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 2021: compare Puerto Rico to Chicago flight prices with the expected peak season, weather and rainfall in Chicago.
How far in advance should I book a flight from Puerto Rico to Chicago?

Users have found that booking a flight from Puerto Rico to Chicago at least 20 days early can save you up to 10% on average compared to booking a flight this week. If booking 20 days before your flight isn’t an option for you, users have found flights from Puerto Rico to Chicago for as little as $137 when booking for a departure date within the next two weeks. You can also check prices now. Some users have found airline tickets as low as $157 for flights departing within the next 3 days.

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

April can be a great time to fly to Chicago from Puerto Rico with a flight ticket averaging about $135. Cheapflights users have found deals in the month of April for as cheap as $33. The most expensive prices can be found in the month of December.

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

The best prices found for Puerto Rico to CHI flights for May, June
10 May - 16 May
$135pp
SJU
San Juan Luis Munoz Marin Intl
Multiple Airlines
Non-Stop
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Frontier
Non-Stop
SJU
San Juan Luis Munoz Marin Intl
13 May - 15 May
$136pp
SJU
San Juan Luis Munoz Marin Intl
Multiple Airlines
Non-Stop
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Frontier
Non-Stop
SJU
San Juan Luis Munoz Marin Intl
20 May - 23 May
$138pp
SJU
San Juan Luis Munoz Marin Intl
Multiple Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Frontier
Non-Stop
SJU
San Juan Luis Munoz Marin Intl

Puerto Rico to Chicago 2021 flight deals

Cheap flights to Chicago from Puerto Rico found for this year
10 May - 16 May
$135pp
SJU
San Juan Luis Munoz Marin Intl
Multiple Airlines
Non-Stop
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Frontier
Non-Stop
SJU
San Juan Luis Munoz Marin Intl
13 May - 15 May
$136pp
SJU
San Juan Luis Munoz Marin Intl
Multiple Airlines
Non-Stop
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Frontier
Non-Stop
SJU
San Juan Luis Munoz Marin Intl
20 May - 23 May
$138pp
SJU
San Juan Luis Munoz Marin Intl
Multiple Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Frontier
Non-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
10 May - 16 May
$135pp
SJU
San Juan Luis Munoz Marin Intl
Multiple Airlines
Non-Stop
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Frontier
Non-Stop
SJU
San Juan Luis Munoz Marin Intl
13 May - 15 May
$136pp
SJU
San Juan Luis Munoz Marin Intl
Multiple Airlines
Non-Stop
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Frontier
Non-Stop
SJU
San Juan Luis Munoz Marin Intl
14 May - 15 May
$141pp
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
10 May - 16 May
$135pp
SJU
San Juan Luis Munoz Marin Intl
Multiple Airlines
Non-Stop
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Frontier
Non-Stop
SJU
San Juan Luis Munoz Marin Intl
13 May - 15 May
$136pp
SJU
San Juan Luis Munoz Marin Intl
Multiple Airlines
Non-Stop
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Frontier
Non-Stop
SJU
San Juan Luis Munoz Marin Intl
13 May - 23 May
$139pp
SJU
San Juan Luis Munoz Marin Intl
United Airlines
Non-Stop
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
United 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
10:46 am - 7:34 pm
Delta
1 Stop
9h 48m
SJU - ORD
Delta
$72
Delta
10:39 pm - 3:22 am
Multiple Airlines
2 Stops
29h 43m
SJU - ORD
Multiple Airlines
$106
Kiwi.com
12:18 pm - 4:42 pm
American Airlines
Nonstop
5h 24m
SJU - ORD
American Airlines

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

Are flight prices decreasing from Puerto Rico to Chicago 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 Puerto Rico and Chicago 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 Puerto Rico to Chicago to control the spread of COVID-19?

New policies can now be found on Delta to help keep travelers safe while flying. Airline carriers are regularly disinfecting and sanitizing their aircraft. Masks are provided and are mandatory while on board. Pre-flight testing for symptoms and antibodies, alongside socially distanced seating (for a limited time) will work towards keeping travelers safer while flying from Puerto Rico to Chicago. Policies will vary by airline.

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 Multiple Airlines for just $134, but on average you can expect to pay $152.

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 $172.

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 days are nonstop flights available from Puerto Rico to Chicago?

You can find nonstop flights on the following days: Wednesday.

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

The most popular airlines flying from Puerto Rico to Chicago are American Airlines, JetBlue and Delta. Something to consider prior to booking your flight.

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

Most travelers choose San Juan Luis Munoz Marin Intl - Chicago O'Hare Intl, San Juan Luis Munoz Marin Intl - Chicago Midway or Aguadilla Borinquen - Chicago O'Hare Intl when deciding on the best route from Puerto Rico to Chicago.

What are the cheapest Flights from Puerto Rico to Chicago?

Looking at all options, your cheapest flight can be booked for $117. While the most popular route (San Juan Luis Munoz Marin Intl - Chicago O'Hare Intl) can be booked for $163 on average our data indicates $511 when flying from Puerto Rico to Chicago

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

Before booking your flight to Chicago from Puerto Rico, check out the most reliable airlines to get you to your destination on time: Frontier (97%), United Airlines (92%), Air Canada( 89%).

How long is the flight from Puerto Rico to Chicago?

A quick flight from Puerto Rico to Chicago can take about 5h 10m. United Airlines provides one of the quickest options available for as low as $139. This flight may include one or multiple stops.

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

According to our current data, United Airlines ($139), Frontier ($141), and Delta ($144) offers the cheapest pricing from Puerto Rico to Chicago.

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

The cheapest airlines for a one-way flight from Puerto Rico to Chicago are American Airlines ($68), Frontier ($71), and Delta ($72).

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
5h 05m
Average temperature for May in Chicago
71.6 °F
Avg rainfall for May in Chicago
4.3 ″

Airports servicing

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

Airports servicing Chicago

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%
JetBlue
$174 $340 No cancel fee 62%
United Airlines
$183 $435 No cancel fee 69%
American Airlines
$182 $470 No cancel fee 71%
Delta
$164 $522 No cancel fee N/A
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