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 7% by booking at least 19 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 $262.

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, August can be a great choice for travel to Puerto Rico. Flights to Puerto Rico from Chicago Midway in August are about $313 on average during August, but can be found for as low as $121.

Cheap flights from Chicago Midway to Puerto Rico in March, April 2021

23 Mar - 26 May
$176pp
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
16 Mar - 23 Mar
$186pp
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
30 Mar - 6 Apr
$226pp
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

Chicago Midway to Puerto Rico 2021 flight deals

23 Mar - 26 May
$176pp
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
16 Mar - 23 Mar
$186pp
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
18 May - 25 May
$217pp
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

16 Mar - 23 Mar
$186pp
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
16 Mar - 23 Mar
$317pp
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
16 Mar - 20 Mar
$329pp
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

8:41 am - 6:04 pm
Delta
1 Stop
8h 23m
MDW - SJU
Delta
$83
Delta
10:21 am - 6:56 pm
Delta
1 Stop
7h 35m
MDW - SJU
Delta
$92
Delta
10:21 am - 6:56 pm
Delta
1 Stop
7h 35m
MDW - SJU
Delta
$93
Delta

Related info for your journey

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?

Delta is one 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 $200 on Cheapflights?

Yes, there are multiple flights from Chicago Midway to Puerto Rico for under $200. The cheapest flight booked recently is on Delta for just $176, but on average you can expect to pay $259.

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

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

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 $310, 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 $186 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 6h 16m. 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 $176, 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 $83.

Destination points for flights from Chicago Midway to Puerto Rico

Destination information for 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