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Puerto Rico

$115+ 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 3/5. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — SJU
Jan 17 — Jan 241
Sat 1/17
Sat 1/24
1 adult, Economy
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Cheap 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 December 18, 2025.

This Expedia deal was found by Cheapflights users on 12/16. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/296:15 amMDW - SJU
1 stop24h 24mFrontier
Sat 1/177:34 pmSJU - MDW
1 stop23h 31mFrontier
Deal found 12/16$250
This CheapOair deal was found by Cheapflights users on 12/16. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/303:10 pmMDW - SJU
1 stop9h 40mFrontier
Thu 1/810:47 pmSJU - MDW
1 stop17h 19mFrontier
Deal found 12/16$255
This Priceline deal was found by Cheapflights users on 12/16. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/313:10 pmMDW - SJU
1 stop9h 40mFrontier
Thu 1/810:47 pmSJU - MDW
1 stop17h 19mFrontier
Deal found 12/16$258
This Priceline deal was found by Cheapflights users on 12/15. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/226:15 amMDW - SJU
1 stop24h 24mFrontier
Thu 12/257:00 amSJU - MDW
1 stop12h 38mFrontier
Deal found 12/15$260
This CheapOair deal was found by Cheapflights users on 12/16. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/226:15 amMDW - SJU
1 stop18h 24mFrontier
Tue 12/237:33 pmSJU - MDW
1 stop21h 04mFrontier
Deal found 12/16$285
This Kiwi.com deal was found by Cheapflights users on 12/16. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/256:12 amMDW - SJU
2 stops24h 27mMultiple Airlines
Fri 1/1611:52 amSJU - MDW
1 stop9h 02mMultiple Airlines
Deal found 12/16$286
This Frontier deal was found by Cheapflights users on 12/16. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/293:10 pmMDW - SJU
1 stop9h 40mFrontier
Fri 1/94:39 pmSJU - MDW
1 stop7h 42mFrontier
Deal found 12/16$288
This Frontier deal was found by Cheapflights users on 12/16. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/318:15 amMDW - SJU
1 stop13h 39mFrontier
Fri 1/94:39 pmSJU - MDW
1 stop7h 42mFrontier
Deal found 12/16$292
This Priceline deal was found by Cheapflights users on 12/16. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/253:10 pmMDW - SJU
1 stop27h 17mFrontier
Mon 12/293:55 amSJU - MDW
1 stop20h 03mFrontier
Deal found 12/16$301

Find 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 December 18, 2025.

Round-trip from

$195
(Priceline)

One-way from

$115
(Priceline)

Popular in

December

Cheapest in

April

Average price

$570
From Chicago Midway to Puerto Rico
Search Deals
One-way flight from Chicago Midway to Puerto Rico
Search Deals
Highest demand for flights based on searches. 10% potential increase in price ($49 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($15 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in December 2025
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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 December 18, 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

Wed 1/21

1:50 pm-12:35 am

2 stops8h 45m

San Juan Luis Munoz Marin Intl

Wed 1/28

5:40 am-2:15 pm

2 stops10h 35m

$265

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Sat 1/24

10:46 am-11:45 pm

1 stop10h 59m

San Juan Luis Munoz Marin Intl

Wed 1/28

3:55 pm-10:22 pm

1 stop8h 27m

$275

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Mon 1/19

6:00 am-5:17 pm

1 stop9h 17m

San Juan Luis Munoz Marin Intl

Fri 1/23

2:15 pm-10:22 pm

1 stop10h 07m

$275

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Mon 1/26

6:50 am-7:05 pm

2 stops10h 15m

San Juan Luis Munoz Marin Intl

Fri 1/30

6:10 am-1:55 pm

2 stops9h 45m

$295

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Sat 1/24

2:45 pm-12:10 am

1 stop7h 25m

San Juan Luis Munoz Marin Intl

Fri 1/30

6:10 am-11:35 am

1 stop7h 25m

$295

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Wed 1/28

6:00 am-5:17 pm

1 stop9h 17m

San Juan Luis Munoz Marin Intl

Tue 2/3

3:55 pm-10:22 pm

1 stop8h 27m

$310

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Sat 1/17

12:45 pm-12:10 am

2 stops9h 25m

San Juan Luis Munoz Marin Intl

Thu 1/22

6:10 am-1:55 pm

2 stops9h 45m

$310

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Thu 1/15

9:50 am-10:25 pm

2 stops10h 35m

San Juan Luis Munoz Marin Intl

Thu 1/22

6:10 am-1:55 pm

2 stops9h 45m

$330

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Thu 1/8

1:50 pm-12:35 am

2 stops8h 45m

San Juan Luis Munoz Marin Intl

Thu 1/15

2:20 pm-11:45 pm

1 stop11h 25m

$355

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Sun 1/18

2:20 pm-12:35 am

2 stops8h 15m

San Juan Luis Munoz Marin Intl

Thu 1/22

5:40 am-12:30 pm

2 stops8h 50m

$375

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/16

Showing 1-10 of 23 results
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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, January is the cheapest month in which you can book a flight from Chicago Midway Airport to Puerto Rico (average of $131). Flying from Chicago Midway Airport to Puerto Rico in June is currently the most expensive (average of $298). 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 December 18, 2025.

Unlike at noon, when flights are generally more expensive, you can save up to 54% on flights from Chicago Midway Airport to Puerto Rico by exploring options for tickets in the afternoon.

How often are flights from Chicago to Puerto Rico delayed?

About 23% of weekly flights between Chicago and Puerto Rico have experienced delays in the past year, with the average delay time being 97 minutes.

What is the most punctual flight time for Chicago to Puerto Rico flights?

Historically, flights departing in the morning are less likely to be delayed, whereas flights leaving in the morning tend to experience delays more often.

What day of the week experiences the fewest flight delays on this route?

Saturday tends to have the lowest number of delays on this route, whereas Tuesday has historically faced a higher average of delays compared to other days of the week.

Which airline has the best punctuality record on Chicago to Puerto Rico flights?

Over the last year, Southwest have had the lowest number of delays on this route, with just 23% of flights being delayed.

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 December 18, 2025.
Peruse reviews from past customers who have flown with Southwest, Delta, and Frontier from Chicago Midway Airport to Puerto Rico to help guide your decision. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
7.9
Good
4,249 reviews

Overall

7.9

Boarding

8.1

Crew

8.6

Comfort

8.0

Food

7.0

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
Southwest
7.9
Good
4,249 reviews
Southwest
7.9
Good
4,249 reviews

Overall

7.9

Boarding

8.1

Crew

8.6

Comfort

8.0

Food

7.0

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
Delta
7.9
Good
8,007 reviews
Southwest
7.9
Good
4,249 reviews

Overall

7.9

Boarding

8.1

Crew

8.6

Comfort

8.0

Food

7.0

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
Frontier
5.8
Fair
3,081 reviews
Southwest
7.9
Good
4,249 reviews

Overall

7.9

Boarding

8.1

Crew

8.6

Comfort

8.0

Food

7.0

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am

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.

  • How long is the flight from Chicago Midway Airport to Puerto Rico?

    Airlines like Southwest and Delta fly from Chicago Midway Airport to Puerto Rico in about 8h 45m. The time it takes to get you to your destination can typically vary by up to 2h 14m. Airlines will cover a distance of 2057 mi. This flight may include one or multiple stops.

  • 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, January is the cheapest month in which you can book a flight from Chicago Midway Airport to Puerto Rico (average of $131). Flying from Chicago Midway Airport to Puerto Rico in June is currently the most expensive (average of $298). 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

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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 3 airlines flying from Midway to Puerto Rico

Discover the top 3 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 December 18, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$144Average$294FlexibilityNo cancel feeOn-time62%
DeltaCheapest$325Average$394FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$381Average$495FlexibilityNo cancel feeOn-time63%

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