Cheap flights from Chicago (CHI) to Puerto Rico

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

All the information you need to plan the best CHI to SJU flight in 2021: compare Chicago to Puerto Rico flight prices with the expected peak season, weather and rainfall in 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 19 days in advance to save up to 7% 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 19 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 $262, or $281 for flights within the next 24 hours.

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

Our data shows that August tends to be the cheapest month to fly to Puerto Rico from Chicago. Users have commonly found prices around $313 for the month, but tickets can be as low as $121. Due to multiple factors, prepare for potentially higher prices in December.

Cheap flights from Chicago to Puerto Rico in June, July 2021

The best prices found for CHI to Puerto Rico flights for June, July
20 Jul - 10 Aug
$162pp
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
17 Jul - 21 Jul
$164pp
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
4 Jul - 9 Jul
$175pp
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 2021 flight deals

Cheap flights to Puerto Rico from Chicago found for this year
17 Aug - 25 Aug
$135pp
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
24 Aug - 1 Sep
$136pp
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
18 Aug - 25 Aug
$139pp
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
3 Nov - 2 Dec
$176pp
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
27 Oct - 3 Nov
$180pp
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
6 Nov - 14 Dec
$186pp
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
30 Jun - 21 Jul
$186pp
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
30 Jun - 9 Jul
$207pp
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
30 Jun - 21 Jul
$226pp
ORD
Chicago O'Hare Intl
Multiple Airlines
 
1 STOP
SJU
San Juan Luis Munoz Marin Intl
SJU
San Juan Luis Munoz Marin Intl
Frontier
Non-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 - 9:25 am
Delta
1 Stop
6h 25m
MDW - SJU
Delta
$89
Delta
1:25 am - 1:03 pm
Spirit Airlines
1 Stop
10h 38m
ORD - SJU
Spirit Airlines
$106
mytrip.com
9:29 pm - 3:24 am
Frontier
Nonstop
4h 55m
ORD - SJU
Frontier
$108
SmartFares

Related info for your journey

Useful info, stats and facts about <span class="emphasized">Chicago</span> to <span class="emphasized">Puerto Rico</span> 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 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 $200 on Cheapflights?

Yes, there are multiple flights from Chicago to Puerto Rico for under $200. The cheapest flight booked recently is on Spirit Airlines for just $135, but on average you can expect to pay $158.

Are there nonstop flights from Chicago to Puerto Rico for under $200 on Cheapflights?

Cheapflights has at least 20 direct flights from Chicago to Puerto Rico under $200. A good price for a nonstop flight from Chicago to Puerto Rico is less than $198.

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 days are nonstop flights available from Chicago to Puerto Rico?

Nonstop flights can be found on the following days: Saturday.

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 - Aguadilla Borinquen.

What are the cheapest Flights from Chicago to Puerto Rico?

Looking at all options, your cheapest flight can be booked for $94. While the most popular route (Chicago O'Hare Intl - San Juan Luis Munoz Marin Intl) can be booked for $159 on average our data indicates $677 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 Qatar Airways (97%), Alaska Airlines (94%) and American Airlines (92%).

How long is the flight from Chicago to Puerto Rico?

Departing from Chicago to Puerto Rico will take you 4h 55m. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.

What are the cheapest airlines flying from Chicago to Puerto Rico round-trip?

Flying on Spirit Airlines is currently your cheapest option to Puerto Rico, with prices starting at $135. Additional round-trip tickets that might be worth considering are offered by Frontier and Delta, with the lowest prices starting at $176 and $178, respectively.

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 $66. However, be on the lookout for offers from Frontier and Delta, as they are both options that can get you from Chicago to Puerto Rico for a low price.

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.

Destination information for Puerto Rico

Things to know before you go - useful duration and weather info for your trip from Chicago to Puerto Rico.
Today's exchange rate
$1 = $1.00
Flight duration
5h 08m

Airports servicing Chicago

Chicago Midway (MDW)
Rockford (RFD)

Airports servicing

Culebra (CPX)
Mayagüez Eugenio M De Hostos (MAZ)
Ceiba J. Aponte de la Torre (NRR)
Ponce (PSE)
Vieques (VQS)

Top 6 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.
Airline Cheapest Average Flexibility On-time COVID-19 safety
Spirit Airlines
$112 $300 No cancel fee 65%
JetBlue
$139 $303 No cancel fee 62%
Frontier
$90 $342 No cancel fee 62%
American Airlines
$185 $461 No cancel fee 71%
Delta
$163 $463 No cancel fee N/A
United Airlines
$183 $492 No cancel fee 69%
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