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Midway

$124+ 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 11/18. Fares are subject to change and may not be available on all flights or dates of travel.
SJU — MDW
oct. 17 — oct. 241
vie. 10/17
vie. 10/24
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 septiembre 17, 2025.

Round-trip from

$203
(Frontier)

One-way from

$124
(Kiwi.com)

Popular in

August

Cheapest in

January

Average price

$297

Good one-way deal

$231 or less
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 ($11 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease ($5 potential savings vs. average RT price).
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Average for round-trip flights in September 2025
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Price to beat on a one-way flight from Puerto Rico to Chicago Midway.
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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 septiembre 17, 2025.

This Frontier deal was found by Cheapflights users on 9/16. 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.
sáb. 10/256:22 amSJU - MDW
2 stops17h 25mFrontier
vie. 10/319:32 amMDW - SJU
1 stop10h 52mFrontier
Deal found 9/16$203
This Southwest deal was found by Cheapflights users on 9/17. 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.
jue. 10/235:50 amSJU - MDW
2 stops8h 30mSouthwest
dom. 10/266:55 amMDW - SJU
1 stop7h 55mSouthwest
Deal found 9/17$227
This Frontier deal was found by Cheapflights users on 9/15. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 10/216:22 amSJU - MDW
2 stops17h 58mFrontier
lun. 10/2712:17 pmMDW - SJU
1 stop6h 39mFrontier
Deal found 9/15$244
This Frontier deal was found by Cheapflights users on 9/15. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lun. 10/69:26 pmSJU - MDW
2 stops17h 12mFrontier
vie. 10/1710:33 amMDW - SJU
1 stop8h 23mFrontier
Deal found 9/15$249
This Frontier deal was found by Cheapflights users on 9/15. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 12/43:00 pmSJU - MDW
1 stop10h 25mFrontier
lun. 12/82:15 pmMDW - SJU
1 stop10h 35mFrontier
Deal found 9/15$251
This Kiwi.com deal was found by Cheapflights users on 9/15. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb. 11/156:00 amSJU - MDW
2 stops17h 35mMultiple Airlines
mar. 11/186:26 pmMDW - SJU
1 stop31h 07mMultiple Airlines
Deal found 9/15$253
This Frontier deal was found by Cheapflights users on 9/15. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 10/221:59 amSJU - MDW
2 stops19h 22mFrontier
dom. 10/269:26 pmMDW - SJU
2 stops16h 58mFrontier
Deal found 9/15$255
This Frontier deal was found by Cheapflights users on 9/15. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 9/239:26 pmSJU - MDW
2 stops19h 32mFrontier
vie. 9/266:21 amMDW - SJU
1 stop8h 01mFrontier
Deal found 9/15$256
This Frontier deal was found by Cheapflights users on 9/15. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 10/166:22 amSJU - MDW
2 stops14h 59mFrontier
sáb. 10/186:15 amMDW - SJU
1 stop7h 13mFrontier
Deal found 9/15$261
This Kiwi.com deal was found by Cheapflights users on 9/14. 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.
mié. 10/291:59 amSJU - MDW
1 stop13h 34mFrontier
dom. 11/25:20 amMDW - SJU
1 stop6h 59mFrontier
Deal found 9/14$263
This Priceline deal was found by Cheapflights users on 9/15. 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.
mié. 10/152:59 amBQN - MDW
1 stop8h 47mFrontier
sáb. 10/1811:31 amMDW - BQN
1 stop13h 33mFrontier
Deal found 9/15$286
This Trip.com deal was found by Cheapflights users on 9/16. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 10/222:59 amBQN - MDW
2 stops21h 47mFrontier
jue. 10/306:20 amMDW - BQN
2 stops18h 57mFrontier
Deal found 9/16$303

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 septiembre 17, 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

jue. 11/13

6:40 am-11:25 am

1 stop6h 45m

Chicago Midway

lun. 11/17

12:55 pm-11:20 pm

1 stop8h 25m

$227

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

mié. 11/5

5:45 am-1:05 pm

2 stops9h 20m

Chicago Midway

sáb. 11/8

1:00 pm-12:15 am

1 stop9h 15m

$227

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

mar. 11/4

5:45 am-2:30 pm

1 stop10h 45m

Chicago Midway

sáb. 11/8

1:00 pm-12:15 am

1 stop9h 15m

$227

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

jue. 10/9

1:05 pm-9:55 pm

1 stop9h 50m

Chicago Midway

vie. 10/17

5:50 pm-9:50 am

2 stops15h 00m

$227

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

jue. 10/23

5:50 am-2:20 pm

1 stop9h 30m

Chicago Midway

dom. 10/26

6:55 am-3:50 pm

1 stop7h 55m

$227

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

jue. 10/30

5:50 am-1:20 pm

2 stops8h 30m

Chicago Midway

dom. 11/2

1:40 pm-9:45 pm

1 stop6h 05m

$227

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

jue. 11/13

4:31 pm-10:03 pm

1 stop7h 32m

Chicago Midway

lun. 11/17

6:15 am-3:19 pm

1 stop7h 04m

$272

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

jue. 10/2

10:57 am-11:41 pm

2 stops13h 44m

Chicago Midway

lun. 10/6

6:21 am-3:42 pm

1 stop8h 21m

$278

AguadillaChicago

BQN - MDW

BQNMDW

Aguadilla Borinquen

mié. 10/15

2:59 am-10:46 am

1 stop8h 47m

Chicago Midway

sáb. 10/18

11:31 am-2:04 am

1 stop13h 33m

$286

AguadillaChicago

BQN - MDW

BQNMDW

Aguadilla Borinquen

mié. 10/22

2:59 am-11:46 pm

2 stops21h 47m

Chicago Midway

jue. 10/30

6:20 am-2:17 am

2 stops18h 57m

$303

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/15

Showing 1-10 of 27 results
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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 septiembre 17, 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 septiembre 17, 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
4,242 reviews

Overall

8.0

Boarding

8.1

Crew

8.6

Comfort

8.0

Food

7.0

Entertainment

7.5

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
4,242 reviews
Southwest
8.0
Very good
4,242 reviews

Overall

8.0

Boarding

8.1

Crew

8.6

Comfort

8.0

Food

7.0

Entertainment

7.5

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
3,173 reviews
Southwest
8.0
Very good
4,242 reviews

Overall

8.0

Boarding

8.1

Crew

8.6

Comfort

8.0

Food

7.0

Entertainment

7.5

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 Southwest and Frontier fly from Puerto Rico to Chicago Midway Airport in about 6h 45m. The time it takes to get you to your destination can typically vary by up to 2h 02m. There are 2057 mi between Puerto Rico and Chicago Midway Airport. This flight may include one or multiple stops.

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

    Looking for the cheapest flight from Puerto Rico to Chicago Midway Airport? While on average our users pay $231, our data indicates the cheapest price to be $191. The most popular route (San Juan Luis Munoz Marin Intl - Chicago Midway), is priced around $227.

  • 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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Port Au Prince to Midway flights

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 septiembre 17, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$148Average$234FlexibilityNo cancel feeOn-time62%
SouthwestCheapest$320Average$497FlexibilityNo cancel feeOn-time63%

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