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Midway

$108+ 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 12/25. Fares are subject to change and may not be available on all flights or dates of travel.
SJU — MDW
Dec 6 — Dec 131
Sat 12/6
Sat 12/13
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 November 6, 2025.

Round-trip from

$203
(eDestinos)

One-way from

$108
(Trip.com)

Popular in

August

Cheapest in

January

Average price

$285
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. 0% potential increase in price ($3 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 November 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 November 6, 2025.

This eDestinos deal was found by Cheapflights users on 11/4. 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.
Wed 12/247:30 amSJU - MDW
1 stop16h 42mFrontier
Sat 1/32:24 pmMDW - SJU
1 stop10h 15mFrontier
Deal found 11/4$203
This Frontier deal was found by Cheapflights users on 11/6. 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 12/54:31 pmSJU - MDW
1 stop7h 41mFrontier
Mon 12/86:15 amMDW - SJU
1 stop6h 56mFrontier
Deal found 11/6$211
This Kiwi.com deal was found by Cheapflights users on 11/5. 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.
Tue 12/239:49 amSJU - MDW
1 stop30h 48mFrontier
Fri 1/28:15 amMDW - SJU
1 stop12h 29mFrontier
Deal found 11/5$237
This Kiwi.com deal was found by Cheapflights users on 11/6. 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.
Sun 11/237:10 amSJU - MDW
1 stop12h 05mFrontier
Mon 11/2412:25 pmMDW - SJU
1 stop25h 50mFrontier
Deal found 11/6$239
This CheapOair deal was found by Cheapflights users on 11/5. 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 11/252:25 amSJU - MDW
1 stop17h 55mFrontier
Thu 12/42:16 pmMDW - SJU
1 stop18h 16mFrontier
Deal found 11/5$251
This Kiwi.com deal was found by Cheapflights users on 11/6. 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.
Sun 12/213:54 amSJU - MDW
1 stop12h 11mFrontier
Thu 1/16:33 pmMDW - SJU
1 stop26h 11mFrontier
Deal found 11/6$255
This Kiwi.com deal was found by Cheapflights users on 11/5. 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 11/2012:37 pmSJU - MDW
1 stop8h 54mMultiple Airlines
Mon 11/245:47 pmMDW - SJU
1 stop15h 02mMultiple Airlines
Deal found 11/5$259
This CheapOair deal was found by Cheapflights users on 11/6. 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.
Wed 12/33:55 amSJU - MDW
1 stop20h 03mFrontier
Sun 12/72:59 pmMDW - SJU
1 stop16h 38mFrontier
Deal found 11/6$261
This eDestinos deal was found by Cheapflights users on 11/4. 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.
Thu 11/133:59 amBQN - MDW
1 stop20h 11mFrontier
Tue 11/181:56 pmMDW - BQN
2 stops35h 08mFrontier
Deal found 11/4$333
This Priceline deal was found by Cheapflights users on 11/5. 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.
Fri 11/143:59 amBQN - MDW
1 stop8h 27mFrontier
Sun 11/1610:12 amMDW - BQN
1 stop14h 52mFrontier
Deal found 11/5$354
This Priceline deal was found by Cheapflights users on 11/5. 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 11/193:55 amBQN - MDW
1 stop14h 35mFrontier
Mon 11/245:47 pmMDW - BQN
1 stop7h 16mFrontier
Deal found 11/5$374
This Frontier deal was found by Cheapflights users on 11/4. 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 11/123:59 amBQN - MDW
1 stop7h 13mFrontier
Thu 11/205:30 pmMDW - BQN
1 stop7h 33mFrontier
Deal found 11/4$384

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 November 6, 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

Fri 1/23

7:30 am-12:01 pm

1 stop6h 31m

Chicago Midway

Tue 2/3

12:48 pm-8:57 pm

1 stop6h 09m

$227

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Wed 12/24

4:16 pm-5:38 pm

1 stop27h 22m

Chicago Midway

Sat 1/3

2:24 pm-2:39 am

1 stop10h 15m

$245

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Fri 2/13

6:30 am-1:20 pm

2 stops8h 50m

Chicago Midway

Tue 2/17

1:35 pm-12:05 am

2 stops8h 30m

$287

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Fri 2/13

6:30 am-1:20 pm

2 stops8h 50m

Chicago Midway

Sun 2/22

7:20 pm-10:30 am

1 stop13h 10m

$287

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Fri 11/21

9:30 pm-4:57 pm

1 stop21h 27m

Chicago Midway

Mon 11/24

12:25 pm-2:54 am

2 stops12h 29m

$297

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Sat 1/24

6:00 am-1:40 pm

2 stops9h 40m

Chicago Midway

Tue 1/27

7:35 am-8:55 pm

1 stop11h 20m

$311

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Thu 11/20

7:15 am-4:30 pm

1 stop11h 15m

Chicago Midway

Sun 11/23

12:25 pm-9:40 am

2 stops19h 15m

$312

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Tue 11/25

2:25 am-6:20 pm

1 stop17h 55m

Chicago Midway

Sun 11/30

5:30 pm-11:44 pm

2 stops28h 14m

$372

AguadillaChicago

BQN - MDW

BQNMDW

Aguadilla Borinquen

Wed 11/19

3:55 am-4:30 pm

1 stop14h 35m

Chicago Midway

Mon 11/24

5:47 pm-3:03 am

1 stop7h 16m

$374

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Thu 11/27

9:54 pm-7:31 pm

1 stop23h 37m

Chicago Midway

Mon 12/1

7:10 pm-12:49 am

1 stop27h 39m

$381

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/5

Showing 1-10 of 23 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, December is the cheapest month in which you can book a flight from Puerto Rico to Chicago Midway Airport (average of $154). Flying from Puerto Rico to Chicago Midway Airport in March is currently the most expensive (average of $427). 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 November 6, 2025.

Unlike in the afternoon, when flights are generally more expensive, you can save up to 40% on flights from Puerto Rico to Chicago Midway Airport by exploring options for tickets in the morning.

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 November 6, 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
4,241 reviews

Food

7.0

Entertainment

7.5

Comfort

8.0

Crew

8.6

Boarding

8.1

Overall

8.0

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
4,241 reviews
Southwest
8.0
Very good
4,241 reviews

Food

7.0

Entertainment

7.5

Comfort

8.0

Crew

8.6

Boarding

8.1

Overall

8.0

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
3,116 reviews
Southwest
8.0
Very good
4,241 reviews

Food

7.0

Entertainment

7.5

Comfort

8.0

Crew

8.6

Boarding

8.1

Overall

8.0

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 Delta, Frontier, and Southwest fly from Puerto Rico to Chicago Midway Airport in about 6h 31m. The time it takes to get you to your destination can typically vary by up to 20h 51m. There are 2057 mi between Puerto Rico and Chicago Midway Airport. This flight may include one or multiple stops.

  • What are the cheapest airlines to fly from Puerto Rico to Chicago Midway Airport one-way?

    For one-way options, check prices for Southwest. According to our data, you can fly for as low as $114. Users have also found prices from $114 and $177 on Delta and Frontier, respectively.

  • 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, December is the cheapest month in which you can book a flight from Puerto Rico to Chicago Midway Airport (average of $154). Flying from Puerto Rico to Chicago Midway Airport in March is currently the most expensive (average of $427). 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
Lansing
Hammond
Porter
Benton Harbor
Merrillville

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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
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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 November 6, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$148Average$265FlexibilityNo cancel feeOn-time62%
SouthwestCheapest$394Average$566FlexibilityNo cancel feeOn-time63%

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