Cheap flights from Puerto Rico to Chicago (CHI)

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

All the information you need to plan the best null to CHI flight in 2022: compare Puerto Rico to Chicago flight prices with the expected peak season, weather and rainfall in Chicago.
What is the cheapest month to fly from Puerto Rico to Chicago?

Our data shows that August tends to be the cheapest month to fly to Chicago from Puerto Rico. Users have commonly found prices around $266 for the month, but tickets can be as low as $102. Due to multiple factors, prepare for potentially higher prices in December.

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

Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Puerto Rico to Chicago as you normally would.

Cheap flights from Puerto Rico to Chicago in January, February 2022

The best prices found for Puerto Rico to CHI flights for January, February
25 Feb - 1 Mar
$116pp
SJU
San Juan Luis Munoz Marin Intl
Spirit Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Spirit Airlines
 
1 STOP
SJU
San Juan Luis Munoz Marin Intl
26 Jan - 29 Jan
$125pp
SJU
San Juan Luis Munoz Marin Intl
Multiple Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Frontier
 
1 STOP
SJU
San Juan Luis Munoz Marin Intl
2 Feb - 6 Feb
$127pp
SJU
San Juan Luis Munoz Marin Intl
Spirit Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Spirit Airlines
 
1 STOP
SJU
San Juan Luis Munoz Marin Intl

Puerto Rico to Chicago 2022 flight deals

Cheap flights to Chicago from Puerto Rico found for this year
25 Feb - 1 Mar
$116pp
SJU
San Juan Luis Munoz Marin Intl
Spirit Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Spirit Airlines
 
1 STOP
SJU
San Juan Luis Munoz Marin Intl
26 Jan - 29 Jan
$125pp
SJU
San Juan Luis Munoz Marin Intl
Multiple Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Frontier
 
1 STOP
SJU
San Juan Luis Munoz Marin Intl
2 Feb - 6 Feb
$127pp
SJU
San Juan Luis Munoz Marin Intl
Spirit Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Spirit Airlines
 
1 STOP
SJU
San Juan Luis Munoz Marin Intl

Non-stop flights to Chicago from Puerto Rico

Save time with Puerto Rico to Chicago direct flight deals
22 Feb - 27 Feb
$129pp
SJU
San Juan Luis Munoz Marin Intl
Frontier
Non-Stop
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Frontier
Non-Stop
SJU
San Juan Luis Munoz Marin Intl
22 Feb - 27 Feb
$132pp
SJU
San Juan Luis Munoz Marin Intl
Frontier
Non-Stop
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Frontier
Non-Stop
SJU
San Juan Luis Munoz Marin Intl
23 Feb - 27 Feb
$135pp
SJU
San Juan Luis Munoz Marin Intl
Frontier
Non-Stop
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Frontier
Non-Stop
SJU
San Juan Luis Munoz Marin Intl

Last minute flights from Puerto Rico to Chicago

Late deals on round-trip flights to Chicago from Puerto Rico, departing today and this week
26 Jan - 29 Jan
$125pp
SJU
San Juan Luis Munoz Marin Intl
Multiple Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Frontier
 
1 STOP
SJU
San Juan Luis Munoz Marin Intl
27 Jan - 2 Feb
$132pp
SJU
San Juan Luis Munoz Marin Intl
Spirit Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Spirit Airlines
 
1 STOP
SJU
San Juan Luis Munoz Marin Intl
24 Jan - 1 Feb
$135pp
SJU
San Juan Luis Munoz Marin Intl
Multiple Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Spirit Airlines
 
1 STOP
SJU
San Juan Luis Munoz Marin Intl

One-way flights to Chicago from Puerto Rico

The cheapest one-way flights from Puerto Rico to Chicago
10:29 pm - 5:30 pm
Multiple Airlines
1 Stop
21h 01m
SJU - ORD
Multiple Airlines
$83
Kiwi.com
10:47 pm - 2:12 am
Frontier
Nonstop
5h 25m
SJU - ORD
Frontier
$92
SmartFares
1:00 am - 5:04 am
Spirit Airlines
2 Stops
30h 04m
SJU - ORD
Spirit Airlines
$93
Gotogate

Related info for your journey

Useful info, stats and facts about <span class="emphasized">Puerto Rico</span> to <span class="emphasized">Chicago</span> flights.

Flight FAQs

From Puerto Rico to Chicago

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

Some of our airline partners flying from Puerto Rico to Chicago have new flexible policies in place due to COVID-19. United Airlines, Spirit Airlines, and American Airlines are some of the carriers where you may find flexible cancellation policies. You can use our site to filter for airlines like United Airlines with this kind of flexibility.

Can I find flights from Puerto Rico to Chicago for under $200 on Cheapflights?

Yes, there are multiple flights from Puerto Rico to Chicago for under $200. The cheapest flight booked recently is on Spirit Airlines for just $114, but on average you can expect to pay $133.

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

Cheapflights has at least 20 direct flights from Puerto Rico to Chicago under $200. A good price for a nonstop flight from Puerto Rico to Chicago is less than $161.

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

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

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

No one likes to see their flight delayed. When booking a flight from Puerto Rico to Chicago consider choosing American Airlines (90%), Alaska Airlines (90%) or Air Canada (88%) as they are the most reliable in getting you off to your destination on time.

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

The most popular route from Puerto Rico to Chicago is San Juan Luis Munoz Marin Intl - Chicago O'Hare Intl. You may also consider San Juan Luis Munoz Marin Intl - Chicago Midway or Aguadilla Borinquen - Chicago O'Hare Intl.

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

Consider American Airlines, JetBlue or Delta when booking your flight. These represent the most popular airlines when flying from Puerto Rico to Chicago.

What are the cheapest flights from Puerto Rico to Chicago?

The cheapest flight price from Puerto Rico to Chicago is $46. On average you can expect to pay $393. The most popular route, (San Juan Luis Munoz Marin Intl - Chicago O'Hare Intl), can usually be booked for $132.

COVID Restrictions

View COVID Travel Restrictions for Chicago, IL

Do I need a COVID test to fly to Chicago from Puerto Rico?

Information is based on travel restrictions from Puerto Rico to Chicago

Most visitors from Puerto Rico need to provide a negative COVID-19 test result and/or quarantine to enter Chicago.

COVID-19 testing requirements
Visitors from Puerto Rico must present a negative RT-PCR (NAAT) or Antigen (quick-test) test taken 24 hours before departing to Chicago.

Quarantine requirements
Visitors from Puerto Rico are not required to quarantine after entering Chicago.

Do I need a test to fly back to Puerto Rico from Chicago?

Returning to Puerto Rico from Chicago

COVID-19 testing requirements
Visitors from Chicago must present a negative RT-PCR (NAAT) test taken 72 for RT-PCR (NAAT) and 24 Antigen (quick-test) hours before departing to Puerto Rico.

Quarantine requirements
Visitors from Chicago are not required to quarantine after entering Puerto Rico.

Hide COVID Travel Restrictions for Chicago, IL

Destination information for Chicago

Things to know before you go - useful duration and weather info for your trip from Puerto Rico to Chicago.
Today's exchange rate
$1 = $1.00
Flight duration from Puerto Rico to Chicago
5h 01m
Average temperature for January in Chicago
33.8 °F
Avg rainfall for January in Chicago
0.7 ″

Airports servicing

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

Airports servicing Chicago

Midway (MDW)
Rockford (RFD)

Top 6 airlines flying from Puerto Rico to Chicago

The chart below displays the airlines Cheapflights users traveling from Puerto Rico to Chicago 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
Frontier
$85 $226 No cancel fee 62%
Spirit Airlines
$118 $277 No cancel fee 65%
Delta
$164 $522 No cancel fee N/A
JetBlue
$174 $340 No cancel fee 62%
American Airlines
$182 $470 No cancel fee 71%
United Airlines
$183 $435 No cancel fee 69%
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