Cheap flights from Chicago (CHI) to San Juan

CHI — SJU
Feb 7 — Feb 141

How to find the cheapest flight from Chicago (CHI) to San Juan

All the information you need to plan the best CHI to PR1 flight in 2023: compare Chicago to San Juan flight prices with the expected peak season, weather and rainfall in San Juan.

CHI - SJU

Price

$275 - $578

SJU

Temperature

77 - 82.4 °F

SJU

Rainfall

2.2 - 6.1 inches

Popular inDecemberHigh demand for flights, 30% potential price rise
Cheapest inFebruaryBest time to find cheap flights, 32% potential price drop
Round-trip from$275From Chicago (CHI) to San Juan
One-way from$94One-way flight from Chicago (CHI) to San Juan

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

Travelers have found it’s best to book a flight 38 days in advance to save up to 16% compared to booking the same week of travel. As your travel date approaches, the cost of this flight route may potentially increase. While opting to book 38 days out may not be an option for all, there are still additional ways to secure a deal in the near future. You might find a flight from Chicago to San Juan 1-2 weeks in advance for as low as $402, or $467 for flights within the next 24 hours.

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

The best pricing can be found in the month of February. Prices to San Juan from Chicago average $403. You can even find prices in February for less than $403, as users have found deals to San Juan from as low as $168. The month of December appears to be one of the more expensive times to travel to San Juan from Chicago. Flying in the targeted month can save you up to 43%.

When is the cheapest time to fly from Chicago to San Juan (CHI - SJU)?

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

Cheap flights from Chicago to San Juan in February, March 2023

The best prices found for CHI to San Juan flights for February, March
Mar 1 - Mar 8
ORD

Chicago O'Hare Intl

SJU

San Juan Luis Munoz Marin Intl

1 stop

17h 31m
SJU

San Juan Luis Munoz Marin Intl

ORD

Chicago O'Hare Intl

1 stop

20h 04m
$148

Multiple Airlines

Pick Dates

Deal found 1/30

Feb 7 - Feb 14
MDW

Chicago Midway

SJU

San Juan Luis Munoz Marin Intl

1 stop

8h 57m
SJU

San Juan Luis Munoz Marin Intl

MDW

Chicago Midway

1 stop

26h 51m
$150

Frontier

Pick Dates

Deal found 1/30

Feb 6 - Mar 8
ORD

Chicago O'Hare Intl

SJU

San Juan Luis Munoz Marin Intl

1 stop

12h 42m
SJU

San Juan Luis Munoz Marin Intl

ORD

Chicago O'Hare Intl

1 stop

15h 05m
$151

Frontier

Pick Dates

Deal found 1/30

Chicago to San Juan 2023 flight deals

Cheap flights to San Juan from Chicago found for this year
Mar 1 - Mar 8
ORD

Chicago O'Hare Intl

SJU

San Juan Luis Munoz Marin Intl

1 stop

17h 31m
SJU

San Juan Luis Munoz Marin Intl

ORD

Chicago O'Hare Intl

1 stop

20h 04m
$148

Multiple Airlines

Pick Dates

Deal found 1/30

Feb 7 - Feb 14
MDW

Chicago Midway

SJU

San Juan Luis Munoz Marin Intl

1 stop

8h 57m
SJU

San Juan Luis Munoz Marin Intl

MDW

Chicago Midway

1 stop

26h 51m
$150

Frontier

Pick Dates

Deal found 1/30

Feb 6 - Mar 8
ORD

Chicago O'Hare Intl

SJU

San Juan Luis Munoz Marin Intl

1 stop

12h 42m
SJU

San Juan Luis Munoz Marin Intl

ORD

Chicago O'Hare Intl

1 stop

15h 05m
$151

Frontier

Pick Dates

Deal found 1/30

Cheap Frontier flights from Chicago to San Juan

Feb 7 - Feb 14
MDW

Chicago Midway

SJU

San Juan Luis Munoz Marin Intl

1 stop

8h 57m
SJU

San Juan Luis Munoz Marin Intl

MDW

Chicago Midway

1 stop

26h 51m
$150

Frontier

Pick Dates

Deal found 1/30

Feb 7 - Feb 14
MDW

Chicago Midway

SJU

San Juan Luis Munoz Marin Intl

1 stop

18h 51m
SJU

San Juan Luis Munoz Marin Intl

MDW

Chicago Midway

1 stop

26h 51m
$154

Frontier

Pick Dates

Deal found 1/30

Feb 7 - Mar 8
ORD

Chicago O'Hare Intl

SJU

San Juan Luis Munoz Marin Intl

1 stop

15h 50m
SJU

San Juan Luis Munoz Marin Intl

ORD

Chicago O'Hare Intl

1 stop

15h 05m
$156

Frontier

Pick Dates

Deal found 1/30

Cheap Spirit Airlines flights from Chicago to San Juan

Mar 6 - Mar 8
ORD

Chicago O'Hare Intl

SJU

San Juan Luis Munoz Marin Intl

1 stop

13h 49m
SJU

San Juan Luis Munoz Marin Intl

ORD

Chicago O'Hare Intl

1 stop

12h 18m
$168

Spirit Airlines

Pick Dates

Deal found 1/31

Feb 14 - Feb 21
ORD

Chicago O'Hare Intl

SJU

San Juan Luis Munoz Marin Intl

1 stop

14h 53m
SJU

San Juan Luis Munoz Marin Intl

ORD

Chicago O'Hare Intl

2 stops

16h 43m
$169

Spirit Airlines

Pick Dates

Deal found 1/30

Feb 7 - Feb 14
ORD

Chicago O'Hare Intl

SJU

San Juan Luis Munoz Marin Intl

1 stop

14h 01m
SJU

San Juan Luis Munoz Marin Intl

ORD

Chicago O'Hare Intl

2 stops

22h 20m
$176

Spirit Airlines

Pick Dates

Deal found 1/30

Non-stop flights to San Juan from Chicago

Save time with Chicago to San Juan direct flight deals
Apr 22 - Apr 26
ORD

Chicago O'Hare Intl

SJU

San Juan Luis Munoz Marin Intl

Nonstop

4h 46m
SJU

San Juan Luis Munoz Marin Intl

ORD

Chicago O'Hare Intl

Nonstop

5h 15m
$333

Multiple Airlines

Pick Dates

Deal found 2/1

Apr 17 - Apr 26
ORD

Chicago O'Hare Intl

SJU

San Juan Luis Munoz Marin Intl

Nonstop

4h 31m
SJU

San Juan Luis Munoz Marin Intl

ORD

Chicago O'Hare Intl

Nonstop

5h 15m
$363

American Airlines

Pick Dates

Deal found 1/30

Apr 29 - May 10
ORD

Chicago O'Hare Intl

SJU

San Juan Luis Munoz Marin Intl

Nonstop

4h 46m
SJU

San Juan Luis Munoz Marin Intl

ORD

Chicago O'Hare Intl

Nonstop

5h 10m
$378

United Airlines

Pick Dates

Deal found 2/1

Last minute flights from Chicago to San Juan

Late deals on return flights to San Juan from Chicago, departing today and this week
Feb 7 - Feb 14
MDW

Chicago Midway

SJU

San Juan Luis Munoz Marin Intl

1 stop

8h 57m
SJU

San Juan Luis Munoz Marin Intl

MDW

Chicago Midway

1 stop

26h 51m
$150

Frontier

Pick Dates

Deal found 1/30

Feb 7 - Feb 14
MDW

Chicago Midway

SJU

San Juan Luis Munoz Marin Intl

1 stop

18h 51m
SJU

San Juan Luis Munoz Marin Intl

MDW

Chicago Midway

1 stop

26h 51m
$154

Frontier

Pick Dates

Deal found 1/30

Feb 7 - Mar 8
ORD

Chicago O'Hare Intl

SJU

San Juan Luis Munoz Marin Intl

1 stop

15h 50m
SJU

San Juan Luis Munoz Marin Intl

ORD

Chicago O'Hare Intl

1 stop

15h 05m
$156

Frontier

Pick Dates

Deal found 1/30

One-way flights to San Juan from Chicago

The cheapest one-way flights from Chicago to San Juan
Feb 8
MDW

Chicago Midway

SJU

San Juan Luis Munoz Marin Intl

1 stop

13h 10m
$72

Frontier

Pick Dates

Deal found 1/30

Feb 28
MDW

Chicago Midway

SJU

San Juan Luis Munoz Marin Intl

1 stop

17h 42m
$74

Frontier

Pick Dates

Deal found 1/31

Feb 8
MDW

Chicago Midway

SJU

San Juan Luis Munoz Marin Intl

1 stop

12h 41m
$76

Frontier

Pick Dates

Deal found 1/31

Reviews of Airlines Servicing San Juan

Spirit Airlines
6.9
Okay
716 reviews

Crew

7.4

Food

5.6

Boarding

7.2

Entertainment

5.6

Overall

6.9

Comfort

6.4

Reviews

1 / 10

Seats are small, hard and don’t recline. Some arm rests are stationary. Flight took longer on Spirit than other airlines. Baggage claim was ridiculous slow. Took over an hour to get bags in Dallas and Las Vegas. Not worth the small savings! I’ll fly SWA or some other airline.

Spirit Airlines
6.9
Okay
716 reviews
Spirit Airlines
6.9
Okay
716 reviews

Crew

7.4

Food

5.6

Boarding

7.2

Entertainment

5.6

Overall

6.9

Comfort

6.4

Reviews

1 / 10

Seats are small, hard and don’t recline. Some arm rests are stationary. Flight took longer on Spirit than other airlines. Baggage claim was ridiculous slow. Took over an hour to get bags in Dallas and Las Vegas. Not worth the small savings! I’ll fly SWA or some other airline.

Frontier
6.1
Okay
537 reviews
Spirit Airlines
6.9
Okay
716 reviews

Crew

7.4

Food

5.6

Boarding

7.2

Entertainment

5.6

Overall

6.9

Comfort

6.4

Reviews

1 / 10

Seats are small, hard and don’t recline. Some arm rests are stationary. Flight took longer on Spirit than other airlines. Baggage claim was ridiculous slow. Took over an hour to get bags in Dallas and Las Vegas. Not worth the small savings! I’ll fly SWA or some other airline.

Related info for your journey

Useful info, stats and facts about Chicago to San Juan flights.

Which airlines flying from Chicago to San Juan have flexible cancellations due to COVID-19?

Some of the carriers operating flights from Chicago to San Juan that may be offering flexible cancellation policies are American Airlines, United Airlines, and Frontier. Our site will let you filter for all airlines offering greater flexibility due to COVID-19.

Can I find flights from Chicago to San Juan for under $200 on Cheapflights?

Yes, there are multiple flights from Chicago to San Juan for under $200. The cheapest flight booked recently is on Multiple Airlines for just $148, but on average you can expect to pay $161.

Are there nonstop flights from Chicago to San Juan for under $400 on Cheapflights?

Cheapflights has at least 20 direct flights from Chicago to San Juan under $400. A good price for a nonstop flight from Chicago to San Juan is less than $428.

Are there last-minute flights available from Chicago to San Juan for under $200?

There are currently 20+ open flights from Chicago to San Juan within the next 7 days for less than $200.

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 $156. Another airline that can offer you cheap pricing is Spirit Airlines. Frontier is priced at 61% lower than the current average price of a flight leaving 3 months from now.

What are the most popular airlines that fly from Chicago to San Juan?

Consider American Airlines, Alaska Airlines or JetBlue when booking your flight. These represent the most popular airlines when flying from Chicago to San Juan.

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: Air Canada (85%), Air New Zealand (85%), American Airlines (77%).

What are the cheapest flights from Chicago to San Juan?

Looking at all options, your cheapest flight can be booked for $185. While the most popular route (Chicago O'Hare Intl - San Juan Luis Munoz Marin Intl) can be booked for $161 on average our data indicates $1,038 when flying from Chicago to San Juan.

Top 8 airlines flying from Chicago to San Juan

The chart below displays the airlines Cheapflights users traveling from Chicago to San Juan choose most often. Cheapest and average prices are based on aggregated data from the past 12 months.
AirlineCheapestAverageFlexibilityOn-timeCOVID-19 safety
Juneyao AirlinesCheapest$11Average$21FlexibilityNo cancel feeOn-time66%COVID-19 safety
Search Juneyao Airlines flights
JetBlueCheapest$134Average$431FlexibilityNo cancel feeOn-time62%COVID-19 safety
Search JetBlue flights
Spirit AirlinesCheapest$159Average$351FlexibilityNo cancel feeOn-time65%COVID-19 safety
Search Spirit Airlines flights
FrontierCheapest$160Average$303FlexibilityNo cancel feeOn-time62%COVID-19 safety
Search Frontier flights
DeltaCheapest$166Average$597FlexibilityNo cancel feeOn-timeN/ACOVID-19 safety
Search Delta flights
United AirlinesCheapest$227Average$668FlexibilityNo cancel feeOn-time69%COVID-19 safety
Search United Airlines flights
American AirlinesCheapest$234Average$509FlexibilityNo cancel feeOn-time71%COVID-19 safety
Search American Airlines flights
Alaska AirlinesCheapest$396Average$572FlexibilityNo cancel feeOn-time75%COVID-19 safety
Search Alaska Airlines flights

Hourly flight availability from Chicago to San Juan

See what time of day planes typically take off from Chicago to San Juan
1%of flight departuresEarly morningMidnight to 6 am
44%of flight departuresMorning6 am to noon
55%of flight departuresAfternoonNoon to 6 pm
0%of flight departuresEvening6 pm to midnight
Midnight
6 AM
Noon
6 PM

Weekly flight availability from Chicago to San Juan

See how many times per day planes take to the skies headed from Chicago to San Juan
Sunday7daily flights
Monday9daily flights
Tuesday9daily flights
Wednesday9daily flights
Thursday9daily flights
Friday9daily flights
Saturday7daily flights
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