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Puerto Rico

$88+ 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 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
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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 November 20, 2024.

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 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 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 2,629,791 searches. Data last updated November 20, 2024.

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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 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 $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 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 November 20, 2024.

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 November 20, 2024.
Read through reviews of airlines operating flights from Chicago to Puerto Rico, such as Frontier, Delta and Southwest. 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
5,014 reviews

Crew

8.7

Comfort

8.1

Overall

8.1

Entertainment

7.7

Food

7.2

Boarding

8.2

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

Crew

8.7

Comfort

8.1

Overall

8.1

Entertainment

7.7

Food

7.2

Boarding

8.2

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

Crew

8.7

Comfort

8.1

Overall

8.1

Entertainment

7.7

Food

7.2

Boarding

8.2

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

Crew

8.7

Comfort

8.1

Overall

8.1

Entertainment

7.7

Food

7.2

Boarding

8.2

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 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 ($88), Southwest ($105), and Delta ($162).

  • 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 $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.

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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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O'Hare Intl to Saint Thomas Island flights
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Midway to Nassau flights
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O'Hare Intl to Puerto Plata flights
Midway to Providenciales flights
Midway to Simpson Bay flights
O'Hare Intl to Kralendijk flights
Midway to George Town flights
O'Hare Intl to St. John's flights
O'Hare Intl to Basseterre flights
O'Hare Intl to Kingston flights
Midway to Santo Domingo flights
O'Hare Intl to Santiago de los Caballeros flights
O'Hare Intl to Gregory Town flights
O'Hare Intl to St. George's flights
O'Hare Intl to Georgetown flights
Midway to Castries flights
O'Hare Intl to Freeport flights
O'Hare Intl to Road Town flights
O'Hare Intl to Port of Spain flights
Midway to Kingston flights
O'Hare Intl to Castries flights
O'Hare Intl to Fort-de-France flights
O'Hare Intl to The Valley flights
Midway to Santiago de los Caballeros flights
O'Hare Intl to Havana flights
Midway to Georgetown flights
O'Hare Intl to Pointe-à-Pitre flights
O'Hare Intl to Port Au Prince flights
O'Hare Intl to Marsh Harbour flights
O'Hare Intl to Gustavia flights
O'Hare Intl to Kingstown 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 2,629,791 searches. Data last updated November 20, 2024.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$119Average$299FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$199Average$277FlexibilityNo cancel feeOn-time65%
SouthwestCheapest$275Average$416FlexibilityNo cancel feeOn-time63%
DeltaCheapest$374Average$674FlexibilityNo cancel feeOn-timeN/A
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