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Cheap flights from Chicago (CHI) to Puerto Rico

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Cheap flights from Chicago to Puerto Rico in May, June 2020

The best prices found for ORD to Puerto Rico flights for May, June
3 Jun - 11 Jun
$129pp
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
28 May - 5 Jun
$130pp
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 Jun - 18 Jun
$138pp
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
3 Jun - 11 Jun
$129pp
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
28 May - 5 Jun
$130pp
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 Jun - 18 Jun
$138pp
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
9 Jul - 12 Jul
$251pp
ORD
Chicago O'Hare Intl
$self.airline
Non-Stop
SJU
San Juan Luis Munoz Marin Intl
SJU
San Juan Luis Munoz Marin Intl
United Airlines
Non-Stop
ORD
Chicago O'Hare Intl
7 Aug - 14 Aug
$261pp
ORD
Chicago O'Hare Intl
$self.airline
Non-Stop
SJU
San Juan Luis Munoz Marin Intl
SJU
San Juan Luis Munoz Marin Intl
United Airlines
Non-Stop
ORD
Chicago O'Hare Intl
23 Jul - 26 Jul
$282pp
ORD
Chicago O'Hare Intl
$self.airline
Non-Stop
SJU
San Juan Luis Munoz Marin Intl
SJU
San Juan Luis Munoz Marin Intl
United Airlines
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
28 May - 4 Jun
$130pp
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
28 May - 1 Jun
$150pp
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
28 May - 5 Jun
$159pp
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
4:00 am - 9:06 am
Spirit Airlines
1 Stop
28h 06m
ORD - SJU
Spirit Airlines
$66
Fareboom
4:00 am - 9:06 am
Spirit Airlines
1 Stop
28h 06m
ORD - SJU
Spirit Airlines
$67
Bookingwiz.co.th
11:58 am - 10:39 am
Spirit Airlines
1 Stop
21h 41m
ORD - SJU
Spirit Airlines
$68
Fareboom

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.

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 $129, but on average you can expect to pay $155.

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

Cheapflights has at least 3 direct flights from Chicago to Puerto Rico under $300. A good price for a nonstop flight from Chicago to Puerto Rico is less than $264.

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

There are currently 3+ open flights from Chicago to Puerto Rico within the next 7 days for less than $200.

How popular is this flight route?

This flight path from Chicago to Puerto Rico was viewed by 538 users in the past month. Keep an eye out for changes in search interest prior to high and low season.

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 JetBlue, Delta or Frontier 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 $60. 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 $441 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 Air Canada (73%), United Airlines (73%) and Air New Zealand (73%).

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)