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Cheap flights from Chicago Midway (MDW) to Puerto Rico

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

How far in advance should I book a flight from Chicago Midway to Puerto Rico?

Find a great deal and save up to 11% by booking at least 41 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 Midway to Puerto Rico within the next two weeks, with the cheapest ticket starting at $380.

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

Due to multiple factors, expect to potentially pay more when booking in December. For low rates, September can be a great choice for travel to Puerto Rico. Flights to Puerto Rico from Chicago Midway in September are about $380 on average during September, but can be found for as low as $194.

Cheap flights from Chicago Midway to Puerto Rico in October, November 2020

The best prices found for MDW to Puerto Rico flights for October, November
2 Nov - 16 Nov
$298pp
MDW
Chicago Midway
Multiple Airlines
 
1 STOP
SJU
San Juan Luis Munoz Marin Intl
SJU
San Juan Luis Munoz Marin Intl
Multiple Airlines
   
2 STOPS
MDW
Chicago Midway
10 Nov - 17 Nov
$310pp
MDW
Chicago Midway
Delta
 
1 STOP
SJU
San Juan Luis Munoz Marin Intl
SJU
San Juan Luis Munoz Marin Intl
Delta
 
1 STOP
MDW
Chicago Midway
5 Nov - 12 Nov
$314pp
MDW
Chicago Midway
Multiple Airlines
   
2 STOPS
SJU
San Juan Luis Munoz Marin Intl
SJU
San Juan Luis Munoz Marin Intl
Multiple Airlines
   
2 STOPS
MDW
Chicago Midway

Chicago Midway to Puerto Rico 2020 flight deals

Cheap flights to Puerto Rico from Chicago Midway found for this year
2 Nov - 16 Nov
$298pp
MDW
Chicago Midway
Multiple Airlines
 
1 STOP
SJU
San Juan Luis Munoz Marin Intl
SJU
San Juan Luis Munoz Marin Intl
Multiple Airlines
   
2 STOPS
MDW
Chicago Midway
12 Dec - 20 Dec
$309pp
MDW
Chicago Midway
Multiple Airlines
   
2 STOPS
SJU
San Juan Luis Munoz Marin Intl
SJU
San Juan Luis Munoz Marin Intl
Multiple Airlines
   
2 STOPS
MDW
Chicago Midway
10 Nov - 17 Nov
$310pp
MDW
Chicago Midway
Delta
 
1 STOP
SJU
San Juan Luis Munoz Marin Intl
SJU
San Juan Luis Munoz Marin Intl
Delta
 
1 STOP
MDW
Chicago Midway

Last minute flights from Chicago Midway to Puerto Rico

Late deals on round-trip flights to Puerto Rico from Chicago Midway, departing today and this week
25 Oct - 31 Oct
$363pp
MDW
Chicago Midway
Multiple Airlines
   
2 STOPS
SJU
San Juan Luis Munoz Marin Intl
SJU
San Juan Luis Munoz Marin Intl
Multiple Airlines
   
2 STOPS
MDW
Chicago Midway
26 Oct - 13 Nov
$405pp
MDW
Chicago Midway
Delta
 
1 STOP
SJU
San Juan Luis Munoz Marin Intl
SJU
San Juan Luis Munoz Marin Intl
Delta
 
1 STOP
MDW
Chicago Midway
28 Oct - 9 Nov
$425pp
MDW
Chicago Midway
Delta
 
1 STOP
SJU
San Juan Luis Munoz Marin Intl
SJU
San Juan Luis Munoz Marin Intl
Delta
 
1 STOP
MDW
Chicago Midway

One-way flights to Puerto Rico from Chicago Midway

The cheapest one-way flights from Chicago Midway to Puerto Rico
1:15 am - 10:36 am
Delta
1 Stop
7h 21m
MDW - SJU
Delta
$155
Delta
7:41 am - 5:54 pm
Delta
1 Stop
8h 13m
MDW - SJU
Delta
$180
Delta
6:27 am - 6:40 pm
Delta
1 Stop
10h 13m
MDW - SJU
Delta
$200
Delta

Related info for your journey

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

Flight FAQs

From Chicago Midway to Puerto Rico

Are flight prices decreasing from Chicago Midway 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 Midway 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.

What safety measures are being taken by airlines flying from Chicago Midway to Puerto Rico to control the spread of COVID-19?

JetBlue and Delta are some of the many airlines that have implemented additional safety measures to control the spread of COVID-19. New policies for travelers booking flights from Chicago Midway to Puerto Rico include masks being provided and required on board, daily cleaning and sanitization, use of HEPA filters, pre-flight testing for antibodies and symptoms, and socially distanced seating (for a limited time). Keep in mind that policies will vary by airline.

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

Due to the rapidly changing circumstances due to COVID-19, airlines like Delta, United Airlines, and American Airlines flying from Chicago Midway to Puerto Rico have implemented new flexible cancellation policies.

Can I find flights from Chicago Midway to Puerto Rico for under $300 on Cheapflights?

Yes, there are multiple flights from Chicago Midway to Puerto Rico for under $300. The cheapest flight booked recently is on Multiple Airlines for just $298, but on average you can expect to pay $349.

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

There are no nonstop flights from Chicago Midway to Puerto Rico, but Cheapflights can provide you with all the information you need to find the fastest route with the fewest stops.

Are there last-minute flights available from Chicago Midway to Puerto Rico for under $400?

There are currently 16+ open flights from Chicago Midway to Puerto Rico within the next 7 days for less than $400.

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

American Airlines, JetBlue and Delta are the most popular airlines when flying from Chicago Midway to Puerto Rico.

What are the cheapest Flights from Chicago Midway to Puerto Rico?

While on average a flight from Chicago Midway to Puerto Rico is generally $375, our data shows the cheapest flight currently is $201. When looking at the most popular route, (Chicago Midway - San Juan Luis Munoz Marin Intl), you can expect to pay $310 for that flight.

How long is the flight from Chicago Midway to Puerto Rico?

Airlines like Delta fly from Chicago Midway to Puerto Rico in about 5h 51m. The time it takes to get you to your destination can typically vary by up to .

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

Currently priced at $310, Delta will fly you from Chicago Midway to Puerto Rico and back. In addition to Delta, many other airlines offer competitively priced options for your trip.

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

For one-way options, check prices for Delta. According to our data, you can fly for as low as $155.

Arrival points for flights from Chicago Midway to Puerto Rico

Destination information for Puerto Rico

Things to know before you go. Useful info for your trip from Chicago Midway to Puerto Rico
Today's exchange rate
$1 = $1.00

Airports servicing Chicago

Airports servicing

Culebra (CPX)
Mayaguez (MAZ)
Ceiba J. Aponte de la Torre (NRR)
Ponce (PSE)
Vieques (VQS)
Home Caribbean Puerto Rico Cheap flights from Chicago Midway to Puerto Rico