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Cheap flights from Chicago (CHI) to Puerto Rico

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How to find the cheapest flight from
Chicago (CHI) to Puerto Rico

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

Travelers have found it’s best to book a flight 41 days in advance to save up to 11% 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 41 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 Puerto Rico 1-2 weeks in advance for as low as $380, or $415 for flights within the next 24 hours.

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

Our data shows that September tends to be the cheapest month to fly to Puerto Rico from Chicago. Users have commonly found prices around $380 for the month, but tickets can be as low as $194. Due to multiple factors, prepare for potentially higher prices in December.

Cheap flights from Chicago to Puerto Rico in October, November 2020

The best prices found for CHI to Puerto Rico flights for October, November
9 Nov - 10 Nov
$98pp
ORD
Chicago O'Hare Intl
Spirit Airlines
 
1 STOP
SJU
San Juan Luis Munoz Marin Intl
SJU
San Juan Luis Munoz Marin Intl
Spirit Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
10 Nov - 11 Nov
$101pp
ORD
Chicago O'Hare Intl
Spirit Airlines
 
1 STOP
SJU
San Juan Luis Munoz Marin Intl
SJU
San Juan Luis Munoz Marin Intl
Spirit Airlines
   
2 STOPS
ORD
Chicago O'Hare Intl
3 Nov - 6 Nov
$102pp
ORD
Chicago O'Hare Intl
Spirit Airlines
 
1 STOP
SJU
San Juan Luis Munoz Marin Intl
SJU
San Juan Luis Munoz Marin Intl
Spirit Airlines
 
1 STOP
ORD
Chicago O'Hare Intl

Chicago to Puerto Rico 2020 flight deals

Cheap flights to Puerto Rico from Chicago found for this year
9 Nov - 10 Nov
$98pp
ORD
Chicago O'Hare Intl
Spirit Airlines
 
1 STOP
SJU
San Juan Luis Munoz Marin Intl
SJU
San Juan Luis Munoz Marin Intl
Spirit Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
10 Nov - 11 Nov
$101pp
ORD
Chicago O'Hare Intl
Spirit Airlines
 
1 STOP
SJU
San Juan Luis Munoz Marin Intl
SJU
San Juan Luis Munoz Marin Intl
Spirit Airlines
   
2 STOPS
ORD
Chicago O'Hare Intl
3 Nov - 6 Nov
$102pp
ORD
Chicago O'Hare Intl
Spirit Airlines
 
1 STOP
SJU
San Juan Luis Munoz Marin Intl
SJU
San Juan Luis Munoz Marin Intl
Spirit Airlines
 
1 STOP
ORD
Chicago O'Hare Intl

Non-stop flights to Puerto Rico from Chicago

Save time with Chicago to Puerto Rico direct flight deals
21 Jan - 25 Jan
$217pp
ORD
Chicago O'Hare Intl
Frontier
Non-Stop
SJU
San Juan Luis Munoz Marin Intl
SJU
San Juan Luis Munoz Marin Intl
Frontier
Non-Stop
ORD
Chicago O'Hare Intl
28 Dec - 9 Jan
$223pp
ORD
Chicago O'Hare Intl
Frontier
Non-Stop
SJU
San Juan Luis Munoz Marin Intl
SJU
San Juan Luis Munoz Marin Intl
Frontier
Non-Stop
ORD
Chicago O'Hare Intl
29 Dec - 9 Jan
$228pp
ORD
Chicago O'Hare Intl
Frontier
Non-Stop
SJU
San Juan Luis Munoz Marin Intl
SJU
San Juan Luis Munoz Marin Intl
Frontier
Non-Stop
ORD
Chicago O'Hare Intl

Last minute flights from Chicago to Puerto Rico

Late deals on round-trip flights to Puerto Rico from Chicago, departing today and this week
3 Nov - 6 Nov
$102pp
ORD
Chicago O'Hare Intl
Spirit Airlines
 
1 STOP
SJU
San Juan Luis Munoz Marin Intl
SJU
San Juan Luis Munoz Marin Intl
Spirit Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
3 Nov - 6 Nov
$104pp
ORD
Chicago O'Hare Intl
Spirit Airlines
 
1 STOP
SJU
San Juan Luis Munoz Marin Intl
SJU
San Juan Luis Munoz Marin Intl
Spirit Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
2 Nov - 5 Nov
$110pp
ORD
Chicago O'Hare Intl
Spirit Airlines
 
1 STOP
SJU
San Juan Luis Munoz Marin Intl
SJU
San Juan Luis Munoz Marin Intl
Spirit Airlines
 
1 STOP
ORD
Chicago O'Hare Intl

One-way flights to Puerto Rico from Chicago

The cheapest one-way flights from Chicago to Puerto Rico
2:00 am - 11:56 am
Frontier
1 Stop
8h 56m
ORD - SJU
Frontier
$64
Expedia
2:00 am - 5:12 pm
American Airlines
1 Stop
13h 12m
ORD - SJU
American Airlines
5:25 pm - 4:36 pm
Spirit Airlines
3 Stops
45h 11m
ORD - SJU
Spirit Airlines
$81
Kiwi.com

Related info for your journey

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

Flight FAQs

From Chicago to Puerto Rico

Are flight prices decreasing from Chicago to Puerto Rico due to COVID-19 (coronavirus)?

At this time, Cheapflights has noticed price decreases for many domestic flights due to COVID-19. Travel is not necessarily recommended at this time, and flights may be prone to cancellation: please check with local authorities in both Chicago and Puerto Rico for travel alerts, and be sure to review the airline's cancellation policy and travel advisories before booking. For more information, please view our post on what to know about COVID-19 (coronavirus) and travel.

What safety measures are being taken by airlines flying from Chicago to Puerto Rico to control the spread of COVID-19?

New policies can now be found on Alaska Airlines, JetBlue, and Delta to help keep travelers safe while flying. New policies for travelers booking flights from Chicago to Puerto Rico include masks being provided and required on board, daily cleaning and sanitization, use of HEPA filters, pre-flight testing for antibodies and symptoms, and socially distanced seating (for a limited time). Keep in mind that policies will vary by airline.

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 United Airlines, American Airlines, and Spirit Airlines flying from Chicago to Puerto Rico have implemented new flexible cancellation policies.

Can I find flights from Chicago to Puerto Rico for under $100 on Cheapflights?

Yes, there are multiple flights from Chicago to Puerto Rico for under $100. The cheapest flight booked recently is on Spirit Airlines for just $98, but on average you can expect to pay $111.

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 $263.

Are there last-minute flights available from Chicago to Puerto Rico for under $200?

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

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 Major Airline, American Airlines or Alaska Airlines as they are the most popular for this route.

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 - Culebra.

What are the cheapest Flights from Chicago to Puerto Rico?

Looking at all options, your cheapest flight can be booked for $122. While the most popular route (Chicago O'Hare Intl - San Juan Luis Munoz Marin Intl) can be booked for $106 on average our data indicates $302 when flying from Chicago to Puerto Rico

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

The top 3 most reliable airlines when flying from Chicago to Puerto Rico are American Airlines (100%), Alaska Airlines (100%) and Iberia (100%).

How long is the flight from Chicago to Puerto Rico?

Departing from Chicago to Puerto Rico will take you 6h 05m. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.

What is the cheapest airline to fly from Chicago to Puerto Rico round-trip?

Flying on Spirit Airlines is currently your cheapest option to Puerto Rico, with prices starting at $98.

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

The cheapest airline one-way is Spirit Airlines, with whom users have recently found tickets for as low as $47. However, be on the lookout for offers from Frontier and American Airlines, as they are both options that can get you from Chicago to Puerto Rico for a low price.

Destination information for Puerto Rico

Things to know before you go. Useful info for your trip from Chicago to Puerto Rico
Today's exchange rate
$1 = $1.00

Airports servicing Chicago

Chicago Midway (MDW)
Rockford (RFD)

Airports servicing

Culebra (CPX)
Mayaguez (MAZ)
Ceiba J. Aponte de la Torre (NRR)
Ponce (PSE)
Vieques (VQS)
Home Caribbean Puerto Rico Cheap flights from Chicago to Puerto Rico