pm-11:39 pm

1 stop7h 49m

$227

ChampaignSan Juan

CMI - SJU

CMISJU

Champaign University-Willard

Wed 1/21

6:00 am-9:39 pm

1 stop13h 39m

San Juan Luis Munoz Marin Intl

Wed 1/28

6:00 am-8:27 pm

2 stops16h 27m

$235

BloomingtonSan Juan

BMI - SJU

BMISJU

Bloomington-Normal

Mon 1/26

8:50 am-9:39 pm

1 stop10h 49m

San Juan Luis Munoz Marin Intl

Sat 1/31

6:00 am-10:16 pm

2 stops18h 16m

$235

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Sun 1/18

1:50 pm-12:35 am

2 stops8h 45m

San Juan Luis Munoz Marin Intl

Thu 1/22

6:10 am-1:55 pm

2 stops9h 45m

$267

St. LouisSan Juan

STL - SJU

STLSJU

Lambert-St Louis

Tue 1/20

1:15 pm-12:36 am

2 stops9h 21m

San Juan Luis Munoz Marin Intl

Tue 1/27

7:45 am-5:43 pm

2 stops11h 58m

$271

MolineSan Juan

MLI - SJU

MLISJU

Moline Quad-City

Mon 4/27

6:41 pm-4:05 pm

2 stops20h 24m

San Juan Luis Munoz Marin Intl

Fri 5/1

3:45 pm-2:17 pm

2 stops23h 32m

$295

PeoriaSan Juan

PIA - SJU

PIASJU

Greater Peoria

Mon 4/27

6:41 pm-2:35 pm

2 stops18h 54m

San Juan Luis Munoz Marin Intl

Fri 5/1

6:25 am-11:45 pm

2 stops18h 20m

$295

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/2

Showing 1-10 of 60 results
1
2
3
...
6

Best time to book a flight from Illinois to San Juan

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

What is the cheapest month to book a flight from Illinois to San Juan?

Currently, February is the cheapest month in which you can book a flight from Illinois to San Juan (average of $127). Flying from Illinois 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 IL to SJU?

Find hourly flight availability from Illinois 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 3, 2025.

When flying from Illinois to San Juan, the time of day you fly usually plays a role in the price. Save by searching for a flight in the evening, which can drop the price by up to 40% versus a flight in the morning.

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

Use this chart to determine the cheapest time to fly round-trip from Illinois to San Juan. Price data was last updated on December 16, 2024.

Travelers seeking maximum savings on their Illinois 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 Illinois to San Juan

Explore weekly flight availability from Illinois 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 3, 2025.

The most flights from USIL 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 Illinois to San Juan?

Related info for your journey

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

    Airlines like United Airlines, Delta, and Southwest fly from Illinois to San Juan in about 4h 45m. The time it takes to get you to your destination can typically vary by up to 2h 54m. The distance from Illinois to San Juan is about 2073 mi. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.

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

    $84 is the cheapest one-way deal found within the past few days, from Frontier. You may also be able to find cheap deals on Delta and United Airlines, with prices starting from $113 and $113, respectively.

  • What are the most popular routes from Illinois to San Juan?

    When deciding which route to take from Illinois to San Juan consider Chicago O'Hare Intl - San Juan Luis Munoz Marin Intl, Chicago Midway - San Juan Luis Munoz Marin Intl or Lambert-St Louis - San Juan Luis Munoz Marin Intl as they are the most popular.

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

    No one likes to see their flight delayed. When booking a flight from Illinois to San Juan consider choosing American Airlines (94%), Alaska Airlines (89%) or Spirit Airlines (72%) as they are the most reliable in getting you off to your destination on time.

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

    The cheapest flight price from Illinois to San Juan is $124. On average you can expect to pay $813. The most popular route, (Chicago O'Hare Intl - San Juan Luis Munoz Marin Intl), can usually be booked for $176.

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

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

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

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

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

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

    Currently, February is the cheapest month in which you can book a flight from Illinois to San Juan (average of $127). Flying from Illinois 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

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for Illinois to San Juan

See prices for flight routes from nearby airports that may be better suited for you.
John F Kennedy Intl to Luis Munoz Marin Intl flights
Newark to Luis Munoz Marin Intl flights
Dulles Intl to Luis Munoz Marin Intl flights
Orlando to Luis Munoz Marin Intl flights
O'Hare Intl to Luis Munoz Marin Intl flights
Baltimore to Luis Munoz Marin Intl flights
LaGuardia to Luis Munoz Marin Intl flights
Boston to Luis Munoz Marin Intl flights
Reagan-National to Luis Munoz Marin Intl flights
Philadelphia to Luis Munoz Marin Intl flights
Atlanta to Luis Munoz Marin Intl flights
Hartford to Luis Munoz Marin Intl flights
Dallas/Fort Worth to Luis Munoz Marin Intl flights
Tampa to Luis Munoz Marin Intl flights
Minneapolis to Luis Munoz Marin Intl flights
Hobby to Luis Munoz Marin Intl flights
Detroit to Luis Munoz Marin Intl flights
Raleigh to Luis Munoz Marin Intl flights
George Bush Intcntl to Luis Munoz Marin Intl flights
Fort Lauderdale to Luis Munoz Marin Intl flights
Midway to Luis Munoz Marin Intl flights
Denver to Luis Munoz Marin Intl flights
John F Kennedy Intl to Aguadilla flights
Miami to Luis Munoz Marin Intl flights
Los Angeles to Luis Munoz Marin Intl flights
Cleveland to Luis Munoz Marin Intl flights
Providence to Luis Munoz Marin Intl flights
Seattle to Luis Munoz Marin Intl flights
Charlotte to Luis Munoz Marin Intl flights
San Francisco to Luis Munoz Marin Intl flights
Orlando to Aguadilla flights
Orlando to Ponce flights
Cincinnati to Luis Munoz Marin Intl flights
Austin to Luis Munoz Marin Intl flights
White Plains to Luis Munoz Marin Intl flights
Trenton to Luis Munoz Marin Intl flights
Milwaukee to Luis Munoz Marin Intl flights
Indianapolis to Luis Munoz Marin Intl flights
John F Kennedy Intl to Ponce flights
Love Field to Luis Munoz Marin Intl flights
Sky Harbor Intl to Luis Munoz Marin Intl flights
Norfolk to Luis Munoz Marin Intl flights
Jacksonville to Luis Munoz Marin Intl flights
Columbus to Luis Munoz Marin Intl flights
Pittsburgh to Luis Munoz Marin Intl flights
Islip to Luis Munoz Marin Intl flights
New Orleans to Luis Munoz Marin Intl flights
San Antonio to Luis Munoz Marin Intl flights
St. Louis to Luis Munoz Marin Intl flights
Atlantic City to Luis Munoz Marin Intl flights

Top 7 airlines flying from Illinois to San Juan

Discover the top 7 airlines that operate flights from Illinois 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 3, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$106Average$285FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$140Average$317FlexibilityNo cancel feeOn-time65%
DeltaCheapest$196Average$406FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$225Average$577FlexibilityNo cancel feeOn-time71%
JetBlueCheapest$271Average$406FlexibilityNo cancel feeOn-time62%
United AirlinesCheapest$273Average$509FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$380Average$490FlexibilityNo cancel feeOn-time63%

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.