Cheap flights from Chicago (CHI) to Puerto Rico

CHI — SJU
May 25 — Jun 11

How far in advance should I book a flight from Chicago to Puerto Rico?

Find a great deal and save up to 13% by booking at least 18 days prior to your desired departure date, rather than waiting until the week of travel. According to our data, there are a number of flights available from Chicago to Puerto Rico within the next two weeks, with the cheapest ticket starting at $256.

What is the cheapest month to fly from Chicago to Puerto Rico?

August is one of the best times of the year to fly to Puerto Rico from Chicago. Prices for August average $307 per person but you can even find prices for as low as $118. The most expensive prices can be found in the month of December. Opting for a August flight can save you 81% on your journey compared to booking in December

When is the cheapest time to fly from Chicago to Puerto Rico (CHI - PR)?

When flying from Chicago to Puerto Rico, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

Cheap flights from Chicago to Puerto Rico in May, June 2022

The best prices found for CHI to Puerto Rico flights for May, June
May 21 - May 26
ORD

Chicago O'Hare Intl

SJU

San Juan Luis Munoz Marin Intl

Nonstop

4h 47m
SJU

San Juan Luis Munoz Marin Intl

ORD

Chicago O'Hare Intl

Nonstop

5h 12m
$258

Frontier

View Deal

Deal found 18/5/22

May 21 - May 26
ORD

Chicago O'Hare Intl

SJU

San Juan Luis Munoz Marin Intl

1 stop

7h 59m
SJU

San Juan Luis Munoz Marin Intl

ORD

Chicago O'Hare Intl

Nonstop

5h 12m
$267

Frontier

View Deal

Deal found 18/5/22

May 23 - May 26
ORD

Chicago O'Hare Intl

SJU

San Juan Luis Munoz Marin Intl

Nonstop

4h 47m
SJU

San Juan Luis Munoz Marin Intl

ORD

Chicago O'Hare Intl

Nonstop

5h 12m
$270

Frontier

View Deal

Deal found 18/5/22

Chicago to Puerto Rico 2022 flight deals

Cheap flights to Puerto Rico from Chicago found for this year
Oct 24 - Oct 27
MDW

Chicago Midway

SJU

San Juan Luis Munoz Marin Intl

1 stop

8h 22m
SJU

San Juan Luis Munoz Marin Intl

MDW

Chicago Midway

1 stop

10h 15m
$219

Delta

View Deal

Deal found 18/5/22

Sep 13 - Sep 20
ORD

Chicago O'Hare Intl

SJU

San Juan Luis Munoz Marin Intl

1 stop

8h 56m
SJU

San Juan Luis Munoz Marin Intl

ORD

Chicago O'Hare Intl

1 stop

10h 39m
$219

Delta

View Deal

Deal found 17/5/22

Oct 22 - Oct 26
ORD

Chicago O'Hare Intl

SJU

San Juan Luis Munoz Marin Intl

1 stop

9h 35m
SJU

San Juan Luis Munoz Marin Intl

ORD

Chicago O'Hare Intl

1 stop

11h 07m
$229

Delta

View Deal

Deal found 17/5/22

Cheap Delta flights from Chicago to Puerto Rico

Oct 24 - Oct 27
MDW

Chicago Midway

SJU

San Juan Luis Munoz Marin Intl

1 stop

8h 22m
SJU

San Juan Luis Munoz Marin Intl

MDW

Chicago Midway

1 stop

10h 15m
$219

Delta

View Deal

Deal found 18/5/22

Oct 22 - Oct 26
ORD

Chicago O'Hare Intl

SJU

San Juan Luis Munoz Marin Intl

1 stop

9h 35m
SJU

San Juan Luis Munoz Marin Intl

ORD

Chicago O'Hare Intl

1 stop

11h 07m
$229

Delta

View Deal

Deal found 17/5/22

Oct 1 - Oct 8
ORD

Chicago O'Hare Intl

SJU

San Juan Luis Munoz Marin Intl

1 stop

9h 35m
SJU

San Juan Luis Munoz Marin Intl

ORD

Chicago O'Hare Intl

1 stop

7h 48m
$239

Delta

View Deal

Deal found 18/5/22

Cheap Spirit Airlines flights from Chicago to Puerto Rico

Sep 10 - Sep 13
ORD

Chicago O'Hare Intl

SJU

San Juan Luis Munoz Marin Intl

1 stop

17h 13m
SJU

San Juan Luis Munoz Marin Intl

ORD

Chicago O'Hare Intl

1 stop

20h 40m
$245

Spirit Airlines

View Deal

Deal found 19/5/22

Sep 13 - Sep 20
ORD

Chicago O'Hare Intl

SJU

San Juan Luis Munoz Marin Intl

1 stop

25h 10m
SJU

San Juan Luis Munoz Marin Intl

ORD

Chicago O'Hare Intl

1 stop

20h 40m
$246

Spirit Airlines

View Deal

Deal found 18/5/22

Oct 12 - Oct 15
ORD

Chicago O'Hare Intl

SJU

San Juan Luis Munoz Marin Intl

1 stop

7h 33m
SJU

San Juan Luis Munoz Marin Intl

ORD

Chicago O'Hare Intl

1 stop

8h 22m
$248

Spirit Airlines

View Deal

Deal found 17/5/22

Non-stop flights to Puerto Rico from Chicago

Save time with Chicago to Puerto Rico direct flight deals
Nov 1 - Nov 11
ORD

Chicago O'Hare Intl

SJU

San Juan Luis Munoz Marin Intl

Nonstop

4h 36m
SJU

San Juan Luis Munoz Marin Intl

ORD

Chicago O'Hare Intl

Nonstop

5h 30m
$285

Multiple Airlines

View Deal

Deal found 19/5/22

Oct 29 - Nov 5
ORD

Chicago O'Hare Intl

SJU

San Juan Luis Munoz Marin Intl

Nonstop

4h 44m
SJU

San Juan Luis Munoz Marin Intl

ORD

Chicago O'Hare Intl

Nonstop

5h 11m
$298

United Airlines

View Deal

Deal found 17/5/22

Oct 1 - Oct 8
ORD

Chicago O'Hare Intl

SJU

San Juan Luis Munoz Marin Intl

Nonstop

4h 44m
SJU

San Juan Luis Munoz Marin Intl

ORD

Chicago O'Hare Intl

Nonstop

5h 07m
$299

Multiple Airlines

View Deal

Deal found 17/5/22

Last minute flights from Chicago to Puerto Rico

Late deals on return flights to Puerto Rico from Chicago, departing today and this week
May 28 - Jun 5
ORD

Chicago O'Hare Intl

SJU

San Juan Luis Munoz Marin Intl

Nonstop

4h 47m
SJU

San Juan Luis Munoz Marin Intl

ORD

Chicago O'Hare Intl

Nonstop

5h 12m
$304

Frontier

View Deal

Deal found 18/5/22

May 26 - May 28
ORD

Chicago O'Hare Intl

SJU

San Juan Luis Munoz Marin Intl

Nonstop

4h 47m
SJU

San Juan Luis Munoz Marin Intl

ORD

Chicago O'Hare Intl

1 stop

14h 58m
$324

Multiple Airlines

View Deal

Deal found 18/5/22

May 26 - Jun 2
ORD

Chicago O'Hare Intl

SJU

San Juan Luis Munoz Marin Intl

Nonstop

4h 47m
SJU

San Juan Luis Munoz Marin Intl

ORD

Chicago O'Hare Intl

Nonstop

5h 12m
$330

Frontier

View Deal

Deal found 19/5/22

One-way flights to Puerto Rico from Chicago

The cheapest one-way flights from Chicago to Puerto Rico
Sep 27
ORD

Chicago O'Hare Intl

SJU

San Juan Luis Munoz Marin Intl

1 stop

8h 56m
$110

Delta

View Deal

Deal found 18/5/22

Oct 8
MDW

Chicago Midway

SJU

San Juan Luis Munoz Marin Intl

1 stop

8h 22m
$120

Delta

View Deal

Deal found 18/5/22

Sep 14
ORD

Chicago O'Hare Intl

BQN

Aguadilla Borinquen

1 stop

7h 54m
$123

Spirit Airlines

View Deal

Deal found 17/5/22

Related info for your journey

Useful info, stats and facts about Chicago to Puerto Rico flights.

Which airlines flying from Chicago to Puerto Rico have flexible cancellations due to COVID-19?

Due to the rapidly changing circumstances due to COVID-19, airlines like Frontier, American Airlines, and United Airlines flying from Chicago to Puerto Rico have implemented new flexible cancellation policies.

Can I find flights from Chicago to Puerto Rico for under $300 on Cheapflights?

Yes, there are multiple flights from Chicago to Puerto Rico for under $300. The cheapest flight booked recently is on Delta for just $219, but on average you can expect to pay $240.

Are there nonstop flights from Chicago to Puerto Rico for under $300 on Cheapflights?

Cheapflights has at least 20 direct flights from Chicago to Puerto Rico under $300. A good price for a nonstop flight from Chicago to Puerto Rico is less than $335.

Are there last-minute flights available from Chicago to Puerto Rico for under $400?

There are currently 20+ open flights from Chicago to Puerto Rico within the next 7 days for less than $400.

What are the cheapest airlines to fly from Chicago to Puerto Rico one-way?

To fly one-way, consider booking your trip with Delta, which is currently one of the cheapest options available, starting at $110. Spirit Airlines flights start at $123 while deals on United Airlines start at $135 one-way.

What are the most popular routes from Chicago to Puerto Rico?

The most popular flight routes from Chicago to Puerto Rico are Chicago O'Hare Intl - San Juan Luis Munoz Marin Intl, Chicago Midway - San Juan Luis Munoz Marin Intl and Chicago O'Hare Intl - Ponce Mercedita.

What are the most popular airlines that fly from Chicago to Puerto Rico?

When booking a flight from Chicago to Puerto Rico, you may want to consider flying on American Airlines, Alaska Airlines or JetBlue as they are the most popular for this route.

What are the most reliable airlines from Chicago to Puerto Rico?

Before booking your flight to Puerto Rico from Chicago, check out the most reliable airlines to get you to your destination on time: Qatar Airways (94%), Air Canada (90%), Air New Zealand( 90%).

What are the cheapest flights from Chicago to Puerto Rico?

On average you can expect to pay $691 for a flight from Chicago to Puerto Rico. The cheapest flight overall is $125 while the most popular route, (Chicago O'Hare Intl - San Juan Luis Munoz Marin Intl) is currently priced at $219.

Destination points for flights from Chicago to Puerto Rico

Select to see more specific information for flights from Chicago to all places in Puerto Rico

Top 5 airlines flying from Chicago to Puerto Rico

The chart below displays the airlines Cheapflights users traveling from Chicago to Puerto Rico choose most often. Cheapest and average prices are based on aggregated data from the past 12 months.
AirlineCheapestAverageFlexibilityOn-timeCOVID-19 safety
Juneyao AirlinesCheapest$12Average$21FlexibilityNo cancel feeOn-time66%COVID-19 safety
Search Juneyao Airlines flights
Spirit AirlinesCheapest$85Average$216FlexibilityNo cancel feeOn-time65%COVID-19 safety
Search Spirit Airlines flights
JetBlueCheapest$101Average$417FlexibilityNo cancel feeOn-time62%COVID-19 safety
Search JetBlue flights
FrontierCheapest$116Average$349FlexibilityNo cancel feeOn-time62%COVID-19 safety
Search Frontier flights
United AirlinesCheapest$124Average$483FlexibilityNo cancel feeOn-time69%COVID-19 safety
Search United Airlines flights

Hourly flight availability from Chicago to Puerto Rico

See what time of day planes typically take off from Chicago to Puerto Rico
18%of flight departuresEarly morningMidnight to 6 am
1%of flight departuresMorning6 am to noon
61%of flight departuresAfternoonNoon to 6 pm
20%of flight departuresEvening6 pm to midnight
Midnight
6 AM
Noon
6 PM