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$145+ 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 5/19. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — SJU
Apr 22 — Apr 291
Tue 4/22
Tue 4/29
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 April 17, 2025.

Round-trip from

$298
(Frontier)

One-way from

$145
(Trip.com)

Popular in

December

Cheapest in

August

Average price

$351

Good round-trip deal

$397 or less

Good one-way deal

$288 or less
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 ($68 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 April 2025
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Price to beat on a round-trip flight from Chicago Midway to Puerto Rico.
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Price to beat on a 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 April 17, 2025.

This Frontier deal was found by Cheapflights users on 4/17. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/212:15 pmMDW - SJU
1 stop12h 35mFrontier
Mon 5/510:46 amSJU - MDW
1 stop14h 01mFrontier
Deal found 4/17$298
This Southwest deal was found by Cheapflights users on 4/17. 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.
Sat 5/171:35 pmMDW - SJU
1 stop7h 50mSouthwest
Sat 5/241:00 pmSJU - MDW
Nonstop5h 20mSouthwest
Deal found 4/17$377
This Delta deal was found by Cheapflights users on 4/16. 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.
Wed 5/1410:25 amMDW - SJU
1 stop8h 23mDelta
Wed 5/286:15 amSJU - MDW
1 stop6h 38mDelta
Deal found 4/16$391
This Mytrip deal was found by Cheapflights users on 4/15. 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.
Thu 5/2911:03 amMDW - SJU
3 stops31h 04mMultiple Airlines
Sun 6/18:12 pmSJU - MDW
2 stops24h 02mMultiple Airlines
Deal found 4/15$470

Cheapflights Fare Finder

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 April 17, 2025.
Use the filters below to find and compare flights from Chicago Midway Airport to Puerto Rico that are best for you.

Fly from

Midway

Fly to

Puerto Rico

Route

Depart

Return

Price

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Fri 5/2

1:19 pm-10:01 pm

1 stop7h 42m

San Juan Luis Munoz Marin Intl

Sun 5/4

9:58 pm-5:28 pm

1 stop20h 30m

$298

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Sat 5/17

1:35 pm-10:25 pm

1 stop7h 50m

San Juan Luis Munoz Marin Intl

Sat 5/24

1:00 pm-5:20 pm

Nonstop5h 20m

$377

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Wed 5/14

10:25 am-7:48 pm

1 stop8h 23m

San Juan Luis Munoz Marin Intl

Wed 5/28

6:15 am-11:53 am

1 stop6h 38m

$391

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Thu 5/29

11:03 am-7:07 pm

3 stops31h 04m

San Juan Luis Munoz Marin Intl

Sun 6/1

8:12 pm-7:14 pm

2 stops24h 02m

$470

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Mon 5/19

1:19 pm-10:01 pm

1 stop7h 42m

$145

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Sat 6/14

8:00 am-7:45 pm

1 stop10h 45m

$156

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Tue 5/20

2:40 pm-11:55 pm

2 stops8h 15m

$191

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Tue 4/29

6:04 am-4:01 pm

1 stop8h 57m

$216

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/17

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.

Cheapflights Insights

Everything you need to know about your flight from Chicago Midway Airport to Puerto Rico

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 December is currently the most expensive (average of $336). 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 April 17, 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 April 17, 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
8.0
Very good
4,280 reviews

Boarding

8.2

Crew

8.6

Food

7.1

Entertainment

7.6

Comfort

8.0

Overall

8.0

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
Southwest
8.0
Very good
4,280 reviews
Southwest
8.0
Very good
4,280 reviews

Boarding

8.2

Crew

8.6

Food

7.1

Entertainment

7.6

Comfort

8.0

Overall

8.0

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
Delta
8.0
Very good
7,917 reviews
Southwest
8.0
Very good
4,280 reviews

Boarding

8.2

Crew

8.6

Food

7.1

Entertainment

7.6

Comfort

8.0

Overall

8.0

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
Frontier
6.0
Okay
3,281 reviews
Southwest
8.0
Very good
4,280 reviews

Boarding

8.2

Crew

8.6

Food

7.1

Entertainment

7.6

Comfort

8.0

Overall

8.0

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.

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 ($145), Southwest ($191), and Delta ($216).

  • What are the cheapest flights from Chicago Midway Airport to Puerto Rico?

    Looking for the cheapest flight from Chicago Midway Airport to Puerto Rico? While on average our users pay $362, our data indicates the cheapest price to be $243. The most popular route (Chicago Midway - San Juan Luis Munoz Marin Intl), is priced around $261.

  • 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 December is currently the most expensive (average of $336). 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.
O'Hare Intl to Luis Munoz Marin Intl flights
O'Hare Intl to Punta Cana flights
Midway to Luis Munoz Marin Intl flights
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Midway to Montego Bay flights
Midway to Punta Cana flights
O'Hare Intl to Nassau flights
O'Hare Intl to Saint Thomas Island flights
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Midway to Oranjestad flights
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Midway to Nassau flights
O'Hare Intl to Providenciales flights
Midway to Saint Thomas Island flights
O'Hare Intl to Kingston flights
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O'Hare Intl to Bridgetown flights
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Midway to Simpson Bay flights
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O'Hare Intl to Gregory Town flights
Midway to Kingston flights
O'Hare Intl to Freeport flights
O'Hare Intl to Culebra flights
O'Hare Intl to Basseterre flights
O'Hare Intl to The Valley flights
O'Hare Intl to Castries flights
O'Hare Intl to St. George's flights
O'Hare Intl to Aguadilla flights
O'Hare Intl to Kingstown flights
O'Hare Intl to Gustavia flights
O'Hare Intl to Marsh Harbour flights
O'Hare Intl to Georgetown flights
Midway to Castries flights
O'Hare Intl to Pointe-à-Pitre flights
O'Hare Intl to Port Royal 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 April 17, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$133Average$334FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$174Average$280FlexibilityNo cancel feeOn-time65%
DeltaCheapest$325Average$469FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$342Average$469FlexibilityNo cancel feeOn-time63%

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