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Midway

$119+ Cheap flights from Puerto Rico to Midway (MDW)

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 10/4. Fares are subject to change and may not be available on all flights or dates of travel.
SJU — MDW
Aug 26 — Sep 21
Tue 8/26
Tue 9/2
1 adult, Economy
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Cheap flight deals from Puerto Rico to Midway

Keep the following information in mind while searching for Puerto Rico to Midway flight deals. Data was last updated August 21, 2025.

Round-trip from

$238
(Mytrip)

One-way from

$119
(Priceline)

Popular in

June

Cheapest in

January

Average price

$292
From Puerto Rico to Chicago Midway
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One-way flight from Puerto Rico to Chicago Midway
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Highest demand for flights based on searches. 3% potential increase in price ($10 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease ($6 potential savings vs. average RT price).
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Average for round-trip flights in August 2025
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Find flight deals from Puerto Rico to Midway

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

This Mytrip deal was found by Cheapflights users on 8/21. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/123:39 amSJU - MDW
1 stop7h 12mFrontier
Sat 9/2010:51 amMDW - SJU
1 stop12h 08mFrontier
Deal found 8/21$238
This Priceline deal was found by Cheapflights users on 8/21. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/241:06 pmSJU - MDW
1 stop19h 05mFrontier
Fri 9/269:48 amMDW - SJU
1 stop15h 46mFrontier
Deal found 8/21$258
This Priceline deal was found by Cheapflights users on 8/19. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/2412:28 amSJU - MDW
1 stop7h 43mFrontier
Sat 9/276:15 amMDW - SJU
1 stop6h 56mFrontier
Deal found 8/19$259
This Booking.com deal was found by Cheapflights users on 8/19. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/412:28 amSJU - MDW
1 stop7h 43mFrontier
Sat 9/2710:51 amMDW - SJU
1 stop20h 11mFrontier
Deal found 8/19$261
This OneTravel deal was found by Cheapflights users on 8/20. 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 OneTravel is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/313:31 pmSJU - MDW
1 stop7h 37mFrontier
Sun 11/26:06 pmMDW - SJU
1 stop17h 16mFrontier
Deal found 8/20$269
This Mytrip deal was found by Cheapflights users on 8/21. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/2512:28 amSJU - MDW
1 stop7h 43mFrontier
Sun 9/286:20 amMDW - SJU
1 stop6h 51mFrontier
Deal found 8/21$278
This Priceline deal was found by Cheapflights users on 8/19. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/163:40 amSJU - MDW
1 stop13h 40mFrontier
Mon 10/209:45 amMDW - SJU
1 stop12h 44mFrontier
Deal found 8/19$279
This Booking.com deal was found by Cheapflights users on 8/21. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/296:25 amSJU - MDW
1 stop7h 45mFrontier
Sun 8/313:36 pmMDW - SJU
1 stop7h 18mFrontier
Deal found 8/21$281
This Mytrip deal was found by Cheapflights users on 8/21. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/238:23 pmSJU - MDW
1 stop12h 59mFrontier
Sun 8/313:36 pmMDW - SJU
1 stop7h 18mFrontier
Deal found 8/21$283
This Gotogate deal was found by Cheapflights users on 8/21. 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 Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/228:13 pmSJU - MDW
1 stop14h 41mFrontier
Sun 8/313:36 pmMDW - SJU
1 stop7h 18mFrontier
Deal found 8/21$284
This Mytrip deal was found by Cheapflights users on 8/19. 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.
Fri 8/228:13 pmSJU - MDW
1 stop14h 41mFrontier
Sun 8/249:17 amMDW - SJU
1 stop16h 33mFrontier
Deal found 8/19$289
This SmartFares deal was found by Cheapflights users on 8/19. 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 SmartFares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/113:16 pmSJU - MDW
1 stop9h 04mFrontier
Sun 9/146:20 amMDW - SJU
1 stop6h 51mFrontier
Deal found 8/19$290

Cheapflights Fare Finder

 
Customize your flight search to find flights from Puerto Rico to Midway 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 August 21, 2025.
Use the filters below to find and compare flights from Puerto Rico to Chicago Midway Airport that are best for you.

Fly from

Puerto Rico

Fly to

Midway

Route

Depart

Return

Price

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Sat 9/13

3:16 pm-11:17 pm

1 stop9h 01m

Chicago Midway

Sat 9/20

10:51 am-11:59 pm

1 stop12h 08m

$238

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Sat 9/27

3:16 pm-11:17 pm

1 stop9h 01m

Chicago Midway

Mon 9/29

6:20 am-2:11 pm

1 stop6h 51m

$258

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Wed 9/24

1:06 pm-7:11 am

1 stop19h 05m

Chicago Midway

Fri 9/26

9:48 am-2:34 am

1 stop15h 46m

$258

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Wed 10/15

1:26 pm-7:25 am

1 stop18h 59m

Chicago Midway

Mon 10/20

6:15 am-2:06 pm

1 stop6h 51m

$258

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Sat 10/11

4:22 pm-10:47 pm

1 stop7h 25m

Chicago Midway

Mon 10/13

5:28 pm-2:30 am

1 stop8h 02m

$258

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Wed 9/24

12:28 am-7:11 am

1 stop7h 43m

Chicago Midway

Sat 9/27

6:15 am-2:11 pm

1 stop6h 56m

$259

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Thu 9/4

12:28 am-7:11 am

1 stop7h 43m

Chicago Midway

Sat 9/27

10:51 am-8:02 am

1 stop20h 11m

$261

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Fri 9/26

3:39 am-9:51 am

1 stop7h 12m

Chicago Midway

Sun 10/5

6:20 am-2:11 pm

1 stop6h 51m

$261

AguadillaChicago

BQN - MDW

BQNMDW

Aguadilla Borinquen

Fri 10/3

3:32 am-9:18 am

1 stop30h 46m

Chicago Midway

Mon 10/6

8:19 am-2:08 am

1 stop16h 49m

$346

AguadillaChicago

BQN - MDW

BQNMDW

Aguadilla Borinquen

Sat 10/4

11:41 am-9:18 am

1 stop22h 37m

Chicago Midway

Mon 10/6

9:47 pm-2:04 am

2 stops27h 17m

$378

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/21

Showing 1-10 of 22 results
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2
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Best time to book a flight from Puerto Rico to Midway

Have a flexible travel schedule? Discover the best time to fly to Midway from Puerto Rico 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 Puerto Rico to Chicago Midway Airport

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

Currently, April is the cheapest month in which you can book a flight from Puerto Rico to Chicago Midway Airport (average of $160). Flying from Puerto Rico to Chicago Midway Airport in November is currently the most expensive (average of $249). 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 PR to MDW?

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

When flying from Puerto Rico to Chicago Midway Airport, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

Reviews of airlines servicing Midway

Get insights into the airlines that provide service to Midway. 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 Midway. Reviews last updated August 21, 2025.
Read reviews from past customers who have flown Southwest and Frontier from Puerto Rico to Chicago Midway Airport. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,245 reviews

Overall

8.0

Food

7.0

Entertainment

7.5

Comfort

8.0

Boarding

8.1

Crew

8.6

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Southwest
8.0
Very good
4,245 reviews
Southwest
8.0
Very good
4,245 reviews

Overall

8.0

Food

7.0

Entertainment

7.5

Comfort

8.0

Boarding

8.1

Crew

8.6

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Frontier
5.8
Fair
3,207 reviews
Southwest
8.0
Very good
4,245 reviews

Overall

8.0

Food

7.0

Entertainment

7.5

Comfort

8.0

Boarding

8.1

Crew

8.6

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines

Related info for your journey

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

    Airlines like Frontier fly from Puerto Rico to Chicago Midway Airport in about 9h 01m. The time it takes to get you to your destination can typically vary by up to . There are 2057 mi between Puerto Rico and Chicago Midway Airport.

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

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

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

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

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

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

    Currently, April is the cheapest month in which you can book a flight from Puerto Rico to Chicago Midway Airport (average of $160). Flying from Puerto Rico to Chicago Midway Airport in November is currently the most expensive (average of $249). 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

Traveling to a place near Chicago Midway Airport?

Book flights to Chicago Midway Airport if you plan to visit one of these locations
Merrillville
Lansing
Hammond
Benton Harbor
Porter
Chesterton

Browse thousands of different options on Cheapflights for your next trip

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Alternative routes for Puerto Rico to Midway

See prices for flight routes from nearby airports that may be better suited for you.
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Top 2 airlines flying from Puerto Rico to Midway

Discover the top 2 airlines that operate flights from Puerto Rico to Midway. 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 August 21, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$148Average$234FlexibilityNo cancel feeOn-time62%
SouthwestCheapest$312Average$463FlexibilityNo cancel feeOn-time63%

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