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$84+ 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 5/5. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — SJU
Feb 25 — Mar 41
Tue 2/25
Tue 3/4
1 adult, Economy
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Cheap flight deals from Midway to Puerto Rico

Keep the following information in mind while searching for Midway to Puerto Rico flight deals. Data was last updated February 20, 2025.

Round-trip from

$168
(Mytrip)

One-way from

$84
(Cheapflightsfares)

Popular in

December

Cheapest in

April

Average price

$372
From Chicago Midway to Puerto Rico
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One-way flight from Chicago Midway to Puerto Rico
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Highest demand for flights based on searches. 15% potential increase in price ($69 potential increase over avg. RT price).
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Cheapest flight prices on average. 5% potential price decrease ($19 potential savings vs. average RT price).
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Average for round-trip flights in February 2025
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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 February 20, 2025.

This Mytrip deal was found by Cheapflights users on 2/19. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/54:20 pmMDW - SJU
1 stop26h 50mFrontier
Tue 3/116:00 amSJU - MDW
1 stop10h 32mFrontier
Deal found 2/19$168
This Delta deal was found by Cheapflights users on 2/20. 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 3/1112:51 pmMDW - SJU
1 stop9h 16mDelta
Tue 3/1812:54 pmSJU - MDW
1 stop10h 29mDelta
Deal found 2/20$271
This Southwest deal was found by Cheapflights users on 2/20. 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.
Thu 3/611:00 amMDW - SJU
1 stop11h 30mSouthwest
Tue 3/115:35 amSJU - MDW
2 stops8h 45mSouthwest
Deal found 2/20$378

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 February 20, 2025.

Fly from

Midway

Fly to

Puerto Rico

Route

Depart

Return

Price

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Wed 3/5

4:20 pm-9:10 pm

1 stop26h 50m

San Juan Luis Munoz Marin Intl

Tue 3/11

6:00 am-3:32 pm

1 stop10h 32m

$168

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Tue 3/11

12:51 pm-11:07 pm

1 stop9h 16m

San Juan Luis Munoz Marin Intl

Tue 3/18

12:54 pm-10:23 pm

1 stop10h 29m

$271

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Thu 3/6

11:00 am-12:30 am

1 stop11h 30m

San Juan Luis Munoz Marin Intl

Tue 3/11

5:35 am-1:20 pm

2 stops8h 45m

$378

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Mon 5/5

6:15 am-2:47 pm

1 stop7h 32m

$84

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Wed 4/23

12:48 pm-11:15 pm

1 stop9h 27m

$136

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Tue 3/4

1:45 pm-12:40 am

2 stops8h 55m

$161

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Mon 3/31

8:40 am-4:34 pm

3 stops30h 54m

$184

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/20

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 $363). 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 February 20, 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 February 20, 2025.
Read through reviews of airlines operating flights from Chicago to Puerto Rico, such as Southwest, Delta and Frontier. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.1
Very good
4,411 reviews

Crew

8.7

Overall

8.1

Entertainment

7.6

Boarding

8.2

Comfort

8.1

Food

7.1

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

Southwest
8.1
Very good
4,411 reviews
Southwest
8.1
Very good
4,411 reviews

Crew

8.7

Overall

8.1

Entertainment

7.6

Boarding

8.2

Comfort

8.1

Food

7.1

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

Delta
8.0
Very good
8,220 reviews
Southwest
8.1
Very good
4,411 reviews

Crew

8.7

Overall

8.1

Entertainment

7.6

Boarding

8.2

Comfort

8.1

Food

7.1

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

Frontier
6.0
Okay
3,355 reviews
Southwest
8.1
Very good
4,411 reviews

Crew

8.7

Overall

8.1

Entertainment

7.6

Boarding

8.2

Comfort

8.1

Food

7.1

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

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 ($84), Delta ($136), and Southwest ($161).

  • 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 $363). 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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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 February 20, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$134Average$298FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$174Average$277FlexibilityNo cancel feeOn-time65%
DeltaCheapest$325Average$483FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$332Average$475FlexibilityNo cancel feeOn-time63%
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