Cheap flights from Chicago (CHI) to Puerto Rico
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
Chicago O'Hare Intl
San Juan Luis Munoz Marin Intl
Nonstop
4h 47mSan Juan Luis Munoz Marin Intl
Chicago O'Hare Intl
Nonstop
5h 12mFrontier
Chicago O'Hare Intl
San Juan Luis Munoz Marin Intl
1 stop
7h 59mSan Juan Luis Munoz Marin Intl
Chicago O'Hare Intl
Nonstop
5h 12mFrontier
Chicago O'Hare Intl
San Juan Luis Munoz Marin Intl
Nonstop
4h 47mSan Juan Luis Munoz Marin Intl
Chicago O'Hare Intl
Nonstop
5h 12mFrontier
Chicago to Puerto Rico 2022 flight deals
Cheap flights to Puerto Rico from Chicago found for this year
Chicago Midway
San Juan Luis Munoz Marin Intl
1 stop
8h 22mSan Juan Luis Munoz Marin Intl
Chicago Midway
1 stop
10h 15mDelta
Chicago O'Hare Intl
San Juan Luis Munoz Marin Intl
1 stop
8h 56mSan Juan Luis Munoz Marin Intl
Chicago O'Hare Intl
1 stop
10h 39mDelta
Chicago O'Hare Intl
San Juan Luis Munoz Marin Intl
1 stop
9h 35mSan Juan Luis Munoz Marin Intl
Chicago O'Hare Intl
1 stop
11h 07mDelta
Cheap Delta flights from Chicago to Puerto Rico
Chicago Midway
San Juan Luis Munoz Marin Intl
1 stop
8h 22mSan Juan Luis Munoz Marin Intl
Chicago Midway
1 stop
10h 15mDelta
Chicago O'Hare Intl
San Juan Luis Munoz Marin Intl
1 stop
9h 35mSan Juan Luis Munoz Marin Intl
Chicago O'Hare Intl
1 stop
11h 07mDelta
Chicago O'Hare Intl
San Juan Luis Munoz Marin Intl
1 stop
9h 35mSan Juan Luis Munoz Marin Intl
Chicago O'Hare Intl
1 stop
7h 48mDelta
Cheap Spirit Airlines flights from Chicago to Puerto Rico
Chicago O'Hare Intl
San Juan Luis Munoz Marin Intl
1 stop
17h 13mSan Juan Luis Munoz Marin Intl
Chicago O'Hare Intl
1 stop
20h 40mSpirit Airlines
Chicago O'Hare Intl
San Juan Luis Munoz Marin Intl
1 stop
25h 10mSan Juan Luis Munoz Marin Intl
Chicago O'Hare Intl
1 stop
20h 40mSpirit Airlines
Chicago O'Hare Intl
San Juan Luis Munoz Marin Intl
1 stop
7h 33mSan Juan Luis Munoz Marin Intl
Chicago O'Hare Intl
1 stop
8h 22mSpirit Airlines
Non-stop flights to Puerto Rico from Chicago
Save time with Chicago to Puerto Rico direct flight deals
Chicago O'Hare Intl
San Juan Luis Munoz Marin Intl
Nonstop
4h 36mSan Juan Luis Munoz Marin Intl
Chicago O'Hare Intl
Nonstop
5h 30mMultiple Airlines
Chicago O'Hare Intl
San Juan Luis Munoz Marin Intl
Nonstop
4h 44mSan Juan Luis Munoz Marin Intl
Chicago O'Hare Intl
Nonstop
5h 11mUnited Airlines
Chicago O'Hare Intl
San Juan Luis Munoz Marin Intl
Nonstop
4h 44mSan Juan Luis Munoz Marin Intl
Chicago O'Hare Intl
Nonstop
5h 07mMultiple Airlines
Last minute flights from Chicago to Puerto Rico
Late deals on return flights to Puerto Rico from Chicago, departing today and this week
Chicago O'Hare Intl
San Juan Luis Munoz Marin Intl
Nonstop
4h 47mSan Juan Luis Munoz Marin Intl
Chicago O'Hare Intl
Nonstop
5h 12mFrontier
Chicago O'Hare Intl
San Juan Luis Munoz Marin Intl
Nonstop
4h 47mSan Juan Luis Munoz Marin Intl
Chicago O'Hare Intl
1 stop
14h 58mMultiple Airlines
Chicago O'Hare Intl
San Juan Luis Munoz Marin Intl
Nonstop
4h 47mSan Juan Luis Munoz Marin Intl
Chicago O'Hare Intl
Nonstop
5h 12mFrontier
One-way flights to Puerto Rico from Chicago
The cheapest one-way flights from Chicago to Puerto Rico
Chicago O'Hare Intl
San Juan Luis Munoz Marin Intl
1 stop
8h 56mDelta
Chicago Midway
San Juan Luis Munoz Marin Intl
1 stop
8h 22mDelta
Chicago O'Hare Intl
Aguadilla Borinquen
1 stop
7h 54mSpirit Airlines
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.
Flights to Puerto Rico from Chicago
Can I fly to Puerto Rico from Chicago right now?
Most visitors from Chicago can enter Puerto Rico without restrictions.
COVID-19 testing requirements
Visitors from Chicago are not required to present a negative COVID-19 PCR test or antigen result upon entering Puerto Rico.
Quarantine requirements
Visitors from Chicago are not required to quarantine after entering Puerto Rico.
Documents
Travel Declaration Form - Must be completed prior to travel to Puerto Rico.
Can I fly back to Chicago from Puerto Rico?
COVID-19 testing requirements
Visitors from Puerto Rico are not required to present a negative COVID-19 PCR test or antigen result upon entering Chicago.
Quarantine requirements
Visitors from Puerto Rico are not required to quarantine after entering Chicago.
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.
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 departures | Early morningMidnight to 6 am |
|---|---|
| 1%of flight departures | Morning6 am to noon |
| 61%of flight departures | AfternoonNoon to 6 pm |
| 20%of flight departures | Evening6 pm to midnight |