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

All the information you need to plan the best MDW to SJU flight in 2021: compare Chicago Midway to Puerto Rico flight prices with the expected peak season, weather and rainfall in 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 June, July 2021

The best prices found for MDW to Puerto Rico flights for June, July
28 Jul - 11 Aug
$318pp
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
31 Jul - 11 Aug
$341pp
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 Jul - 4 Aug
$378pp
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

Cheap flights to Puerto Rico from Chicago Midway found for this year
21 Sep - 25 Sep
$178pp
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 Sep - 15 Sep
$198pp
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
17 Aug - 24 Aug
$218pp
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
28 Jun - 3 Jul
$458pp
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 Jun - 4 Jul
$498pp
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 Jun - 17 Jul
$501pp
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
2:00 am - 9:25 am
Delta
1 Stop
6h 25m
MDW - SJU
Delta
$89
Delta
2:00 am - 12:07 pm
Delta
1 Stop
9h 07m
MDW - SJU
Delta
$109
Delta
8:35 am - 7:30 pm
Delta
1 Stop
9h 55m
MDW - SJU
Delta
$129
Delta

Related info for your journey

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

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 $178, but on average you can expect to pay $284.

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 $500?

There are currently 20+ open flights from Chicago Midway to Puerto Rico within the next 7 days for less than $500.

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

Nonstop flights are available for this route on the following days: Saturday.

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 $309, our data shows the cheapest flight currently is $218. When looking at the most popular route, (Chicago Midway - San Juan Luis Munoz Marin Intl), you can expect to pay $178 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 23m. 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 $178, 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 $89.

Destination points for flights from Chicago Midway to Puerto Rico

Select to see more specific information for flights from Chicago Midway to all places in Puerto Rico.

Destination information for Puerto Rico

Things to know before you go - useful duration and weather info for your trip from Chicago Midway to Puerto Rico.
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Airports servicing Chicago

Airports servicing

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