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Cheap flights from Puerto Rico to Chicago (CHI)

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

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 37 days early can save you up to 10% on average compared to booking a flight this week. If booking 37 days before your flight isn’t an option for you, users have found flights from Puerto Rico to Chicago for as little as $177 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 $177 for flights departing within the next 3 days.

Cheap flights from Puerto Rico to Chicago in August, September 2020

The best prices found for Puerto Rico to CHI flights for August, September
27 Jul - 5 Aug
$75pp
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
27 Jul - 4 Aug
$76pp
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
13 Aug - 17 Aug
$77pp
BQN
Aguadilla Borinquen
Spirit Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Spirit Airlines
 
1 STOP
BQN
Aguadilla Borinquen

Puerto Rico to Chicago 2020 flight deals

Cheap flights to Chicago from Puerto Rico found for this year
27 Jul - 5 Aug
$75pp
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
27 Jul - 4 Aug
$76pp
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
13 Aug - 17 Aug
$77pp
BQN
Aguadilla Borinquen
Spirit Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Spirit Airlines
 
1 STOP
BQN
Aguadilla Borinquen

Non-stop flights to Chicago from Puerto Rico

Save time with Puerto Rico to Chicago direct flight deals
25 Aug - 8 Sep
$276pp
SJU
San Juan Luis Munoz Marin Intl
Multiple Airlines
Non-Stop
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
United Airlines
Non-Stop
SJU
San Juan Luis Munoz Marin Intl
8 Aug - 4 Oct
$281pp
SJU
San Juan Luis Munoz Marin Intl
Multiple Airlines
Non-Stop
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
United Airlines
Non-Stop
SJU
San Juan Luis Munoz Marin Intl
6 Nov - 14 Nov
$284pp
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

Last minute flights from Puerto Rico to Chicago

Late deals on round-trip flights to Chicago from Puerto Rico, departing today and this week
27 Jul - 5 Aug
$75pp
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
27 Jul - 4 Aug
$76pp
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
28 Jul - 4 Aug
$81pp
SJU
San Juan Luis Munoz Marin Intl
Spirit Airlines
   
2 STOPS
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
11:23 pm - 5:27 am
Spirit Airlines
1 Stop
7h 04m
SJU - ORD
Spirit Airlines
$38
FlightNetwork
9:42 am - 4:16 pm
Spirit Airlines
1 Stop
7h 34m
SJU - ORD
Spirit Airlines
$43
FlyFar
11:23 pm - 6:16 am
Spirit Airlines
1 Stop
7h 53m
SJU - ORD
Spirit Airlines
$45
Spirit

Related info for your journey

Useful info, stats and facts about Puerto Rico to Chicago 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.

Can I find flights from Puerto Rico to Chicago for under $100 on Cheapflights?

Yes, there are multiple flights from Puerto Rico to Chicago for under $100. The cheapest flight booked recently is on Spirit Airlines for just $75, but on average you can expect to pay $91.

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

Cheapflights has at least 11 direct flights from Puerto Rico to Chicago under $300. A good price for a nonstop flight from Puerto Rico to Chicago is less than $544.

Are there last-minute flights available from Puerto Rico to Chicago for under $100?

There are currently 20+ open flights from Puerto Rico to Chicago within the next 7 days for less than $100.

What days are nonstop flights available from Puerto Rico to Chicago?

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

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 Midway 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 $119. While the most popular route (San Juan Luis Munoz Marin Intl - Chicago O'Hare Intl) can be booked for $75 on average our data indicates $237 when flying from Puerto Rico to Chicago

How long is the flight from Puerto Rico to Chicago?

A quick flight from Puerto Rico to Chicago can take about 6h 57m. Delta provides one of the quickest options available for as low as $849. This flight may include one or multiple stops.

What is the cheapest airline to fly from Puerto Rico to Chicago round-trip?

According to our current data, Spirit Airlines ($75), 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 airline for a one-way flight from Puerto Rico to Chicago is Spirit Airlines ($38).

Destination information for Chicago

Things to know before you go. Useful info for your trip from Puerto Rico to Chicago
Today's exchange rate
$1 = $1.00
Average temperature for August in Chicago
82.4 °F
Avg rainfall for August in Chicago
3.9 ″

Airports servicing

Culebra (CPX)
Mayaguez (MAZ)
Ceiba J. Aponte de la Torre (NRR)
Ponce (PSE)
Vieques (VQS)

Airports servicing Chicago

Chicago Midway (MDW)
Rockford (RFD)
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