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

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

All the information you need to plan the best SJU to MDW flight in 2022: compare San Juan to Midway flight prices with the expected peak season, weather and rainfall in Midway.
SJU - MDW
Price
$298 - $769
MDW
Temperature
23 - 73.4 °F
MDW
Rainfall
1.7 - 4.9 inches

Popular in

November

High demand for flights, 34% potential price rise

Cheapest in

January

Best time to find cheap flights, 41% potential price drop

Round-trip from

$298

From San Juan to Chicago Midway

One-way from

$155

One-way flight from San Juan to Chicago Midway

Flight route prices based on searches on Cheapflights within the last 3 days, monthly prices based on aggregated historical data.
When is the cheapest time to fly from San Juan to Chicago Midway Airport (SJU - MDW)?

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

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

Flights from San Juan to Chicago Midway Airport lean towards being more expensive in June. Prices are generally better when you fly from San Juan to Chicago Midway Airport in October, with the cheapest ticket starting at $104.

How far in advance should I book a flight from San Juan to Chicago Midway Airport?

To save on the cost of your flight from San Juan to Chicago Midway Airport, book at least 43 days before your planned departure. Booking around this time can save you about 29% on the cost of this flight compared to booking a flight leaving this week. We have found prices from $343 if you need a flight within two weeks. For flights within the next 72 hours, you can find tickets from as low as $386.

Cheap flights from San Juan to Midway in June, July 2022

The best prices found for SJU to MDW flights for June, July
11 Jul - 14 Jul
$399pp
SJU
San Juan Luis Munoz Marin Intl
Multiple Airlines
 
1 STOP
MDW
Chicago Midway
MDW
Chicago Midway
Frontier
 
1 STOP
SJU
San Juan Luis Munoz Marin Intl
18 Jul - 25 Jul
$402pp
SJU
San Juan Luis Munoz Marin Intl
Multiple Airlines
 
1 STOP
MDW
Chicago Midway
MDW
Chicago Midway
Frontier
 
1 STOP
SJU
San Juan Luis Munoz Marin Intl
18 Jul - 20 Jul
$405pp
SJU
San Juan Luis Munoz Marin Intl
Multiple Airlines
 
1 STOP
MDW
Chicago Midway
MDW
Chicago Midway
Frontier
 
1 STOP
SJU
San Juan Luis Munoz Marin Intl

San Juan to Midway 2022 flight deals

Cheap flights to Midway from San Juan found for this year
14 Sep - 20 Sep
$365pp
SJU
San Juan Luis Munoz Marin Intl
Multiple Airlines
 
1 STOP
MDW
Chicago Midway
MDW
Chicago Midway
Multiple Airlines
   
2 STOPS
SJU
San Juan Luis Munoz Marin Intl
12 Aug - 16 Aug
$382pp
SJU
San Juan Luis Munoz Marin Intl
Multiple Airlines
   
2 STOPS
MDW
Chicago Midway
MDW
Chicago Midway
Frontier
 
1 STOP
SJU
San Juan Luis Munoz Marin Intl
19 Aug - 22 Aug
$383pp
SJU
San Juan Luis Munoz Marin Intl
Multiple Airlines
 
1 STOP
MDW
Chicago Midway
MDW
Chicago Midway
Frontier
 
1 STOP
SJU
San Juan Luis Munoz Marin Intl

Non-stop flights to Midway from San Juan

Save time with San Juan to Midway direct flight deals
8 Jul - 11 Jul
$2,925pp
SJU
San Juan Luis Munoz Marin Intl
Major Airline
Non-Stop
MDW
Chicago Midway
MDW
Chicago Midway
Major Airline
Non-Stop
SJU
San Juan Luis Munoz Marin Intl
8 Jul - 11 Jul
$2,928pp
SJU
San Juan Luis Munoz Marin Intl
Major Airline
Non-Stop
MDW
Chicago Midway
MDW
Chicago Midway
Major Airline
Non-Stop
SJU
San Juan Luis Munoz Marin Intl
8 Jul - 11 Jul
$2,936pp
SJU
San Juan Luis Munoz Marin Intl
Major Airline
Non-Stop
MDW
Chicago Midway
MDW
Chicago Midway
Major Airline
Non-Stop
SJU
San Juan Luis Munoz Marin Intl

Last minute flights from San Juan to Midway

Late deals on round-trip flights to Midway from San Juan, departing today and this week
8 Jul - 11 Jul
$429pp
SJU
San Juan Luis Munoz Marin Intl
Multiple Airlines
   
2 STOPS
MDW
Chicago Midway
MDW
Chicago Midway
Frontier
 
1 STOP
SJU
San Juan Luis Munoz Marin Intl
8 Jul - 11 Jul
$430pp
SJU
San Juan Luis Munoz Marin Intl
Multiple Airlines
   
2 STOPS
MDW
Chicago Midway
MDW
Chicago Midway
Frontier
 
1 STOP
SJU
San Juan Luis Munoz Marin Intl
8 Jul - 11 Jul
$446pp
SJU
San Juan Luis Munoz Marin Intl
Multiple Airlines
   
2 STOPS
MDW
Chicago Midway
MDW
Chicago Midway
Frontier
 
1 STOP
SJU
San Juan Luis Munoz Marin Intl

One-way flights to Midway from San Juan

The cheapest one-way flights from San Juan to Midway
3:00 am - 12:16 pm
Delta
1 Stop
10h 16m
SJU - MDW
Delta
$155
Delta
10:26 pm - 2:38 am
Frontier
1 Stop
29h 12m
SJU - MDW
Frontier
$233
Kiwi.com
6:17 am - 4:10 am
Multiple Airlines
3 Stops
22h 53m
SJU - MDW
Multiple Airlines
$234
Kiwi.com

Related info for your journey

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

Flight FAQs

From San Juan to Midway

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

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

Can I find flights from San Juan to Chicago Midway Airport for under $400 on Cheapflights?

Yes, there are multiple flights from San Juan to Chicago Midway Airport for under $400. The cheapest flight booked recently is on Multiple Airlines for just $365, but on average you can expect to pay $399.

Are there nonstop flights from San Juan to Chicago Midway Airport for under $3,000 on Cheapflights?

Cheapflights has at least 3 direct flights from San Juan to Chicago Midway Airport under $3,000. A good price for a nonstop flight from San Juan to Chicago Midway Airport is less than $2,929.

Are there last-minute flights available from San Juan to Chicago Midway Airport for under $500?

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

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

Flying on Frontier is currently your cheapest option to Chicago Midway Airport, with prices starting at $414. You may be able to fly from San Juan to Chicago Midway Airport for 18% less than the average price by searching for this airline.

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

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

Related searches

Flights to Midway from San Juan
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Rent a Car

Car Rentals at Midway Car Rentals in Illinois

COVID Restrictions

View COVID Travel Restrictions for Midway (MDW)

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

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

Most visitors from San Juan can enter Chicago Midway without restrictions.

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.

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

Returning to San Juan from Chicago Midway

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.

Hide COVID Travel Restrictions for Midway (MDW)

Destination information for Midway

Things to know before you go - useful duration and weather info for your trip from San Juan to Midway.
Today's exchange rate
$1 = $1.00
Average temperature for June in Midway
78.8 °F
Avg rainfall for June in Midway
3.4 ″

Airports servicing San Juan

San Juan Isla Grande (SIG)

Airports servicing Chicago

Hourly flight availability from San Juan to Midway

See what time of day planes typically take off from San Juan towards Midway.
Early morning Midnight to 6 AM 100% of SJU to MDW departures
Morning 6 AM to noon 0% of SJU to MDW departures
Afternoon Noon to 6 PM 0% of SJU to MDW departures
Evening 6 PM to midnight 0% of SJU to MDW departures
Midnight
6 AM
Noon
6 PM
Weekly flight availability
from San Juan to Midway
See how many times per day planes take to the skies headed from San Juan to Midway.
Sunday
2 daily flights
Monday
2 daily flights
Tuesday
2 daily flights
Wednesday
2 daily flights
Thursday
2 daily flights
Friday
2 daily flights
Saturday
0 flights