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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 July, August 2020

The best prices found for MDW to Puerto Rico flights for July, August
2 Jul - 7 Jul
$479pp
MDW
Chicago Midway
Multiple Airlines
   
2 STOPS
SJU
San Juan Luis Munoz Marin Intl
SJU
San Juan Luis Munoz Marin Intl
Multiple Airlines
     
3 STOPS
MDW
Chicago Midway
28 Jun - 10 Jul
$488pp
MDW
Chicago Midway
Multiple Airlines
   
2 STOPS
SJU
San Juan Luis Munoz Marin Intl
SJU
San Juan Luis Munoz Marin Intl
Multiple Airlines
     
3 STOPS
MDW
Chicago Midway
25 Jun - 30 Jun
$494pp
MDW
Chicago Midway
Multiple Airlines
     
3 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
21 Sep - 28 Sep
$330pp
MDW
Chicago Midway
Multiple Airlines
   
2 STOPS
SJU
San Juan Luis Munoz Marin Intl
SJU
San Juan Luis Munoz Marin Intl
Multiple Airlines
 
1 STOP
MDW
Chicago Midway
17 Sep - 25 Sep
$347pp
MDW
Chicago Midway
Multiple Airlines
   
2 STOPS
SJU
San Juan Luis Munoz Marin Intl
SJU
San Juan Luis Munoz Marin Intl
Multiple Airlines
 
1 STOP
MDW
Chicago Midway
7 Aug - 19 Aug
$365pp
MDW
Chicago Midway
Multiple Airlines
     
3 STOPS
SJU
San Juan Luis Munoz Marin Intl
SJU
San Juan Luis Munoz Marin Intl
Multiple Airlines
     
3 STOPS
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 - 10 Jul
$488pp
MDW
Chicago Midway
Multiple Airlines
   
2 STOPS
SJU
San Juan Luis Munoz Marin Intl
SJU
San Juan Luis Munoz Marin Intl
Multiple Airlines
     
3 STOPS
MDW
Chicago Midway
25 Jun - 30 Jun
$494pp
MDW
Chicago Midway
Multiple Airlines
     
3 STOPS
SJU
San Juan Luis Munoz Marin Intl
SJU
San Juan Luis Munoz Marin Intl
Multiple Airlines
   
2 STOPS
MDW
Chicago Midway
28 Jun - 10 Jul
$518pp
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

One-way flights to Puerto Rico from Chicago Midway

The cheapest one-way flights from Chicago Midway to Puerto Rico
3:45 pm - 3:19 pm
Multiple Airlines
2 Stops
46h 34m
MDW - SJU
Multiple Airlines
$277
Kiwi.com
11:21 am - 9:06 am
Multiple Airlines
2 Stops
44h 45m
MDW - SJU
Multiple Airlines
$278
Kiwi.com
9:08 am - 6:28 am
Multiple Airlines
2 Stops
20h 20m
MDW - SJU
Multiple Airlines
$291
FlyFar

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.

Can I find flights from Chicago Midway to Puerto Rico for under $400 on Cheapflights?

Yes, there are multiple flights from Chicago Midway to Puerto Rico for under $400. The cheapest flight booked recently is on Multiple Airlines for just $330, but on average you can expect to pay $464.

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 $500?

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

How popular is this flight route?

Within the past month, 763 users have taken a look at flights from Chicago Midway to Puerto Rico.

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

American Airlines, JetBlue and Frontier 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 $543, our data shows the cheapest flight currently is $204. When looking at the most popular route, (Chicago Midway - San Juan Luis Munoz Marin Intl), you can expect to pay $265 for that flight.

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)