Cheap flights from Midway (MDW) to San Juan (SJU)

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How to find the cheapest flight from
Midway (MDW) to San Juan (SJU)

All the information you need to plan the best MDW to SJU flight in 2021: compare Midway to San Juan flight prices with the expected peak season, weather and rainfall in San Juan.
MDW - PR1
Price
$281 - $985
PR1
Temperature
77 - 82.4 °F
PR1
Precipitation
2.2 - 6.1 inches

Popular in

May

High demand for flights, 49% potential price rise

Cheapest in

July

Best time to find cheap flights, 44% potential price drop

Average price

$586

Average for round-trip flights in December 2021

Round-trip from

$281

From Chicago Midway to San Juan

Flight route prices based on searches on Cheapflights within the last 3 days, monthly prices based on aggregated historical data.
How far in advance should I book a flight from Chicago Midway Airport to San Juan?

To save on the cost of your flight from Chicago Midway Airport to San Juan, book at least 18 days before your planned departure. Booking around this time can save you about 13% on the cost of this flight compared to booking a flight leaving this week. We have found prices from $256 if you need a flight within two weeks. For flights within the next 72 hours, you can find tickets from as low as $302.

When is the cheapest time to fly from Chicago Midway Airport to San Juan (MDW - PR1)?

Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Chicago Midway Airport to San Juan as you normally would.

What is the cheapest month to fly from Chicago Midway Airport to San Juan?

Our data shows that August tends to be the cheapest month to fly to San Juan from Chicago Midway Airport. Users have commonly found prices around $307 for the month, but tickets can be as low as $118. Due to multiple factors, prepare for potentially higher prices in December.

Cheap flights from Midway to San Juan in December, January 2022

The best prices found for MDW to SJU flights for December, January
26 Jan - 1 Feb
$255pp
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
20 Jan - 26 Jan
$258pp
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 Jan - 24 Jan
$265pp
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

Chicago Midway to San Juan 2022 flight deals

Cheap flights to San Juan from Midway found for this year
13 Dec - 19 Dec
$323pp
MDW
Chicago Midway
Multiple Airlines
 
1 STOP
SJU
San Juan Luis Munoz Marin Intl
SJU
San Juan Luis Munoz Marin Intl
Multiple Airlines
 
1 STOP
MDW
Chicago Midway
11 Dec - 18 Dec
$326pp
MDW
Chicago Midway
Multiple Airlines
     
3 STOPS
SJU
San Juan Luis Munoz Marin Intl
SJU
San Juan Luis Munoz Marin Intl
Multiple Airlines
 
1 STOP
MDW
Chicago Midway
13 Dec - 19 Dec
$331pp
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

Non-stop flights to San Juan from Midway

Save time with Midway to San Juan direct flight deals
1 Jan - 8 Jan
$693pp
MDW
Chicago Midway
Frontier
Non-Stop
SJU
San Juan Luis Munoz Marin Intl
SJU
San Juan Luis Munoz Marin Intl
Frontier
Non-Stop
MDW
Chicago Midway
27 Dec - 30 Dec
$927pp
MDW
Chicago Midway
Frontier
Non-Stop
SJU
San Juan Luis Munoz Marin Intl
SJU
San Juan Luis Munoz Marin Intl
Frontier
Non-Stop
MDW
Chicago Midway
27 Dec - 1 Jan
$1,037pp
MDW
Chicago Midway
Frontier
Non-Stop
SJU
San Juan Luis Munoz Marin Intl
SJU
San Juan Luis Munoz Marin Intl
Frontier
Non-Stop
MDW
Chicago Midway

Last minute flights from Midway to San Juan

Late deals on round-trip flights to San Juan from Midway, departing today and this week
13 Dec - 19 Dec
$323pp
MDW
Chicago Midway
Multiple Airlines
 
1 STOP
SJU
San Juan Luis Munoz Marin Intl
SJU
San Juan Luis Munoz Marin Intl
Multiple Airlines
 
1 STOP
MDW
Chicago Midway
11 Dec - 18 Dec
$326pp
MDW
Chicago Midway
Multiple Airlines
     
3 STOPS
SJU
San Juan Luis Munoz Marin Intl
SJU
San Juan Luis Munoz Marin Intl
Multiple Airlines
 
1 STOP
MDW
Chicago Midway
13 Dec - 19 Dec
$331pp
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

One-way flights to San Juan from Chicago Midway

The cheapest one-way flights from Midway to San Juan
1:00 am - 12:10 pm
Delta
1 Stop
9h 10m
MDW - SJU
Delta
$389
Delta
1:05 am - 12:45 pm
Frontier
1 Stop
9h 40m
MDW - SJU
Frontier
$393
flightschannel
2:44 am - 8:03 pm
Multiple Airlines
3 Stops
15h 19m
MDW - SJU
Multiple Airlines
$398
mytrip.com

Related info for your journey

Useful info, stats and facts about <span class="emphasized">Midway</span> to <span class="emphasized">San Juan</span> flights.

Flight FAQs

From Midway to San Juan

Which airlines flying from Chicago Midway to San Juan have flexible cancellations due to COVID-19?

Some of the carriers operating flights from Chicago Midway to San Juan that may be offering flexible cancellation policies are Delta, United Airlines, and American Airlines. Our site will let you filter for all airlines offering greater flexibility due to COVID-19.

Can I find flights from Chicago Midway Airport to San Juan for under $300 on Cheapflights?

Yes, there are multiple flights from Chicago Midway Airport to San Juan for under $300. The cheapest flight booked recently is on Multiple Airlines for just $255, but on average you can expect to pay $276.

Are there nonstop flights from Chicago Midway Airport to San Juan for under $700 on Cheapflights?

Cheapflights has at least 3 direct flights from Chicago Midway Airport to San Juan under $700. A good price for a nonstop flight from Chicago Midway Airport to San Juan is less than $885.

Are there last-minute flights available from Chicago Midway Airport to San Juan for under $400?

There are currently 20+ open flights from Chicago Midway Airport to San Juan within the next 7 days for less than $400.

What is the cheapest airline to fly from Chicago Midway Airport to San Juan round-trip?

Delta, at $258, was found to be the cheapest airline from Chicago Midway Airport to San Juan.. You may be able to fly from Chicago Midway Airport to San Juan for 48% less than the average price by searching for this airline.

What are the cheapest flights from Chicago Midway Airport to San Juan?

The cheapest flight price from Chicago Midway Airport to San Juan is $126. On average you can expect to pay $273. The most popular route, (Chicago Midway - San Juan Luis Munoz Marin Intl), can usually be booked for $258.

What are the most popular airlines that fly from Chicago Midway Airport to San Juan?

The most popular airlines flying from Chicago Midway Airport to San Juan are American Airlines, JetBlue and Delta. Something to consider prior to booking your flight.

COVID Restrictions

View COVID Travel Restrictions for San Juan, Puerto Rico

Do I need a COVID test to fly to San Juan from Midway?

Information is based on travel restrictions from Chicago Midway to San Juan

Most visitors from Chicago Midway need to provide a negative COVID-19 test result and/or quarantine to enter San Juan.

COVID-19 testing requirements
Visitors from Chicago Midway must present a negative RT-PCR (NAAT) test taken 72 hours before departing to San Juan.

Quarantine requirements
Visitors from Chicago Midway are not required to quarantine after entering San Juan.

Documents
Travel Declaration Form - Must be completed prior to travel to Puerto Rico.


Do I need a test to fly back to Midway from San Juan?

Returning to Chicago Midway from San Juan

COVID-19 testing requirements
Visitors from San Juan must present a negative RT-PCR (NAAT) or Antigen (quick-test) test taken 24 hours before departing to Chicago Midway.

Quarantine requirements
Visitors from San Juan are not required to quarantine after entering Chicago Midway.

Hide COVID Travel Restrictions for San Juan, Puerto Rico

Alternative routes for Midway to San Juan

See prices for flight routes from nearby airports that may be better suited for you.

Destination information for San Juan

Things to know before you go - useful duration and weather info for your trip from Midway to San Juan.
Today's exchange rate
$1 = $1.00
Average temperature for December in San Juan
84.2 °F
Avg rainfall for December in San Juan
4.2 ″

Airports servicing Chicago

Airports servicing San Juan

San Juan Isla Grande (SIG)

Hourly flight availability from Midway to San Juan

See what time of day planes typically take off from Midway towards San Juan.
Early morning Midnight to 6 AM 84% of MDW to SJU departures
Morning 6 AM to noon 16% of MDW to SJU departures
Afternoon Noon to 6 PM 0% of MDW to SJU departures
Evening 6 PM to midnight 0% of MDW to SJU departures
Midnight
6 AM
Noon
6 PM
Weekly flight availability
from Midway to San Juan
See how many times per day planes take to the skies headed from Midway to San Juan.
Sunday
0 flights
Monday
1 daily flight
Tuesday
1 daily flight
Wednesday
1 daily flight
Thursday
1 daily flight
Friday
1 daily flight
Saturday
2 daily flights
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