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 2022: compare Midway to San Juan flight prices with the expected peak season, weather and rainfall in San Juan.
MDW - SJU
Price
$329 - $741
SJU
Temperature
77 - 82.4 °F
SJU
Rainfall
2.2 - 6.1 inches

Popular in

July

High demand for flights, 30% potential price rise

Cheapest in

November

Best time to find cheap flights, 37% potential price drop

Round-trip from

$329

From Chicago Midway to San Juan

One-way from

$101

One-way flight 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?

When searching for a good deal, it’s best to be prepared for potential fluctuations in price. We recommend booking at least 61 days in advance, which can save you up to 20% on flights from Chicago Midway Airport to San Juan compared to booking the week you need them. Waiting 61 days out may not be for everyone, so we have options available for flights within the next two weeks, with the lowest price starting at $357. For sooner than that we have options available in the next 3 days from $410.

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

Due to multiple factors, expect to potentially pay more when booking in June. For low rates, September can be a great choice for travel to San Juan. Flights to San Juan from Chicago Midway Airport in September are about $328 on average during September, but can be found for as low as $124.

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

When flying from Chicago Midway Airport to San Juan, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

Cheap flights from Midway to San Juan in August, September 2022

The best prices found for MDW to SJU flights for August, September
24 Aug - 30 Aug
$201pp
MDW
Chicago Midway
Frontier
 
1 STOP
SJU
San Juan Luis Munoz Marin Intl
SJU
San Juan Luis Munoz Marin Intl
Frontier
 
1 STOP
MDW
Chicago Midway
3 Sep - 7 Oct
$209pp
MDW
Chicago Midway
Frontier
 
1 STOP
SJU
San Juan Luis Munoz Marin Intl
SJU
San Juan Luis Munoz Marin Intl
Frontier
 
1 STOP
MDW
Chicago Midway
14 Sep - 20 Sep
$211pp
MDW
Chicago Midway
Frontier
 
1 STOP
SJU
San Juan Luis Munoz Marin Intl
SJU
San Juan Luis Munoz Marin Intl
Frontier
 
1 STOP
MDW
Chicago Midway

Chicago Midway to San Juan 2022 flight deals

Cheap flights to San Juan from Midway found for this year
24 Aug - 30 Aug
$201pp
MDW
Chicago Midway
Frontier
 
1 STOP
SJU
San Juan Luis Munoz Marin Intl
SJU
San Juan Luis Munoz Marin Intl
Frontier
 
1 STOP
MDW
Chicago Midway
3 Sep - 7 Oct
$209pp
MDW
Chicago Midway
Frontier
 
1 STOP
SJU
San Juan Luis Munoz Marin Intl
SJU
San Juan Luis Munoz Marin Intl
Frontier
 
1 STOP
MDW
Chicago Midway
14 Sep - 20 Sep
$211pp
MDW
Chicago Midway
Frontier
 
1 STOP
SJU
San Juan Luis Munoz Marin Intl
SJU
San Juan Luis Munoz Marin Intl
Frontier
 
1 STOP
MDW
Chicago Midway

Cheap Frontier flights from Midway to San Juan

24 Aug - 30 Aug
$201pp
MDW
Chicago Midway
Frontier
 
1 STOP
SJU
San Juan Luis Munoz Marin Intl
SJU
San Juan Luis Munoz Marin Intl
Frontier
 
1 STOP
MDW
Chicago Midway
3 Sep - 7 Oct
$209pp
MDW
Chicago Midway
Frontier
 
1 STOP
SJU
San Juan Luis Munoz Marin Intl
SJU
San Juan Luis Munoz Marin Intl
Frontier
 
1 STOP
MDW
Chicago Midway
19 Oct - 25 Oct
$217pp
MDW
Chicago Midway
Frontier
 
1 STOP
SJU
San Juan Luis Munoz Marin Intl
SJU
San Juan Luis Munoz Marin Intl
Frontier
 
1 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
24 Aug - 30 Aug
$201pp
MDW
Chicago Midway
Frontier
 
1 STOP
SJU
San Juan Luis Munoz Marin Intl
SJU
San Juan Luis Munoz Marin Intl
Frontier
 
1 STOP
MDW
Chicago Midway
25 Aug - 30 Aug
$215pp
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
25 Aug - 30 Aug
$222pp
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

One-way flights to San Juan from Chicago Midway

The cheapest one-way flights from Midway to San Juan
4:00 pm - 4:20 pm
Frontier
1 Stop
23h 20m
MDW - SJU
Frontier
$101
Kiwi.com
3:47 pm - 4:20 pm
Frontier
1 Stop
23h 33m
MDW - SJU
Frontier
$102
Kiwi.com
2:44 pm - 3:36 pm
Frontier
1 Stop
23h 52m
MDW - SJU
Frontier
$104
Kiwi.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, American Airlines, and Frontier. 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 Frontier for just $209, but on average you can expect to pay $230.

Are there last-minute flights available from Chicago Midway Airport to San Juan for under $300?

There are currently 20+ open flights from Chicago Midway Airport to San Juan within the next 7 days for less than $300.

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

Frontier, at $209, 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 59% 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 $16. On average you can expect to pay $309. The most popular route, (Chicago Midway - San Juan Luis Munoz Marin Intl), can usually be booked for $220.

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, Alaska Airlines and JetBlue. 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 can enter San Juan without restrictions.

COVID-19 testing requirements
Visitors from Chicago Midway are not required to present a negative COVID-19 PCR test or antigen result upon entering 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 are not required to present a negative COVID-19 PCR test or antigen result upon entering 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.

Top 5 airlines flying from Chicago Midway to San Juan

The chart below displays the airlines Cheapflights users traveling from Midway to San Juan choose most often. Cheapest and average prices are based on aggregated data from the past 12 months.
Airline Cheapest Average Flexibility On-time COVID-19 safety
Juneyao Airlines
$11 $20 No cancel fee 66%

We couldn't confirm the COVID-19 safety measures taken by Juneyao Airlines. Please check directly on their website for additional information.

Frontier
$234 $410 No cancel fee 62%
Delta
$257 $756 No cancel fee N/A
American Airlines
$343 $400 No cancel fee 71%
United Airlines
$450 $785 No cancel fee 69%
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