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$82+ Cheap flights from Midway (MDW) to Puerto Rico

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 3/2. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — SJU
Jan 26 — Feb 21
Sun 1/26
Sun 2/2
1 adult, Economy
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Cheap flight deals from Midway to Puerto Rico

Discover tips and strategies to find the most affordable flight options for your journey from Midway (MDW) to Puerto Rico (PR0). 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 January 21, 2025.

Round-trip from

$160
(FlightHub)

One-way from

$83
(Cheapflightsfares)
From Chicago Midway to Puerto Rico
Search Deals
One-way flight from Chicago Midway to Puerto Rico
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Find flight deals from Midway to Puerto Rico

Cheapest flights from Midway to Puerto Rico
Explore the most affordable flight options available from Midway to Puerto Rico. Find the lowest fares from popular airlines and budget airlines, with prices last updated on January 21, 2025.

This FlightHub deal was found by Cheapflights users on 1/21. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/12:36 pmMDW - SJU
1 stop8h 18mFrontier
Mon 4/75:01 amSJU - MDW
1 stop15h 45mFrontier
Deal found 1/21$160
This Southwest deal was found by Cheapflights users on 1/20. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 2/21:20 pmMDW - SJU
2 stops9h 30mSouthwest
Fri 2/71:45 pmSJU - MDW
1 stop10h 15mSouthwest
Deal found 1/20$235
This Delta deal was found by Cheapflights users on 1/21. 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 1/286:00 amMDW - SJU
1 stop9h 14mDelta
Fri 2/77:30 amSJU - MDW
1 stop10h 50mDelta
Deal found 1/21$325

Find flights from Midway to Puerto Rico within your budget

Customize your flight search to find flights from Midway to Puerto Rico 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 2,558,603 searches. Data last updated January 21, 2025.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Tue 4/1

2:36 pm-11:54 pm

1 stop8h 18m

San Juan Luis Munoz Marin Intl

Mon 4/7

5:01 am-7:46 pm

1 stop15h 45m

$160

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

Fri 2/7

1:45 pm-10:00 pm

1 stop10h 15m

$235

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Tue 5/6

10:10 am-7:39 pm

1 stop8h 29m

San Juan Luis Munoz Marin Intl

Thu 5/8

6:15 am-2:54 pm

1 stop9h 39m

$325

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Sun 3/2

4:19 pm-10:44 am

1 stop16h 25m

$82

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Tue 1/28

10:05 am-12:25 am

2 stops12h 20m

$118

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Tue 1/28

10:57 am-11:46 pm

1 stop10h 49m

$163

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Mon 5/5

8:35 am-4:05 pm

3 stops30h 30m

$255

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/21

Best time to book a flight from Midway to Puerto Rico

Have a flexible travel schedule? Discover the best time to fly to Puerto Rico 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 Puerto Rico

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

What is the cheapest month to book a flight from Chicago Midway Airport to Puerto Rico?

Currently, September is the cheapest month in which you can book a flight from Chicago Midway Airport to Puerto Rico (average of $254). Flying from Chicago Midway Airport to Puerto Rico in March is currently the most expensive (average of $378). 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 PR?

Find hourly flight availability from Midway to Puerto Rico. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated January 21, 2025.

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 Puerto Rico as you normally would.

Rainfall in Puerto Rico by month

Plan your trip to Puerto Rico by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Puerto Rico 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 Puerto Rico when rainfall is around 2.2 in.

Temperature in Puerto Rico by month

Plan your trip to Puerto Rico by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Puerto Rico, 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 Puerto Rico

Get insights into the airlines that provide service to Puerto Rico. 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 Puerto Rico. Reviews last updated January 21, 2025.
Southwest
8.1
Very good
4,662 reviews

Comfort

8.1

Boarding

8.2

Crew

8.7

Entertainment

7.7

Overall

8.1

Food

7.2

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

Southwest
8.1
Very good
4,662 reviews
Southwest
8.1
Very good
4,662 reviews

Comfort

8.1

Boarding

8.2

Crew

8.7

Entertainment

7.7

Overall

8.1

Food

7.2

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

Delta
8.0
Very good
8,521 reviews
Southwest
8.1
Very good
4,662 reviews

Comfort

8.1

Boarding

8.2

Crew

8.7

Entertainment

7.7

Overall

8.1

Food

7.2

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

Frontier
6.1
Okay
3,443 reviews
Southwest
8.1
Very good
4,662 reviews

Comfort

8.1

Boarding

8.2

Crew

8.7

Entertainment

7.7

Overall

8.1

Food

7.2

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

Related info for your journey

Find useful and relevant information for your journey from Midway to Puerto Rico. 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 to fly from Chicago Midway Airport to Puerto Rico one-way?

    The cheapest airlines for a one-way flight from Chicago Midway Airport to Puerto Rico are Frontier ($83), Southwest ($118), and Delta ($163).

  • Can I find deals for flights from Midway to Puerto Rico that include hotel bookings?

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

  • How can I find direct flights from Midway to Puerto Rico?

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

  • Can I find deals for business class flights from Midway to Puerto Rico?

    Yes. Cheapflights offers flight deals from Midway to Puerto Rico 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 Puerto Rico?

    Currently, September is the cheapest month in which you can book a flight from Chicago Midway Airport to Puerto Rico (average of $254). Flying from Chicago Midway Airport to Puerto Rico in March is currently the most expensive (average of $378). 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

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Alternative routes for Midway to Puerto Rico

See prices for flight routes from nearby airports that may be better suited for you.
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Midway to Georgetown flights
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Midway to Santiago de los Caballeros flights

Top 4 airlines flying from Midway to Puerto Rico

Discover the top 4 airlines that operate flights from Midway to Puerto Rico. 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 2,558,603 searches. Data last updated January 21, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$128Average$300FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$199Average$284FlexibilityNo cancel feeOn-time65%
SouthwestCheapest$317Average$475FlexibilityNo cancel feeOn-time63%
DeltaCheapest$354Average$580FlexibilityNo cancel feeOn-timeN/A
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