HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
San Juan

$88+ Cheap flights from Midway (MDW) to San Juan

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 1/10. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — SJU
Nov 25 — Dec 21
Mon 11/25
Mon 12/2
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Midway to San Juan with Cheapflights

1. Tell us where you want to go
Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”
2. Select your favorite providers
We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.
3. Compare prices and book
Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

The best prices from Chicago Midway to San Juan are usually found in January or May, booked 66 days in advance, depart on a Sunday or Tuesday and return on a Sunday

Cheap flight deals from Midway to San Juan

Discover tips and strategies to find the most affordable flight options for your journey from Midway (MDW) to San Juan (PR1). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated November 20, 2024.

Popular in

March

Cheapest in

January

Round-trip from

$174
(Trip.com)

One-way from

$88
(Trip.com)
High demand for flights, 25% potential price rise
Search Deals
Best time to find cheap flights, 30% potential price drop
Search Deals
From Chicago Midway to San Juan
Search Deals
One-way flight from Chicago Midway to San Juan
Search Deals

Find flight deals from Midway to San Juan

Cheapest flights from Midway to San Juan
Explore the most affordable flight options available from Midway to San Juan. Find the lowest fares from popular airlines and budget airlines, with prices last updated on November 20, 2024.

This Trip.com deal was found by Cheapflights users on 11/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/167:25 amMDW - SJU
1 stop16h 32mFrontier
Thu 12/193:59 amSJU - MDW
1 stop7h 32mFrontier
Deal found 11/20$174
This eDestinos deal was found by Cheapflights users on 11/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/1512:36 pmMDW - SJU
2 stops35h 21mMultiple Airlines
Wed 1/224:53 pmSJU - MDW
2 stops27h 33mMultiple Airlines
Deal found 11/19$240
This Southwest deal was found by Cheapflights users on 11/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/121:30 pmMDW - SJU
1 stop9h 15mSouthwest
Sat 12/147:20 amSJU - MDW
2 stops8h 50mSouthwest
Deal found 11/19$297
This Delta deal was found by Cheapflights users on 11/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/106:00 amMDW - SJU
1 stop9h 15mDelta
Mon 12/163:25 pmSJU - MDW
1 stop8h 41mDelta
Deal found 11/20$379

Find flights from Midway to San Juan within your budget

Customize your flight search to find flights from Midway to San Juan that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,629,791 searches. Data last updated November 20, 2024.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Mon 12/16

7:25 am-1:57 am

1 stop16h 32m

San Juan Luis Munoz Marin Intl

Fri 12/20

6:00 am-1:06 pm

1 stop9h 06m

$174

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Sun 2/2

1:20 pm-12:50 am

2 stops9h 30m

San Juan Luis Munoz Marin Intl

Wed 2/5

2:55 pm-7:45 pm

1 stop6h 50m

$210

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Thu 1/9

3:04 pm-6:02 pm

1 stop24h 58m

San Juan Luis Munoz Marin Intl

Sat 1/25

8:00 am-11:29 pm

2 stops17h 29m

$239

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Tue 1/28

6:00 am-2:20 pm

1 stop6h 20m

San Juan Luis Munoz Marin Intl

Fri 2/7

2:02 pm-10:20 pm

1 stop10h 18m

$334

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Fri 1/10

6:45 am-1:57 am

1 stop17h 12m

$88

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Wed 1/22

10:05 am-12:25 am

2 stops12h 20m

$105

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Sat 1/4

4:08 pm-10:47 am

2 stops40h 39m

$124

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Tue 1/14

6:00 am-2:20 pm

1 stop6h 20m

$162

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Sat 3/22

9:20 am-1:05 pm

2 stops26h 45m

$409

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/19

Best time to book a flight from Midway to San Juan

Have a flexible travel schedule? Discover the best time to fly to San Juan from Midway with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Travel insights for flights from Midway to San Juan

Get recent, data-driven insights about flights from Midway to San Juan including ideal travel times, pricing trends, and more.

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

Use this chart to determine the optimal time to book a round-trip flight from Midway to San Juan. Price data was last updated on November 15, 2024.

The best time to book flights from Chicago Midway Airport to San Juan is 66 days before your desired departure date. The cost of your flight will likely increase significantly if you book two weeks in advance of your flight.

What is the cheapest month to book a flight from Chicago Midway Airport to San Juan?

Currently, September is the cheapest month in which you can book a flight from Chicago Midway Airport to San Juan (average of $254). Flying from Chicago Midway Airport to San Juan in March is currently the most expensive (average of $335). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

What is the cheapest time of day to fly from MDW to SJU?

Find hourly flight availability from Midway to San Juan. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated November 20, 2024.

It’s typically best to fly out from Chicago Midway Airport to San Juan in the morning. Doing so could potentially save you 27% on the flight price compared to flying at noon, which is usually more expensive.

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

Use this chart to determine the cheapest time to fly round-trip from Midway to San Juan. Price data was last updated on November 18, 2024.

Travelers seeking maximum savings on their Chicago Midway Airport to San Juan flight should consider departing on Tuesday evenings when fares are most often at their lowest. Tuesday at noon flights should be avoided if possible as fares are typically the most expensive at this time.

Rainfall in San Juan by month

Plan your trip to San Juan by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in San Juan ranges from 2.2 - 6.1 inches per month. November is typically the wettest month, when rainfall can reach 6.1 in. February is typically the driest time to visit San Juan when rainfall is around 2.2 in.

Temperature in San Juan by month

Plan your trip to San Juan by taking into account the average temperature totals by month.

If weather is an important factor for your trip to San Juan, use this chart to help with planning. For those seeking warmer temperatures, June is the ideal time of year to visit, when temperatures reach an average of 82.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 77.0 F).

Reviews of airlines servicing San Juan

Get insights into the airlines that provide service to San Juan. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to San Juan. Reviews last updated November 20, 2024.
Read reviews from past customers who have flown Frontier, Delta and Southwest from Chicago to San Juan. In addition to providing an overall rating, users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.1
Very good
5,014 reviews

Boarding

8.2

Overall

8.1

Crew

8.7

Entertainment

7.7

Comfort

8.1

Food

7.2

Reviews

1 / 10

Great service throughout our flight. Easy boarding with early bird check in

Southwest
8.1
Very good
5,014 reviews
Southwest
8.1
Very good
5,014 reviews

Boarding

8.2

Overall

8.1

Crew

8.7

Entertainment

7.7

Comfort

8.1

Food

7.2

Reviews

1 / 10

Great service throughout our flight. Easy boarding with early bird check in

Delta
8.0
Very good
8,756 reviews
Southwest
8.1
Very good
5,014 reviews

Boarding

8.2

Overall

8.1

Crew

8.7

Entertainment

7.7

Comfort

8.1

Food

7.2

Reviews

1 / 10

Great service throughout our flight. Easy boarding with early bird check in

Frontier
6.1
Okay
3,539 reviews
Southwest
8.1
Very good
5,014 reviews

Boarding

8.2

Overall

8.1

Crew

8.7

Entertainment

7.7

Comfort

8.1

Food

7.2

Reviews

1 / 10

Great service throughout our flight. Easy boarding with early bird check in

Related info for your journey

Find useful and relevant information for your journey from Midway to San Juan. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What are the cheapest airlines flying from Chicago Midway Airport to San Juan round-trip?

    Frontier, at $174, was found to be the cheapest airline from Chicago Midway Airport to San Juan.Alternate airlines to your destination round-trip include Southwest and Delta. You may be able to fly from Chicago Midway Airport to San Juan for 48% less than the average price by searching for these airlines.

  • What are the cheapest airlines to fly from Chicago Midway Airport to San Juan one-way?

    $88 is the cheapest one-way deal found within the past few days, from Frontier. You may also be able to find cheap deals on Southwest and Delta, with prices starting from $105 and $162, respectively.

  • Can I find deals for flights from Midway to San Juan that include hotel bookings?

    Yes. In addition to deals on Midway to San Juan flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Midway to San Juan?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Midway to San Juan.

  • Can I find deals for business class flights from Midway to San Juan?

    Yes. Cheapflights offers flight deals from Midway to San Juan by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Chicago Midway Airport to San Juan?

    Currently, September is the cheapest month in which you can book a flight from Chicago Midway Airport to San Juan (average of $254). Flying from Chicago Midway Airport to San Juan in March is currently the most expensive (average of $335). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Top 4 airlines flying from Midway to San Juan

Discover the top 4 airlines that operate flights from Midway to San Juan. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,629,791 searches. Data last updated November 20, 2024.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$119Average$280FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$199Average$277FlexibilityNo cancel feeOn-time65%
SouthwestCheapest$275Average$416FlexibilityNo cancel feeOn-time63%
DeltaCheapest$374Average$674FlexibilityNo cancel feeOn-timeN/A
100% Free
Cheapflights is completely free to use, so you can start saving the moment you arrive.
Book with Flexibility
Our users can plan ahead with confidence and find flights with no change fees
Travel Smart
Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.
View all available airlines