San Juan

$96+ 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 5/1. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — SJU
Apr 8 — Apr 151
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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 April 3, 2025.

Round-trip from

$174
(Cheapflightsfares)

One-way from

$96
(CheapOair)

Popular in

December

Cheapest in

August

Average price

$312
From Illinois to San Juan
One-way flight from Illinois to San Juan
Highest demand for flights based on searches. 15% potential increase in price ($69 potential increase over avg. RT price).
Cheapest flight prices on average. 5% potential price decrease ($19 potential savings vs. average RT price).
Average for round-trip flights in April 2025

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 April 3, 2025.

This Cheapflightsfares deal was found by Cheapflights users on 4/2. 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 4/138:45 amORD - SJU
1 stop14h 01mSpirit Airlines
Fri 4/189:30 pmSJU - ORD
1 stop11h 34mSpirit Airlines
Deal found 4/2$202
This American Airlines deal was found by Cheapflights users on 4/1. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/36:36 pmSPI - SJU
2 stops20h 44mAmerican Airlines
Tue 9/93:55 pmSJU - SPI
2 stops21h 49mAmerican Airlines
Deal found 4/1$215
This CheapOair deal was found by Cheapflights users on 4/2. 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.
Sat 4/1211:45 amORD - SJU
1 stop11h 01mMultiple Airlines
Thu 4/175:30 amSJU - ORD
1 stop10h 36mMultiple Airlines
Deal found 4/2$241
This Delta deal was found by Cheapflights users on 4/2. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/34:15 pmSTL - SJU
1 stop6h 00mDelta
Sat 5/104:15 pmSJU - STL
1 stop8h 11mDelta
Deal found 4/2$261
This American Airlines deal was found by Cheapflights users on 4/2. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/104:30 pmMLI - SJU
2 stops19h 15mAmerican Airlines
Thu 9/113:58 pmSJU - MLI
2 stops19h 55mAmerican Airlines
Deal found 4/2$285
This Cheapflightsfares deal was found by Cheapflights users on 4/2. 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.
Wed 4/93:00 pmMDW - SJU
1 stop6h 53mFrontier
Thu 4/105:30 amSJU - MDW
1 stop7h 13mFrontier
Deal found 4/2$286
This American Airlines deal was found by Cheapflights users on 4/3. 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.
Sat 5/35:27 pmSTL - SJU
1 stop10h 33mAmerican Airlines
Sat 5/175:25 amSJU - STL
1 stop8h 02mAmerican Airlines
Deal found 4/3$286
This Frontier deal was found by Cheapflights users on 4/2. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/92:00 pmORD - SJU
1 stop7h 53mFrontier
Thu 4/105:30 amSJU - ORD
1 stop10h 36mFrontier
Deal found 4/2$291
This Frontier deal was found by Cheapflights users on 4/1. 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.
Tue 4/154:57 pmSTL - SJU
1 stop7h 53mFrontier
Fri 4/182:20 pmSJU - STL
1 stop10h 26mFrontier
Deal found 4/1$296
This United Airlines deal was found by Cheapflights users on 4/2. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/39:40 amSTL - SJU
2 stops13h 17mUnited Airlines
Fri 5/91:05 amSJU - STL
2 stops15h 42mUnited Airlines
Deal found 4/2$299
This CheapOair deal was found by Cheapflights users on 4/2. 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.
Fri 5/25:55 pmSTL - SJU
1 stop7h 56mMultiple Airlines
Tue 5/69:25 amSJU - STL
1 stop8h 50mMultiple Airlines
Deal found 4/2$305
This JetBlue deal was found by Cheapflights users on 4/2. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/68:45 amORD - SJU
1 stop8h 20mJetBlue
Fri 5/91:58 pmSJU - ORD
1 stop8h 56mJetBlue
Deal found 4/2$324

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 April 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

Sun 4/13

8:45 am-11:46 pm

1 stop14h 01m

San Juan Luis Munoz Marin Intl

Fri 4/18

9:30 pm-8:04 am

1 stop11h 34m

$202

PeoriaSan Juan

PIA - SJU

PIASJU

Greater Peoria

Sun 9/28

4:36 pm-12:45 pm

2 stops19h 09m

San Juan Luis Munoz Marin Intl

Mon 10/6

5:27 pm-10:48 am

2 stops18h 21m

$215

SpringfieldSan Juan

SPI - SJU

SPISJU

Springfield Capital

Wed 9/3

6:36 pm-4:20 pm

2 stops20h 44m

San Juan Luis Munoz Marin Intl

Tue 9/9

3:55 pm-12:44 pm

2 stops21h 49m

$215

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Sat 4/12

11:45 am-11:46 pm

1 stop11h 01m

San Juan Luis Munoz Marin Intl

Tue 4/15

9:28 am-7:04 pm

1 stop10h 36m

$251

St. LouisSan Juan

STL - SJU

STLSJU

Lambert-St Louis

Sat 5/3

4:15 pm-11:15 pm

1 stop6h 00m

San Juan Luis Munoz Marin Intl

Wed 5/7

1:55 pm-8:49 pm

1 stop7h 54m

$261

MolineSan Juan

MLI - SJU

MLISJU

Moline Quad-City

Wed 9/10

4:30 pm-12:45 pm

2 stops19h 15m

San Juan Luis Munoz Marin Intl

Thu 9/11

3:58 pm-10:53 am

2 stops19h 55m

$285

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Wed 4/9

3:00 pm-10:53 pm

1 stop6h 53m

San Juan Luis Munoz Marin Intl

Thu 4/10

5:30 am-11:43 am

1 stop7h 13m

$286

St. LouisSan Juan

STL - SJU

STLSJU

Lambert-St Louis

Sat 5/3

5:27 pm-5:00 am

1 stop10h 33m

San Juan Luis Munoz Marin Intl

Sat 5/17

5:25 am-12:27 pm

1 stop8h 02m

$286

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Wed 4/9

2:00 pm-10:53 pm

1 stop7h 53m

San Juan Luis Munoz Marin Intl

Thu 4/10

5:30 am-3:06 pm

1 stop10h 36m

$291

St. LouisSan Juan

STL - SJU

STLSJU

Lambert-St Louis

Tue 4/15

4:57 pm-1:50 am

1 stop7h 53m

San Juan Luis Munoz Marin Intl

Fri 4/18

2:20 pm-11:46 pm

1 stop10h 26m

$296

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/1

Showing 1-10 of 45 results
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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, September is the cheapest month in which you can book a flight from Illinois to San Juan (average of $254). Flying from Illinois to San Juan in December is currently the most expensive (average of $336). 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 April 3, 2025.

Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Illinois to San Juan as you normally would.

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 April 3, 2025.

The most flights from USIL to PR1 are scheduled on a Monday (10 on average). You will have fewer flight options on Friday, which is when the least amount of flights are scheduled (8 on average).

Rainfall in San Juan by month

Plan your trip to San Juan by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in San Juan ranges from 2.2 - 6.1 inches per month. November is typically the wettest month, when rainfall can reach 6.1 in. February is typically the driest time to visit San Juan when rainfall is around 2.2 in.

Temperature in San Juan by month

Plan your trip to San Juan by taking into account the average temperature totals by month.

If weather is an important factor for your trip to San Juan, use this chart to help with planning. For those seeking warmer temperatures, June is the ideal time of year to visit, when temperatures reach an average of 82.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 77.0 F).

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 April 3, 2025.
See what other customers who have flown with Southwest, Delta and United Airlines from Illinois to San Juan have to say. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.

Overall

8.0

Entertainment

7.6

Boarding

8.2

Crew

8.6

Food

7.1

Comfort

8.0

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.

Overall

8.0

Entertainment

7.6

Boarding

8.2

Crew

8.6

Food

7.1

Comfort

8.0

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
8.0
Very good

Overall

8.0

Entertainment

7.6

Boarding

8.2

Crew

8.6

Food

7.1

Comfort

8.0

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.

Overall

8.0

Entertainment

7.6

Boarding

8.2

Crew

8.6

Food

7.1

Comfort

8.0

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.

Overall

8.0

Entertainment

7.6

Boarding

8.2

Crew

8.6

Food

7.1

Comfort

8.0

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.

Overall

8.0

Entertainment

7.6

Boarding

8.2

Crew

8.6

Food

7.1

Comfort

8.0

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.

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

    $96 is the cheapest one-way deal found within the past few days, from Spirit Airlines. You may also be able to find cheap deals on Southwest and American Airlines, with prices starting from $100 and $105, respectively.

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

  • 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 United Airlines (88%), Air Canada (82%) or Air New Zealand (82%) 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 $69. On average you can expect to pay $823. The most popular route, (Chicago O'Hare Intl - San Juan Luis Munoz Marin Intl), can usually be booked for $172.

  • 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, September is the cheapest month in which you can book a flight from Illinois to San Juan (average of $254). Flying from Illinois to San Juan in December is currently the most expensive (average of $336). 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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Alternative routes for Illinois to San Juan

See prices for flight routes from nearby airports that may be better suited for you.

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 April 3, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$124Average$265FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$144Average$273FlexibilityNo cancel feeOn-time65%
American AirlinesCheapest$194Average$549FlexibilityNo cancel feeOn-time71%
DeltaCheapest$235Average$435FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$271Average$525FlexibilityNo cancel feeOn-time69%
JetBlueCheapest$293Average$399FlexibilityNo cancel feeOn-time62%
SouthwestCheapest$342Average$479FlexibilityNo cancel feeOn-time63%

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